Oxford Homes with Pool

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: 4106733344

$5,295,000

4 Beds ⋅ 7 Baths

First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

5381 Morgans Point Dr, Oxford

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

$569,000

5 Beds ⋅ 4 Baths

Nestled in the serene Meadowbrook subdivision, this wonderful Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. It offers easy access to route 272 whether you are headed south to MD and Delaware or north to Chester or Lancaster Counties. Spanning 1.3 acres, this property boasts a well maintained exterior with vinyl siding and beautifully landscaped grounds, creating an inviting first impression. The roofs on the house and both sheds were just replaced along with many other recent upgrades ensuring a turn key home with no worries. Step inside to discover a thoughtfully designed interior that exudes warmth and sophistication. The spacious layout features five generously sized bedrooms and three and a half bathrooms, ensuring ample space for relaxation and privacy. The 4 second floor bedrooms all have new LVP flooring and the stairs have new carpet. The heart of the home is the gourmet kitchen, complete with an eat-in area, an island for culinary creativity, and high-end appliances including a built-in microwave, self-cleaning oven, and a sleek dishwasher. The adjoining dining area is perfect for hosting intimate gatherings or festive celebrations. Natural light floods the living spaces through bay and bow windows, enhancing the inviting atmosphere. The main floor laundry adds convenience to daily living, while the fully finished daylight basement offers additional space for an in-law suite, grown kids or even a private office. Step outside to your private oasis, where an above-ground pool awaits, relax on a spacious deck ideal for summer barbecues or tranquil evenings under the stars. The expansive lot features a level yard with open spaces, perfect for outdoor activities or gardening enthusiasts. Two sheds provide ample storage for all your outdoor equipment and toys. Parking is a breeze with a side-entry attached garage and additional driveway space, ensuring that guests are always welcome. This home is not just a residence; it's a lifestyle choice, offering the perfect blend of luxury, comfort, and outdoor enjoyment. Experience the tranquility of Meadowbrook while enjoying the convenience of nearby amenities. This property is a true gem, ready to welcome you home.

21 Jason Dr, Oxford

Listing courtesy of Realty One Group Restore. Contact: 3024636548

$1,700,000

3 Beds ⋅ 3 Baths

Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for relaxing, entertaining and enjoying life on the water. Inside, a gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Property is offered as part of an estate and is being sold as is.

104 Myrtle St, Oxford

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

$4,495,000

5 Beds ⋅ 4 Baths

Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

4335 World Farm Rd, Oxford

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

$1,350,000

4 Beds ⋅ 2 Baths

Welcome to Brownstone Farm, a stunning equestrian training center and historic residence set on 12.7± beautifully maintained acres. Originally constructed circa 1772, this solid brick three-story farmhouse blends timeless architecture with modern updates and offers an exceptional opportunity for both gracious country living and professional equestrian pursuits. The main residence invites you in with a wide 10-foot front porch and a grand entry hall flanked by elegant parlors. The remodeled kitchen (2018) features custom cabinetry with a hand-painted finish, soapstone countertops, a farmhouse sink, subway tile backsplash, stainless steel appliances, and a butcher-block center island with prep sink. A cozy breakfast area with a wall of windows and exposed brick adds warmth and light. Adjacent, the formal dining room boasts built-in china cabinets and a charming corner wood-burning fireplace. Additional living spaces include a great room with arched openings, hardwood floors, and a fireplace plus a formal parlor ideal for entertaining with another fireplace. The first floor also offers a convenient laundry room with utility sink and a full bath featuring a soapstone vanity. Upstairs, the second floor hosts four generously sized bedrooms and a full bath with clawfoot tub. The third floor provides THREE additional bedrooms with adjoining sitting or sewing rooms / flexible spaces that can serve as offices, craft rooms, or extra storage. Step outside to your own private retreat. The L-shaped Anthony Sylvan in-ground pool (8’ deep) with adjoining hot tub is surrounded by a 25’ x 15’ patio, an island-themed pool house, fire pit area, and a sports court with basketball hoop. Raised flower beds and mature landscaping complete this peaceful setting. A two bedroom loft apartment with downstairs studio offers full amenities and is currently leased & perfect for generating supplemental income or accommodating guests. Equestrians will appreciate the exceptional facilities: Main Barn (built 2009): 35 stalls with windows, two tack rooms, three wash stalls (2 heated) with hot/cold water, three tack-up stalls, feed room, hay and straw storage, heated office, heated bathroom, and laundry. Second Barn: Seven additional stalls, wash stall with hot/cold water, tack and feed rooms, blanket storage & machine storage bays. Indoor Riding Arena (built 2010): 80’ x 200’, sand footing, LED lighting, heated viewing room, and spectator seating. Outdoor Ring (built 2020): 100’ x 240’, excellent base with sand footing, observation deck with electric and ceiling fan. Fenced paddocks and open pasture complete the setup for a working equestrian facility. Hacking path around the perimeter of the property. Brownstone Farm is as functional as it is picturesque, offering an established setting for lessons, training, and equestrian shows with proven cash flow potential. Whether you’re seeking a turnkey equestrian operation, a country retreat, or a blend of both—this remarkable property delivers history, character, and opportunity in equal measure.

845 Waterway Rd, Oxford

Listing courtesy of BHHS Fox & Roach-Kennett Sq. Contact: (610) 444-9090

$5,350,000

4 Beds ⋅ 6 Baths

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!

Morgans Point Dr, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$1,350,000

4 Beds ⋅ 2 Baths

Welcome to Brownstone Farm, a stunning equestrian training center and historic residence set on 12.7± beautifully maintained acres. Originally constructed circa 1772, this solid brick three-story farmhouse blends timeless architecture with modern updates and offers an exceptional opportunity for both gracious country living and professional equestrian pursuits. The main residence invites you in with a wide 10-foot front porch and a grand entry hall flanked by elegant parlors. The remodeled kitchen (2018) features custom cabinetry with a hand-painted finish, soapstone countertops, a farmhouse sink, subway tile backsplash, stainless steel appliances, and a butcher-block center island with prep sink. A cozy breakfast area with a wall of windows and exposed brick adds warmth and light. Adjacent, the formal dining room boasts built-in china cabinets and a charming corner wood-burning fireplace. Additional living spaces include a great room with arched openings, hardwood floors, and a fireplace plus a formal parlor ideal for entertaining with another fireplace. The first floor also offers a convenient laundry room with utility sink and a full bath featuring a soapstone vanity. Upstairs, the second floor hosts four generously sized bedrooms and a full bath with clawfoot tub. The third floor provides THREE additional bedrooms with adjoining sitting or sewing rooms / flexible spaces that can serve as offices, craft rooms, or extra storage. Step outside to your own private retreat. The L-shaped Anthony Sylvan in-ground pool (8’ deep) with adjoining hot tub is surrounded by a 25’ x 15’ patio, an island-themed pool house, fire pit area, and a sports court with basketball hoop. Raised flower beds and mature landscaping complete this peaceful setting. A two bedroom loft apartment with downstairs studio offers full amenities and is currently leased & perfect for generating supplemental income or accommodating guests. Equestrians will appreciate the exceptional facilities: Main Barn (built 2009): 35 stalls with windows, two tack rooms, three wash stalls (2 heated) with hot/cold water, three tack-up stalls, feed room, hay and straw storage, heated office, heated bathroom, and laundry. Second Barn: Seven additional stalls, wash stall with hot/cold water, tack and feed rooms, blanket storage & machine storage bays. Indoor Riding Arena (built 2010): 80’ x 200’, sand footing, LED lighting, heated viewing room, and spectator seating. Outdoor Ring (built 2020): 100’ x 240’, excellent base with sand footing, observation deck with electric and ceiling fan. Fenced paddocks and open pasture complete the setup for a working equestrian facility. Hacking path around the perimeter of the property. Brownstone Farm is as functional as it is picturesque, offering an established setting for lessons, training, and equestrian shows with proven cash flow potential. Whether you’re seeking a turnkey equestrian operation, a country retreat, or a blend of both—this remarkable property delivers history, character, and opportunity in equal measure.

845 Waterway Rd, Oxford

Listing courtesy of BHHS Fox & Roach-Kennett Sq. Contact: (610) 444-9090

Oxford Homes with Pool

Newest Oxford Homes with Pool