604 properties for sale in Oxford town, District 3 Trappe Talbot County Maryland

Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of Choptank. Every inch of this home has been thoughtfully updated from top to bottom, blending modern finishes with classic Eastern Shore charm. Pella windows. Heat pump. Updated Septic. Previously used as a rental home, this home offers investment potential or the perfect retreat. Walking distance to Choptank Marina. Enjoy local crabbing, fishing, and boating nearby. Peaceful, small-town setting on Maryland’s scenic Eastern Shore. Whether you’re looking for a primary residence, weekend getaway, or income-producing property, this move-in-ready home

Located in the desirable Algonquin neighborhood, this 4 bedroom, 2 bath home offers a quiet, private setting with community water access. Features include a 1-car detached garage, 12x16 shed and new central HVAC (2026). Enjoy access to the community waterfront area for only $60/year, including use of the pier, small beach area, and potential boat slip availability. Possible off-season boat trailer storage. Interior photos coming soon!

Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles Rivera treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electr

A storybook waterfront home with privacy, and timeless old-world charm. This Tilghman Island waterfront property carries a gracious, welcoming spirit: peaceful, and full of character. Large rooms, tall presence, mature trees, and a beautiful wraparound porch give the home a timeless, almost cinematic quality. Set down a long private driveway on Broad Cove, which connects to Harris Creek, this secluded 4-bedroom, 2.5-bath home offers 3,037 square feet of generous living space, 438+ feet of shoreline and a swimming pool. Inside, the home offers expansive gathering spaces, including a large living room with a grand wood-burning fireplace, a spacious family room, a kitchen with a wood stove, and a generous primary bedroom with its own wood-burning fireplace. There is warmth and scale throughout. Old charm, big rooms, and the kind of relaxed elegance that is hard to recreate. A dock is in place and in need of repair, offering the next owner the opportunity to restore and customize the water

Tilghman island. Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite countertops, stylish modern appliances, a large center island, and an oversized walk-in pantryperfect for both everyday cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, where a stunning gas fireplace creates a warm and inviting atmosphere for daily living and special gatherings. Upstairs, you will find a thoughtfully designed layout offering comfort and privacy. The expansive primary suite is a true retreat, complete with two separate walk-in closets and a luxurious en-suite bath. An additional generously sized ensuite bedroom provides excellent flexibility for

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a b

Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners completed a full renovation in 2023. Designer finishes throughout. Attention to detail, light placement and thoughtful preservation of its original style. The screened front porch welcomes you in with it's beautiful woodwork and sets the pace for this Chic, move-in ready Shore Home. Situated on a double lot with room for a pool. Fenced rear yard for room to run. One block to the Community pier on San Domingo Creek, kayak racks and walking path. Full details on the whole renovation are in the documents file. Note.Heated square footage is 1914 sq. Ft

New price! This home just got better—now offered at $499,900 with a brand-new heat pump installed on the first floor! Welcome to Algonquin, a stunning home featuring three spacious bedrooms and 2.5 baths. The primary bedroom offers a beautiful bath and plenty of closet space. Multi levels create a bright, open feel accented by beautiful woodwork, moldings, and wood flooring. Enjoy a gourmet kitchen with granite countertops and a central island, alongside a formal dining room, living room, den, and office. For the fireplace lover, this home features both a cozy gas fireplace and a classic wood-burning fireplace to enjoy! Additional features include a convenient main-floor laundry, an attached garage, and a shed for extra storage. Embrace a peaceful lifestyle and enjoy your morning coffee or al fresco dining on the deck (complete with a retractable awning) or the patio with beautiful brick walkways. The partially fenced backyard is a dream, carefully cultivated to offer something in bloo

Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shores most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat, featu

Online Bidding Open: High Visibility Corner Property on Busy Route 50. Perfect for Living & Business! Exceptional Opportunity in Cordova, MD! This stunning corner property boasts almost 1.5 acres of land on Route 50, offering high visibility and traffic flow. This renovated home is perfect for owner living and operating a good-sized low profile retail business, such as a real estate, insurance agency, law firm, veterinarian, doctor, travel agency, potential billboard signage, solar panels, agricultural products sales, backyard appliances & furniture, sheds, construction and show room co. Renovated from Top to Bottom 2021-2025. New Roof. New Windows. Modern Kitchens. Updated Bathrooms. New Electrical Fixtures. Top-of-the-Line Appliances. And much more! Land and Zoning: Plenty of room for parking and outdoor displays. Prime Location: Corner of Old Skipton Rd and Ocean Gateway. Across from Councell Farms, a well-known agricultural landmark. High traffic flow on Route 50 Don't Miss Out! Th

Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. More info and photos to follow

Are you looking for serenity? Tucked away at the end of a picturesque crepe myrtlelined drive is a breath of fresh air with its peacefully remote surroundings that many people are looking for. 12 miles to St. Michaels, close to Easton and Oxford, This exceptional waterview retreat offers a rare combination of privacy, scenic beauty, and convenience. The property is overlooking Black Walnut Creek, with glimpses of the Chesapeake Bay beyond, this property delivers a true sense of escape. Whether you are seeking a full-time residence, a weekend getaway, or an income-producing short-term rental, the setting and lifestyle here are simply unmatched. Even better, there is no HOA, allowing you the freedom to fully enjoy and personalize your property. Located in FEMA Flood Zone X, with no history of water intrusion, this home provides both peace of mind and long-term value in one of the Eastern Shores most desirable destinations. Inside, thoughtful design meets everyday comfort. The home welcom

This charming Tilghman Island cottage was originally built in 1953 and thoughtfully renovated in 2020, including updated plumbing and electric. The home features durable luxury vinyl plank flooring throughout and the roof was replaced with 45-year architectural shingles for added peace of mind. The kitchen offers stainless steel appliances, space for a dining table and flows seamlessly into the spacious living room, ideal for everyday living and entertaining. The flexible floor plan includes 23 bedrooms and a full bath with a shower. The attic presents an opportunity for expansion, perfect for creating a loft or additional bedroom. Outside, enjoy a partially fenced backyard complete with a large shed equipped with electric, ideal for storage, hobbies or a workshop. Situated on scenic Tilghman Island, this property is just moments from marinas and public boat landings, providing easy access to the Chesapeake Bay and surrounding waterways for boating, fishing, and waterfront dining

Widgeon Place is a charming townhome enclave within the desirable Martingham community, offering effortless comfort and nearly maintenance-free living. Just minutes from the historic waterfront town of St. Michaels, this home is ideally suited for year-round living, a relaxing weekend retreat, or a smart investment opportunity. Martingham overlooks the renowned Links at Perry Cabin Golf Courseoriginally designed by Pete Dye Sr. And thoughtfully reimagined by Pete Dye Jr. Providing a picturesque and prestigious setting and this location is one of the few buildings overlooking the golf course. Inside the residence features hardwood floors throughout the entry, living, dining, and sunroom areas and ceramic tile in the entry, half-bath and kitchen. The upper level offers two en-suite bedrooms, including a spacious primary suite with a private deck. A rear patio extends from the sunroom, creating additional outdoor living space, and a convenient half bath is located on the main level. Each

Select photos have been virtually staged to help visualize room layout and design possibilities. Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck. Ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool, enhancing the home's outdoor living potential. Comfortable, functional and perfectly suited for enjoying the Eastern Shore lifestyle

Cambridge. Located in the Algonquin community, this lovely brick rancher offers two living spaces and two fireplaces! Hardwood floors in most of the house give it a bright feel. Formal living room with fireplace. Kitchen with loads of cabinets and updated appliances. The dining area also has a fireplace. Large all season sun room looks over the back yard. There is something blooming all year long! The primary bedroom features two closets and a full bath. Large laundry room and attached garage. There is a custom built shed with electric for hobbies and storage. This home also offer a surprising amount of storage. Brand new roof and there are replacement windows. Community water rights are available

If no contract by April 24, 2026, Seller will be removing home from market. Looking for a home with a private setting, water views, a pool, and no HOA all within easy reach of the charm and activities of St. Michaels and Easton? Interested in a quiet home retreat or a short term rental? Look no further! Enjoy privacy, water views, and the freedom of no HOA at this tucked-away property located at the end of a Crepe Myrtlelined drive. Surrounded by mature trees and overlooking Black Walnut Creek with glimpses of the Chesapeake Bay, this home offers a peaceful setting that feels like a private retreat while still being close to the vibrant waterfront towns of St. Michaels and Easton, known for their dining, shopping, boating, and year-round events. Located in FEMA Flood Zone X (no flood insurance required and no history of water intrusion), the property also offers excellent potential as a weekend getaway, second home, or short-term rental in one of the Eastern Shores most desirable desti

Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved parking, mature landscaping, pool, 4+ mlw water depth and pier. A short 5 minute drive to downtown St. Michaels. Please see notes about the ALARM

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deckperfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awningan ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a

A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyer’s preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-appro

Price improvement*. Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marinaperfect for boating, entertaining, and leisure. Whether youre looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! New roof & fireplace 2024, new appliances 2019

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family me

Welcome to 9 Hatsawap Road, a beautifully appointed home where comfort, style, and location come together seamlessly. Nestled in a desirable setting, this residence offers the perfect blend of modern living and timeless charmideal for full-time living, a second home, or an investment opportunity. Step inside to discover a thoughtfully designed interior featuring spacious living areas filled with natural light, creating a warm and inviting atmosphere. The well-equipped kitchen serves as the heart of the home, complete with quality finishes, ample cabinetry, and an easy flow for both everyday living and entertaining. The home boasts three ample sized bedrooms and two well-appointed bathrooms, offering both comfort and privacy. Step outside to a thoughtfully designed outdoor living space that truly sets this property apart. A rear deck provides the perfect setting for morning coffee or elevated entertaining, while the adjoining patio with a fire pit invites relaxed evenings under the star

This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth of July fireworks and thirsty Thursday with your new neighbors. Less than 3 miles to downtown St. Michaels Fine Dining and Shopping. More photos to come

Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled interior featuring soaring vaulted ceilings and an open-concept floor plan designed for effortless everyday living and entertaining. Rich hardwood flooring flows throughout, complemented by a beautifully appointed chefs kitchen, three well-proportioned bedrooms, and two elegantly finished full bathsall conveniently situated on a single level. Virtually every component of the home has been renewed, allowing the next owner to enjoy a truly turnkey property with the peace of mind that comes with comprehensive renovation. Outside, professionally designed landscaping surrounds a private backyard, creat