Oxford MD Homes For Sale

Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

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

$1,849,000

4 Beds ⋅ 4 Baths

Simpley 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

$275,000

Location, location, location! It doesn't get much better than this. Nestled on a private, wooded 2.3-acre lot between Easton and Oxford, this property has everything you need to move forward with building your dream home. The sellers are even willing to include their house plans! This perc-approved lot is approved for a 4-bedroom home and is accessed from Almshouse Road via an existing right-of-way. The site has already been cleared and is ready for the permit application process. See documents for the site plan, architectural plans, conservation plan, and stormwater management plan. They aren't making any more land—don't miss this opportunity to secure a beautiful homesite in a sought-after location. Buy now and start building your dream home!

Almshouse ( Lot 2) Rd, Oxford

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$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

$875,000

3 Beds ⋅ 2 Baths

The Rose Cottage was first built in 1890 and owned by a waterman. With barely 1,200 square feet, the house served many generations of Oxford families. Fast forward for about 100 years, the house was raised and the foundation was modernized in the late 1990s. With plumbing and electrical upgrades, the house became a modern historical home. When the current owners bought the Cottage in 2004, they continued with upgrades and additions that continued that modernization, culminating with 2 major upgrades and an 800 square foot addition that made the house 2000 square feet and quite comfortable by today’s standards. The first major addition and upgrade was to the living room. Owners added a new fireplace and chimney, 2 new Marvin windows and oak flooring in 2006. The front porch received a new decking with Trex decking in 2005. In 2011 the most significant upgrade came to date, taking a full year to complete. Starting with an architectural review and plan, the owners worked closely with Oxford’s Historical Board and added 800 square feet to the total footprint and much modernization. Here are some of the highlights: GMB Foundation Review New Foundation for “Bump out” addition Extensive teardown of interior walls, exterior siding, back kitchen, suspect framing and much more. New build of the “Bump out” section with 2 levels Rotation of the stairs to the second story with complete rebuild Upgraded kitchen with new appliances, granite countertops and more Widening the living room to dining room entry New wood floors throughout both stories New on-demand water heater Security system and surround sound system Floors in attic for better storage use and foam insulation with an “insulating the shell” approach to the entire house Cementitious product planking on the exterior for superior protection and durability looks like wood planks but won’t need painting for 30 years. Crawl space mitigation with 10mil plastic, closed foam insulation, sump pump and dehumidifier. Continual service and monitoring with termite and pest control. Virtually every square inch of the Rose Cottage has been upgraded and modernized except for the historic front bedroom. Detached shed with upright freezer with workbench and storage The Rose Cottage is now a comfortable, fully modernized home that is practically maintenance free. With off-street parking for two cars and ideally located next to the restored Wesleyan Church, the cottage is ideally located in Oxford’s historic district.

228 South St, Oxford

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

$169,000

Oxford Lot in the heart of town in the Historic District. Lot size .20 acre +/-. Build your ideal home. A few blocks to Town Creek and Tree Avon River, restaurants, ferry dock, park, town market and more. Buyers to perform own feasibility study and due diligence for intended use. You may contact the town of Oxford Planning and Zoning.

105 Tilghman St, Oxford

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

$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

$749,900

3 Beds ⋅ 2 Baths

Beautifully crafted “Oxford Cottage,” just a few blocks from waterfront park access, downtown Oxford, the Oxford Bellevue Ferry, and the Strand beach. Built in 2023, this builder’s personal home is being offered for the first time. Upstairs features two spacious bedrooms, a full bath, and a convenient laundry area. The main level offers flexible living space with the option for an additional bedroom, home office, or expanded living area, along with a full bath. Enjoy the inviting eat-in kitchen that opens to a large screened porch—perfect for relaxing or entertaining. The property also includes a detached garage with plenty of room for both your vehicle and recreational gear. Outside, cedar-raised flower beds beautifully frame the home, while the welcoming front porch is ideal for unwinding and enjoying the peaceful surroundings.

101 Tilghman St, Oxford

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

$1,195,000

5 Beds ⋅ 6 Baths

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

110 N Morris St, Oxford

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

$1,195,000

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 weekend showings. If weekday is only possibility, please allow 24 hours. Thank you

110 N Morris St, Oxford

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

$1,250,000

3 Beds ⋅ 4 Baths

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.

115 W Pier St, Oxford

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

$655,000

4 Beds ⋅ 3 Baths

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.

209 Third St, Oxford

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

$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

$2,250,000

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 Dr, Oxford

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

$1,945,000

Your Custom Dream Waterfront Home Awaits! This rare, build-ready lot offers a blank canvas for you to craft your perfect Eastern Shore estate with spectacular, panoramic views! The 2.9 acre waterfront lot in the Bachelor Pt section of Oxford offers 180 degree panoramic views stretching across the majestic Choptank River. Enjoy the peace of mind of a recently installed rip-rap shoreline over an estimated 569 feet of protected waterfront, providing long-term erosion protection and maintaining your valuable waterfront. The property also includes a new dock setup, featuring a heavy-duty 16,000 lb boat lift and two additional lifts perfect for jet skis. The lot is located within Oxford town limits, offering the advantage of access to public water and sewer hook-ups. Final approval has been given from the Oxford Planning Board for the building plans the current owner proposed providing a massive head start on your construction timeline. Those plans can be included in the sale of the lot and while you may modify them to suit your taste, having approved plans means the property is truly "build-ready." Simply choose your builder and start constructing your dream!

4480 Bachelors Point Rd, Oxford

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

$262,000

Exceptional 2.18 acre residential lot. Ready to go with approved 4 Bedroom perc. Locate in the very desirable Sailors Retreat neighborhood with a beautiful setting and high-end homes. This parcel offers a high elevation (Zone X). Build your dream home on this last remaining parcel in this coveted neighborhood. See conceptual house plans and site plan in the photos. House plans are available. Click on the movie camera icon for the Virtual Tour*

Sailors Retreat Rd, Oxford

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