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SECOND WIND is a remarkable Eastern Shore sanctuary where history, privacy, and the beauty of the water define everyday living. As noted in The Eastern Shore Dependent in 1963, “Nature provided the idyllic setting.” Set amid nearly 3 acres of magnificent landscaping, with more than 400 feet of protected and licensed shoreline, this property captures sweeping broad water views and unforgettable sunsets from almost every room. The historic c. 1800 two-story section enjoys random width Georgia pine floors, two bedrooms and a full bath. The additions include multiple living areas offering a welcoming blend of historic character and comfortable living, including living/dining room with fireplace, a fireside den with built-in bookcases, a private office with fireplace and a main level primary three bedrooms and multiple living spaces offer a welcoming blend of historic character and comfortable living, including a living/dining room with fireplace, a fireside den with built-in bookcases, a private office with fireplace, and a main-level primary suite with vaulted beamed ceiling and en-suite bath. The kitchen features a breakfast bar and casual dining area, opening to a patio and heated pool and spa—an inviting setting for relaxation and entertaining. A private pier and protected shoreline incorporating a living shoreline enhance the waterfront setting, while magnificent perennial gardens, an attached garage, a detached workshop with artist studio above, and several outbuildings add to the property's appeal. Recent improvements include a new roof. Lovingly maintained and exceptionally private, SECOND WIND offers a rare opportunity to own a truly distinctive waterfront property steeped in Eastern Shore history.

5704 Irish Creek Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$499,888

Welcome to Tilghman on Chesapeake! Discover this peaceful community in a serene setting away from the crowds of traditional beach towns, yet conveniently located near the charming waterfront town of St. Michaels and the amenities of Easton, Maryland. This beautiful Sussex floorplan features 3 bedrooms, 2 full bathrooms, cozy front porch and a 2-car garage. The home includes beautiful quartz countertops, stainless steel appliances, a large island and a spacious family room highlighted by a gas fireplace. The private owner’s retreat offers a relaxing escape, including a Venetian-style private bathroom. Complete with a new home warranty for added peace of mind, this home combines modern finishes, everyday comfort, and the appeal of Eastern Shore living. Enjoy an exceptional community lifestyle with amenities including a waterfront clubhouse, swimming pool, picnic area, and community pier. Boat slips are also available for purchase or lease, making it easy to embrace the Chesapeake Bay lifestyle.

Welcome to Tilghman on Chesapeake! Discover this peaceful community in a serene setting away from the crowds of traditional beach towns, yet conveniently located near the charming waterfront town of St. Michaels and the amenities of Easton, Maryland. This beautiful Sussex floorplan features 3 bedrooms, 2 full bathrooms, cozy front porch and a 2-car garage. The home includes beautiful quartz countertops, stainless steel appliances, a large island and a spacious family room highlighted by a gas fireplace. The private owner’s retreat offers a relaxing escape, including a Venetian-style private bathroom. Complete with a new home warranty for added peace of mind, this home combines modern finishes, everyday comfort, and the appeal of Eastern Shore living. Enjoy an exceptional community lifestyle with amenities including a waterfront clubhouse, swimming pool, picnic area, and community pier. Boat slips are also available for purchase or lease, making it easy to embrace the Chesapeake Bay lifestyle.

5648 Trafalgar Cir, Tilghman

Listing courtesy of Mary Ann Hammel. Contact:

$3,600,000

Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and you’re met with direct water views that can be seen from virtually every room in the home. You’ll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the home’s three fireplaces. Upstairs, you’ll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across the driveway is a detached garage with two car bays, a workshop, and a storage area. Above the garage, you’ll find a separate in-law suite or apartment space with a living area, bedroom, full bathroom, and kitchenette. Around the back of the home is an entertaining space that makes for the perfect Eastern Shore weekend. A beautifully done gunite pool overlooks your 1,600 feet of shoreline. A private dock with a boat lift (insert weight capacity) provides easy access for an afternoon cruise or evening fishing expedition. With privacy from your neighbors and close proximity to historic downtown St. Michaels, this home provides the ultimate secluded Chesapeake Bay oasis.

Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and you’re met with direct water views that can be seen from virtually every room in the home. You’ll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the home’s three fireplaces. Upstairs, you’ll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across the driveway is a detached garage with two car bays, a workshop, and a storage area. Above the garage, you’ll find a separate in-law suite or apartment space with a living area, bedroom, full bathroom, and kitchenette. Around the back of the home is an entertaining space that makes for the perfect Eastern Shore weekend. A beautifully done gunite pool overlooks your 1,600 feet of shoreline. A private dock with a boat lift (insert weight capacity) provides easy access for an afternoon cruise or evening fishing expedition. With privacy from your neighbors and close proximity to historic downtown St. Michaels, this home provides the ultimate secluded Chesapeake Bay oasis.

7116 Pea Neck Rd, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$480,000

Discover the charm of this beautifully renovated ranch-style home, set to impress with its major renovations completed in 2026. This home boasts 4 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and comfort. The open layout seamlessly connects the living areas, creating a warm atmosphere perfect for gatherings or quiet evenings at home. The heart of the home features a modern kitchen equipped white cabinets and sleek quartz countertops. Enjoy the convenience of an attached garage 2 car garage with and additional storage. The expansive lot, spanning over 0.61 acres, offers plenty of outdoor space for gardening, play, or simply enjoying the fresh air. This home was designed with a focus on comfort and functionality. Sit on the front porch and enjoy the serene views of the rural farmlands, this property is perfect for those seeking a peaceful retreat while still being close to local shopping and dining. Experience the perfect blend of modern living and timeless charm in this delightful home. Don't miss the opportunity to make this your own!

Discover the charm of this beautifully renovated ranch-style home, set to impress with its major renovations completed in 2026. This home boasts 4 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and comfort. The open layout seamlessly connects the living areas, creating a warm atmosphere perfect for gatherings or quiet evenings at home. The heart of the home features a modern kitchen equipped white cabinets and sleek quartz countertops. Enjoy the convenience of an attached garage 2 car garage with and additional storage. The expansive lot, spanning over 0.61 acres, offers plenty of outdoor space for gardening, play, or simply enjoying the fresh air. This home was designed with a focus on comfort and functionality. Sit on the front porch and enjoy the serene views of the rural farmlands, this property is perfect for those seeking a peaceful retreat while still being close to local shopping and dining. Experience the perfect blend of modern living and timeless charm in this delightful home. Don't miss the opportunity to make this your own!

8760 Black Dog Aly, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

$3,995,000

Located at the end of Market Street in sought-after Oxford, this distinctive waterfront estate on Town Creek combines Victorian elegance, boating amenities, and the convenience of a downtown setting. Designed by Linda Serabian of SOMA Architects, the property offers privacy and expansive creek views just moments from local restaurants, boutique shops, the park, and marinas. The four-bedroom, three-and-a-half-bath main house showcases timeless architecture and thoughtful craftsmanship, with extensive custom millwork, warm wood floors, and four gas fireplaces. A grand tiled foyer with radiant heated floors welcomes you into the home. The well-appointed kitchen and inviting living spaces overlook the pool and Town Creek, while the second-floor deck offers elevated views of the water. Recent improvements include new Marvin windows and French doors, updated HVAC components, fresh interior and exterior paint, and a remodeled full bath. The guest house offers two bedrooms and two full baths, providing a private and versatile extension of the property. Custom millwork, three hidden Murphy beds throughout and a newly updated kitchenette make hosting family and friends effortless. Recent improvements include a new HVAC system, water heater, encapsulated crawl space, and refreshed rear patio. The grounds are equally impressive, with a gunite pool featuring an electric cover, a refreshed poolside patio, and extensive landscaping. Along Town Creek, a well-protected dock accommodates three boats, with water and electric service and mean low water of four feet or greater. A brick driveway, two-car garage with generous shop and storage space, and inviting outdoor gathering areas complete the offering. With its distinctive architecture, separate guest accommodations, dock with three slips, and coveted in-town Oxford location, this is a rare opportunity to experience the best of Eastern Shore waterfront living.

Located at the end of Market Street in sought-after Oxford, this distinctive waterfront estate on Town Creek combines Victorian elegance, boating amenities, and the convenience of a downtown setting. Designed by Linda Serabian of SOMA Architects, the property offers privacy and expansive creek views just moments from local restaurants, boutique shops, the park, and marinas. The four-bedroom, three-and-a-half-bath main house showcases timeless architecture and thoughtful craftsmanship, with extensive custom millwork, warm wood floors, and four gas fireplaces. A grand tiled foyer with radiant heated floors welcomes you into the home. The well-appointed kitchen and inviting living spaces overlook the pool and Town Creek, while the second-floor deck offers elevated views of the water. Recent improvements include new Marvin windows and French doors, updated HVAC components, fresh interior and exterior paint, and a remodeled full bath. The guest house offers two bedrooms and two full baths, providing a private and versatile extension of the property. Custom millwork, three hidden Murphy beds throughout and a newly updated kitchenette make hosting family and friends effortless. Recent improvements include a new HVAC system, water heater, encapsulated crawl space, and refreshed rear patio. The grounds are equally impressive, with a gunite pool featuring an electric cover, a refreshed poolside patio, and extensive landscaping. Along Town Creek, a well-protected dock accommodates three boats, with water and electric service and mean low water of four feet or greater. A brick driveway, two-car garage with generous shop and storage space, and inviting outdoor gathering areas complete the offering. With its distinctive architecture, separate guest accommodations, dock with three slips, and coveted in-town Oxford location, this is a rare opportunity to experience the best of Eastern Shore waterfront living.

307 Market St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

$939,900

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

5734 Poplar Ln, Royal Oak

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

$1,595,000

Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

Nestled in the prestigious Canterbury subdivision, this exquisite Cape Cod home offers a harmonious blend of luxury and comfort. Spanning over 4,600 square feet, the interior boasts elegant wood floors and an inviting layout, featuring a spacious kitchen with upgraded countertops and a six-burner stove, perfect for culinary enthusiasts. The dining area and cozy built-ins create an ideal setting for gatherings, while the three fireplaces, adorned with charming mantels, add warmth and sophistication. Retreat to the primary suite, complete with a luxurious bath, or enjoy the convenience of an entry-level bedroom. The thoughtful design includes a laundry chute for effortless living. Outside, the expansive 2.44-acre lot is beautifully landscaped, providing a serene backdrop for relaxation. With an attached two-car garage and a commitment to quality, this home embodies an exclusive lifestyle, inviting you to create cherished memories in a space that truly feels like home.

6385 Canterbury Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$789,900

Discover the charm of historic Easton with this beautifully designed new construction home, ideally located within walking distance of downtown's wonderful shops, restaurants, and attractions. Thoughtfully designed to blend timeless architectural appeal with modern comfort, this custom-built residence offers the perfect combination of quality, convenience, and style. Featuring a desirable main-level primary suite, a spacious two-car garage, and an inviting backyard, this home is designed for both everyday living and effortless entertaining. Enjoy the benefits of brand-new construction, with beautiful finishes and thoughtful details throughout. Whether you're searching for a full-time residence or a weekend retreat, this exceptional property offers the opportunity to enjoy the best of Eastern Shore living in one of Maryland's most charming historic towns. Completion is anticipated for the first week of November. Don't miss your opportunity to own a beautiful new home in the heart of Easton, where small-town charm meets modern luxury!

1 Beds ⋅ 2 Baths

Discover the charm of historic Easton with this beautifully designed new construction home, ideally located within walking distance of downtown's wonderful shops, restaurants, and attractions. Thoughtfully designed to blend timeless architectural appeal with modern comfort, this custom-built residence offers the perfect combination of quality, convenience, and style. Featuring a desirable main-level primary suite, a spacious two-car garage, and an inviting backyard, this home is designed for both everyday living and effortless entertaining. Enjoy the benefits of brand-new construction, with beautiful finishes and thoughtful details throughout. Whether you're searching for a full-time residence or a weekend retreat, this exceptional property offers the opportunity to enjoy the best of Eastern Shore living in one of Maryland's most charming historic towns. Completion is anticipated for the first week of November. Don't miss your opportunity to own a beautiful new home in the heart of Easton, where small-town charm meets modern luxury!

422 North St, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$2,495,000

Experience the best of waterfront living on picturesque Trippe Creek, where breathtaking sunsets and sweeping views of the neighboring nature conservancy create an idyllic setting. Nestled in the private Pirates Cove community of Oxford, Maryland, this peaceful retreat offers exceptional privacy, tranquility, and abundant wildlife. Designed for effortless one-level living, this inviting 4-bedroom home features beautiful hardwood and brick flooring, 3 fireplaces (one double sided so feels like 4), and expansive water views. A waterside screened porch provides the perfect setting to relax and enjoy the natural surroundings, while the saltwater pool overlooking the creek offers a wonderful space for outdoor entertaining. Capital improvements to the property 2019 - installed new septic system, enclosed 1-bay of the garage and converted into a finished office/studio. 2020 - installed a new driveway, reset the patio bricks on the back porch. 2021 - completed substantial pool renovation, including both the pool and surround improvements, reset the front walkway/patio brickwork, upgraded the HVAC system. 2023 - new refrigerator. 2024 - new wine refrigerator, constructed a new walkway. 2025 - installed brand new roof, replaced all toilets throughout the home. Through the years of ownership continuously invested in extensive landscaping and site improvements. Boating enthusiasts will appreciate the private pier with approximately 3 feet of mean low water (MLW), providing convenient access to the beautiful waterways of the Eastern Shore. A two-car garage plus a workspace for a studio adds everyday convenience. Offered turnkey with most furnishings included, this exceptional waterfront property also could convey with a 17-foot Scout center console boat with acceptable offer—allowing you to begin enjoying the Eastern Shore lifestyle from day one. Whether you're seeking a full-time residence or a relaxing weekend escape, this special property offers the perfect combination of waterfront recreation, natural beauty, and peaceful coastal living.

Experience the best of waterfront living on picturesque Trippe Creek, where breathtaking sunsets and sweeping views of the neighboring nature conservancy create an idyllic setting. Nestled in the private Pirates Cove community of Oxford, Maryland, this peaceful retreat offers exceptional privacy, tranquility, and abundant wildlife. Designed for effortless one-level living, this inviting 4-bedroom home features beautiful hardwood and brick flooring, 3 fireplaces (one double sided so feels like 4), and expansive water views. A waterside screened porch provides the perfect setting to relax and enjoy the natural surroundings, while the saltwater pool overlooking the creek offers a wonderful space for outdoor entertaining. Capital improvements to the property 2019 - installed new septic system, enclosed 1-bay of the garage and converted into a finished office/studio. 2020 - installed a new driveway, reset the patio bricks on the back porch. 2021 - completed substantial pool renovation, including both the pool and surround improvements, reset the front walkway/patio brickwork, upgraded the HVAC system. 2023 - new refrigerator. 2024 - new wine refrigerator, constructed a new walkway. 2025 - installed brand new roof, replaced all toilets throughout the home. Through the years of ownership continuously invested in extensive landscaping and site improvements. Boating enthusiasts will appreciate the private pier with approximately 3 feet of mean low water (MLW), providing convenient access to the beautiful waterways of the Eastern Shore. A two-car garage plus a workspace for a studio adds everyday convenience. Offered turnkey with most furnishings included, this exceptional waterfront property also could convey with a 17-foot Scout center console boat with acceptable offer—allowing you to begin enjoying the Eastern Shore lifestyle from day one. Whether you're seeking a full-time residence or a relaxing weekend escape, this special property offers the perfect combination of waterfront recreation, natural beauty, and peaceful coastal living.

5718 Pirates Cove Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

$693,900

BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Privacy, a gunite pool, and two acres on Tilghman Island, just 12 miles from St. Michaels. A long, crepe myrtle-lined driveway leads to 4957 Bar Neck Road, surrounded by mature landscaping and expansive lawn with no HOA. The property offers flexibility as a full-time residence, weekend retreat, or potential income-producing short-term rental. Two leaded-glass doors provide separate entrances. The main entrance opens to the foyer, while the second leads to the breezeway and laundry area with a utility sink, storage, and access to a full bath. The main level features hardwood floors, a parlor with built-ins, formal dining room, and family room centered around a wood-burning fireplace. Exposed brick from the fireplace extends upward along the staircase to the second floor, adding warmth and architectural character. Sliding glass doors open directly to the deck, patio, and pool. The kitchen includes granite countertops, stainless steel appliances, light wood cabinetry, and a breakfast bar. Upstairs are three bedrooms, including a spacious primary suite with generous storage and an en-suite bath. A closet-lined passage leads from the bedroom to the bath, which features an oversized jetted tub, double vanity, and abundant natural light. An expansive finished bonus room adds another dimension to the home, with a wood-clad vaulted ceiling, built-in workspace and storage, and a separate mini-split. The space offers tremendous flexibility as an office, den, studio, recreation room, or additional retreat. Outside, the in-ground gunite pool anchors a private outdoor living area surrounded by two acres of open lawn and mature landscaping. A deck, patio, pergola, fire pit, and multiple gathering areas provide plenty of room for relaxing and entertaining. An oversized two-car garage provides additional parking and storage. Improvements include a newer roof, AZEK front decking and steps with vinyl railings, encapsulated crawlspace with concrete floor, tankless water heater, Bosch heating system, and updated primary bath. The home also features two security systems, fire and carbon monoxide detection, and a custom exterior camera system. The property is not located in a flood zone. With two acres, privacy, a gunite pool, generous indoor and outdoor living spaces, and no HOA, 4957 Bar Neck Road offers a distinctive opportunity for year-round living, a second home, or potential short-term rental near St. Michaels and the Chesapeake Bay.

BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Privacy, a gunite pool, and two acres on Tilghman Island, just 12 miles from St. Michaels. A long, crepe myrtle-lined driveway leads to 4957 Bar Neck Road, surrounded by mature landscaping and expansive lawn with no HOA. The property offers flexibility as a full-time residence, weekend retreat, or potential income-producing short-term rental. Two leaded-glass doors provide separate entrances. The main entrance opens to the foyer, while the second leads to the breezeway and laundry area with a utility sink, storage, and access to a full bath. The main level features hardwood floors, a parlor with built-ins, formal dining room, and family room centered around a wood-burning fireplace. Exposed brick from the fireplace extends upward along the staircase to the second floor, adding warmth and architectural character. Sliding glass doors open directly to the deck, patio, and pool. The kitchen includes granite countertops, stainless steel appliances, light wood cabinetry, and a breakfast bar. Upstairs are three bedrooms, including a spacious primary suite with generous storage and an en-suite bath. A closet-lined passage leads from the bedroom to the bath, which features an oversized jetted tub, double vanity, and abundant natural light. An expansive finished bonus room adds another dimension to the home, with a wood-clad vaulted ceiling, built-in workspace and storage, and a separate mini-split. The space offers tremendous flexibility as an office, den, studio, recreation room, or additional retreat. Outside, the in-ground gunite pool anchors a private outdoor living area surrounded by two acres of open lawn and mature landscaping. A deck, patio, pergola, fire pit, and multiple gathering areas provide plenty of room for relaxing and entertaining. An oversized two-car garage provides additional parking and storage. Improvements include a newer roof, AZEK front decking and steps with vinyl railings, encapsulated crawlspace with concrete floor, tankless water heater, Bosch heating system, and updated primary bath. The home also features two security systems, fire and carbon monoxide detection, and a custom exterior camera system. The property is not located in a flood zone. With two acres, privacy, a gunite pool, generous indoor and outdoor living spaces, and no HOA, 4957 Bar Neck Road offers a distinctive opportunity for year-round living, a second home, or potential short-term rental near St. Michaels and the Chesapeake Bay.

4957 Bar Neck Rd, Tilghman

Listing courtesy of Compass. Contact:

$520,000

Chesapeake by Del Webb. This one owner Merion model is sited on an end lot overlooking a pond and community open space. Living room/office, family room with gas fireplace and wood flooring, formal dining room, kitchen with breakfast area, stainless appliances and granite countertops. 1st floor primary bedroom with trey ceiling and walk-in closet, primary bath with walk-in shower, soaking tub and double vanities, powder room and main floor laundry. 2nd floor features a loft and 2 guest bedrooms and bath. Large attached front loading garage with walk-up storage, lawn irrigation, patio with awning and beautiful landscaping. Prime lot on quiet street. Community amenities: Clubhouse with library, billiards room, meeting room, exercise rooms and game room plus outdoor pool and picnic areas, tennis/pickleball courts, bocce ball and exercise paths. 55+ age-restricted section. Close to downtown Easton, medical facilities, shopping, churches and restaurants. *Professional photos to come.

Chesapeake by Del Webb. This one owner Merion model is sited on an end lot overlooking a pond and community open space. Living room/office, family room with gas fireplace and wood flooring, formal dining room, kitchen with breakfast area, stainless appliances and granite countertops. 1st floor primary bedroom with trey ceiling and walk-in closet, primary bath with walk-in shower, soaking tub and double vanities, powder room and main floor laundry. 2nd floor features a loft and 2 guest bedrooms and bath. Large attached front loading garage with walk-up storage, lawn irrigation, patio with awning and beautiful landscaping. Prime lot on quiet street. Community amenities: Clubhouse with library, billiards room, meeting room, exercise rooms and game room plus outdoor pool and picnic areas, tennis/pickleball courts, bocce ball and exercise paths. 55+ age-restricted section. Close to downtown Easton, medical facilities, shopping, churches and restaurants. *Professional photos to come.

7196 Bobs Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$478,940

New main‑level primary bedroom home is about to start construction for a spring move‑in! This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms and is located in amenity filled, Lakeside at Trappe! The open main level features volume ceilings in the great room, creating an airy and inviting living space. Gourmet kitchen with stainless steel appliances including hood. The main‑level primary suite is a true retreat, complete with a deluxe bath including a separate soaking tub and shower. Located in Lakeside at Trappe, an amenity‑rich, master‑planned community just minutes from Easton, residents enjoy a lifestyle designed for connection and recreation including Resort‑style swimming pool, Bathhouse with fitness room, Ping pong & cornhole, Playground & sports courts, Dedicated Bark Park plus an immersive lakeside experience is planned, offering even more opportunities to enjoy the outdoors and waterfront lifestyle. With easy access to Easton, Cambridge, and surrounding areas, Lakeside at Trappe combines small‑town charm with everyday convenience in the heart of the growing Chesapeake Bay region. Please note that the photos are of a model as this home has not yet finished construction, and the photos may show additional options that are not included. ✨ Ask about builder incentives!

New main‑level primary bedroom home is about to start construction for a spring move‑in! This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms and is located in amenity filled, Lakeside at Trappe! The open main level features volume ceilings in the great room, creating an airy and inviting living space. Gourmet kitchen with stainless steel appliances including hood. The main‑level primary suite is a true retreat, complete with a deluxe bath including a separate soaking tub and shower. Located in Lakeside at Trappe, an amenity‑rich, master‑planned community just minutes from Easton, residents enjoy a lifestyle designed for connection and recreation including Resort‑style swimming pool, Bathhouse with fitness room, Ping pong & cornhole, Playground & sports courts, Dedicated Bark Park plus an immersive lakeside experience is planned, offering even more opportunities to enjoy the outdoors and waterfront lifestyle. With easy access to Easton, Cambridge, and surrounding areas, Lakeside at Trappe combines small‑town charm with everyday convenience in the heart of the growing Chesapeake Bay region. Please note that the photos are of a model as this home has not yet finished construction, and the photos may show additional options that are not included. ✨ Ask about builder incentives!

285 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

$389,999

Beautifully maintained and thoughtfully updated, this move-in-ready home offers a comfortable layout with LVP flooring, plantation shutters, and an inviting kitchen featuring quartz countertops, stainless steel appliances, a large island, and a breakfast area. The spacious living room offers plenty of room for a separate dining area. Upstairs, the primary suite features a full bath and two large walk-in closets, along with two additional bedrooms and a full bath. The finished lower level adds a family room, a separate office/bonus room with French doors, a powder room, and a laundry room with washer and dryer. Outside, enjoy a rear patio overlooking the private backyard, a paved driveway, and a storage shed that conveys as-is. Roof replaced October 2019, A/C 2018, Water heater 2013. Recently replace flooring with LVP, carpet replaced, kitchen cabinets painted and new hardware Oct 2026 . All bathrooms recently renovated. Located in a popular neighborhood close to downtown Easton and its many amenities! Don't miss this move in ready home.

Beautifully maintained and thoughtfully updated, this move-in-ready home offers a comfortable layout with LVP flooring, plantation shutters, and an inviting kitchen featuring quartz countertops, stainless steel appliances, a large island, and a breakfast area. The spacious living room offers plenty of room for a separate dining area. Upstairs, the primary suite features a full bath and two large walk-in closets, along with two additional bedrooms and a full bath. The finished lower level adds a family room, a separate office/bonus room with French doors, a powder room, and a laundry room with washer and dryer. Outside, enjoy a rear patio overlooking the private backyard, a paved driveway, and a storage shed that conveys as-is. Roof replaced October 2019, A/C 2018, Water heater 2013. Recently replace flooring with LVP, carpet replaced, kitchen cabinets painted and new hardware Oct 2026 . All bathrooms recently renovated. Located in a popular neighborhood close to downtown Easton and its many amenities! Don't miss this move in ready home.

29214 Corbin Pkwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$479,000

This 4-bedroom, 2.5-bath home offers a bright, open floor plan, well-designed living spaces, and a great location close to downtown Easton. Situated on a corner lot, the property features a beautifully landscaped backyard, Trex deck and storage shed. The main level includes formal living and dining rooms, an eat-in kitchen with abundant cabinetry, a custom center island with breakfast bar, stainless steel appliances, and butler’s pantry. A side-entry, attached two-car garage connects to a spacious mudroom. Upstairs, the large primary suite features a three walk-in closets and remodeled en-suite bath with a custom-tiled shower, along with three additional bedrooms and a full bath. Concrete crawl space. Enjoy direct access to the Rails to Trails, plus convenient access to a public boat ramp, community pool, and parks. The HOA includes common area maintenance and snow removal. Located just minutes from downtown Easton’s shopping, dining, YMCA, and local amenities, this home offers the space you need and the lifestyle that makes the Eastern Shore special.

This 4-bedroom, 2.5-bath home offers a bright, open floor plan, well-designed living spaces, and a great location close to downtown Easton. Situated on a corner lot, the property features a beautifully landscaped backyard, Trex deck and storage shed. The main level includes formal living and dining rooms, an eat-in kitchen with abundant cabinetry, a custom center island with breakfast bar, stainless steel appliances, and butler’s pantry. A side-entry, attached two-car garage connects to a spacious mudroom. Upstairs, the large primary suite features a three walk-in closets and remodeled en-suite bath with a custom-tiled shower, along with three additional bedrooms and a full bath. Concrete crawl space. Enjoy direct access to the Rails to Trails, plus convenient access to a public boat ramp, community pool, and parks. The HOA includes common area maintenance and snow removal. Located just minutes from downtown Easton’s shopping, dining, YMCA, and local amenities, this home offers the space you need and the lifestyle that makes the Eastern Shore special.

201 Coleman Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$769,000

Built in 2019 by Covell Builders and located in the charming community of Easton Village, this home places you just minutes from both downtown Easton and Saint Michaels, convenient to nearby shopping, restaurants, art galleries, and more. Step inside this 4-bedroom, 4-bathroom home, and you’re greeted by a multifunctional den or office space off the foyer. Toward the back of the house is an open-concept layout connecting the kitchen, dining room, and living room. Upstairs, you’ll find a laundry room and 3 well-appointed bedrooms, including a large primary suite with dual-sink vanities and a walk-in shower. Additional home features include a gas fireplace, hardwood floors throughout, and a fenced-in yard. Above the 2-car garage, you’ll find a fully finished apartment suite with an en-suite bathroom. Community amenities include a pool, clubhouse with fitness center, kayak launch, and community pier overlooking the Tred Avon River.

Built in 2019 by Covell Builders and located in the charming community of Easton Village, this home places you just minutes from both downtown Easton and Saint Michaels, convenient to nearby shopping, restaurants, art galleries, and more. Step inside this 4-bedroom, 4-bathroom home, and you’re greeted by a multifunctional den or office space off the foyer. Toward the back of the house is an open-concept layout connecting the kitchen, dining room, and living room. Upstairs, you’ll find a laundry room and 3 well-appointed bedrooms, including a large primary suite with dual-sink vanities and a walk-in shower. Additional home features include a gas fireplace, hardwood floors throughout, and a fenced-in yard. Above the 2-car garage, you’ll find a fully finished apartment suite with an en-suite bathroom. Community amenities include a pool, clubhouse with fitness center, kayak launch, and community pier overlooking the Tred Avon River.

8021 Fox Squirrel Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$325,000

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

4 Beds ⋅ 2 Baths

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

619 Goldsborough St, Easton

Listing courtesy of Next Step Realty. Contact:

$5,750,000

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and full bath on the main level, with two spacious bedrooms and a large hall bath upstairs. This thoughtfully designed space is ideal for guests, extended family, or a private retreat. The outdoor amenities are equally impressive. A large, stocked pond is home to hybrid bass, largemouth bass, and bluegill, offering a private setting for fishing and recreation. Along Broad Creek, the substantial dock features water and electric, approximately 3.5 feet mean low water, a boat lift, and multiple slips, providing excellent access for boating and waterfront activities. Additional improvements include a large block outbuilding ideal for equipment, storage, hobbies, or workshop use; an in-ground pool; irrigation system; and two generators. The sale includes a separate 0.146-acre waterfront lot on Harris Creek, and two additional, platted waterfront lots, providing more possibilities for the new owner. (Please note there is potentially an Eagles' Nest on the property). Pine Point Farm is a truly exceptional waterfront estate, combining 77+ acres, two newly constructed residences, extensive waterfront amenities, recreational features, and remarkable privacy—all in one extraordinary offering.

2 Beds ⋅ 3 Baths

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and full bath on the main level, with two spacious bedrooms and a large hall bath upstairs. This thoughtfully designed space is ideal for guests, extended family, or a private retreat. The outdoor amenities are equally impressive. A large, stocked pond is home to hybrid bass, largemouth bass, and bluegill, offering a private setting for fishing and recreation. Along Broad Creek, the substantial dock features water and electric, approximately 3.5 feet mean low water, a boat lift, and multiple slips, providing excellent access for boating and waterfront activities. Additional improvements include a large block outbuilding ideal for equipment, storage, hobbies, or workshop use; an in-ground pool; irrigation system; and two generators. The sale includes a separate 0.146-acre waterfront lot on Harris Creek, and two additional, platted waterfront lots, providing more possibilities for the new owner. (Please note there is potentially an Eagles' Nest on the property). Pine Point Farm is a truly exceptional waterfront estate, combining 77+ acres, two newly constructed residences, extensive waterfront amenities, recreational features, and remarkable privacy—all in one extraordinary offering.

23505 Pine Point Rd, Bozman

Listing courtesy of Meredith Fine Properties. Contact:

$465,000

NEW HOME FEELING WITHOUT THE WAIT! Why wait for new construction when you can move right into this nearly new home, less than two years young! Enjoy a beautiful open floor plan, stylish stone countertops, a spacious kitchen island, and plenty of room to spread out. The fourth bedroom makes an ideal home office, guest room, or flex space to fit your lifestyle. Park in your finished garage and keep your car safe from the snow this winter! Step outside to a nice, level backyard with room to entertain, celebrate special occasions, enjoy outdoor activities, or simply relax. Skip the construction delays and make this beautiful home yours! Don't miss your opportunity to enjoy the benefits of a nearly new home without the wait.

4 Beds ⋅ 2 Baths

NEW HOME FEELING WITHOUT THE WAIT! Why wait for new construction when you can move right into this nearly new home, less than two years young! Enjoy a beautiful open floor plan, stylish stone countertops, a spacious kitchen island, and plenty of room to spread out. The fourth bedroom makes an ideal home office, guest room, or flex space to fit your lifestyle. Park in your finished garage and keep your car safe from the snow this winter! Step outside to a nice, level backyard with room to entertain, celebrate special occasions, enjoy outdoor activities, or simply relax. Skip the construction delays and make this beautiful home yours! Don't miss your opportunity to enjoy the benefits of a nearly new home without the wait.

31336 Dukes Bridge Rd, Cordova

Listing courtesy of RE/MAX United Real Estate. Contact:

$799,000

Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe. Time to make your personal selections. Make this home your personal statement. Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more. Make this your dream home.

Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe. Time to make your personal selections. Make this home your personal statement. Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more. Make this your dream home.

Lot 16A Meadow, Saint Michaels

Listing courtesy of Keller Williams Flagship. Contact:

$1,195,000

Welcome home to 28641 Hope Circle, an elegant 4BR/3.5BA Federal-style residence nestled in the highly sought after Village section of Cooke’s Hope. Spanning 4,772 sq ft of meticulously maintained living space, this property blends timeless Eastern Shore charm with modern luxury. The thoughtful layout offers unmatched flexibility, featuring dual primary suites with one on the main level and one on the upper level, making it perfect for multi-generational living or an exceptional guest arrangement. The upper primary suite serves as a true sanctuary boasting a luxury bath and a private outdoor deck overlooking the serene surroundings. A welcoming foyer leads to formal dining room (currently being used as a living room) with custom wainscoting, and a private home office/study complete with high-end built-in cabinetry. The heart of the home flows into a sunlit breakfast area, a bright laundry room, and a spacious mudroom with custom coat and shoe organizational shelving. From there, a second staircase leads to an incredible, fully equipped media/theater room featuring reclining stadium seating, a movie projector, and an integrated screen. Expanding the living space even further, a fully finished, heated and air-conditioned third-floor bonus room provides endless possibilities for a yoga studio, playroom, gym, or hobby shop. Outside your door, enjoy the prestigious Cooke’s Hope lifestyle, which offers miles of scenic walking trails, a fitness center, tennis courts, a kayak launch, and the community’s signature pastures home to resident Belted Galloway cows, all while being just minutes from historic downtown Easton’s premiers dining and shopping.

Welcome home to 28641 Hope Circle, an elegant 4BR/3.5BA Federal-style residence nestled in the highly sought after Village section of Cooke’s Hope. Spanning 4,772 sq ft of meticulously maintained living space, this property blends timeless Eastern Shore charm with modern luxury. The thoughtful layout offers unmatched flexibility, featuring dual primary suites with one on the main level and one on the upper level, making it perfect for multi-generational living or an exceptional guest arrangement. The upper primary suite serves as a true sanctuary boasting a luxury bath and a private outdoor deck overlooking the serene surroundings. A welcoming foyer leads to formal dining room (currently being used as a living room) with custom wainscoting, and a private home office/study complete with high-end built-in cabinetry. The heart of the home flows into a sunlit breakfast area, a bright laundry room, and a spacious mudroom with custom coat and shoe organizational shelving. From there, a second staircase leads to an incredible, fully equipped media/theater room featuring reclining stadium seating, a movie projector, and an integrated screen. Expanding the living space even further, a fully finished, heated and air-conditioned third-floor bonus room provides endless possibilities for a yoga studio, playroom, gym, or hobby shop. Outside your door, enjoy the prestigious Cooke’s Hope lifestyle, which offers miles of scenic walking trails, a fitness center, tennis courts, a kayak launch, and the community’s signature pastures home to resident Belted Galloway cows, all while being just minutes from historic downtown Easton’s premiers dining and shopping.

28641 Hope Cir, Easton

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

$449,500

JUST LISTED in Downtown Historic Easton! Fall in love with 25 S. Hanson St., a masterfully restored 1910 colonial farmhouse that balances timeless charm with contemporary luxury. What you'll love: an incredible wraparound front porch perfect for morning coffee or evening wine, a state-of-the art kitchen featuring premium countertops, beautifully refinished hardwood floors throughout, an unfinished basement with endless possibilities, an unbeatable downtown location where evertyhing is just minutes away.

JUST LISTED in Downtown Historic Easton! Fall in love with 25 S. Hanson St., a masterfully restored 1910 colonial farmhouse that balances timeless charm with contemporary luxury. What you'll love: an incredible wraparound front porch perfect for morning coffee or evening wine, a state-of-the art kitchen featuring premium countertops, beautifully refinished hardwood floors throughout, an unfinished basement with endless possibilities, an unbeatable downtown location where evertyhing is just minutes away.

25 S Hanson St, Easton

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

$1,350,000

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

7582 Leadenham Cove Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

$349,900

Recently updated and move-in ready, this one-level home offers 3 bedrooms and 2 full baths with LVP flooring throughout most of the home, kitchen with newer appliances, separate dining area, and a spacious living room. The primary bedroom includes a private bath. Major 2025 -2026 improvements include a new HVAC system with updated ductwork and vents, an encapsulated crawl space, a new roof, new siding, new windows, and new doors. Outside, you'll find a storage shed and a gravel driveway with ample parking. Conveniently located near downtown Trappe with fabulous dining options and two parks..See list of improvements. Close to public boat ramp. This home is ideally situated between Easton and Cambridge. A well-maintained, updated home offering excellent value and easy living on Maryland's Eastern Shore.

Recently updated and move-in ready, this one-level home offers 3 bedrooms and 2 full baths with LVP flooring throughout most of the home, kitchen with newer appliances, separate dining area, and a spacious living room. The primary bedroom includes a private bath. Major 2025 -2026 improvements include a new HVAC system with updated ductwork and vents, an encapsulated crawl space, a new roof, new siding, new windows, and new doors. Outside, you'll find a storage shed and a gravel driveway with ample parking. Conveniently located near downtown Trappe with fabulous dining options and two parks..See list of improvements. Close to public boat ramp. This home is ideally situated between Easton and Cambridge. A well-maintained, updated home offering excellent value and easy living on Maryland's Eastern Shore.

4072 Main St, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$2,495,000

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

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

28910 Jennings Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$425,000

Step into a piece of Eastern Shore history with this charming, beautifully maintained American Four Square, where original craftsmanship and timeless character create a home that feels truly special. Original doors, staircase, picture windows, plaster and lath walls, beautiful trim and floors, classic built-ins, and a welcoming wraparound porch evoke a simpler pace of life. Adding to the property's unique story is the retired U.S. Post Office building, a remarkable historic feature that gives this property a sense of place and a connection to the town’s rich history. With its own parking, the Post Office offers an excellent opportunity for an on-site professional office or cottage industry. Inside the house, 3 bedrooms and 2.5 baths are complemented by a country kitchen with newer appliances, downstairs laundry, parlor, living room, and formal dining room with built-in cabinetry. Upstairs, the original bath has been renovated and features an antique mahogany vanity matched with the original tub, to which a shower has been added. A second spacious bath has been renovated and features an antique walnut vanity with marble countertop and a step-in shower. A new heat pump upstairs and a split unit downstairs were added in 2023. The water heater was replaced this summer. There is a screened rear porch off the kitchen that backs to woods and a fenced yard. The entire property is complemented by mature landscaping, including many natives, a small water feature, plus pawpaw, persimmon, and fig trees, making it the perfect setting for entertaining, birdwatching. Programmable landscape lighting shows off the property each evening. Additionally, the cellar, attic, storage shed with lofts, and detached garage with workbench and loft add versatility and plenty of storage. Conveniently located on Alt. Rt. 404 near Rt. 309, the property offers quick access to the boat ramp at Hillsboro, Adkins Arboretum, Frederick Douglass Park, and nearby Tuckahoe State Park. Annapolis is only 45 minutes away, and BWI Airport is approximately 75 minutes away. More than a home, this is a rare opportunity to own a distinctive century property and make it part of your own story.

Step into a piece of Eastern Shore history with this charming, beautifully maintained American Four Square, where original craftsmanship and timeless character create a home that feels truly special. Original doors, staircase, picture windows, plaster and lath walls, beautiful trim and floors, classic built-ins, and a welcoming wraparound porch evoke a simpler pace of life. Adding to the property's unique story is the retired U.S. Post Office building, a remarkable historic feature that gives this property a sense of place and a connection to the town’s rich history. With its own parking, the Post Office offers an excellent opportunity for an on-site professional office or cottage industry. Inside the house, 3 bedrooms and 2.5 baths are complemented by a country kitchen with newer appliances, downstairs laundry, parlor, living room, and formal dining room with built-in cabinetry. Upstairs, the original bath has been renovated and features an antique mahogany vanity matched with the original tub, to which a shower has been added. A second spacious bath has been renovated and features an antique walnut vanity with marble countertop and a step-in shower. A new heat pump upstairs and a split unit downstairs were added in 2023. The water heater was replaced this summer. There is a screened rear porch off the kitchen that backs to woods and a fenced yard. The entire property is complemented by mature landscaping, including many natives, a small water feature, plus pawpaw, persimmon, and fig trees, making it the perfect setting for entertaining, birdwatching. Programmable landscape lighting shows off the property each evening. Additionally, the cellar, attic, storage shed with lofts, and detached garage with workbench and loft add versatility and plenty of storage. Conveniently located on Alt. Rt. 404 near Rt. 309, the property offers quick access to the boat ramp at Hillsboro, Adkins Arboretum, Frederick Douglass Park, and nearby Tuckahoe State Park. Annapolis is only 45 minutes away, and BWI Airport is approximately 75 minutes away. More than a home, this is a rare opportunity to own a distinctive century property and make it part of your own story.

32301 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact:

$465,000

One of the best lots in Matthewstown Run! This 4 bedroom, 2.5 bath home backs up to a farm field with peaceful open views and no neighbors behind you. It has a country, secluded feel and is still close to everything Easton has to offer. The open living room and kitchen share a wood-burning fireplace, perfect for chilly nights. The primary suite has a soaking tub and a large walk-in closet. The 10x20 back porch was enclosed and conditioned with a mini-split, beautiful hickory floors, a closet and privacy doors, so it works as an office, playroom, or bonus room. Outside, the fenced backyard and hardscape patio are made for entertaining, and there’s an attached 2-car garage. Recent updates include a new tankless water heater, new stove, and 5 new upstairs windows. Schedule your showing today, this house will go quickly!