Oxford MD Real Estate & Homes for Sale

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.

Fantastic summer getaway or full-time residence just minutes from all of Oxford's amenities which include famous restaurants, marinas, tennis/pickle ball courts, the Oxford Museum, the active Community Center and wonderful nature trails. Located only one block from a public access sitting area overlooking Town Creek. The standout features include all new flooring throughout, the fabulous screened porch, the open floor plan, many windows offering lots of natural light, plenty of off street parking, the primary bedroom with en-suite bathroom and two additional bedrooms share a second full bathroom, making it a great option for hosting guests. Tour this renovated and updated home before it's too late.

Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

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

New to the market, this well-maintained 4-bedroom, 2.5-bath Cape Cod offers the perfect blend of comfort and Eastern Shore charm in the heart of Oxford. Tucked away on a quiet cul-de-sac, this inviting home features welcoming indoor and outdoor living spaces - ideal for year-round living or a relaxing weekend escape. Step into the foyer and discover spacious living and dining areas highlighted by beautiful Brazilian hardwood floors, vaulted ceilings, and abundant natural light. The comfortable living room flows seamlessly into a large kitchen with an adjacent dining area and a bright breakfast room perfect for casual mornings or gathering with family and friends. Off the kitchen you will find a large family room with access to the spacious back yard. Upstairs, the primary suite offers a peaceful retreat with a large walk-in closet and ensuite bathroom featuring double sinks, jacuzzi tub and a walk-in shower. Two additional bedrooms share a generous full hall bath with double sinks and a tub/shower combination. Finishing off the second floor is a loft, ideal for a home office or home gym. Outdoor living is just as appealing. Unwind on the front deck or entertain in the fully fenced backyard complete with a deck, patio, and fire pit - perfect for relaxing evenings or weekend gatherings. One of the largest backyards in the neighborhood and plenty of room for a pool! Located just a short stroll from downtown Oxford, you'll enjoy easy access to local shops, restaurants, the waterfront park, Oxford Market, and the beloved Scottish Highland Creamery. 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 in August 2025, all stainless steel appliances are less than two years old

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

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.

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!

Considerable price reduction! Located just outside of Oxford and situated on almost 7 mostly wooded acres. This 3 bedroom, 2 bath ranch has been updated with a new metal roof, gutters, flooring, appliances, countertops, water heater, well pump, interior doors and has been freshly painted. Enjoy a quiet evening sitting by the fire, dining on the screened porch or lounging around the Gunite pool. Only a short drive to Oxford dining and marinas.

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.