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Turn-key waterfront home with spectacular views from every room. The entire house has been taken down to the studs: exterior and interior walls reframed; shed dormers installed; glass doors and windows placed in every wall; renovated kitchen with quartz countertops, semi-custom cabinets, new appliances, a Butler's Pantry, two new staircases, all new plumbing, electric, HVAC, built-ins, hardi-plank siding, Azek trim, composite decking, custom garage doors -- the list goes on. "Tilghman on Chesapeake" has coveted amenities including a clubhouse and outdoor pool on the water, piers, boat-slips, and sweeping views of the watermen departing at sun-rise. Restaurants and daily amenities are nearby including groceries, liquor, a deli and the best cup of coffee on the Eastern Shore served at the Country Store. Spectacular views, and laid-back community charm, is the timeless appeal that makes Tilghman Island so special. The home can convey furnished if desired.

21525 Island Club Rd, Tilghman

Listing courtesy of Sell Your Home Services. Contact:

$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.

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:

$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:

$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:

$3,295,000

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

5 Beds ⋅ 5 Baths

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

104 East St, Oxford

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

$1,150,000

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

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

7040 Old School House Ln, Easton

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

$2,195,000

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

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

27476 Travelers Rest Ct, Easton

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

$979,000

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

4 Beds ⋅ 4 Baths

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

32675 Discovery Dr, Easton

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

$1,399,000

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

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

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact:

$1,500,000

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

4 Beds ⋅ 3 Baths

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:

$5,995,000

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

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

8612 Tilghman Island Rd, Wittman

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

$7,900,000

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

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

8612 Tilghman Island Rd, Wittman

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

$5,995,000

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

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

8612 Tilghman Island Rd, Wittman

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

$965,000

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

4 Beds ⋅ 5 Baths

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

13446 Blackberry Ln, Wye Mills

Listing courtesy of Coldwell Banker Realty. Contact:

$365,000

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a fourth bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

4 Beds ⋅ 3 Baths

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a fourth bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

408 Crowberry Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$675,000

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

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

32930 Oyster Bank Ter, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$598,000

Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

204 Lincoln, Saint Michaels

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

$5,895,000

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

5 Beds ⋅ 6 Baths

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

9170 Hunting Creek Ln, Easton

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

$7,900,000

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

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

8612 Tilghman Island Rd, Wittman

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

$799,000

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

21560 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$649,000

New $10k price improvement and ready by September, this one-of-a-kind Ryan model is set to be the largest one-story home constructed on Sandy Lane, brought to life by Developer Sandy Lane, LLC and renowned local builders Stansbury and Sons. Like all ten homes in this thoughtfully designed new downtown Easton community, the Ryan will be a custom, stick-built residence backed by a one-year builder’s warranty and outfitted with brand-new appliances and systems—allowing homeowners to enjoy their new space without the constant burden of "old house" maintenance. The Ryan's convenient single-level layout includes three bedrooms, two full baths, and a spacious living room with vaulted ceilings that flows seamlessly into the dining area and a beautifully appointed kitchen. A cook's dream, the kitchen features custom cabinetry, including a large pantry cabinet, solid surface countertops, and stainless-steel appliances. The luxurious primary suite offers a private bath with a tiled shower, double sink vanity and a generous walk-in closet. The two additional bedrooms on the opposite side of the floorplan share a stylish hall bath with tub/shower. There is also a dedicated laundry area—strategically placed between the kitchen, primary suite and garage entrance—which completes the interior. Outside, the home boasts a one-car attached garage with an electric car charger, a concrete driveway with parking for two, custom front foundation landscaping, a fully sodded yard, and a rear patio. Sandy Lane homes are built with premium features such as encapsulated, climate-controlled crawl spaces suitable for storage, superior framing and finish work, certified IECC Energy Efficient insulation (R-49 ceiling, R-21 walls), luxury vinyl flooring throughout, ample closet space, and multiple contemporary ceiling fans and fixtures. The Ryan’s flexible design makes it ideal for retirees, remote workers, singles and families alike. All infrastructure costs—including surveys, permits, site work, utilities, and street improvements—have been prepaid by the developer, eliminating typical new construction extended yearly front foot fees for buyers. Located off N Washington Street in Easton, Sandy Lane offers easy access to downtown amenities such as Easton Utilities (electric, water, sewer, cable, and high-speed internet), weekly trash and recycling pickup, and a wealth of recreational options including parks, sports fields, trails, playgrounds, tennis and pickleball courts, a community pool, and a dog park. Easton and Talbot County provide abundant waterfront access, fire and police services, medical facilities, cultural attractions such as the Avalon Theater, The Academy Art Museum, and Maritime Museum, premium shopping, and some of the best dining on the East Coast. The community is subject to Covenants and Restrictions but carries no HOA or associated fees. Developer: Sandy Lane, LLC (MHBR 9512). Builder: Stansbury and Sons Home Improvement Inc. (MHBR 8351). Builder Contract required.