Oxford MD Real Estate & Homes for Sale

This charming Victorian house is located in the Historic District of Oxford and has resided with the current owner for several decades. A front porch overlooks a beautifully landscaped garden and lawn while the rear lawn is surrounded by gardens for beauty and privacy. A stunning water fountain with trickling water works perfectly for a quiet time on the sun porch or the second floor deck with sliding shades for the late afternoon sun. A garden shed/shop and a single car garage with a studio/apartment on the second floor round out this beautifully decorated home. A full size modern kitchen with top of the line appliances, dining room, and formal living room are on the first floor. Three bedrooms and two modern baths are located on the second floor. The house enjoys the benefits of a geothermal well system, 9' ceilings and two fireplaces. The garage and garden shed are accessed by an alley which also allows for additional off street parking, a rarity in the Historic District. All of this sits on high ground in the X flood zone. Enjoy easy access to local shops, restaurants, the waterfront park, Oxford Market, and the beloved Scottish Highland Creamery.

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.

Set in the highly sought-after Patrick's Plains community, 28211 Brick Row Drive is an exceptionally maintained and thoughtfully appointed waterfront residence overlooking the serene waters of Island Creek. Bathed in natural light, the home welcomes you with a stunning foyer and living room featuring floor-to-ceiling windows, skylights, and a gas fireplace, seamlessly connecting to the expansive deck. Designed for both everyday living and elegant entertaining, the home offers a formal dining area and beautiful hardwood flooring throughout. The gourmet kitchen is a true centerpiece, boasting a massive island, Viking gas range, Sub-Zero refrigerator, stainless steel appliances, and abundant pantry storage. Just off the kitchen, the family room impresses with cathedral ceilings, a gas fireplace, sweeping water views, and direct access to a screened-in porch. The main-level primary suite is a private retreat, complete with a spacious walk-in closet and direct access to the back deck, where you can enjoy tranquil poolside and waterfront views. The luxurious primary bath features a cathedral ceiling, a standalone soaking tub, and a glass-enclosed shower. The lower level offers incredible flexibility as a poolside retreat or in-law suite, with its own living room, recreation space, bedroom, full bath, and kitchenette. Completing the home is a rare three-car garage, adding both convenience and functionality. The owner has completed many upgrades, including a new pool, pier improvements, three new HVAC systems, a new driveway, and a water treatment system, along with many other enhancements (full list available). With its prime waterfront setting, abundant natural light, and exceptional living spaces, this home offers a truly elevated lifestyle in one of the area's most desirable communities.

Welcome to 705 S Morris St in the heart of charming Oxford, Maryland - one of the Eastern Shore's most desirable waterfront towns, known for its maritime heritage, relaxed pace, and timeless coastal appeal. This classic 2-bedroom, 2-bath Captain's House offers approximately 1,200 square feet of thoughtfully designed living space on a rare and spacious 0.4-acre lot. A hallmark of Oxford's nautical history, the Captain's House style is prized for its efficient layout, coastal character, and enduring charm - making it especially appealing to both homeowners and visitors alike. Inside, the home features a bright, welcoming interior with comfortable living spaces and well-appointed bedrooms, ideal for everyday living or weekend escapes. The expansive lot provides ample room for outdoor entertaining, gardening, or future expansion - an uncommon feature within town limits. Location is where this property truly shines. Enjoy exceptional walkability to Oxford's beloved waterfront restaurants, marinas, and local attractions. Even better, a town beach is just a one-minute walk directly across the street - offering effortless access to the water and some of the best sunset views on the Eastern Shore. Previously operated as a successful Airbnb, this home has received consistently positive guest feedback for its peaceful setting, unbeatable location, and comfortable accommodations. Short-term rentals are permitted, offering an excellent opportunity for buyers seeking supplemental income or a flexible-use property. Adding to its turnkey appeal, most furnishings are included, allowing the next owner to seamlessly continue short-term rental operations or immediately begin enjoying the home as a fully furnished coastal retreat. Whether you're searching for a primary residence, weekend getaway, or investment property with proven rental potential, 705 S Morris St delivers a rare opportunity to own a piece of Oxford's historic waterfront lifestyle.

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.

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.

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.