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Prime Oxford Road location! This distinctive one level contemporary home offers a desirable split bedroom floor plan and an exceptional setting just minutes from Talbot Country Club, Easton, and Oxford. Set on a wooded lot, the property combines privacy and comfortable one-level living. Inside beautiful wood floors extend throughout the main living spaces. The thoughtfully designed layout offers a comfortable family room and dining area, along with a large living room with fireplace. A dedicated office/library provides a quiet space for work or study, while two primary owner suites offer exceptional flexibility and privacy. With 3 bedrooms and 3 full baths, the home provides ample room for guests and everyday living. Outdoor living takes center stage with covered front and rear porches and an in-ground swimming pool. A rare four-car garage provides exceptional space for vehicles, storage, hobbies, or recreational equipment. A sought after Oxford Road address, generous indoor and outdoor spaces, and convenient access to both Easton and Oxford make this a special Eastern Shore opportunity. Deep Well - Replaced in 2016. Roof replaced in 2024. Recently replaced sliding doors. Property being sold as-is. Inspections for informational purposes only.

6028 Millington Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,289,000

Fabulous home in Oaklands, ideally located along the highly desirable Oxford Road corridor! Beautifully updated and designed for effortless entertaining, this four-bedroom Colonial offers light-filled interiors, hardwood floors, geothermal heating and cooling and exceptional indoor-outdoor living. The living room features a fireplace flanked by custom built-ins and a large bay window. A separate family room provides a more relaxed setting with exposed wood beams and raised-hearth brick fireplace. At the heart of the home, the renovated kitchen features an oversized island, abundant cabinetry, a gas range, generous storage and a dining area. Just beyond, the light-filled sunroom is a standout with a wet bar, beamed ceiling and custom built-ins making it an inviting space for gatherings throughout the year. Upstairs, the oversized primary suite includes an updated ensuite bath and expansive walk-in closet. The second bedroom features hardwood floors and its own sitting area, while two additional bedrooms and an updated full bath complete the second floor. Outside, the backyard is an entertainer’s dream, featuring a saltwater in-ground pool, outdoor kitchen, fire pit and an impressive 1,532 square feet of terraced patio space. Two sheds offer additional storage and versatility, while a separate pump house accommodates the pool equipment. An oversized attached two-car garage provides ample space for vehicles, storage and hobbies. Residents of Oaklands also enjoy community water access and use of the community pier, completing this exceptional Oxford Road property. Please do not go down driveway without an appointment.

8410 Bozman Neavitt Rd, Bozman

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,195,000

Fabulous home in Oaklands, ideally located along the highly desirable Oxford Road corridor! Beautifully updated and designed for effortless entertaining, this four-bedroom Colonial offers light-filled interiors, hardwood floors, geothermal heating and cooling and exceptional indoor-outdoor living. The living room features a fireplace flanked by custom built-ins and a large bay window. A separate family room provides a more relaxed setting with exposed wood beams and raised-hearth brick fireplace. At the heart of the home, the renovated kitchen features an oversized island, abundant cabinetry, a gas range, generous storage and a dining area. Just beyond, the light-filled sunroom is a standout with a wet bar, beamed ceiling and custom built-ins making it an inviting space for gatherings throughout the year. Upstairs, the oversized primary suite includes an updated ensuite bath and expansive walk-in closet. The second bedroom features hardwood floors and its own sitting area, while two additional bedrooms and an updated full bath complete the second floor. Outside, the backyard is an entertainer’s dream, featuring a saltwater in-ground pool, outdoor kitchen, fire pit and an impressive 1,532 square feet of terraced patio space. Two sheds offer additional storage and versatility, while a separate pump house accommodates the pool equipment. An oversized attached two-car garage provides ample space for vehicles, storage and hobbies. Residents of Oaklands also enjoy community water access and use of the community pier, completing this exceptional Oxford Road property. Please do not go down driveway without an appointment.

28372 Canvasback Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$9,950,000

Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

4 Beds ⋅ 6 Baths

Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

6920 Travelers Rest Cir, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,695,000

Refined waterfront offering on Maryland’s Eastern Shore, 7871 Avon Court has been completely transformed into a sophisticated modern farmhouse blending timeless design and convenience. Thoughtfully renovated to a like-new standard, the residence offers approximately 2,000 square feet with 3 bedrooms, 2.5 baths and a private office/flex space. Dramatic vaulted living spaces, wide-plank flooring, custom finishes and a beautifully reimagined kitchen create interiors that feel both elevated and inviting. Expansive windows frame views of the Tred Avon River from nearly every room, seamlessly connecting the home to its exceptional waterfront setting. Set on a high-bank waterfront site with approximately 360± feet of shoreline and 3± feet MLW, the property is ideally suited for boating, kayaking, paddleboarding and waterfront entertaining. Private pier, sandy beach, mature trees and expansive lawn create a rare park-like setting just minutes from downtown Easton and within easy reach of Washington, Northern Virginia, Philadelphia and surrounding Mid-Atlantic destinations. A compelling waterfront retreat offering privacy, style and effortless Eastern Shore living. Room for pool subject approvals.

Refined waterfront offering on Maryland’s Eastern Shore, 7871 Avon Court has been completely transformed into a sophisticated modern farmhouse blending timeless design and convenience. Thoughtfully renovated to a like-new standard, the residence offers approximately 2,000 square feet with 3 bedrooms, 2.5 baths and a private office/flex space. Dramatic vaulted living spaces, wide-plank flooring, custom finishes and a beautifully reimagined kitchen create interiors that feel both elevated and inviting. Expansive windows frame views of the Tred Avon River from nearly every room, seamlessly connecting the home to its exceptional waterfront setting. Set on a high-bank waterfront site with approximately 360± feet of shoreline and 3± feet MLW, the property is ideally suited for boating, kayaking, paddleboarding and waterfront entertaining. Private pier, sandy beach, mature trees and expansive lawn create a rare park-like setting just minutes from downtown Easton and within easy reach of Washington, Northern Virginia, Philadelphia and surrounding Mid-Atlantic destinations. A compelling waterfront retreat offering privacy, style and effortless Eastern Shore living. Room for pool subject approvals.

7871 Avon Ct, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$13,750,000

Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. **CALL listing agent for more information! The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. The 12,000+ sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exemplifies the pinnacle of luxury living. Built by Ilex Construction, striking architectural details and unparalleled craftsmanship are demonstrated throughout, seamlessly integrating with the breathtaking beauty of the landscape. This magnificent home is filled with an abundance of natural light and boasts panoramic views, thanks to soaring glass walls that overlook the tranquil waters of Pickering Creek, expansive fields, and picturesque vineyards. The thoughtfully curated interior includes spacious living areas, a stunning owner's wing that offers privacy and comfort, and a separate guest wing that features a full kitchen, providing ideal accommodations for family and visitors. High-end features abound, including a gourmet kitchen, recreation room complete with kitchen and bar for entertaining, full exercise room, 5 car garages, elevator, heated limestone floors, Venetian plaster walls, and multiple outdoor decks. At every turn, this property exudes the loving care it has received. Outside, the resort-style amenities include a large, heated infinity pool, complete with waterfall and hot tub, stunning pool pavilion with full outdoor kitchen, stone fireplace, and two TV’s and AV system. Along with the waterside tennis/pickleball court, tranquil koi pond, and private pier with 4-5’MLW, the opportunities for outdoor fun and relaxation are boundless. In addition is the beautifully renovated 4-bedroom guesthouse with views of the vineyards, providing comfortable accommodations for family and friends. A well-equipped 9-stall barn includes a tack room/office, kitchenette, and a riding ring, complemented by 20 acres of fenced pastures. There is also a 3-4 BR caretaker's home, a fully outfitted greenhouse, large equipment barn complete with an office and full workshop, and hay barn for storage. The property also offers excellent hunting opportunities, making it a versatile retreat for outdoor enthusiasts. The highlights of this extraordinary property continue through every acre, including sweeping landscapes and hardscapes, 200 acres of working farmland, 5 acres of vineyards, and a 6-acre stocked pond with private island. Unparalleled in its mix of tranquility and luxury, the opportunity to experience the very best of the Eastern Shore’s refined lifestyle and natural beauty is only possible at Stock Range Farm. Please don't drive in driveway as there are security cameras and alarm. All appointments must be made with listing agent and additional information and details are available upon request.

5 Beds ⋅ 9 Baths

Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. **CALL listing agent for more information! The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. The 12,000+ sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exemplifies the pinnacle of luxury living. Built by Ilex Construction, striking architectural details and unparalleled craftsmanship are demonstrated throughout, seamlessly integrating with the breathtaking beauty of the landscape. This magnificent home is filled with an abundance of natural light and boasts panoramic views, thanks to soaring glass walls that overlook the tranquil waters of Pickering Creek, expansive fields, and picturesque vineyards. The thoughtfully curated interior includes spacious living areas, a stunning owner's wing that offers privacy and comfort, and a separate guest wing that features a full kitchen, providing ideal accommodations for family and visitors. High-end features abound, including a gourmet kitchen, recreation room complete with kitchen and bar for entertaining, full exercise room, 5 car garages, elevator, heated limestone floors, Venetian plaster walls, and multiple outdoor decks. At every turn, this property exudes the loving care it has received. Outside, the resort-style amenities include a large, heated infinity pool, complete with waterfall and hot tub, stunning pool pavilion with full outdoor kitchen, stone fireplace, and two TV’s and AV system. Along with the waterside tennis/pickleball court, tranquil koi pond, and private pier with 4-5’MLW, the opportunities for outdoor fun and relaxation are boundless. In addition is the beautifully renovated 4-bedroom guesthouse with views of the vineyards, providing comfortable accommodations for family and friends. A well-equipped 9-stall barn includes a tack room/office, kitchenette, and a riding ring, complemented by 20 acres of fenced pastures. There is also a 3-4 BR caretaker's home, a fully outfitted greenhouse, large equipment barn complete with an office and full workshop, and hay barn for storage. The property also offers excellent hunting opportunities, making it a versatile retreat for outdoor enthusiasts. The highlights of this extraordinary property continue through every acre, including sweeping landscapes and hardscapes, 200 acres of working farmland, 5 acres of vineyards, and a 6-acre stocked pond with private island. Unparalleled in its mix of tranquility and luxury, the opportunity to experience the very best of the Eastern Shore’s refined lifestyle and natural beauty is only possible at Stock Range Farm. Please don't drive in driveway as there are security cameras and alarm. All appointments must be made with listing agent and additional information and details are available upon request.

27772 Sharp Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$3,295,000

Unrivaled Architecture and Design! Exceptional waterfront living on picturesque Town Creek in the historic village of Oxford. Built in 2023 and privately set on 1.71 acres—an extraordinary offering in Oxford—this 5-bedroom, 4.5-bath residence is surrounded by mature trees, refined landscaping, and beautifully executed hardscaping. Designed with exceptional attention to detail, the home features soaring vaulted ceilings, expansive windows, and multiple decks and balconies that frame tranquil water views throughout. The grand living room with gas fireplace opens to the dining area and extraordinary chef’s kitchen, appointed with a substantial center island, casual dining area, and butler’s pantry. A screened porch extends directly from the kitchen, creating an effortless setting for outdoor dining and entertaining. The main-level primary suite is a private retreat with a spa-inspired bath, separate sitting room, and direct access to a screened waterside porch. A private office with adjacent full bath offers flexibility as a fifth bedroom or guest suite. The second floor offers three additional bedrooms, including an ensuite guest room with private balcony, and two bedrooms connected by a Jack-and-Jill bath. Outside, a waterside slate terrace takes full advantage of the setting, while a new pier with two slips and 4' MLW provides convenient boating access. The property also features an integrated rainwater harvesting and management system as part of its environmental site design. Just a short stroll from downtown Oxford, this exceptional property offers a rare combination of architectural distinction, privacy, acreage, and waterfront access. Built outside the flood zone; elevation certificate available. Room for a pool, with plans available for a pool and pool house.

5 Beds ⋅ 5 Baths

Unrivaled Architecture and Design! Exceptional waterfront living on picturesque Town Creek in the historic village of Oxford. Built in 2023 and privately set on 1.71 acres—an extraordinary offering in Oxford—this 5-bedroom, 4.5-bath residence is surrounded by mature trees, refined landscaping, and beautifully executed hardscaping. Designed with exceptional attention to detail, the home features soaring vaulted ceilings, expansive windows, and multiple decks and balconies that frame tranquil water views throughout. The grand living room with gas fireplace opens to the dining area and extraordinary chef’s kitchen, appointed with a substantial center island, casual dining area, and butler’s pantry. A screened porch extends directly from the kitchen, creating an effortless setting for outdoor dining and entertaining. The main-level primary suite is a private retreat with a spa-inspired bath, separate sitting room, and direct access to a screened waterside porch. A private office with adjacent full bath offers flexibility as a fifth bedroom or guest suite. The second floor offers three additional bedrooms, including an ensuite guest room with private balcony, and two bedrooms connected by a Jack-and-Jill bath. Outside, a waterside slate terrace takes full advantage of the setting, while a new pier with two slips and 4' MLW provides convenient boating access. The property also features an integrated rainwater harvesting and management system as part of its environmental site design. Just a short stroll from downtown Oxford, this exceptional property offers a rare combination of architectural distinction, privacy, acreage, and waterfront access. Built outside the flood zone; elevation certificate available. Room for a pool, with plans available for a pool and pool house.

104 East St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact:

$3,495,000

Located at the end of a private, gated, park-like lane, mid-way between Easton and Oxford: This gracious home is situated on one of the premier sites in Talbot County, MD...2.3-acre point of land, providing Westerly (SUNSET) views looking directly down Trippe Creek toward the Tred Avon River. The tastefully updated brick home provides exceptional water views from most rooms, especially from the living room, dining room and brick-floored glassed "River Room." The floor plan (see downstairs and upstairs plans in the attached photos) features 2-bedrooms down stairs (including a "Primary" Bedroom) and 2 bedrooms upstairs (Including another "Primary" - take your pick!). A total of four large bedrooms, four bathrooms and one half-bath. Lots of living and entertaining spaces downstairs, including a spacious living room, family room, library and River Room. Recent updates include a new BAT septic system; encapsulated crawl space; refinished wood floors throughout; fresh paint inside and out; new kitchen countertops; new kitchen appliances; updated bathrooms and more. This is a true "turn-key" home. For boating, there is a substantial private pier (6' x 135') which provides 6+ ft of depth at low tide (MLW). By boat, the town of Oxford and the open waters of the Choptank River are just a short, scenic 5-mile boat ride downstream. By car, this prime location is conveniently located approx. 5-miles to Easton or 5-miles to Oxford. The Talbot Country Club is less than 2-miles away. A new survey confirms there is room to install a swimming pool. There is a perfect future pool site, providing views of the dock and Trippe Creek.

4 Beds ⋅ 5 Baths

Located at the end of a private, gated, park-like lane, mid-way between Easton and Oxford: This gracious home is situated on one of the premier sites in Talbot County, MD...2.3-acre point of land, providing Westerly (SUNSET) views looking directly down Trippe Creek toward the Tred Avon River. The tastefully updated brick home provides exceptional water views from most rooms, especially from the living room, dining room and brick-floored glassed "River Room." The floor plan (see downstairs and upstairs plans in the attached photos) features 2-bedrooms down stairs (including a "Primary" Bedroom) and 2 bedrooms upstairs (Including another "Primary" - take your pick!). A total of four large bedrooms, four bathrooms and one half-bath. Lots of living and entertaining spaces downstairs, including a spacious living room, family room, library and River Room. Recent updates include a new BAT septic system; encapsulated crawl space; refinished wood floors throughout; fresh paint inside and out; new kitchen countertops; new kitchen appliances; updated bathrooms and more. This is a true "turn-key" home. For boating, there is a substantial private pier (6' x 135') which provides 6+ ft of depth at low tide (MLW). By boat, the town of Oxford and the open waters of the Choptank River are just a short, scenic 5-mile boat ride downstream. By car, this prime location is conveniently located approx. 5-miles to Easton or 5-miles to Oxford. The Talbot Country Club is less than 2-miles away. A new survey confirms there is room to install a swimming pool. There is a perfect future pool site, providing views of the dock and Trippe Creek.

28161 Harleigh Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

$3,000,000

FALL IN LOVE WITH LIFE IN ST. MICHAELS! As summer fades, the Eastern Shore becomes even more captivating. Just one mile from vibrant downtown St. Michaels, this meticulously renovated waterfront residence offers easy access to seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities. Designed for effortless one-level living, the home combines thoughtful design and relaxed comfort in a resort-like setting. Its westerly orientation provides expansive water views, spectacular sunsets and abundant wildlife. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs convey. Additional features include a saltwater pool, pool house, three-car garage and a separate, fenced “tiny house” for the dogs!

FALL IN LOVE WITH LIFE IN ST. MICHAELS! As summer fades, the Eastern Shore becomes even more captivating. Just one mile from vibrant downtown St. Michaels, this meticulously renovated waterfront residence offers easy access to seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities. Designed for effortless one-level living, the home combines thoughtful design and relaxed comfort in a resort-like setting. Its westerly orientation provides expansive water views, spectacular sunsets and abundant wildlife. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs convey. Additional features include a saltwater pool, pool house, three-car garage and a separate, fenced “tiny house” for the dogs!

23820 Mount Pleasant Lndg, Saint Michaels

Listing courtesy of Engel & Volkers Annapolis. Contact:

$1,150,000

Beautifully positioned on a quiet cul-de-sac in the sought-after community of Cooke’s Hope, this distinguished brick residence offers timeless architecture, generously scaled interiors, a beautifully landscaped private garden with green house, and a detached two-car garage with a private studio above. Designed for both everyday comfort and elegant entertaining, the home is filled with natural light and features a thoughtfully planned floor plan. The welcoming living room is defined by high ceilings, a gas fireplace, and ample space for multiple seating areas, including room for a grand piano. At the heart of the home, the expansive kitchen combines exceptional storage with a large center island, Corian countertops, quality appliances, and a casual dining area. A spacious library/family room with custom built-in shelving provides an inviting retreat, while the adjoining enclosed sunroom overlooks the garden and creates a seamless connection to the outdoors. An elevator provides convenient access to the second level (new carpet throughout), where the spacious primary suite features a tray ceiling and a large well-appointed bath with two walk-in closets, separate vanities, a generous walk-in shower, and towel warmers. Two additional bedrooms offer abundant closet space and share a skylit hall bath. Easily accessible attic space provides excellent additional storage. The mudroom and laundry room is thoughtfully equipped with built-in cabinetry, a utility sink, and direct access to the garden. Outside, mature landscaping, brick hardscaping, and a fountain create a private and tranquil setting. Above the detached garage, the studio with half bath offers exceptional flexibility as a home office, guest suite, fitness room, or creative workspace. Residents of Cooke’s Hope enjoy an outstanding collection of amenities, including scenic walking trails, ponds, tennis and pickleball courts, a fitness room, community gathering spaces, and a waterfront dock with slips and kayak storage. A rare opportunity to own a beautifully maintained home that offers timeless design, exceptional versatility, and the distinctive lifestyle of one of Easton’s premier communities.

Beautifully positioned on a quiet cul-de-sac in the sought-after community of Cooke’s Hope, this distinguished brick residence offers timeless architecture, generously scaled interiors, a beautifully landscaped private garden with green house, and a detached two-car garage with a private studio above. Designed for both everyday comfort and elegant entertaining, the home is filled with natural light and features a thoughtfully planned floor plan. The welcoming living room is defined by high ceilings, a gas fireplace, and ample space for multiple seating areas, including room for a grand piano. At the heart of the home, the expansive kitchen combines exceptional storage with a large center island, Corian countertops, quality appliances, and a casual dining area. A spacious library/family room with custom built-in shelving provides an inviting retreat, while the adjoining enclosed sunroom overlooks the garden and creates a seamless connection to the outdoors. An elevator provides convenient access to the second level (new carpet throughout), where the spacious primary suite features a tray ceiling and a large well-appointed bath with two walk-in closets, separate vanities, a generous walk-in shower, and towel warmers. Two additional bedrooms offer abundant closet space and share a skylit hall bath. Easily accessible attic space provides excellent additional storage. The mudroom and laundry room is thoughtfully equipped with built-in cabinetry, a utility sink, and direct access to the garden. Outside, mature landscaping, brick hardscaping, and a fountain create a private and tranquil setting. Above the detached garage, the studio with half bath offers exceptional flexibility as a home office, guest suite, fitness room, or creative workspace. Residents of Cooke’s Hope enjoy an outstanding collection of amenities, including scenic walking trails, ponds, tennis and pickleball courts, a fitness room, community gathering spaces, and a waterfront dock with slips and kayak storage. A rare opportunity to own a beautifully maintained home that offers timeless design, exceptional versatility, and the distinctive lifestyle of one of Easton’s premier communities.

7040 Old School House Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$599,000

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities.

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities.

6280 Bellevue Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$2,195,000

Coveted location between Easton and St. Michaels with breathtaking Tred Avon River views!!!!Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick home enjoys water views from nearly every room. The thoughtfully designed one-level floor plan is comfortable and easy to live in, while the classic character of the original home has been complemented by extensive updates from the current owners. A substantial attic runs the full length of the house, offering excellent storage and the potential for future expansion. The three-bedroom, three-bath home has been updated throughout, with beautiful hardwood floors, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new deck, 2017 roof, and numerous other improvements. The spacious waterside primary suite has a generous ensuite bath, ample closet space, and additional storage, while two privately situated bedrooms share a full bath for family or guests. The living spaces are warm and inviting, with large windows bringing the river setting indoors. The living room centers around a wood-burning fireplace framed by custom built-in bookshelves, and the formal dining room is well suited for entertaining. The renovated kitchen, with its large center island and premium appliances, flows into the comfortable family room and the waterside enclosed sunroom, complete with a full bath and beautiful river views. An adjoining bonus room offers additional flexibility for a butler’s pantry, hobby or craft room, or storage. An oversized attached two-car garage connects conveniently to the expansive attic, while a detached, climate-controlled studio provides wonderful flexibility for an art studio, home office, workshop, or other uses. The outdoor spaces make the most of the waterfront setting. A gunite pool, added in 2020, is surrounded by hardscape and fencing and offers a private place to relax and entertain. The dock was completely rebuilt in 2024 and includes two slips, a floating dock, and approximately 6' MLW, providing excellent access to the Tred Avon River and by boat to Oxford and the Choptank River. With its beautiful setting, extensive improvements, exceptional boating access, and convenient location between Easton and St. Michaels, this is a special Eastern Shore property that offers privacy, character, and an easy waterfront lifestyle.

Coveted location between Easton and St. Michaels with breathtaking Tred Avon River views!!!!Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick home enjoys water views from nearly every room. The thoughtfully designed one-level floor plan is comfortable and easy to live in, while the classic character of the original home has been complemented by extensive updates from the current owners. A substantial attic runs the full length of the house, offering excellent storage and the potential for future expansion. The three-bedroom, three-bath home has been updated throughout, with beautiful hardwood floors, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new deck, 2017 roof, and numerous other improvements. The spacious waterside primary suite has a generous ensuite bath, ample closet space, and additional storage, while two privately situated bedrooms share a full bath for family or guests. The living spaces are warm and inviting, with large windows bringing the river setting indoors. The living room centers around a wood-burning fireplace framed by custom built-in bookshelves, and the formal dining room is well suited for entertaining. The renovated kitchen, with its large center island and premium appliances, flows into the comfortable family room and the waterside enclosed sunroom, complete with a full bath and beautiful river views. An adjoining bonus room offers additional flexibility for a butler’s pantry, hobby or craft room, or storage. An oversized attached two-car garage connects conveniently to the expansive attic, while a detached, climate-controlled studio provides wonderful flexibility for an art studio, home office, workshop, or other uses. The outdoor spaces make the most of the waterfront setting. A gunite pool, added in 2020, is surrounded by hardscape and fencing and offers a private place to relax and entertain. The dock was completely rebuilt in 2024 and includes two slips, a floating dock, and approximately 6' MLW, providing excellent access to the Tred Avon River and by boat to Oxford and the Choptank River. With its beautiful setting, extensive improvements, exceptional boating access, and convenient location between Easton and St. Michaels, this is a special Eastern Shore property that offers privacy, character, and an easy waterfront lifestyle.

27476 Travelers Rest Ct, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$979,000

No showings until Aug. 25, 2026. Stunning and spacious, this 4703-square-foot residence rests gracefully on a meticulously landscaped 2-acre parcel adorned with majestic trees. A tranquil goldfish pond, home to over 40 fish, adds a serene touch and can remain with the property, or the owner can rehome the fish. Upon entering, you're greeted by soaring 9+ foot ceilings and an impressive cathedral ceiling in the great room, complemented by recessed lighting throughout the home. The home features cutting-edge Geo-thermal heating and central air conditioning for comfort in all seasons. Entertainment options abound, with a well-appointed wet bar complete with a fridge. Luxurious flooring finishes include marble, hardwood, and Berber carpet upstairs. Dual primary bedroom suites on the main level offer versatility, one boasting a private deck overlooking the picturesque fishpond and gas fireplace. Each suite includes a spacious walk-in closet. The home offers an intercom. A large loft with a catwalk offers a commanding view of the main living area, enhanced by a striking window wall. Relax on the screened porch or enjoy the outdoors from the expansive front porch adorned with stately columns. Or the rear exterior charm is found on the deck with brick façade and wrought-iron railings. The home office/den and convenient laundry room are on the main level for added functionality. With four bedrooms—two upstairs and two downstairs—and 3.5 bathrooms, there's ample space for family and guests alike. Crown mouldings in the lower level and large columns throughout the interior add a touch of elegance. The gourmet kitchen is a chef's delight, featuring granite countertops, all-new stainless-steel appliances, and a double-wall oven. A breakfast room and formal dining room, open and defined by elegant columns, provide flexible dining options. This home offers an open main level, kitchen, breakfast area, living room, dining room, great room and large foyer. Blacktop Driveway and parking area, and 3 car garage. Additional features are the unique advantage of being one of only three properties excluded from HOA fees. This exceptional property offers a rare blend of luxury, functionality, and serene surroundings, making it truly one-of-a-kind.

4 Beds ⋅ 4 Baths

No showings until Aug. 25, 2026. Stunning and spacious, this 4703-square-foot residence rests gracefully on a meticulously landscaped 2-acre parcel adorned with majestic trees. A tranquil goldfish pond, home to over 40 fish, adds a serene touch and can remain with the property, or the owner can rehome the fish. Upon entering, you're greeted by soaring 9+ foot ceilings and an impressive cathedral ceiling in the great room, complemented by recessed lighting throughout the home. The home features cutting-edge Geo-thermal heating and central air conditioning for comfort in all seasons. Entertainment options abound, with a well-appointed wet bar complete with a fridge. Luxurious flooring finishes include marble, hardwood, and Berber carpet upstairs. Dual primary bedroom suites on the main level offer versatility, one boasting a private deck overlooking the picturesque fishpond and gas fireplace. Each suite includes a spacious walk-in closet. The home offers an intercom. A large loft with a catwalk offers a commanding view of the main living area, enhanced by a striking window wall. Relax on the screened porch or enjoy the outdoors from the expansive front porch adorned with stately columns. Or the rear exterior charm is found on the deck with brick façade and wrought-iron railings. The home office/den and convenient laundry room are on the main level for added functionality. With four bedrooms—two upstairs and two downstairs—and 3.5 bathrooms, there's ample space for family and guests alike. Crown mouldings in the lower level and large columns throughout the interior add a touch of elegance. The gourmet kitchen is a chef's delight, featuring granite countertops, all-new stainless-steel appliances, and a double-wall oven. A breakfast room and formal dining room, open and defined by elegant columns, provide flexible dining options. This home offers an open main level, kitchen, breakfast area, living room, dining room, great room and large foyer. Blacktop Driveway and parking area, and 3 car garage. Additional features are the unique advantage of being one of only three properties excluded from HOA fees. This exceptional property offers a rare blend of luxury, functionality, and serene surroundings, making it truly one-of-a-kind.

32675 Discovery Dr, Easton

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

$1,399,000

This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! ACCESS BY APPT ONLY, surveillance cameras.

This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact:

$1,500,000

A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact:

$6,375,000

Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

2 Beds ⋅ 3 Baths

Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

6150 Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$5,995,000

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

$7,900,000

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

$5,995,000

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

$2,995,000

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

4 Beds ⋅ 4 Baths

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

26279 Deep Water Harbor Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$410,000

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

21406 Dogwood Cove Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

$675,000

Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal for everyday living and entertaining. The second floor offers a nice loft / bonus area with fireplace, spacious owners suite with WIC and attached bath, plus a walk-in attic with potential for additional living space. Step outside to your own private retreat featuring a fenced rear yard, in-ground swimming pool, full pool bath with exterior access, and an expansive composite deck with vinyl railing—perfect for summer gatherings. Additional highlights include a new roof in 2025, new water heater April 2026, Polaris pool pimp replaced Fall 2025. attached 2-car garage with workbench. New shower in primary bathroom 2025, Chesapeake Crawl space Nov 2024,. Enjoy peaceful country living while remaining close to downtown amenities. Less than a mile to Kingston Landing – a public boat ramp for easy access to the water. Fence as-is.

Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal for everyday living and entertaining. The second floor offers a nice loft / bonus area with fireplace, spacious owners suite with WIC and attached bath, plus a walk-in attic with potential for additional living space. Step outside to your own private retreat featuring a fenced rear yard, in-ground swimming pool, full pool bath with exterior access, and an expansive composite deck with vinyl railing—perfect for summer gatherings. Additional highlights include a new roof in 2025, new water heater April 2026, Polaris pool pimp replaced Fall 2025. attached 2-car garage with workbench. New shower in primary bathroom 2025, Chesapeake Crawl space Nov 2024,. Enjoy peaceful country living while remaining close to downtown amenities. Less than a mile to Kingston Landing – a public boat ramp for easy access to the water. Fence as-is.

32930 Oyster Bank Ter, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$5,995,000

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

6 Beds ⋅ 6 Baths

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$5,895,000

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

5 Beds ⋅ 6 Baths

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

9170 Hunting Creek Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact:

$2,495,000

Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

4 Beds ⋅ 4 Baths

Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

28910 Jennings Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$7,900,000

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact:

$6,890,000

An Exceptional Eastern Shore Estate - 145 Acres of Waterfront, Farmland & Timeless Beauty. There are properties that offer a beautiful setting and then there are properties that possess an unmistakable sense of place. This extraordinary 145 acre estate in coveted Royal Oak is one of the latter - a private waterfront sanctuary where expansive farmland and pasture, mature trees, tranquil ponds and sweeping waterviews converge to create a setting of rare distinction. From the gated drive, the experience is extraordinary. A gracefully paved approach winds through a pastoral landscape of open vistas, three ponds, white-fenced fields and paddocks, and a magnificent canopy of mature sawtooth oaks. Beyond the landscape, the elegant Colonial-style main residence reveals itself, perfectly positioned to capture the serenity of Fox Hole Creek and its long view toward the Tred Avon River. The architecture is gracious and beautifully proportioned. The two-and-a-half-story central section is framed by side wings that step down elegantly to one-story elevations, creating a classic country estate character. Inside, generous proportions, heart pine floors, and natural light complement the home's timeless design. A compelling feature of the residence is its relationship to the water. On the main level, the sunroom, breakfast room, living room, family room, and primary suite all enjoy direct visual connections to the waterfront and open to a sweeping brick terrace extending the length of the house. It is an extraordinary setting for entertaining or simply enjoying the seasons of the Eastern Shore. The second-floor stair hall opens onto a substantial private deck, creating an elevated vantage point overlooking the water and surrounding acreage. Two-bedroom suites and two offices occupy this level, while an additional bedroom suite on the third floor provides comfortable accommodations for guests. The grounds unfold as a collection of distinct destinations. A two-bedroom guest house offers privacy for visitors while the detached garage with apartment above provides versatile space. The resort-style pool is complemented by an elegant pool house featuring a sauna, bath, kitchenette, porch, and lounging areas. A private pier and small boathouse extend the experience to the water, while a greenhouse with its own sitting area offers a tranquil retreat for gardening or quiet reflection. The estate includes a handsome five-stall barn with tack room, washroom, and fenced paddocks. A second barn has been transformed into an impressive garage accommodating classic automobiles—an exceptional amenity that could serve a collector or those seeking extraordinary workspace. Outdoor living is woven throughout the property. The front porch welcomes guests; the expansive covered brick terrace provides an exceptional setting for waterfront entertaining; and a covered brick walkway connects the main residence to the pool and pool house. At the pool, a pergola-shaded lounging area creates an intimate outdoor room designed for long afternoons and summer evenings. The estate is impeccably maintained and equipped for modern living, including a new composite roof, geothermal HVAC, wine cellar, sprinkler system, and high-speed connectivity. Starlink internet is in place, broadband cable is available, and Easton Velocity service is available for hookup. A gated main entrance and separate farm entrance provide convenience and privacy. The Bellevue Ferry to Oxford is nearby, while Easton and St. Michaels are approximately equidistant. Annapolis is approximately 50 miles, Washington, D.C. approximately 70 miles, and Easton Airport: 12 miles. This is a complete Eastern Shore lifestyle—private, elegant, equestrian, agricultural, and intimately connected to the water. SUBDIVISION POTENTIAL presents an additional opportunity, further enhancing the possibilities of this rare offering.

4 Beds ⋅ 5 Baths

An Exceptional Eastern Shore Estate - 145 Acres of Waterfront, Farmland & Timeless Beauty. There are properties that offer a beautiful setting and then there are properties that possess an unmistakable sense of place. This extraordinary 145 acre estate in coveted Royal Oak is one of the latter - a private waterfront sanctuary where expansive farmland and pasture, mature trees, tranquil ponds and sweeping waterviews converge to create a setting of rare distinction. From the gated drive, the experience is extraordinary. A gracefully paved approach winds through a pastoral landscape of open vistas, three ponds, white-fenced fields and paddocks, and a magnificent canopy of mature sawtooth oaks. Beyond the landscape, the elegant Colonial-style main residence reveals itself, perfectly positioned to capture the serenity of Fox Hole Creek and its long view toward the Tred Avon River. The architecture is gracious and beautifully proportioned. The two-and-a-half-story central section is framed by side wings that step down elegantly to one-story elevations, creating a classic country estate character. Inside, generous proportions, heart pine floors, and natural light complement the home's timeless design. A compelling feature of the residence is its relationship to the water. On the main level, the sunroom, breakfast room, living room, family room, and primary suite all enjoy direct visual connections to the waterfront and open to a sweeping brick terrace extending the length of the house. It is an extraordinary setting for entertaining or simply enjoying the seasons of the Eastern Shore. The second-floor stair hall opens onto a substantial private deck, creating an elevated vantage point overlooking the water and surrounding acreage. Two-bedroom suites and two offices occupy this level, while an additional bedroom suite on the third floor provides comfortable accommodations for guests. The grounds unfold as a collection of distinct destinations. A two-bedroom guest house offers privacy for visitors while the detached garage with apartment above provides versatile space. The resort-style pool is complemented by an elegant pool house featuring a sauna, bath, kitchenette, porch, and lounging areas. A private pier and small boathouse extend the experience to the water, while a greenhouse with its own sitting area offers a tranquil retreat for gardening or quiet reflection. The estate includes a handsome five-stall barn with tack room, washroom, and fenced paddocks. A second barn has been transformed into an impressive garage accommodating classic automobiles—an exceptional amenity that could serve a collector or those seeking extraordinary workspace. Outdoor living is woven throughout the property. The front porch welcomes guests; the expansive covered brick terrace provides an exceptional setting for waterfront entertaining; and a covered brick walkway connects the main residence to the pool and pool house. At the pool, a pergola-shaded lounging area creates an intimate outdoor room designed for long afternoons and summer evenings. The estate is impeccably maintained and equipped for modern living, including a new composite roof, geothermal HVAC, wine cellar, sprinkler system, and high-speed connectivity. Starlink internet is in place, broadband cable is available, and Easton Velocity service is available for hookup. A gated main entrance and separate farm entrance provide convenience and privacy. The Bellevue Ferry to Oxford is nearby, while Easton and St. Michaels are approximately equidistant. Annapolis is approximately 50 miles, Washington, D.C. approximately 70 miles, and Easton Airport: 12 miles. This is a complete Eastern Shore lifestyle—private, elegant, equestrian, agricultural, and intimately connected to the water. SUBDIVISION POTENTIAL presents an additional opportunity, further enhancing the possibilities of this rare offering.

5289 Ferry Neck Rd, Royal Oak

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$470,000

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.