Refine Search
Map
Sort by
$7,000,000
6 Beds ⋅ 13 Baths
Discover an extraordinary 6.8-acre waterfront estate on Morgans Point, meticulously crafted for those who seek modern luxury infused with timeless elegance. This custom-designed residence seamlessly blends sophistication, comfort, and exceptional craftsmanship. A private, tree-lined drive leads to an expansive motor court, setting the stage for the grand two-story foyer that welcomes you inside. Spanning over 24,000 square feet across three levels, this home is designed for both lavish entertaining and relaxed everyday living. The gourmet chef's kitchen (the heartbeat of this home) is equipped with top-tier appliances and custom cabinetry. It flows effortlessly into a spacious covered terrace, offering stunning water views and an ideal space for outdoor living. The main level features a gracious family room, formal dining room, serene sitting room, paneled library, fitness room, sauna, and a glass-enclosed heated indoor pool with a hot tub. A convenient main-level guest suite with patio access adds to the home's versatility, while an elevator connects all floors for ease of movement. The bedroom layout is thoughtfully designed as a private retreat, featuring two luxurious primary suites, three additional ensuite bedrooms, and a separate in-law/au pair suite. The main primary suite is a sanctuary, complete with dual bathrooms (one with heated floors and an "in-mirror TV"), a cozy sitting area, a fireplace, and a large covered balcony overlooking the serene river. Outdoor spaces are designed to maximize the breathtaking water views, with expansive covered areas and a resort-style terrace. The private pier, equipped with two boat lifts, four jet ski lifts, and a floating dock (5' MLW, buyer to verify), offers endless opportunities for waterfront enjoyment. The lower level is an entertainer's dream, featuring a full bar, wine cellar, game room, secondary kitchen, theater room, and a discreetly located safe room with a vault and full bath for added security. Car enthusiasts will appreciate the expansive 73x30 four-car garage with soaring ceilings, complemented by an additional in-law/au pair suite above, complete with a full kitchen and family room. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC, Northern Virginia, Annapolis, and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

5369 Morgans Point Dr, Oxford

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

Selling Office: Benson & Mangold, LLC.

$5,900,000
4 Beds ⋅ 6 Baths
Privacy and proximity! This charming English style cottage is sited on 4.43 professionally landscaped acres on Town Creek and Cemetery Cove and just minutes to both Oxford and Easton. It is move-in ready offering 4 bedrooms and 5 baths with the primary suite located on the first floor. Separate dining room, large beamed family room/kitchen, paneled living room and 3 "flex" rooms make this home extremely livable. The attention to detail is unsurpassed. Great storage areas, pool, additional garage and deepwater dockage with new 20,000 lb. lift complete this exceptional property. Professional photos coming soon.

5419 Morgans Point Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Keller Williams Realty.

$2,795,000
4 Beds ⋅ 4 Baths
Perfectly positioned along the prestigious shores of the Tred Avon River, this extraordinary waterfront estate offers breathtaking water views from nearly every room and an unparalleled blend of luxury, craftsmanship, and cutting-edge sustainability. Designed to embrace its spectacular setting, the three-level main residence features exceptional attention to detail throughout, including rich hardwood flooring, custom millwork, hidden built-in cabinetry, and exquisite finishes at every turn. A gracious main hallway draws your eye directly to the covered waterside porch, creating a seamless connection between the home's elegant interior and its stunning riverfront backdrop. The heart of the home is a chef's kitchen appointed with marble countertops, a spacious center island, and thoughtfully designed gathering spaces that flow effortlessly into the dining room and inviting sitting room with a fireplace. The second-floor primary suite serves as a private retreat, featuring access to its own waterfront balcony overlooking the Tred Avon River. The luxurious primary bath offers a beautiful tiled steam shower with water views, a dedicated vanity area, and an expansive custom walk-in closet with integrated laundry. Outside, an incredible overflow pool creates a resort-like setting where endless river views take center stage. Guests will enjoy complete privacy in the detached guest house, which includes a kitchenette and full bath. A detached one-car garage provides additional storage and convenience. Built with both comfort and efficiency in mind, the property showcases Tesla Solar Roof shingles on both the main residence and guest house, geothermal heating and cooling, radiant floor heating throughout the first and second levels, seven Tesla backup batteries providing power during outages, and elevator access serving the first and second floors. A rare offering in the heart of historic Oxford, 200 West Street represents waterfront living at its finest—where timeless elegance, modern innovation, and spectacular views come together in one unforgettable property. --- {Luxury & Special Features} Waterfront primary suite featuring a private balcony, rain shower, and steam bath | Chef's kitchen with two freezer drawers and built-in plate warmer | Continuous warm water circulation system throughout the home | Dedicated water pressure enhancement system | Elevator serving the first and second floors | Radiant floor heating throughout the first and second levels | Geothermal heating and cooling system | Tesla Solar Roof shingles on the main residence and guest house | Seven Tesla Powerwall backup batteries providing power during outages | Tesla electric vehicle charging station | Resort-style overflow pool overlooking the Tred Avon River | Electric retractable awnings | Detached guest house with kitchenette and full bath | Detached one-car garage

200 West St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,750,000
4 Beds ⋅ 3 Baths
Set on a private point overlooking Boone Creek and the Choptank River in Oxford, this exceptional 4BR/2.5BA modern farmhouse offers panoramic water views and refined coastal living on 2.4 acres. Built in 2018, the home showcases high-end finishes, hardwood flooring throughout, and a light-filled, open design with walls of windows capturing the surrounding waterfront. A welcoming, expansive front porch introduces the main level, where the cathedral-ceiling living room with gas fireplace flows seamlessly into a gourmet kitchen with top-tier appliances—ideal for both everyday living and entertaining. The main-level primary suite enjoys water views and privacy, while the second level overlooks the living space below and features three additional bedrooms and a full hall bath. Outdoor amenities complete the offering, including a waterside deck, new gunite pool (Aqua Pool), private pier with two slips and floating dock, riprapped shoreline, detached two-car garage (transformed and finished into a large office), and beautifully landscaped grounds—perfectly capturing the relaxed elegance and timeless appeal of Eastern Shore living.

4361 Bachelors Point Rd, Oxford

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

Selling Office: TTR Sotheby's International Realty.

$2,695,000
5 Beds ⋅ 6 Baths
Set in the highly sought-after Patrick’s Plains community, 28211 Brick Row Drive is an exceptionally maintained and thoughtfully appointed waterfront residence overlooking the serene waters of Island Creek. Bathed in natural light, the home welcomes you with a stunning foyer and living room featuring floor-to-ceiling windows, skylights, and a gas fireplace, seamlessly connecting to the expansive deck. Designed for both everyday living and elegant entertaining, the home offers a formal dining area and beautiful hardwood flooring throughout. The gourmet kitchen is a true centerpiece, boasting a massive island, Viking gas range, Sub-Zero refrigerator, stainless steel appliances, and abundant pantry storage. Just off the kitchen, the family room impresses with cathedral ceilings, a gas fireplace, sweeping water views, and direct access to a screened-in porch. The main-level primary suite is a private retreat, complete with a spacious walk-in closet and direct access to the back deck, where you can enjoy tranquil poolside and waterfront views. The luxurious primary bath features a cathedral ceiling, a standalone soaking tub, and a glass-enclosed shower. The lower level offers incredible flexibility as a poolside retreat or in-law suite, with its own living room, recreation space, bedroom, full bath, and kitchenette. Completing the home is a rare three-car garage, adding both convenience and functionality. The owner has completed many upgrades, including a new pool, pier improvements, three new HVAC systems, a new driveway, and a water treatment system, along with many other enhancements (full list available). With its prime waterfront setting, abundant natural light, and exceptional living spaces, this home offers a truly elevated lifestyle in one of the area’s most desirable communities.

28211 Brick Row Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$2,600,000
4 Beds ⋅ 6 Baths
‘Eagle’s Nest’ is an exceptional waterfront retreat overlooking Island Creek, just minutes from historic Oxford. Prime location with guest house and deep water (6.5' MLW). Privately sited on more than four acres amid mature trees and meticulously landscaped grounds, this impressive main residence (5324 SF)—completely rebuilt by Ilex Construction in 2008—offers four bedrooms, four full baths, and two half baths. Every room is generously sized and thoughtfully designed to capture expansive water views while providing elegant yet comfortable living. The main level features beautifully appointed living spaces, including a formal living room with coffered ceiling, wood-burning fireplace, custom built-ins, wet bar, and sliding doors opening to the waterside patio. A formal dining room, enclosed by French doors, offers an inviting setting for entertaining. At the heart of the home, the gourmet kitchen showcases a cathedral ceiling, large center island, top-of-the-line appliances, gas fireplace, spacious walk-in pantry, and custom built-ins—creating a warm and functional gathering space. The adjoining sunroom is filled with natural light and features vaulted ceilings, slate tile flooring, and sweeping water views, with glass doors opening to the patio and pool area. Nearby, a well-equipped mudroom, laundry room, and half bath add everyday convenience, along with a covered breezeway to the two-car garage. The desirable main-level primary suite serves as a private retreat with tranquil water views, dual walk-in closets, and a luxurious en suite bath. Just off the primary suite corridor, a private office with custom built-ins and an additional powder room enhance the home’s thoughtful design. Upstairs, three generously sized guest bedrooms each include en suite baths. A comfortable sitting area opens to a balcony overlooking Island Creek—an ideal place to relax and take in the serene setting. In addition, a coveted one-bedroom, one-and-a-half-bath guest house (968 SF) includes a full kitchen, living room, and attached two-car garage—perfect for visitors, extended family, or flexible use. Outdoor living is equally impressive, highlighted by a gunite swimming pool, expansive brick patio, mature landscaping, and extensive hardscaping designed to complement the waterfront setting. The private pier features two slips and a boat lift with 6.5' MLW along a protected, riprapped shoreline. ‘Eagle’s Nest’ presents a rare opportunity to enjoy refined Eastern Shore waterfront living just moments from Oxford. New roof on main house (2025). New pool cover: Aqua pool service contract paid for-2026

4573 Bringman Farm Rd, Oxford

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

Selling Office: Unrepresented.

$2,600,000
4 Beds ⋅ 5 Baths
Welcome to your private Eastern Shore retreat! This amazing 4-bedroom, 4.5-bath Cape Cod is perfectly situated on a secluded peninsula, offering unparalleled tranquility and breathtaking waterfront views of Boone Creek located in beautiful Oxford, Maryland. The home offers an incredible blend of traditional elegance and modern luxury. An open and airy floor plan is bathed in natural light, with expansive windows framing the stunning water views from nearly every room. The living room has beautiful brick floors and a wood burning fireplace. You will also find a gas fireplace in the spacious family room. The bright and inviting sunroom has cathedral ceilings and walls of glass doors with water, pool, garden and patio views. The gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and a large center island. It flows effortlessly into the formal dining area which includes an additional fireplace for cozy and intimate dining experiences. Beautiful hard wood floors flow into several rooms. The main floor also hosts two private sanctuaries: an ensuite bedroom and a primary bedroom, each with private decks offering stunning water views. The primary suite's closet is a truly incredible, separate dressing room. A laundry room, a full bath, and a half bath complete the main level. Upstairs, two large bedrooms and a shared bath provide comfort and privacy for guests or family. Outside you discover a true entertainer's paradise. The property's unique peninsula location offers a wide expanse of water frontage, perfect for enjoying the Eastern Shore lifestyle. A large, sparkling in-ground pool is the centerpiece of the manicured grounds, surrounded by extensive hardscaping and lush landscaping, creating a resort-like feel. The detached two-car garage is enormous. There are raised beds in a fully fenced garden with a garden shed. The climate-controlled dock house offers endless possibilities for a gym, office, art studio or storage. The private dock provides water access for boating, kayaking, paddleboarding, fishing and crabbing on Boone Creek. With quick water access to Choptank River, Tred Avon River, Chesapeake Bay & Miles River, you can explore the best areas of the shore. This home is more than a residence; it's a lifestyle. Located just minutes from the historic town of Oxford, you'll have easy access to charming shops, restaurants, parks, the beach strand and the Oxford-Bellevue Ferry. This is a rare opportunity to own a piece of paradise on the Eastern Shore.

4500 Boone Creek Rd, Oxford

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$2,405,000
3 Beds ⋅ 3 Baths
Waterfront living at its finest in Pirate’s Cove, tucked along the serene waters of Trippe Creek. Set on 2.71 waterfront acres and beautifully sited across from a nature preserve, this property offers serenity, sophistication, and sweeping water views. Built in 1986 and thoughtfully reimagined with a custom renovation in 2016, the home blends elegant design and modern comforts in a meticulously maintained, one-level layout featuring three bedrooms and three full baths. Vaulted ceilings and walls of windows fill the living spaces with natural light, creating a bright, open atmosphere throughout. Overlooking the water, the gourmet kitchen is a chef’s delight, featuring a Wolf range with warming drawer, Sub-Zero refrigerator, double wall ovens, quartzite countertops, generous cabinetry, and a spacious island perfect for gathering. The living room, kitchen, and primary suite are all sun-drenched and open seamlessly to the deck, providing stunning water views and creating effortless indoor-outdoor living. The primary suite is a tranquil retreat with expansive water views, a large walk-in closet, and a spa-like en-suite bath highlighted by a stone soaking tub, glass-enclosed shower, and a unique laundry-chute window that connects directly to the laundry room for added convenience. Outside, enjoy summer days by the salt water, in-ground pool or stroll down to your private pier with approximately 4' MLW—ideal for boating, kayaking, or simply soaking in the peaceful setting. A large attached three-car garage provides ample space for vehicles, storage, and waterfront gear. This is the essence of Eastern Shore waterfront living—refined, relaxed, and ready to be enjoyed.

5728 Pirates Cove Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,100,000
4 Beds ⋅ 4 Baths
This Island Creek waterfront home located on deep water with a southern exposure and long shoreline is being sold for the first time since built in 1999. Situated on 3.8 acres, every detail was thought out and executed by the owners and a top rate builder. The house consists of 4,469 sq. ft. of living space plus a two car garage. The house has an open floor plan, featuring a large eat in kitchen with views over Island Creek, the dock and an expansive well landscaped lawn that drops to the shoreline. The kitchen is well appointed with top end appliances, tons of storage areas, pantry and is close to the laundry room and shop. There is a primary bedroom suite on the first floor, a second bath, and three bedrooms and two full baths on the second floor. There is a deck, patio and screened porch facing SW, all meticulously maintained. The property is located in the “X” flood zone. This is an extraordinary waterfront property located in the Oxford zip code on one of the best deep water creeks in Talbot County.

27877 Bent Farm Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$1,875,000
Welcome to an amazing farm opportunity located 3 miles from Oxford, Maryland, one of the Eastern Shore’s most treasured waterfront towns, where timeless charm meets an exceptional opportunity to create your dream home. Set along the shores of Goldsborough Creek, this premier waterfront parcel offers northwestern exposure, delivering breathtaking sunset views across tranquil waters. The preferred waterfront building site allows for construction with a 100-foot setback, providing nearly 180 degrees of waterfront views on Goldsborough Creek. A proposed 150-foot private dock site would provide approximately 2.5 feet at mean low tide. A recent septic application with the Talbot County Health Department has been submitted for a four-bedroom residence. Soil evaluations indicate excellent conditions for a generous sewage disposal area, offering flexibility for a substantial home and the potential for future improvements. Engineering analysis also supports the possibility of identifying additional SDA locations should subdivision be pursued, subject to county approvals. Preliminary estimates show the potential for 2 waterfront and 1 inland building site, to be confirmed with Talbot County Planning and Zoning. The farm is located within a historic waterfowl staging area providing habitat for wintering Canada Geese and Ducks. Adjacent woodland and contiguous farm fields complement this coveted rural setting with ample opportunity to enhance the natural features and create a haven for the outdoors and nature enthusiasts. This unique waterfront farm opportunity provides an extraordinary setting to design and build a custom waterfront retreat in a location defined by the natural beauty where land and water combine.

Oxford Road, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

$1,800,000
4 Beds ⋅ 4 Baths
Simply Sensational! Sunrise views over Town Creek set the tone for this beautifully designed four-bedroom waterfront home, where contemporary architecture meets the warmth of a waterfront cottage. The main living areas include a formal living room and dining room, each with a fireplace, a bright eat-in kitchen and an inviting family room, where walls of windows frame the water views and fill the home with natural light. Two first-floor bedrooms offer the convenience of main-level living. Upstairs, two ensuite bedrooms open to the second-floor sun deck, including a spacious primary suite with floor-to-ceiling windows overlooking Town Creek.An expansive waterside patio and pool create the perfect setting for relaxing and entertaining. The separate one-bedroom guest house/pool house and detached workshop provide additional space for family, guests, hobbies or a home office. The private pier, complete with a boat lift and floating dock for kayaks and paddleboards, provides easy access to the Tred Avon River and the Chesapeake Bay. Located in the historic waterfront village of Oxford, this exceptional home captures the beauty, charm and relaxed waterfront lifestyle that define Maryland's Eastern Shore. The property is offered with its furniture allowing for an effortless transition.

106 E Division St, Oxford

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

Selling Office: TTR Sotheby's International Realty.

$1,800,000
3 Beds ⋅ 3 Baths
Discover your own Eastern Shore retreat at 4491 Bachelors Point Road in Oxford, MD. This exceptional 29-acre waterfront estate offers unrivaled privacy, 2,100 feet of pristine shoreline on Boone Creek, and effortless access to the Choptank River. The thoughtfully designed residence—completed initially in 2003 and extensively updated—features over 2,000± sq. ft., three bedrooms, and a newly completed 2023 primary suite with a walk-in closet and spa-style bath. Enjoy sweeping water and wildlife views from the expansive screened porch and spacious deck. A separate apartment above the detached garage provides flexible space for guests, a home office, or rental income. The property also includes a 100-foot dock with water and electric (replanked in 2025) and sheltered waters ideal for small boats, kayaking, paddleboarding, and swimming. Set within the highly sought-after Bachelor’s Point community, residents enjoy proximity to deepwater boat slips, a full-service boatyard, and Oxford’s charming boutiques, restaurants, festivals, and recreational amenities. Mature trees, abundant wildlife, and protected conservation acreage create a serene, low-maintenance setting perfect for a private getaway, hunting retreat, or investment opportunity.

4491 Bachelors Point Rd, Oxford

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

Selling Office: Benson & Mangold, LLC.

$1,800,000
3 Beds ⋅ 3 Baths
Nantucket-Style Waterfront Retreat on a Private Peninsula Near Oxford Discover this enchanting Nantucket-style cottage, gracefully positioned on its own private 2.6-acre peninsula at the confluence of the Choptank River and Boone Creek. Just minutes from the historic town of Oxford, this 3,196 sq ft home offers approximately 1,000 feet of pristine waterfront and panoramic western views—perfect for savoring Chesapeake Bay sunsets . Built in 1986, the residence has been thoughtfully updated by West and Callahan, featuring a new roof, siding, Trex decking, and numerous new windows to enhance both comfort and efficiency . Zillow Main Level Highlights: A spacious kitchen that flows into a large dining area, opening to a side screened porch—ideal for alfresco dining. A versatile double room serving as a living area and library/study or potential game room. A second screened porch overlooking the in-ground pool, offering a serene space to relax. Upper Level Features: Three bedrooms and two full baths. The primary suite boasts vaulted ceilings and breathtaking views across the Choptank River. The second bedroom features high ceilings and picturesque vistas. The third bedroom includes a cozy desk alcove and a charming sleeping porch . Additional Amenities: An artist's studio equipped with water and electricity, situated adjacent to the in-ground pool. A private pier on Boone Creek with an electric lift, accommodating small watercraft. This unique property combines timeless design with modern updates, offering a tranquil waterfront lifestyle just a short drive from Oxford's shops, dining, and cultural attractions.

26319 Chanticleer Rd, Oxford

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

Selling Office: Benson & Mangold, LLC.

$1,700,100
3 Beds ⋅ 3 Baths
Located in the sought-after Oxford neighborhood of Sailors Retreat, this well-maintained brick and siding home offers easy one-level living in a peaceful, natural setting. The home features 3 bedrooms plus a separate office, beautifully updated bathrooms, and an upgraded kitchen with modern finishes. Hardwood floors run throughout the main living areas. Enjoy the outdoors with a private in-ground pool, mature landscaping, and access to deep water, perfect for boating, paddleboarding, kayaking, or simply enjoying the view. Sailors Retreat is a quiet, waterfront community known for its natural beauty, and proximity to both downtown Oxford and Easton. Whether you're searching for a full-time home or a weekend getaway, this property offers the perfect blend of comfort, convenience, and Eastern Shore charm. Call for list of improvements

4721 Sailors Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,695,000
3 Beds ⋅ 3 Baths
Welcome to Tred Avon Point, an extraordinary waterfront property on a stunning point of land in the picturesque, historic town of Oxford, MD. Strategically sited only 25 feet to the waters edge on three sides to capture breathtaking views of the Tred Avon River & amazing western sunsets! Maritime inspired post & beam, open design visually connects the views to the space. The character & depth of the architecture blurs the lines between indoor & outdoor living. The abundance of the wood toned palette play with the hue & saturation of the natural landscape. The space easily transitions from entertaining friends & family to a respite for homeowners. The perfect vantage point to watch the boats, sailing races & watermen go by. Two primary suites on each level can be reached by the nautically designed wood spiral staircase or elevator. Gorgeous custom designed kitchen renovation done in 2019. The guest suite on the first level enjoys the views from its private deck. The rooftop cupula offers a stunning 360 degree birdseye view of the town & water. All season beauty can be enjoyed even in winter in front of the recently installed, high-end brick fireplace. The property includes a shared lot with a 7ft MLW deepwater multislip dock with lift. Perfectly located near dining, yacht club & marinas yet still invoking quiet & privacy. The included furniture, fine art & accessories create a move-in ready primary, 2nd home or vacation rental. Truly a one of a kind home!

121 Pier, Oxford

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

Selling Office: Benson & Mangold, LLC.

$1,650,000
Discover the rare opportunity to own one of the Eastern Shore's finest waterfront parcels: Lot 5, an exceptional 4.18-acre homesite in the exclusive Morgan's Point community of Oxford, Maryland. This home site has an approved prec, and flood insurance is not required. Tucked along the serene Tred Avon River, this buildable waterfront gem offers expansive privacy and boundless potential, thanks to its generous scale and direct river access with 389 feet of rip-rap shoreline. Perfect for your custom estate, family compound, or legacy retreat, this sanctuary marries natural splendor with the refined charm of Talbot County's coastal haven. Spanning 4.18 acres, a fully usable lot provides versatile space to build your future home with breathtaking river vistas. Boasting direct frontage on the Tred Avon River with ample mean low water depth In a market where waterfront estates command premiums, this rare 4+ acre offering represents an unparalleled canvas for your vision. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

Morgans Point Drive, Oxford

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

Selling Office: Benson & Mangold, LLC.

$1,650,000
5 Beds ⋅ 5 Baths
This charming cape cod is located in Oxford on Town Creek just outside the Historic District on a quiet dead end street. Downstairs is a home office (with full bath, could also be used as a primary), a built-in bar, cozy den with gas fireplace, bright sunroom and fabulous screened porch. Upstairs, freshly carpeted and painted, are four bedrooms and three full baths. The awning-covered deck just off the Primary gives the feeling of a tree house with expansive Creek views. In the backyard sits a waterside cottage, “The Boathouse,” with amazing breezes all summer and in the winter it’s a prime viewing spot for the spectacular Oxford Christmas Dock tree display. Got boats? The dock has 4 slips, one currently occupied by a floating dock (conveys). The fenced yard is perfect for your furry friends. The crawl space was recently encapsulated and the attic newly re-insulated (2025). This wonderful house has it all and is as charming as it gets.

111 First St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,625,000
4 Beds ⋅ 4 Baths
Oxford Cove – A truly rare offering, this extraordinary waterfront property is a study in serenity, privilege, and timeless eastern shore beauty. Surrounded by sweeping, uninterrupted water views to the south and east, the property captures the beautiful sunrise, immersing you in the everchanging light and rhythm of the tides. The main residence- graciously scaled with four bedrooms-embraces a refined yet relaxed aesthetic, designed for effortless living and seamless indoor-outdoor flow. Expansive terrace with a waterside pool, creates an idyllic setting for both quiet reflection and elegant entertaining. A charming one bedroom guest house/pool house offers a private haven for visitors, while a separate workshop provides space for creativity or collection. For the avid mariner, the property is exceptionally equipped with a private pier with a boat lift and a floating dock for kayaks and canoes- delivering immediate access to the finest waters of the Chesapeake Bay. Set in the historic village of Oxford,, one of the Eastern Shore’s most treasured enclaves, “Oxford Cove” offers a rare balance of seclusion and proximity. Here, life is defined by understated luxury, natural beauty, and the enduring allure of the waterfront.

106 E Division St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,495,000
4 Beds ⋅ 4 Baths
Welcome to this beautifully maintained 4/5 BR/3.5BA waterfront residence in desirable Oxford, offering timeless coastal appeal and the relaxed lifestyle that defines Maryland's Eastern Shore. Thoughtfully designed for both comfortable everyday living and gracious entertaining, the home features a desirable main-level primary suite with tranquil water views, a large walk-in closet, and a spacious ensuite bath with double-sink vanity. Upstairs, a second primary suite, two additional guest bedrooms, a full bath, and a versatile bonus room provide exceptional flexibility for family and guests. Filled with natural light, the home offers a seamless blend of traditional design and inviting gathering spaces. The gourmet kitchen features a center island, custom glass-front cabinetry, and opens to a charming breakfast room where peaceful water views create the perfect backdrop for morning coffee. A formal dining room is ideal for special occasions, while the dramatic vaulted living room showcases a gas-burning fireplace with custom surround and built-in entertainment center. Double sliding doors open to the patio and gardens, creating an effortless connection between indoor and outdoor living. A separate mudroom provides convenient interior access to the attached 2-car garage, which also offers a full staircase to wonderful attic storage above. Outside, a waterside screened porch invites you to relax and enjoy gentle Eastern Shore breezes and ever-changing views across Boone Creek. The beautifully landscaped grounds are enhanced by mature trees, flowering gardens, and expansive lawn leading to the water's edge. Complete with a private pier featuring two slips and a boat lift, approximately 3.5+ feet of MLW, riprapped shoreline, and picturesque views along Boone Creek, this exceptional waterfront property offers an ideal setting for boating, entertaining, and embracing the best of Oxford's waterfront lifestyle.

26226 Langs Landing Rd, Oxford

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

Selling Office: Benson & Mangold, LLC.

$1,400,000
5 Beds ⋅ 5 Baths
This one-of-a-kind executive estate blends timeless Cape Cod architecture with modern sophistication, set high on over 10 rolling acres to capture the very best of Chester County living. A sweeping covered flagstone porch (10x50) welcomes you into a grand foyer, where custom-milled hardwood floors, crown molding, nine-foot ceilings, and rich stonework set the tone for the exceptional quality throughout. Built without compromise, this home was designed for one-level living and is wheelchair-accessible on the main level, highlighted by a luxurious owner’s suite with a spa-inspired bath featuring a state-of-the-art walk-in shower, dual custom vanities with marble tops, and a custom walk-in closet with organizer. The chef’s kitchen is an entertainer’s dream, featuring granite countertops, extensive cabinetry, an oversized island with prep sink, a Thermador six-burner gas range with double ovens, SubZero refrigerator, Miele drawer dishwasher, trash compactor, and built-in pull-out pantry, all flowing seamlessly into both formal and casual dining spaces with French doors opening to outdoor living. The living room impresses with a gorgeous stone fireplace with wood stove insert, custom built-ins, window seats, and arched doorways, while a breathtaking library with custom-built, floor-to-ceiling wood shelving and French doors to the covered stone porch offers warmth and refinement. Completing the main level are a spacious guest bath designed for poolside convenience, a commercial-grade sauna, and a radiant-heated floors! Huge mudroom/laundry with abundant storage. Upstairs, you’ll find four generously sized bedrooms (one en suite), a hall bath, a media lounge with a 10-foot drop-down screen and projector, and a huge private au pair/guest suite with wet bar that opens to a versatile bonus room with surround sound and balcony views. Additional highlights include an oversized three-car garage with 8-foot wooden doors, a tiled game and entertainment room with French doors to the pool, two newer HVAC systems, surround sound throughout the main floor, a whole-house water treatment system, and countless custom touches. Outdoors, the property lives like a private resort with a sparkling swimming pool, multiple flagstone terraces, lush lawns, and more than five wooded acres with walking trails. Nestled among Amish farms and horse country, this remarkable estate offers a rare opportunity to experience refined living, natural beauty, and everyday tranquility.

930 Saginaw Rd, Oxford

Listing courtesy of Realty One Group Restore. Contact:

Selling Office: RE/MAX Associates-Hockessin.

$1,350,000
3 Beds ⋅ 4 Baths
Beyond the white picket fence, a storybook garden unfolds—lush, curated, and unmistakably Oxford. Perfectly positioned just moments from the beach, ferry, and waterfront park, 208 Factory Street offers a rare blend of timeless village charm and sophisticated modern comfort. Thoughtfully enhanced with updated mechanical systems since 2019, this three-bedroom residence has been meticulously maintained and beautifully reimagined for effortless living. Sunlight pours into the airy, open- concept living, dining, and kitchen spaces, where hardwood flooring flows seamlessly throughout and every room feels connected to the outdoors. Designed with exceptional flexibility, the home features two private primary suites—one conveniently located on the main level and a second occupying the upper floor. The upstairs retreat serves as a true sanctuary, complemented by a beautifully renovated spa-inspired bath featuring a glass-enclosed porcelain tile steam shower. The main-level suite offers its own renovated bath and charming loft area, creating an equally inviting private escape. Just off the kitchen, a dedicated office provides the ideal work-from-home setting, while multiple outdoor living spaces invite relaxation and entertaining throughout the seasons. Enjoy quiet mornings on the intimate sitting porch overlooking the pool, gather with friends on the screened porch, or simply savor the beauty of the impeccably landscaped cottage gardens that envelop the property. Completing the offering is a detached one-car garage and an enviable location in the heart of Oxford. A home that captures the very essence of Eastern Shore living—elegant yet approachable, refined yet welcoming, and perfectly connected to one of Maryland’s most treasured waterfront communities. Here, every detail has been thoughtfully curated to create a lifestyle as beautiful as its surroundings. ---{Luxury & Special Features} Electric retractable awnings | Heated floor in second-floor primary bath | Glass-enclosed steam shower with rain shower in second-floor primary bath | Towel warmer in second-floor primary bath | Tesla charger in detached garage | Moen smart water shutoff valve | Water pressure booster pump | Lawn irrigation system | Updated mechanical systems since 2019 | Hardwood flooring throughout | Two primary suites, including a main-level primary | Dedicated office/flex room | Screened porch | Poolside sitting porch | Detached one-car garage | Cottage gardens and white picket fence setting |

208 Factory St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,320,000
4 Beds ⋅ 4 Baths
Discover the charm of 213 S Morris Street, an exquisite residence nestled in Oxford, MD's historic district. Originally built in 1870 by a skilled shipwright, this home was meticulously restored with a "down to the studs" renovation, seamlessly blending historic charm with modern luxury. The property boasts a gated brick and river stone driveway, providing off-street parking. The property is fully enclosed by both a historic brick wall and an Oxford-style picket fence ensuring privacy. The grounds are professionally landscaped and irrigated for natural beauty and feature a large blue slate patio for outdoor living. The home features a separate heated and air-conditioned studio/office, perfect for creative pursuits or remote work. Inside, the beautifully decorated interior offers a primary bedroom (with en-suite bath) on the first floor and three additional bedrooms upstairs. With three bathrooms—including two on the second floor, one on the first, plus a powder room—comfort and convenience are paramount. Enjoy cozy evenings by one of the four gas fireplaces or entertain in the stunning family room with vaulted ceilings and clerestory windows that adjoins a gourmet kitchen equipped with a six-burner Wolf stove and top-of-the-line appliances. The home is bathed in natural light, with top-quality windows and doors, and features pristine pine floors throughout. It's a "happy house," radiating warmth and elegance, and its reproduction costs in today's market would far exceed the list price.

213 S Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$1,280,000
2 Beds ⋅ 3 Baths
Prime waterfront home in Oxford’s beautiful historic district, faces west overlooking the Tred Avon River. Offering the best in Oxford waterfront with prevailing SW summer breezes, fantastic year-round sunsets, a long dock, patio, old growth large trees, extensive hardscape and off-street parking make this property unique. It has a carport and is located on a significant tree-lined street and lies with the “X” zone on the flood maps. On the first floor is an open, well equipped kitchen that opens to the great room with views overlooking the patio, gardens and the river. One full bath on the first floor with a library/den and front entrance. There is a primary bedroom suite on the second level adjoining a screened porch and deck with views to the Tred Avon beyond. The views are extraordinary! In addition, there is a second bedroom and bath on this level.

102 Tred Avon Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,270,000
4 Beds ⋅ 4 Baths
Tucked in a lovely Oxford location just steps from in-town amenities, this completely redone 4 bedroom, 3.5-bath residence offers quaint Eastern Shore living with exceptional charm and flexibility. The light-filled main home features a formal dining room, private office/bedroom, inviting family room with gas fireplace and wet bar with custom built-ins, and a top-of-the-line gourmet kitchen with cathedral ceiling, generous cabinetry, center island, and an adjacent mudroom with additional appliances. Upstairs, the spacious primary suite overlooks the beautifully landscaped rear grounds , pool and features vaulted ceilings, custom built-ins, and a walk-in closet. There is a comfortable guest bedroom and full bath. Outdoor living features a fabulous rear deck overlooking an in-ground swimming pool and manicured gardens—perfect for entertaining or quiet relaxation. A separate guest cottage with murphy bed, full bath and kitchenette adds even more versatility, ideal for guests, extended stays, or a private retreat. Only a couple blocks to town owned waterfront, shops, restaurants, parks, marinas and the local market. Move in ready home.

103 Tred Avon Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Compass.

$1,225,000
4 Beds ⋅ 5 Baths
Luxury Living Meets Versatile Workspace on 12.3 Gated Acres Welcome to 15 Wood Valley Lane—an extraordinary Chester County estate offering the perfect blend of refined living and functional space. Set on 12.3 private, gated acres of scenic countryside, this one-of-a-kind property features a beautifully appointed 4-bedroom, 5-bath main residence, a inground pool and hot tub, and an impressive 60'x100' steel shop with a fully integrated 3-bedroom apartment. Inside the main home, you'll find expansive, light-filled living areas with tasteful finishes and a warm, inviting atmosphere. The primary suite offers a serene retreat with a luxurious ensuite bath and tranquil views. Each additional bedroom includes its own dedicated bathroom, ideal for family or guests. Step outside to enjoy the manicured grounds, where a luxurious pool and hot tub area await—perfect for entertaining or relaxing in total privacy. The massive steel building is a true standout, offering endless potential for business use, hobbies, or storage, and the attached 3-bedroom apartment provides flexibility for multi-generational living, staff quarters, or rental income. For peace of mind, this property features a hard-wired, whole-house generator. There’s room here for everything—horses, gardening, equipment, or just breathing room to enjoy the land. Located in a quiet, accessible spot not far from major routes, this property is ideal for someone who wants space to grow, live, and work—all in one place.

15 Wood Valley Ln, Oxford

Listing courtesy of Beiler-Campbell Realtors-Kennett Square. Contact:

Selling Office: KW Greater West Chester.

$1,045,000
4 Beds ⋅ 4 Baths
Located in one of the county’s most coveted areas along the Oxford Corridor, this 4-bedroom, 3.5-bathroom custom home offers a spacious layout with a flexible design for modern living. The open floor plan seamlessly connects the kitchen, dining area, and vaulted-ceiling living room with fireplace, creating a functional space ideal for everyday living and entertaining. The updated kitchen features stainless steel appliances, Silestone countertops, an island, and a breakfast nook. Just off the foyer, a private office with French doors provides a quiet workspace, and a formal dining room offers room for gatherings. The main-level primary suite includes two walk-in closets, two vanities, a soaking tub, a walk-in shower, and direct access to the back patio. Upstairs, an en-suite bedroom serves well as a second primary suite, along with two additional bedrooms and a large bonus or recreation room. A cozy sunroom overlooks the elaborate stone patio and outdoor fireplace, offering a peaceful view of the surrounding 2.6± acre property. In addition to the attached 2-car garage, the property includes an oversized detached equipment building—well-suited for boat restoration, woodworking, recreation, or storage. A deeded right of way provides direct water access to Boone Creek, perfect for kayaking or fishing.

26604 E Bonfield Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,025,000
3 Beds ⋅ 2 Baths
A lovely waterfront home located in Sailors Retreat. Three bedrooms and two and half baths. primary bedroom, sunroom, and family room have a beautiful view of Island Creek. Nice deck and patio for relaxing Two car garage with walk upstairs to the attic. The dock can accommodate two boats with a water depth of 3'-4' MLW. Buyer must verify the water depth

4752 Sailors Retreat Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented.

$945,000
4 Beds ⋅ 3 Baths
Best value!! An amazing chance to renovate or construct a new home! This stunning 1.77-acre property sits on the Choptank River, offering breathtaking western views. The house includes a generous great room, a large eat-in kitchen, 4 bedrooms, 3 bathrooms, a den, an office, a recreation room, as well as a carport and storage shed. Enjoy outdoor living with a deck and patio. The septic system was replaced in 2019, and the HVAC was updated in 2020. Revel in spectacular sunset views, a private pier, rip-rap shoreline, and a sandy beach. Located on a private road, it's just a short distance from the historic towns of Oxford and Easton, with nearby parks, marinas, and dining options.

26361 Chanticleer Rd, Oxford

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

Selling Office: Shore Living Real Estate.

$900,000
US RT 1 and Rt 10 interchange. 2.1 acre +/- site available for commercial use. Approximately 300' From Route 1 Bypass Ramps. Excellent visibility & traffic count. property situated on route to Walmart shopping center. Commercial Building has many possibilities as well. 4600 S.F. steel structure, 2 Heat Pumps. . Route 10 Road Frontage Is 175'. Public Sewer, on site well. Opportunity to lease or purchase.

309 Limestone Rd, Oxford

Listing courtesy of BHHS Fox & Roach-Kennett Sq. Contact:

Selling Office: BHHS Fox & Roach-Jennersville.

$875,000
3 Beds ⋅ 3 Baths
This charming Victorian house is located in the Historic District of Oxford and has resided with the current owner for several decades. A front porch overlooks a beautifully landscaped garden and lawn while the rear lawn is surrounded by gardens for beauty and privacy. A stunning water fountain with trickling water works perfectly for a quiet time on the sun porch or the second floor deck with sliding shades for the late afternoon sun. A garden shed/shop and a single car garage with a studio/apartment on the second floor round out this beautifully decorated home. A full size modern kitchen with top of the line appliances, dining room, and formal living room are on the first floor. Three bedrooms and two modern baths are located on the second floor. The house enjoys the benefits of a geothermal well system, 9’ ceilings and two fireplaces. The garage and garden shed are accessed by an alley which also allows for additional off street parking, a rarity in the Historic District. All of this sits on high ground in the “X” flood zone. Enjoy easy access to local shops, restaurants, the waterfront park, Oxford Market, and the beloved Scottish Highland Creamery.

226 S Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.