Refine Search
Map
Sort by
24580 Deepwater Point Dr Unit 3, Saint Michaels
$398,000
2 Beds ⋅ 2 Baths
Nestled in the serene enclave of Gull Wing Villas, this exquisite bungalow-style townhouse offers a harmonious blend of comfort and relaxation. Step inside to discover an inviting open floor plan that seamlessly combines the dining and living areas, perfect for both relaxation and entertaining. The warmth of wood floors and the charm of a brick gas fireplace create an ambiance that feels like home. This residence features two spacious bedrooms, including a primary suite with a luxurious walk-in shower and ample closet space. Recessed lighting and ceiling fans enhance the inviting atmosphere, while the eat-in kitchen beckons culinary creativity. An attic provides additional storage, ensuring that every inch of this home is utilized efficiently. Outside, indulge in the exclusive lifestyle that comes with private for residents only access to the Miles River. Enjoy leisurely afternoons at the waterfront park or embark on adventures with your canoe or kayak, enjoy the picnic area to end the day, foster a sense of connection with neighbors while maintaining your privacy. With two dedicated parking spaces and a well-maintained environment, this property is not just a home; it's a lifestyle choice. Experience the tranquility of this golf community living while enjoying the conveniences of one story living amenities. Embrace the opportunity to make this comfortable retreat your own.

24580 Deepwater Point Dr Unit 3, Saint Michaels

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

301 Lincoln Ave, Saint Michaels
$474,900
3 Beds ⋅ 2 Baths
Worth the wait!! Coming soon in St. Michaels. **OPEN HOUSE Saturday October 17th 11AM-1PM** This charming cottage-styled home is beautifully maintained and truly pristine inside and out. Hardwood floors, a cozy wood-burning fireplace, spacious bedrooms, updated bathrooms and a bright and airy sunroom create a home that feels warm and inviting from the moment you step inside. Outside, enjoy a large private backyard setting with plenty of space to relax and entertain, plus a huge attached garage offering exceptional parking and storage. All just minutes from everything that makes St. Michaels such a special place to call home.

301 Lincoln Ave, Saint Michaels

Listing courtesy of RE/MAX Executive. Contact:

7963 Pond Haven Ct, Saint Michaels
$655,000
3 Beds ⋅ 3 Baths
Charming Coastal Retreat with Endless Potential in Backcreek LandingWelcome to this beautiful two-story home in the highly sought-after Backcreek Landing neighborhood, just minutes from historic St. Michaels. Blending coastal elegance with incredible value, this property features a brand-new roof with lifetime shingles and is attractively priced, leaving you budget flexibility to update the bathrooms to your taste. From the front porch, you can enjoy serene views of the pond right across the street and step directly onto the neighborhood walking trail.The main level offers a private front office, a formal dining room, and a grand living room with dramatic cathedral ceilings and French doors leading to a spacious deck. The casual dining area opens through separate French doors to a wonderful screened porch, creating a seamless flow for indoor-outdoor living. Your main-floor primary suite serves as a private sanctuary, complete with tray ceilings, a walk-in closet, and serene views of a backyard framed by mature crepe myrtles. Upstairs, you will find a massive bonus room equipped with a water hookup, two bright guest bedrooms, a shared full bath, and a large walk-in attic. Complete with a two-car garage, this home is the perfect Maryland Eastern Shore getaway.

7963 Pond Haven Ct, Saint Michaels

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

204 E Marengo St, Saint Michaels
$525,000
2 Beds ⋅ 1 Baths
**OPEN HOUSE, Saturday, 10/10, 10:00am - Noon** Priced to Sell - Huge Price Improvement! Your St. Michaels weekend escape may be more attainable than you think. Trade the traffic and weekly routine for weekends in one of the Eastern Shore’s most beloved waterfront towns. 204 E Marengo Street offers the perfect combination of location, low-maintenance living, and your own private backyard oasis—ideal as a weekend retreat or primary home. Located just outside the Historic District and approximately 1.5 blocks from water access, including a marina and public boat ramp, this move-in-ready cottage puts restaurants, coffee shops, boutiques, waterfront parks, marinas, and all the charm of St. Michaels within easy reach. Inside, enjoy bright, inviting spaces, convenient main-level living, an updated bathroom, and numerous improvements. Major updates include a new roof (2024), upgraded crawl space with French drain, insulation, and vapor barrier (2025), updated plumbing (2025), Thompson Creek windows, HVAC and water heater (2018), plus updated appliances and plantation shutters —meaning less time on projects and more time enjoying the Shore. Outside is where weekends really begin. Spend summer afternoons by the in-ground pool, entertain friends at the beach-inspired outdoor bar with cable TV, or simply unwind after a day on the water. The detached garage with electric offers additional space for bikes, kayaks, water toys, and weekend gear. And because the property is outside the Historic District, you'll have greater flexibility for future improvements without Historic District oversight. Come for the weekends and stay for the lifestyle. Whether you're looking for a primary home, weekend getaway, or your own place to escape and recharge, 204 E Marengo Street is ready to enjoy from day one.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact:

24700 Deepwater Pt Unit 20, Saint Michaels
$385,000
2 Beds ⋅ 3 Baths
Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated cabinetry, granite countertops, and stainless steel appliances in the kitchen. All three bathrooms have been refreshed with new vanities, fixtures, and finishes, offering a clean and modern feel throughout the home. Beyond the cosmetic updates, extensive infrastructure improvements provide peace of mind, including a newer HVAC, upgraded electrical panel, full outlet and switch replacement and enhanced attic efficiency with resealing and R49 insulation installation. Interior finishes have been completely reimagined and updated throughout, including new luxury vinyl plank flooring on the upper level and premium Mohawk carpeting with upgraded padding in the lower bedrooms and on the stairwell (2024). Fresh interior paint throughout the home, along with meticulous restoration of original doors - stripped, primed, and repainted with all new hardware installed in 2024 - add to the home's character and detail. Additionally, the deck was also recently primed and painted. Additional improvements include a new washer and dryer (2024), new sliding glass doors in the bedrooms, and a 60-inch Hunter ceiling fan in the great room. A stand out feature of this unit is the expanded floor plan, offering a more open, functional, and spacious living area not commonly found in similar units. The HOA recently completed significant improvements, including a new roof, decking replacements, and new gutters in 2025. Completely turnkey and thoughtfully upgraded make this property ideal as a full-time residence, weekend retreat or investment property. Come and enjoy the St. Michaels lifestyle today.

24700 Deepwater Pt Unit 20, Saint Michaels

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

204 Lincoln, Saint Michaels
$598,000
3 Beds ⋅ 2 Baths
Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

204 Lincoln, Saint Michaels

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

1215 Washington, Saint Michaels
$499,000
4 Beds ⋅ 4 Baths
RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012942).EDUCED - REDUCED - DO NOT WAIT TO SEE THIS DESIREABLE RIO VISTA LIVING -MOVE IN ONE

1215 Washington, Saint Michaels

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

1211 Washington, Saint Michaels
$499,000
4 Beds ⋅ 4 Baths
Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application and payment of applicable fees. The property features two mirror-image units, each offering: Kitchen with a cozy breakfast area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath This duplex presents an excellent investment opportunity with a strong rental history. Both units are currently tenant-occupied and rent well. Additional opportunity: The neighboring duplex at 1215 is also available for purchase (MLS #MDTA2012950).UST REDUCED - DONT WAIT TO LOOK AT THIS DESIREABLE RIO VISTA LIVING -MOVE

1211 Washington, Saint Michaels

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

9518 Quail Holw Unit 702, Saint Michaels
$455,000
3 Beds ⋅ 3 Baths
Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with fireplace, custom built-ins and seamless access to a private rear patio overlooking peaceful common space. The kitchen has been completely transformed with quartz countertops, soft-close cabinetry, and newer stainless steel appliances. A main-level bedroom with its own ensuite bath provides flexible living options. Upstairs, the spacious owner’s suite features a private balcony, a spa-like bath, and generous closet space, plus a second guest suite and stacked washer and dryer. Additional improvements include fresh interior and exterior paint, a newer HVAC system (within the last five years), updated carpeting, refinished hardwood floors, and recently installed 6” gutters. The property includes a one-car garage with attic storage. Backing to open common area for added privacy and tranquility, and located near The Links at Perry Cabin with no town taxes, this home delivers comfort, convenience, and exceptional value. A gas line is in place for the fireplace, but the fireplace is not currently used. Currently listed for Sale and Rent.

9518 Quail Holw Unit 702, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

no property photo
$368,500
2 Beds ⋅ 2 Baths
Charming one-story Cottage located in Martingham at Gull Wing Villas. Pull up to your own slice of heaven, adorned with a white picket fence, enter into the custom painted Benjamin Moore Blueberry front door, slat foyer and large family room with large sliders overlooking the links at Perry Cabin. Beautiful landscaping with large flowering Cherry Blossom tree just outside your family room slider. Enjoy entertaining on your large patio with views of the golf course and rolling landscape. Each bedroom has an en-suite bath, with walk in closets. Annual HOA fee for Martingham is $225.00. Spend afternoons sitting on the bench/gazebo gazing at the Miles River at the waterfront park for residents only, very close by. This stunning cottage won't last schedule your showing today!

24560 Deepwater Point Dr Unit 4, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: