luxury houses with pool for sale Talbot County, United States

Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU! This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for entertaining or everyday living. Soaring two-story ceilings, skylights, and expansive windows flood the home with natural light, while a gas-burning fireplace is the focal point of this inviting space. The main-level primary suite serves as a private retreat with an ensuite bath, complemented by two walk-in closets. A cozy den and convenient powder room complete the main level. An upper-level loft overlook adds architectural charm and provides additional space for relaxation. Upstairs, one guest bedroom enjoys its own ensuite bath, and two additional bedrooms share a connecting full bath. Outdoors, a beautifully landscaped backyard framed by mature trees provides a tranquil setting, while the attached 2-car garage offers convenience. Cooke’s Hope residents enjoy an unmatched lifestyle with ponds, tennis courts, walking trails, a dog park, fitness center, picnic pavilion, and a community dock—making this one of Easton’s most desirable communities.

Improved Pricing ! Make this Charming Oxford Gem your new home. This well-maintained 4-bedroom, 2.5-bath home offers a comfortable blend of classic style and Eastern Shore charm in a prime Oxford location. Whether you're looking for a first home, a retirement retreat, a weekend escape, or an investment property, this inviting residence is designed to fit a variety of lifestyles. Tucked away on a quiet cul-de-sac, it features welcoming indoor and outdoor spaces ideal for year-round living, with plenty of room to transform/grow and make it your own. Inside, the foyer opens to spacious living and dining areas featuring Brazilian cherry hardwood floors, vaulted ceilings, and abundant natural light. French doors lead to a flexible room that can serve as a first floor guest room or home office. The living room flows into a large kitchen with a bright breakfast room and an adjacent dining area, making it ideal for casual mornings and gatherings with family and friends. Just off the kitchen, a half bath and a large family room provide added convenience and direct access to a spacious backyard. Upstairs, the primary suite offers a peaceful retreat with a large walk-in closet and an en-suite bath featuring double sinks, a Jacuzzi tub, and a walk-in shower. Two additional bedrooms share a generous hall bath with double sinks and a tub-shower combination. A second-floor bonus room adds even more flexibility and can be used as a playroom, home gym, game room, or private retreat. Outdoor living is equally appealing, with a front and back decks, patio with fire pit and a fully fenced backyard. One of the largest yards in the neighborhood, with plenty of room for a pool. Located just a short walk from downtown Oxford, the home offers easy access to local shops, restaurants, the waterfront park, Oxford Market, and Scottish Highland Creamery. Move-in ready and full of character, this Eastern Shore gem delivers exceptional value. Move-in ready and full of character, this Eastern Shore gem offers the best of Oxford living at an exceptional value. Recent Upgrades include: A new roof installed in August 2025, Stainless-steel appliances less than two years old, encapsulated crawlspace.

PRICE IMPROVEMENT*** Discover the charm of Lakelands at Easton, where community spirit meets modern living in this stunning coastal-style townhouse. Built in 2010, this beautifully maintained home boasts 4 spacious bedrooms and 3.5 bathrooms, offering ample space for relaxation and entertainment. The inviting exterior features well-kept sidewalks that encourage evening strolls and friendly neighborly chats. Step outside to enjoy the community amenities, including basketball courts and a refreshing outdoor pool, perfect for summer gatherings and active lifestyles. The vibrant neighborhood is designed for connection, with parks nearby that provide green spaces for picnics, playdates, and outdoor activities. The community's commitment to safety and convenience is evident, with public services readily accessible, making daily life a breeze. Inside, the home features a cozy gas fireplace, ideal for creating warm memories during chilly evenings. The improved basement offers additional living space, while the attached garage and driveway provide ample parking for guests. With a lot size of 0.09 acres, this property strikes the perfect balance between manageable upkeep and outdoor enjoyment. Embrace a lifestyle where community, comfort, and convenience come together seamlessly in Lakelands at Easton. Don't miss your chance to make this delightful townhouse your new home! **New AC 2024, Five New windows with warranty, New Roof Ridge top peak and vents through Marasun 2025, Gas Fireplace-all new parts 2026, 2019 Replaced wood Decking with Trex decking, Only One of 4 units that has 4 bedrooms.**

Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

Absolutely stunning mid-century contemporary estate offering a private, park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor-kitchen, outdoor shower, in-ground hot tub, tennis court, and maintenance-free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with Wi-Fi controlled front/rear irrigation system. The superbly designed and crafted home offers an open floorplan with 4 bedrooms and an office, 3.5 designer baths with heated floors, a magnificent gourmet kitchen, upper and lower-level living areas providing outstanding functionality. Breathtaking water-views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished!

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

PRICE IMPROVEMENT*** Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019

LOCATION and CHARM! Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a stunning gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

Bolton Farm, available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 115-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

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.

Welcome to La Trappe Heights, where this beautifully refreshed 3-bedroom, 2.5-bath Cape Cod is ready to impress. Enjoy new appliances, new durable LVP flooring, and fresh paint throughout. A spacious living room is highlighted by cathedral ceilings and a features cozy wood-burning fireplace. A bright eat-in kitchen with a center island is accented with new granite counter tops. Sliding glass doors lead to a spacious deck and large fenced backyard. The first-floor primary suite offers a walk-in closet, and private bath for added comfort and convenience. Upstairs you have two bedrooms and one full bath. This home is move-in ready and just waiting for you.

Envisioned for a premier waterfront setting along the Tred Avon River, this exceptional TO-BE-BUILT coastal residence by award-winning firm - Pacquin Design Build, presents a rare opportunity to create a refined Eastern Shore retreat on a remarkable 4.18-acre homesite within the exclusive Morgan’s Point community of Oxford. Thoughtfully designed in classic shingle-style architecture, the proposed home is perfectly oriented to capture sweeping river views, abundant natural light, and a seamless connection between indoor and outdoor living. The proposed floor plan balances timeless elegance with everyday comfort, featuring open yet well-defined living spaces that flow effortlessly toward the waterfront. A chef’s kitchen anchors the main level, opening to inviting gathering areas and expansive terraces overlooking the river. Walls of glass frame the ever-changing water views, while a main-level bedroom suite offers flexibility for guests or convenient single-level living. The upper level is designed as a private retreat, highlighted by a serene primary suite with elevated river views and additional bedrooms thoughtfully arranged for family and guests. Outdoors, the concept plan showcases a resort-inspired setting with a waterfront pool, generous patios, and sweeping lawn leading to approximately 389 feet of rip-rap shoreline. Boating, paddleboarding, and relaxed days by the water are central to the lifestyle this property affords. The lot is fully usable, offers ample mean low water depth, has an approved perc, and does not require flood insurance, making it an ideal canvas for a custom estate, family compound, or legacy retreat. Lot can be purchased separately for $2,250,000 (MDTA2012470) Set within the natural beauty and refined charm of Talbot County, and just moments from the Chesapeake Bay, this extraordinary offering combines privacy, scale, and location. A rare chance to bring a bespoke coastal vision to life on one of the Eastern Shore’s most desirable riverfront parcels—perfect as a year-round residence or second-home sanctuary. Located 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!

Brand New Home Ready for Move-In! Step into this stunning two-story home designed for modern living, offering the perfect blend of style, comfort, and functionality. The open-concept layout features upgraded lighting, hardware, and railings throughout, complemented by a premium exterior color package. The gourmet kitchen includes a large island, walk-in pantry, and stainless steel appliances, flowing seamlessly into a bright and spacious family area ideal for entertaining. The main level features a private primary suite with a luxurious en suite bath, along with a convenient half bath and laundry room. Upstairs, you'll find three additional bedrooms and two full baths, providing plenty of space for family or guests. Located in Lakeside at Trappe, just minutes from Easton and Cambridge, this amenity-rich community offers a pool, fitness room, and dog park.

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

Located on a quiet street with walking distance to a Boat yard at end of cul-de sac This home built from the remains of the Oxford Military acadamy and recently updated in 2015 with all new kitchen equipment. This is an estate sale so all items in house, garage and gazebo will convey. Open floor plan and master bedroom with private porch and exterior stairway. Few properties in Oxford have privacy, pool and good depth at the dock with open floor plan. Garage holds additional frige and pool furniture.

Royal Oak - escape to your own Eastern Shore estate. Anderby Hall is part of an original 1680 land grant. This 12 +/- acre parcel features 3,260' +/- of shoreline (mostly rip rapped) including a tidal pond and island (accessed by bridge)to a private peninsula and private cove. The gated driveway leads to the main house- a 3000 +/- sq.ft. Colonial featuring a great room with fireplace, charming old pine floors and hand hewn ceiling beams. Granite kitchen with island. Primary suite with his/her closets and second floor office/den area. Almost every room offers a gorgeous view of Irish Creek. Brick walkways ways lead to the water side pool. The dock has 5'MLW and you are minutes to the Choptank RIver. Additional 2600 sq. foot guest house. Tennis courts (could be picklebal!l) with gazebo. 30x50 detached 3 car garage, and an additional 1 car garage with workshop and a service shed. Licensed shoreline. Geese, ducks, deer, turkey. Convenient to Easton and St. Michaels Enjoy a lifestyle of luxury, privacy, and natural beauty. Embrace the exclusive charm of waterfront living today!