easternshoremdfineproperties.com Search Results

$749,000

Charming and beautifully updated, this circa-1900 Colonial offers an inviting blend of historic character and refined, comfortable living in the heart of downtown Oxford. Surrounded by lovely gardens, mature trees, and established plantings, the property enjoys a picturesque setting just moments from the waterfront, with water views looking down the street and all the charm of this beloved Eastern Shore village close at hand. Inside, beautiful hardwood floors and thoughtfully updated interiors create a warm and welcoming atmosphere. The beautiful sun-lit living room offers a gracious space for relaxing and gathering, while the spacious gourmet kitchen serves as the heart of the home, featuring a large center island, premium stainless appliances, and a generous casual dining and sitting area overlooking the garden. A formal dining room provides an elegant setting for entertaining, while a comfortable sitting room opens to the screened porch, extending the living space outdoors. A full bath with a glass-enclosed shower completes the main level. Upstairs, the private primary suite is distinguished by vaulted, beamed ceilings and an ensuite bath with a double-sink vanity, glass-enclosed shower, two closets, and convenient access to the laundry. Two additional guest bedrooms share a half bath, with plans available upon request for conversion to a full bath. Outside, a wonderful screened porch and adjoining deck overlook the lush gardens and mature trees, creating a peaceful setting for outdoor dining and relaxation. A rare detached one-car garage offers additional workshop space, while the stone driveway provides ample off-street parking. Located in the heart of historic Oxford, the home is ideally positioned for enjoying the town’s waterfront parks, marinas, restaurants, and scenic streets, along with the relaxed pace and enduring character that make Oxford one of the Eastern Shore’s most treasured waterfront communities.

3 Beds ⋅ 3 Baths

Charming and beautifully updated, this circa-1900 Colonial offers an inviting blend of historic character and refined, comfortable living in the heart of downtown Oxford. Surrounded by lovely gardens, mature trees, and established plantings, the property enjoys a picturesque setting just moments from the waterfront, with water views looking down the street and all the charm of this beloved Eastern Shore village close at hand. Inside, beautiful hardwood floors and thoughtfully updated interiors create a warm and welcoming atmosphere. The beautiful sun-lit living room offers a gracious space for relaxing and gathering, while the spacious gourmet kitchen serves as the heart of the home, featuring a large center island, premium stainless appliances, and a generous casual dining and sitting area overlooking the garden. A formal dining room provides an elegant setting for entertaining, while a comfortable sitting room opens to the screened porch, extending the living space outdoors. A full bath with a glass-enclosed shower completes the main level. Upstairs, the private primary suite is distinguished by vaulted, beamed ceilings and an ensuite bath with a double-sink vanity, glass-enclosed shower, two closets, and convenient access to the laundry. Two additional guest bedrooms share a half bath, with plans available upon request for conversion to a full bath. Outside, a wonderful screened porch and adjoining deck overlook the lush gardens and mature trees, creating a peaceful setting for outdoor dining and relaxation. A rare detached one-car garage offers additional workshop space, while the stone driveway provides ample off-street parking. Located in the heart of historic Oxford, the home is ideally positioned for enjoying the town’s waterfront parks, marinas, restaurants, and scenic streets, along with the relaxed pace and enduring character that make Oxford one of the Eastern Shore’s most treasured waterfront communities.

100 Tilghman St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$3,295,000

EXPANSIVE SOUTHWESTERN VIEWS OF THE TRED AVON AND CHOPTANK RIVERS. A distinguished waterfront residence in Oxford, thoughtfully designed to embrace its extraordinary setting. Exceptional craftsmanship is evident throughout, with exquisite moldings and millwork, Brazilian Cherry hardwood floors, elevated and vaulted ceilings, abundant natural light, and an open floor plan oriented toward the water. The main level is equally suited to gracious entertaining and comfortable everyday living. A formal dining room opens to a refined gourmet kitchen with a generous center island and breakfast bar, premium stainless-steel appliances, wine storage, and a six-burner gas range. The kitchen flows seamlessly into the spacious living room with gas fireplace and continues to a screened porch and adjoining covered porch with outdoor grill, overlooking the pool and river. A well-appointed guest bedroom with ensuite bath and powder room complete the main level. Upstairs, a spacious sitting area with custom built-ins provides a quiet retreat. The waterside primary suite is exceptionally private, with a sitting area and gas fireplace, private balcony overlooking the river, and two cedar-lined walk-in closets with custom cabinetry. A discreetly integrated refreshment bar with wet sink and beverage refrigerator adds an elegant touch. The ensuite bath features a jetted tub, dual-sink vanity, and glass-enclosed walk-in shower. Three additional guest bedrooms include two sharing a Jack-and-Jill bath and a third with an ensuite bath. The waterfront grounds are designed for both relaxation and entertaining, with a pool and hot tub positioned to take full advantage of the expansive river views. A natural shoreline, small sandy beach, and private dock with boat lift and approximately 3' MLW extend the living experience to the water. A large two-car garage provides generous parking and storage. An exceptional Oxford offering with commanding river views, refined interiors, extensive outdoor living, and a private waterfront setting—an elegant retreat with all the elements for sophisticated Eastern Shore living.

5 Beds ⋅ 5 Baths

EXPANSIVE SOUTHWESTERN VIEWS OF THE TRED AVON AND CHOPTANK RIVERS. A distinguished waterfront residence in Oxford, thoughtfully designed to embrace its extraordinary setting. Exceptional craftsmanship is evident throughout, with exquisite moldings and millwork, Brazilian Cherry hardwood floors, elevated and vaulted ceilings, abundant natural light, and an open floor plan oriented toward the water. The main level is equally suited to gracious entertaining and comfortable everyday living. A formal dining room opens to a refined gourmet kitchen with a generous center island and breakfast bar, premium stainless-steel appliances, wine storage, and a six-burner gas range. The kitchen flows seamlessly into the spacious living room with gas fireplace and continues to a screened porch and adjoining covered porch with outdoor grill, overlooking the pool and river. A well-appointed guest bedroom with ensuite bath and powder room complete the main level. Upstairs, a spacious sitting area with custom built-ins provides a quiet retreat. The waterside primary suite is exceptionally private, with a sitting area and gas fireplace, private balcony overlooking the river, and two cedar-lined walk-in closets with custom cabinetry. A discreetly integrated refreshment bar with wet sink and beverage refrigerator adds an elegant touch. The ensuite bath features a jetted tub, dual-sink vanity, and glass-enclosed walk-in shower. Three additional guest bedrooms include two sharing a Jack-and-Jill bath and a third with an ensuite bath. The waterfront grounds are designed for both relaxation and entertaining, with a pool and hot tub positioned to take full advantage of the expansive river views. A natural shoreline, small sandy beach, and private dock with boat lift and approximately 3' MLW extend the living experience to the water. A large two-car garage provides generous parking and storage. An exceptional Oxford offering with commanding river views, refined interiors, extensive outdoor living, and a private waterfront setting—an elegant retreat with all the elements for sophisticated Eastern Shore living.

808 S Morris St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$865,000

Built in 2020 by Covell Builders, this customized Monterey Legacy offers 2,600± sq. ft. of finished living space with an appealing combination of first-floor living, flexible guest space, and distinctive architectural detail in Easton Village. The home features 2 bedrooms, 3 full baths, a private study, spacious screened porch, and attached two-car rear/side-entry garage. The private first-floor study is currently staged as a third bedroom, illustrating the versatility of the floor plan. Set on a 0.145± acre lot, the property backs to trees, while a landscaped community common area directly across the street provides an attractive outlook from the front of the home. A traditional foyer introduces the main level, where hardwood floors, crown molding, chair rail, and paneled millwork extend through the principal living areas. The private study is positioned near the entry, while the kitchen occupies the center of the home with white cabinetry, granite countertops, a large center island with seating, stainless steel appliances, and gas cooking. An adjoining butler's pantry provides generous cabinetry and counter space, glass-front display cabinets, built-in wine storage, and an under-counter beverage refrigerator. The living room features a gas fireplace and opens through French doors to a 234± sq. ft. screened porch, creating a comfortable extension of the living space and a convenient connection to the garage. The spacious first-floor primary suite includes a walk-in closet and private bath with double vanity and oversized tiled walk-in shower with frameless glass enclosure. A dedicated laundry room with utility sink and interior access to the conditioned crawlspace add everyday convenience. Upstairs, the second bedroom and full bath are joined by a spacious family room/retreat with a gas fireplace. This flexible upper level provides plenty of room for guests, media, exercise, hobbies, or additional living space. Additional features include natural gas heat and hot water, central air, a 404± sq. ft. attached two-car garage, covered front porch, brick-paver walkway, and established landscaping. Easton Village offers an array of community amenities including a clubhouse, waterside pool, fitness facilities, recreation and nature trails, open space, fishing and crabbing piers, kayak launch and storage, and marina, all convenient to downtown Easton.

2 Beds ⋅ 3 Baths

Built in 2020 by Covell Builders, this customized Monterey Legacy offers 2,600± sq. ft. of finished living space with an appealing combination of first-floor living, flexible guest space, and distinctive architectural detail in Easton Village. The home features 2 bedrooms, 3 full baths, a private study, spacious screened porch, and attached two-car rear/side-entry garage. The private first-floor study is currently staged as a third bedroom, illustrating the versatility of the floor plan. Set on a 0.145± acre lot, the property backs to trees, while a landscaped community common area directly across the street provides an attractive outlook from the front of the home. A traditional foyer introduces the main level, where hardwood floors, crown molding, chair rail, and paneled millwork extend through the principal living areas. The private study is positioned near the entry, while the kitchen occupies the center of the home with white cabinetry, granite countertops, a large center island with seating, stainless steel appliances, and gas cooking. An adjoining butler's pantry provides generous cabinetry and counter space, glass-front display cabinets, built-in wine storage, and an under-counter beverage refrigerator. The living room features a gas fireplace and opens through French doors to a 234± sq. ft. screened porch, creating a comfortable extension of the living space and a convenient connection to the garage. The spacious first-floor primary suite includes a walk-in closet and private bath with double vanity and oversized tiled walk-in shower with frameless glass enclosure. A dedicated laundry room with utility sink and interior access to the conditioned crawlspace add everyday convenience. Upstairs, the second bedroom and full bath are joined by a spacious family room/retreat with a gas fireplace. This flexible upper level provides plenty of room for guests, media, exercise, hobbies, or additional living space. Additional features include natural gas heat and hot water, central air, a 404± sq. ft. attached two-car garage, covered front porch, brick-paver walkway, and established landscaping. Easton Village offers an array of community amenities including a clubhouse, waterside pool, fitness facilities, recreation and nature trails, open space, fishing and crabbing piers, kayak launch and storage, and marina, all convenient to downtown Easton.

28323 Ayres Sq, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$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.

4 Beds ⋅ 3 Baths

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: 4106733344

$2,475,000

Exceptionally rare waterfront property located in the highly sought-after Oaklands neighborhood of Easton, Maryland, in the heart of the Chesapeake Bay region. Perfectly situated just minutes from charming downtown Easton and historic Oxford, you’ll enjoy easy access to renowned restaurants, boutique shopping, marinas, and all the beauty the Eastern Shore has to enjoy whatever the season. This beautiful one-story brick ranch home features an expansive open floor plan designed to capture breathtaking water views from nearly every room. With so much to offer it can easily be a full-time residence, retirement retreat, family home, or luxurious summer retreat - don't let this one get away. Floor-to-ceiling windows span the rear of the home, filling the great room with natural light and showcasing the peaceful beauty of private LeGates Cove off the Tred Avon River. The home offers a split bedroom plan with two oversized bedrooms that share a bath off the main entrance and a Primary bedroom ensuite featuring a full bath with soaking tub, separate shower, and additional closet space. 2 car garage with fixed stairs to storage above, paved driveway, and privacy trees. There's a dedicated office, laundry room, spacious kitchen, living room, and an oversized great room with brand new carpet all overlooking the water — ideal for entertaining family and friends or simply relaxing and enjoying the serene surroundings. Whether your passion is sailing, boating, fishing, or quiet waterfront living, this property offers it all. With approximately 220 feet of bulk headed / rip-rapped water frontage, 100’ dock with 10x30’ “L”, floating dock, water and sink area, the private waterfront is perfectly suited for larger boats to kayaks. The property is further updated with new carpet in the great room, new paint throughout most rooms, tankless water heater new kitchen hardware, Subzero fridge, Wolf oven and cooktop, lighted cabinets, buried 500 gal propane tank, whole house generator and surveillance system, Wi-Fi mesh / terrapin alarm, vapor barrier and floor joist insulation.

3 Beds ⋅ 2 Baths

Exceptionally rare waterfront property located in the highly sought-after Oaklands neighborhood of Easton, Maryland, in the heart of the Chesapeake Bay region. Perfectly situated just minutes from charming downtown Easton and historic Oxford, you’ll enjoy easy access to renowned restaurants, boutique shopping, marinas, and all the beauty the Eastern Shore has to enjoy whatever the season. This beautiful one-story brick ranch home features an expansive open floor plan designed to capture breathtaking water views from nearly every room. With so much to offer it can easily be a full-time residence, retirement retreat, family home, or luxurious summer retreat - don't let this one get away. Floor-to-ceiling windows span the rear of the home, filling the great room with natural light and showcasing the peaceful beauty of private LeGates Cove off the Tred Avon River. The home offers a split bedroom plan with two oversized bedrooms that share a bath off the main entrance and a Primary bedroom ensuite featuring a full bath with soaking tub, separate shower, and additional closet space. 2 car garage with fixed stairs to storage above, paved driveway, and privacy trees. There's a dedicated office, laundry room, spacious kitchen, living room, and an oversized great room with brand new carpet all overlooking the water — ideal for entertaining family and friends or simply relaxing and enjoying the serene surroundings. Whether your passion is sailing, boating, fishing, or quiet waterfront living, this property offers it all. With approximately 220 feet of bulk headed / rip-rapped water frontage, 100’ dock with 10x30’ “L”, floating dock, water and sink area, the private waterfront is perfectly suited for larger boats to kayaks. The property is further updated with new carpet in the great room, new paint throughout most rooms, tankless water heater new kitchen hardware, Subzero fridge, Wolf oven and cooktop, lighted cabinets, buried 500 gal propane tank, whole house generator and surveillance system, Wi-Fi mesh / terrapin alarm, vapor barrier and floor joist insulation.

28082 Oaklands Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$1,295,000

Beautifully maintained 3–4 bedroom home set on lovely park-like grounds in the sought after community of Cooke’s Hope. From the welcoming foyer, the home opens to formal living and dining rooms, followed by an inviting great room with cathedral ceiling, fireplace and wet bar. The spacious kitchen offers an abundance of cabinetry, stainless steel appliances, breakfast bar and a cozy breakfast nook overlooking the beautifully landscaped rear yard. Hardwood floors, crown molding and recessed lighting add warmth and character throughout. The first floor primary suite offers a walk-in closet and spacious bath with separate soaking tub. Upstairs, two additional ensuite bedrooms along with a separate office and family/bonus room with a private balcony. Tons of attic storage. Outdoor living is easy here, with a screened and wraparound porch overlooking the mature landscaping and private rear yard with gazebo. Cooke’s Hope offers an exceptional array of amenities, including scenic walking trails, ponds, tennis and pickleball courts, fitness room, community gathering spaces and a waterfront dock with slips and kayak storage. It is a community that offers both an active lifestyle and a sense of space and privacy. A special property in a highly desirable setting, offering one level living with plenty of additional space for family, guests and hobbies.Close to downtown Historic Easton, YMCA, shopping, museums and grocery stores. Please note: Sellers require a mid-April 2027 settlement. A rent-back agreement will be required if an earlier settlement is requested.

3 Beds ⋅ 4 Baths

Beautifully maintained 3–4 bedroom home set on lovely park-like grounds in the sought after community of Cooke’s Hope. From the welcoming foyer, the home opens to formal living and dining rooms, followed by an inviting great room with cathedral ceiling, fireplace and wet bar. The spacious kitchen offers an abundance of cabinetry, stainless steel appliances, breakfast bar and a cozy breakfast nook overlooking the beautifully landscaped rear yard. Hardwood floors, crown molding and recessed lighting add warmth and character throughout. The first floor primary suite offers a walk-in closet and spacious bath with separate soaking tub. Upstairs, two additional ensuite bedrooms along with a separate office and family/bonus room with a private balcony. Tons of attic storage. Outdoor living is easy here, with a screened and wraparound porch overlooking the mature landscaping and private rear yard with gazebo. Cooke’s Hope offers an exceptional array of amenities, including scenic walking trails, ponds, tennis and pickleball courts, fitness room, community gathering spaces and a waterfront dock with slips and kayak storage. It is a community that offers both an active lifestyle and a sense of space and privacy. A special property in a highly desirable setting, offering one level living with plenty of additional space for family, guests and hobbies.Close to downtown Historic Easton, YMCA, shopping, museums and grocery stores. Please note: Sellers require a mid-April 2027 settlement. A rent-back agreement will be required if an earlier settlement is requested.

28751 Emanuel St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$490,000

With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office. Upstairs are two generous ensuite bedrooms with updated baths. A slider off the primary bedroom leads to a porch overlooking the landscaped grounds. A one-car garage is just outside the front door, and additional parking is available just steps away. All this within a mile of historic St. Michaels (but no town taxes!).

3 Beds ⋅ 3 Baths

With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office. Upstairs are two generous ensuite bedrooms with updated baths. A slider off the primary bedroom leads to a porch overlooking the landscaped grounds. A one-car garage is just outside the front door, and additional parking is available just steps away. All this within a mile of historic St. Michaels (but no town taxes!).

9521 Quail Hollow Dr Unit #605, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$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: (410) 280-5600

$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: 4106733344

$799,950

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants, grocery stores, museums, and downtown shops. A wonderful place to settle in and enjoy the lifestyle that makes St. Michaels so special.

4 Beds ⋅ 4 Baths

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants, grocery stores, museums, and downtown shops. A wonderful place to settle in and enjoy the lifestyle that makes St. Michaels so special.

407 Seymour Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$1,100,000

Location, Location, Location. Oxford corridor with 50 Ft. of waterfront plus a small dock on Peachblossom Creek and a beautiful pond. Peaceful 3.5 acre waterfront lot with plenty of room for a pool and tennis courts. Rancher style home being sold As Is. 4 bedrooms and 3 full baths, oversized garage as well as a large detached garage. First time offered in 50+ years. This property is ready for your design. Bring your architect and make this your forever home.

4 Beds ⋅ 3 Baths

Location, Location, Location. Oxford corridor with 50 Ft. of waterfront plus a small dock on Peachblossom Creek and a beautiful pond. Peaceful 3.5 acre waterfront lot with plenty of room for a pool and tennis courts. Rancher style home being sold As Is. 4 bedrooms and 3 full baths, oversized garage as well as a large detached garage. First time offered in 50+ years. This property is ready for your design. Bring your architect and make this your forever home.

28221 Widgeon Ter, Easton

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

$3,295,000

Welcome to this exceptional 4/5 BR/4.5BA waterfront residence overlooking picturesque Town Creek in the historic waterfront town of Oxford. Built in 2023, this home is privately set on 1.71 acres (very rare for Oxford) surrounded by mature trees, extensive landscaping and thoughtfully designed hardscaping that complement the natural beauty of its serene waterfront setting. Designed with extraordinary attention to detail, the home showcases soaring vaulted ceilings, expansive windows, and multiple decks and balconies that capture tranquil water views from nearly every room. The grand living room, anchored by a gas fireplace, flows effortlessly into the dining area and an extraordinary chef’s kitchen featuring a large center island, separate casual dining space, a well-appointed butler’s pantry, and a screened porch just off the kitchen - perfect for outdoor dining and enjoying the peaceful waterfront setting. A private office with an adjacent full bath offers flexibility as a guest suite. The desirable main-level primary suite is a luxurious retreat, complete with a spa-inspired bath, private sitting room, and sliding doors opening to a peaceful screened waterside porch. The second floor offers three additional guest bedrooms, including one with an ensuite bath and two connected by a Jack & Jill bath, providing comfortable accommodation for family and guests. Outdoor living is equally impressive, featuring a waterside slate patio with expansive views, ideal for relaxing or entertaining while enjoying the serene waterfront setting. A new pier with two slips and 4’ MLW provides convenient boating access, while a thoughtfully integrated rainwater harvesting and management system was incorporated as part of the property’s environmental site design. Located just a short stroll from downtown Oxford, this beautiful waterfront home offers the perfect blend of luxury, comfort, and small-town coastal living. *Home built out of flood zone: Elevation certificate available *Room for pool; plans available for pool and pool house.

5 Beds ⋅ 5 Baths

Welcome to this exceptional 4/5 BR/4.5BA waterfront residence overlooking picturesque Town Creek in the historic waterfront town of Oxford. Built in 2023, this home is privately set on 1.71 acres (very rare for Oxford) surrounded by mature trees, extensive landscaping and thoughtfully designed hardscaping that complement the natural beauty of its serene waterfront setting. Designed with extraordinary attention to detail, the home showcases soaring vaulted ceilings, expansive windows, and multiple decks and balconies that capture tranquil water views from nearly every room. The grand living room, anchored by a gas fireplace, flows effortlessly into the dining area and an extraordinary chef’s kitchen featuring a large center island, separate casual dining space, a well-appointed butler’s pantry, and a screened porch just off the kitchen - perfect for outdoor dining and enjoying the peaceful waterfront setting. A private office with an adjacent full bath offers flexibility as a guest suite. The desirable main-level primary suite is a luxurious retreat, complete with a spa-inspired bath, private sitting room, and sliding doors opening to a peaceful screened waterside porch. The second floor offers three additional guest bedrooms, including one with an ensuite bath and two connected by a Jack & Jill bath, providing comfortable accommodation for family and guests. Outdoor living is equally impressive, featuring a waterside slate patio with expansive views, ideal for relaxing or entertaining while enjoying the serene waterfront setting. A new pier with two slips and 4’ MLW provides convenient boating access, while a thoughtfully integrated rainwater harvesting and management system was incorporated as part of the property’s environmental site design. Located just a short stroll from downtown Oxford, this beautiful waterfront home offers the perfect blend of luxury, comfort, and small-town coastal living. *Home built out of flood zone: Elevation certificate available *Room for pool; plans available for pool and pool house.

104 East St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$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 recently 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.

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 recently 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.

28161 Harleigh Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$3,000,000

Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its westerly orientation delivers spectacular sunsets every evening, complemented by expansive water views 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 even a separate, fenced “tiny house” for the dogs! The property fronts Broad Creek, a tidal tributary of the Choptank River and Chesapeake Bay, and is not located within a FEMA-designated flood zone

4 Beds ⋅ 3 Baths

Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its westerly orientation delivers spectacular sunsets every evening, complemented by expansive water views 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 even a separate, fenced “tiny house” for the dogs! The property fronts Broad Creek, a tidal tributary of the Choptank River and Chesapeake Bay, and is not located within a FEMA-designated flood zone

23820 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$895,000

Oxford. One owner 2,858 sq. ft home built in 2006 is just off the Strand only a block from the Tred Avon River. Features living room and dining rooms, den, family room with woodburning fireplace off open kitchen with island and granite countertops, powder room. Second floor offers 3 spacious bedrooms including a primary suite with walk-in closet and 2 guest bedrooms and guest bath. Exterior offers 2 balconies, HardiPlank siding, paver driveway and more on a .18 acre lot. Hardwood flooring throughout most of the home (except 2 guest bedrooms) and 2 energy efficient heat pumps. Located in the Oxford’s historic district. This home preserves the historic character while offering a modern floor plan with 9’ ceilings and modern upgrades. Professional photos coming in September

3 Beds ⋅ 3 Baths

Oxford. One owner 2,858 sq. ft home built in 2006 is just off the Strand only a block from the Tred Avon River. Features living room and dining rooms, den, family room with woodburning fireplace off open kitchen with island and granite countertops, powder room. Second floor offers 3 spacious bedrooms including a primary suite with walk-in closet and 2 guest bedrooms and guest bath. Exterior offers 2 balconies, HardiPlank siding, paver driveway and more on a .18 acre lot. Hardwood flooring throughout most of the home (except 2 guest bedrooms) and 2 energy efficient heat pumps. Located in the Oxford’s historic district. This home preserves the historic character while offering a modern floor plan with 9’ ceilings and modern upgrades. Professional photos coming in September

104 Stewart Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$1,075,000

This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a tile-surround shower and soaking tub, along with three additional bedrooms, two of which have attached baths. The full basement is a standout feature, offering a dedicated workshop with ample space for projects, tools, and storage. Outside, the entertaining space continues with a large back porch, pool, hot tub, oversized shed, extended driveway, and lush landscaping. With a secluded country feel, generous indoor and outdoor gathering spaces, and easy access to downtown Easton, this property offers an exceptional balance of privacy, space, and convenience.

4 Beds ⋅ 4 Baths

This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a tile-surround shower and soaking tub, along with three additional bedrooms, two of which have attached baths. The full basement is a standout feature, offering a dedicated workshop with ample space for projects, tools, and storage. Outside, the entertaining space continues with a large back porch, pool, hot tub, oversized shed, extended driveway, and lush landscaping. With a secluded country feel, generous indoor and outdoor gathering spaces, and easy access to downtown Easton, this property offers an exceptional balance of privacy, space, and convenience.

29747 Easton Farms, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$749,900

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home in Master's Village at Easton Club. A welcoming wraparound front porch and beautifully landscaped front yard set the tone for the inviting spaces found throughout the home. Hardwood flooring extends through most of the main level, where the light-filled living room features high ceilings, a gas fireplace, and built-in cabinetry. The highly sought-after entry-level primary suite offers a private retreat with direct access from the bedroom to the back deck, along with a spacious bath featuring a soaking tub, separate shower, and double vanities. Just off the kitchen, the sunroom opens to the deck with an awning, creating an ideal space for indoor-outdoor living and entertaining, with a stone patio providing additional outdoor space. Upstairs, the hallway landing doubles as a comfortable sitting area or potential home office and leads to three additional bedrooms. A large bonus room offers plenty of flexibility as a recreation room, family room, or additional gathering space. An additional stairway from the second level leads to a dedicated storage room, providing convenient extra storage. Located in the desirable Easton Club community, residents enjoy access to community amenities including a swimming pool and tennis courts, all just minutes from the conveniences of downtown Easton. Roof New August 2026 HVAC- Downstairs new 2026, upstairs new 2020.

4 Beds ⋅ 3 Baths

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home in Master's Village at Easton Club. A welcoming wraparound front porch and beautifully landscaped front yard set the tone for the inviting spaces found throughout the home. Hardwood flooring extends through most of the main level, where the light-filled living room features high ceilings, a gas fireplace, and built-in cabinetry. The highly sought-after entry-level primary suite offers a private retreat with direct access from the bedroom to the back deck, along with a spacious bath featuring a soaking tub, separate shower, and double vanities. Just off the kitchen, the sunroom opens to the deck with an awning, creating an ideal space for indoor-outdoor living and entertaining, with a stone patio providing additional outdoor space. Upstairs, the hallway landing doubles as a comfortable sitting area or potential home office and leads to three additional bedrooms. A large bonus room offers plenty of flexibility as a recreation room, family room, or additional gathering space. An additional stairway from the second level leads to a dedicated storage room, providing convenient extra storage. Located in the desirable Easton Club community, residents enjoy access to community amenities including a swimming pool and tennis courts, all just minutes from the conveniences of downtown Easton. Roof New August 2026 HVAC- Downstairs new 2026, upstairs new 2020.

7583 Easton Club Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$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.

3 Beds ⋅ 3 Baths

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: 4106733344

$525,000

Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years old. From the moment you step inside, you’ll appreciate the home’s attention to detail, including soaring ceilings and an elegant tray ceiling in the dining room. The warm and welcoming family room is centered around a gas fireplace, creating the perfect setting for relaxing evenings or gathering with family and friends. Designed with convenient main-level living in mind, the spacious primary suite is located on the first floor and is enhanced by a beautiful tray ceiling. The private primary bath features a walk-in shower and soaking tub, creating your own relaxing retreat at the end of the day. At the heart of the home is a spectacular kitchen featuring granite countertops and beautiful 42-inch maple cabinetry, offering plenty of workspace and storage for everyday living and entertaining. The additional sunroom may quickly become one of your favorite places in the home. Enjoy your morning coffee while looking out over the stone patio and surrounding trees, where wild turkeys and deer may be among your morning visitors. Need a little extra space? A room above the garage with both heat and air conditioning provides wonderful flexibility. Create a home office, hobby or craft room, exercise space, media room, or comfortable retreat—the possibilities are yours. Whether you’re ready to simplify your lifestyle, enjoy the benefits of a welcoming 55+ community, or simply find a beautiful home where you can relax and enjoy everything the Eastern Shore has to offer, 29796 Lyons Drive is more than a home—it’s a destination.

3 Beds ⋅ 3 Baths

Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years old. From the moment you step inside, you’ll appreciate the home’s attention to detail, including soaring ceilings and an elegant tray ceiling in the dining room. The warm and welcoming family room is centered around a gas fireplace, creating the perfect setting for relaxing evenings or gathering with family and friends. Designed with convenient main-level living in mind, the spacious primary suite is located on the first floor and is enhanced by a beautiful tray ceiling. The private primary bath features a walk-in shower and soaking tub, creating your own relaxing retreat at the end of the day. At the heart of the home is a spectacular kitchen featuring granite countertops and beautiful 42-inch maple cabinetry, offering plenty of workspace and storage for everyday living and entertaining. The additional sunroom may quickly become one of your favorite places in the home. Enjoy your morning coffee while looking out over the stone patio and surrounding trees, where wild turkeys and deer may be among your morning visitors. Need a little extra space? A room above the garage with both heat and air conditioning provides wonderful flexibility. Create a home office, hobby or craft room, exercise space, media room, or comfortable retreat—the possibilities are yours. Whether you’re ready to simplify your lifestyle, enjoy the benefits of a welcoming 55+ community, or simply find a beautiful home where you can relax and enjoy everything the Eastern Shore has to offer, 29796 Lyons Drive is more than a home—it’s a destination.

29796 Lyons Dr, Easton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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.

3 Beds ⋅ 3 Baths

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: 4108226665

$2,195,000

Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick residence enjoys sweeping views of the Tred Avon River from nearly every room. Thoughtfully designed for one-level living, the home combines classic architectural character with extensive updates by the current owners and a floor plan that is both comfortable and highly functional. The interior has been carefully updated while retaining the character of the original home. Improvements include beautiful hardwood flooring, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new roof (2017), new deck, and numerous additional enhancements. A complete list of improvements is available from the listing agent. The three-bedroom, three-bath residence includes a spacious waterside primary suite with a generous ensuite bath, ample closet space, and additional storage. Two additional bedrooms share a full bath and are privately positioned for family or guests. The main living spaces take full advantage of the river setting. The generously proportioned living room features a wood-burning fireplace framed by custom built-in bookshelves, while the formal dining room provides a gracious setting for entertaining. The renovated kitchen features a large center island and premium appliances and opens directly to the family room, where a wood stove, breakfast area, and wall of built-in bookshelves create a comfortable gathering space. An adjoining bonus room offers exceptional flexibility and could serve as a walk-in butler’s pantry, hobby or craft room. The enclosed sunroom, with its attached full bath, is a particularly appealing space from which to enjoy the expansive water views. An oversized attached two-car garage provides convenient access to extensive attic storage that runs the full length of the house. A detached climate-controlled studio adds valuable additional space for an art studio, home office, workshop, or other uses. Outside, the property is equally well appointed. A gunite pool, added in 2020, is surrounded by extensive hardscape and fencing, offering a private setting for outdoor enjoyment. The new dock, completed in 2024, includes two slips, a floating dock, and approximately 6'MLW, providing excellent access to the Tred Avon River for boating and fishing. With its coveted location, private acreage, substantial improvements, exceptional water access, and panoramic Tred Avon River views, this is a distinctive Eastern Shore waterfront property that offers both privacy and a relaxed, livable setting.

3 Beds ⋅ 3 Baths

Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick residence enjoys sweeping views of the Tred Avon River from nearly every room. Thoughtfully designed for one-level living, the home combines classic architectural character with extensive updates by the current owners and a floor plan that is both comfortable and highly functional. The interior has been carefully updated while retaining the character of the original home. Improvements include beautiful hardwood flooring, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new roof (2017), new deck, and numerous additional enhancements. A complete list of improvements is available from the listing agent. The three-bedroom, three-bath residence includes a spacious waterside primary suite with a generous ensuite bath, ample closet space, and additional storage. Two additional bedrooms share a full bath and are privately positioned for family or guests. The main living spaces take full advantage of the river setting. The generously proportioned living room features a wood-burning fireplace framed by custom built-in bookshelves, while the formal dining room provides a gracious setting for entertaining. The renovated kitchen features a large center island and premium appliances and opens directly to the family room, where a wood stove, breakfast area, and wall of built-in bookshelves create a comfortable gathering space. An adjoining bonus room offers exceptional flexibility and could serve as a walk-in butler’s pantry, hobby or craft room. The enclosed sunroom, with its attached full bath, is a particularly appealing space from which to enjoy the expansive water views. An oversized attached two-car garage provides convenient access to extensive attic storage that runs the full length of the house. A detached climate-controlled studio adds valuable additional space for an art studio, home office, workshop, or other uses. Outside, the property is equally well appointed. A gunite pool, added in 2020, is surrounded by extensive hardscape and fencing, offering a private setting for outdoor enjoyment. The new dock, completed in 2024, includes two slips, a floating dock, and approximately 6'MLW, providing excellent access to the Tred Avon River for boating and fishing. With its coveted location, private acreage, substantial improvements, exceptional water access, and panoramic Tred Avon River views, this is a distinctive Eastern Shore waterfront property that offers both privacy and a relaxed, livable setting.

27476 Travelers Rest Ct, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$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.

3 Beds ⋅ 3 Baths

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: 4102244400

$1,500,000

OPEN HOUSE ON SUNDAY FROM 2:00-4:00PM. 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.

4 Beds ⋅ 3 Baths

OPEN HOUSE ON SUNDAY FROM 2:00-4:00PM. 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: afitzgerald@weichertrealtors.net

$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.

8 Beds ⋅ 6 Baths

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: 4106733344

$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.

8 Beds ⋅ 6 Baths

"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: 4106733344

$1,725,000

Commercial Opportunity– Positioned along S. Talbot Street (Route 33) at the entrance to St. Michaels, this General Commercial (GC) property offers exceptional visibility, convenient access, ample parking, and a flexible three-unit configuration suitable for a variety of commercial uses. The property provides a strong location for an owner-user or investment opportunity with easy access to St. Michaels, Easton, and surrounding Talbot County communities. Three Condominium Units A-C. Unit A– 248' of Road frontage / Showroom Approximately 4,044± SF One-story block construction with storage attic Large display windows Showroom space Office and planning areas Shop and storage areas Central air conditioning 2-zones 10'x8' door Unit B– Warehouse / Flex Space (Heated) Approximately 4,148± SF Metal building Warehouse/light industrial configuration Two 12' × 12' drive-in doors Flexible warehouse and storage space 2nd Floor storage space added Loading and service access Unit C– Workshop / Storage Additional detached commercial unit offering workshop and storage flexibility. Potential Uses– The property's General Commercial zoning and flexible layout make it well suited for a variety of commercial applications, including: Retail Professional office Showroom Automotive/service business Warehouse Marine Businesses Distribution Flex commercial Contractor headquarters Storage Light industrial Investment opportunity Owner-user occupancy

1007 S Talbot St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$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.

8 Beds ⋅ 6 Baths

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: 4106733344

$569,000

Welcome to 11 Londonderry Drive, a thoughtfully updated Easton home in the established Thread Haven neighborhood. Set on more than half an acre with no HOA, this inviting property offers a fenced backyard, two-car garage, wraparound front porch and a private outdoor setting just minutes from downtown Easton. The light-filled main level features an open, comfortable flow for everyday living and entertaining. The kitchen includes a newly constructed pantry, generous workspace and sculpted pendant lighting by award-winning designer Lightexture. Additional improvements include new lighting throughout, a new first-floor coat closet, updated stair railing, concealed laundry doors, and fresh paint on the main level and guest room in July 2026. Upstairs, the primary bedroom features a new ClosetMaid custom closet. Major updates include a new roof in December 2020, crawl-space vapor barrier, energy-efficient water heater in 2022, dishwasher in 2022 and microwave in 2025. Outdoor living is a highlight, with a re-stained deck and front porch, new front porch stairs and railing, refreshed landscaping, and a new fire pit with flagstone path. Enjoy morning coffee on the porch, evenings around the fire pit, and the convenience of nearby shopping, dining, parks, healthcare and all that Easton has to offer. With its spacious lot, thoughtful improvements, garage, outdoor living areas and no HOA, 11 Londonderry Drive offers an appealing combination of comfort, privacy and Eastern Shore lifestyle.

3 Beds ⋅ 3 Baths

Welcome to 11 Londonderry Drive, a thoughtfully updated Easton home in the established Thread Haven neighborhood. Set on more than half an acre with no HOA, this inviting property offers a fenced backyard, two-car garage, wraparound front porch and a private outdoor setting just minutes from downtown Easton. The light-filled main level features an open, comfortable flow for everyday living and entertaining. The kitchen includes a newly constructed pantry, generous workspace and sculpted pendant lighting by award-winning designer Lightexture. Additional improvements include new lighting throughout, a new first-floor coat closet, updated stair railing, concealed laundry doors, and fresh paint on the main level and guest room in July 2026. Upstairs, the primary bedroom features a new ClosetMaid custom closet. Major updates include a new roof in December 2020, crawl-space vapor barrier, energy-efficient water heater in 2022, dishwasher in 2022 and microwave in 2025. Outdoor living is a highlight, with a re-stained deck and front porch, new front porch stairs and railing, refreshed landscaping, and a new fire pit with flagstone path. Enjoy morning coffee on the porch, evenings around the fire pit, and the convenience of nearby shopping, dining, parks, healthcare and all that Easton has to offer. With its spacious lot, thoughtful improvements, garage, outdoor living areas and no HOA, 11 Londonderry Drive offers an appealing combination of comfort, privacy and Eastern Shore lifestyle.

11 Londonderry Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$534,900

Welcome to this beautifully updated two-story Wittman model in the highly sought-after 55+ community of Easton Club East, where thoughtful upgrades and timeless design come together effortlessly. From the moment you step inside, you’ll notice the extensive improvements throughout, from custom paint and upgraded lighting to engineered wood flooring and high-end finishes that elevate every space. The heart of the home is the stunning, fully renovated kitchen (approx. 3 years young), featuring granite countertops, a center island with seating, custom cabinetry with soft-close drawers, and stainless steel appliances. Heated floors add an extra touch of comfort, while the adjoining breakfast nook and sunroom create the perfect setting for morning coffee overlooking the private backyard. The spacious great room is designed for both relaxing and entertaining, complete with a natural gas fireplace, along with built-in wiring for surround sound. A dedicated office provides flexibility for work or hobbies, while the main-level primary suite offers comfort and convenience with an updated bath, walk-in shower, and custom finishes. A guest bedroom and additional full bath on the main level provide ideal space for visitors. Upstairs, a large loft expands your living space, accompanied by an additional bedroom and full bath, perfect for guests or extended stays. Additional upgrades continue throughout the home, including custom window treatments, Hunter Douglas shades, enhanced storage solutions, and a fully insulated garage with built-in cabinetry, workbench, and its own mini-split heating and cooling system. Step outside to enjoy the extended paver patio, complete with a remote-controlled awning, landscape lighting, and irrigation system, creating a beautifully maintained outdoor retreat. Located in Easton Club East, residents enjoy resort-style amenities including a clubhouse, outdoor pool, tennis courts, bocce ball, putting green, scenic walking paths, and picnic areas with gazebos. This is a rare opportunity to own a meticulously maintained and extensively upgraded home in one of Easton’s most desirable communities. Schedule your private showing today and experience it for yourself.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated two-story Wittman model in the highly sought-after 55+ community of Easton Club East, where thoughtful upgrades and timeless design come together effortlessly. From the moment you step inside, you’ll notice the extensive improvements throughout, from custom paint and upgraded lighting to engineered wood flooring and high-end finishes that elevate every space. The heart of the home is the stunning, fully renovated kitchen (approx. 3 years young), featuring granite countertops, a center island with seating, custom cabinetry with soft-close drawers, and stainless steel appliances. Heated floors add an extra touch of comfort, while the adjoining breakfast nook and sunroom create the perfect setting for morning coffee overlooking the private backyard. The spacious great room is designed for both relaxing and entertaining, complete with a natural gas fireplace, along with built-in wiring for surround sound. A dedicated office provides flexibility for work or hobbies, while the main-level primary suite offers comfort and convenience with an updated bath, walk-in shower, and custom finishes. A guest bedroom and additional full bath on the main level provide ideal space for visitors. Upstairs, a large loft expands your living space, accompanied by an additional bedroom and full bath, perfect for guests or extended stays. Additional upgrades continue throughout the home, including custom window treatments, Hunter Douglas shades, enhanced storage solutions, and a fully insulated garage with built-in cabinetry, workbench, and its own mini-split heating and cooling system. Step outside to enjoy the extended paver patio, complete with a remote-controlled awning, landscape lighting, and irrigation system, creating a beautifully maintained outdoor retreat. Located in Easton Club East, residents enjoy resort-style amenities including a clubhouse, outdoor pool, tennis courts, bocce ball, putting green, scenic walking paths, and picnic areas with gazebos. This is a rare opportunity to own a meticulously maintained and extensively upgraded home in one of Easton’s most desirable communities. Schedule your private showing today and experience it for yourself.

7401 Casey Ave, Easton

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$115,000

Great Potential for this cleared lot ! attention Investors , builders, or someone who wants to build the house of their dreams. This buildable Lot has been Perc. Tested , and septic approved by Talbot County Heath dept. 7/13/26 2.41 cleared Flat acres off of Rt 50,. Lot ready to be built . Lot has right of way through lot #2 Buyer responsible for doing diligent research on this residential lot and or other land use .

13433 Ocean Gateway, Queen Anne

Listing courtesy of Samson Properties. Contact: 3017555613