Oxford MD Homes For Sale

Discover the epitome of elegance and tranquility at Old Wintersell, a private retreat on Island Creek just minutes from Oxford and Easton. This 6-bedroom colonial is nestled amidst 14 acres, creating a sanctuary for abundant wildlife and unparalleled privacy. The property boasts a waterside pool, dock, pond, workshop, pump house, and extensive landscaping. Nearby amenities include fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport. The property is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia.

4895 Judiths Garden Rd, Oxford

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

$450,000

3 Beds ⋅ 2 Baths

Oxford Rancher. One story living. 3-4 bedrooms, 2 baths, wood flooring, kitchen/dining with center island and corner seating. Corian countertops and stainless appliances, mud room. Large shed, fenced backyard, brick patio with cover, paved driveway. Heat pump replaced last year. New kitchen sink and inside and outside painting just completed. Room for a garage. Recently painted throughout. Close to town, parks, marinas, churches, restaurants and public landing. Ready for immediate occupancy.

200 Bonfield Ave, Oxford

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

$1,195,000

5 Beds ⋅ 5 Baths

Welcome to the "Valliant House" located in historic Oxford and just a minutes walk to the Tred Avon River, park, shopping, and restaurants. This 5BR/5BA renovated home is sited on .27 acres and offers a large fenced-in yard with mature and attractive landscaping, a gorgeous wrap-around porch, and off-street parking. Built c. 1870, the historic charm is evident with high ceilings, large windows, beautiful hardwood floors, and comfortably scaled rooms. A wonderful chef's kitchen is at the heart of the home with it's large island , stainless appliances, and ample cooking spaces. The living room and library (which could be a first floor bedroom with en-suite bath) both have gas fireplaces, and a separate dining room is adjacent to the kitchen and is wonderful for entertaining. Also on the first floor is an additional full bath and laundry. On the second level, there is the primary suite plus two additional bedrooms and a play room which would make a great office . Both bathrooms have been renovated as well. The third floor is currently used as the 5th bedroom( could also be a large bonus room) and has its own bath and walk-in closet. This property truly is must see! List of improvements available upon request.

302 N Morris St N, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

$4,250,000

Talbot County Farm For Sale – Over 200 acres located between Easton and Oxford at the headwaters of Trippe Creek. ‘Piney Point’s Advantage’ provides 214 acres with agricultural fields, mature woodland, extensive habitat for waterfowl, and upland game along with a recorded four-lot subdivision and eight remaining development rights. Habitat and wetlands restoration began in 2011 with a Soil Conservation and Water Quality Plan. The CRP contracts were renewed in 2020 to help with the sustainable use and sound management of soil, water, and habitat resources. Of the 214 acres of the farm, 58 acres are enrolled in the CRP program, 93 acres are under cultivation and the remainder is woodland, field edges, and waterfront. The farm provides an opportunity for residential use with a recorded four-lot division and eight remaining development rights. Development activity is subject to a re-evaluation by the County Health Department for the four existing perc sites. There is an existing private road built to county standards and governing documents in place satisfying county requirements when development activity begins. Located between Easton and Oxford, Piney Point’s Advantage is impeccably well-kept and maintained to maximize wildlife habitat. This farm provides a rare opportunity for a family compound in a natural setting with substantial infrastructure. Waterfowl impoundments, a private road, and approvals that generate value through a myriad of uses are in place and represent value for the buyer with a vision in mind. Set among large estates, Piney Point’s Advantage is sure to please the discerning buyer, nature lover, and outdoors enthusiast. Farm current farming lease and CRP contracts. Documents are available upon request. Assumption of CRP Contracts by Buyer at Settlement.

Almshouse Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$799,000

Local landmark restaurant in Oxford, Maryland is available For Sale for investors. New 5-year lease. Situated at the entrance to the idyllic town of Oxford, Latitude 38 has served locals and tourists alike for over 33 years. Within walking distance to most marinas and boatyards, the restaurant has become a staple amongst the town's residents, weekenders, and visitors. The restaurant interior was renovated in the spring of 2022 offering 128 seats and a gorgeous 20 chair bar. Many upgrades throughout the facility, including new kitchen equipment, HVAC, and other remodeled elements. Home to coastal living and lifestyle enthusiasts, the Town of Oxford is the "Gold Coast" of the Chesapeake Bay region.

26342 Oxford Rd, Oxford

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440

$3,995,000

3 Beds ⋅ 5 Baths

One of the most unique properties on Maryland’s Eastern Shore, ‘Swan Pointe’ offers the most commanding broad view of Oxford’s vibrant harbor on Town Creek. The property includes the main house and three garage bays in two accessory buildings, all situated on approximately one acre with beautiful landscaping, broad lawns, patios and porches, and mature shade trees, all on city water and sewer. A total of six full and two half baths among the three buildings. Ample off street parking and plenty of room for expansion make this property as unique as the town of Oxford where it is located.

101 East St, Oxford

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

$990,000

Extremely rare waterfront building lot in historic Oxford Maryland. Blocks away from everything Oxford, including shopping, dining, ice cream and parks. Approximately 10,000 +/- square foot lot with lovely views of Town Creek, deep water with pier (shared pier easement is currently in place) in a protected cove. Bulkheaded shoreline, high elevation, and located outside of Federal flood plain (Zone X). Town water and sewer. The lot line depicted in the photo is approximate, consult the plat and survey for exact lot lines.

215B South St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$12,150,000

5 Beds ⋅ 6 Baths

Hidden near the Tred Avon River, along shaded Trippe Creek shores, discover this Oxford jewel where refined luxury blends effortlessly with laid-back coastal charm. Accessible from beyond twenty high-elevation acres and a stately gas-lamp flanked gate, be transported as covered walkways, cobblestone paths, ornamental trees, scenic gardens, and panoramic point of land views enchant. Here, Widgeon Point's original 1938 construction has been beautifully reimagined by skilled artisans and a talented architects designing a warmly-hued residence echoing a River House of timeless elegance. In the home’s heart, sun-filled ceilings highlight intricate millwork, artfully laid hardwoods, heated Tennessee stone floors, built-in cabinetry, and fireplaces of fine craftsmanship where you’ll work, unwind, and dine. In the provincial kitchen, professional-grade appliances, farmhouse sink, and granite-topped counters assist with best-loved meals, while adjacent firelight warms cheerful late night moments with friends. While the dining room’s wet bar serves holiday celebrations, the bar-hosted enclosed gazebo and endless outdoor patios allow for large parties and simple summer pleasures overlooking yachts and memorable sunsets. Picnic or take morning strolls to either of your private ponds, float the summer away in the saltwater pool, tend to chores from within the solar paneled barn, or launch cruises from the deep water lift-fitted dock. After a day of cruising or antiquing in town, retreat to four bedrooms; each guest-perfect with access to the grounds, privacy, and bathrooms of hand selected stone. While the primary refuge boasts one of many serene custom closets, your guests will appreciate the two bedroom guest house, and fully independent over-garage apartment. While on tour, visit the pool house’s kitchen plus bath, caretaker cottage, boathouse, three car garage, and two barns with varying fittings including geothermal HVAC and insulation. Minutes away, historic townships - including Oxford and Easton - offer friendly eateries, romantic restaurants, golf clubs, artful shops, and annual festivals, while coves, rivers, and sanctuaries inspire your inner fisherman, sportsman, or athlete with endless watershed adventure.

5808 Widgeon Point Ln, Oxford

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

$2,795,000

6 Beds ⋅ 5 Baths

This remarkable waterfront property with a large waterside concrete pool within 25' of the Tred Avon River and looks west over the river and across the Chesapeake Bay. Pier with lift, rip-rapped shoreline and southwest breezes and sunsets year round. Located in the heart of Oxford's Historic District. Tree-lined streets on two sides, private, fenced and landscaped. Seller will consider holding a first mortgage to a qualified buyer.

106 Tred Avon Ave, Oxford

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

$1,200,000

Great opportunity to own 32.9480 acres just 2 miles from Oxford where you can build your dream home. The property is currently being farmed. Ideal location for horses, and also hunting geese, deer, and turkeys. Perc approved 4 bedrooms, tax records show 33.5804 acres and the most recent survey shows 32.9480 acres.

Evergreen Rd, Oxford

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

$750,000

Turn-key and established waterfront restaurant featuring transient slips and ample parking located in historic Oxford, MD. Enjoy an established clientele and well run business on day one.

Tilghman St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665