Saint Michaels Real Estate

Saint Michaels Real Estate

Welcome to Saint Michaels, Maryland—a charming waterfront town nestled in the heart of Talbot County on the picturesque Eastern Shore. Known for its rich maritime heritage and stunning natural beauty, Saint Michaels offers a delightful blend of history, culture, and outdoor adventure.

As you stroll through the quaint streets lined with historic homes and boutiques, you’ll discover a vibrant community that celebrates its roots. Originally a shipbuilding hub, the town is now a haven for art enthusiasts and food lovers alike, boasting a variety of galleries, shops, and restaurants that highlight the region's freshest seafood and local produce.

One of the highlights of Saint Michaels is its stunning waterfront, where the Miles River meets the Chesapeake Bay. Whether you’re enjoying a leisurely boat ride, fishing off the docks, or simply soaking in the breathtaking views, the water is a central part of life here. Outdoor enthusiasts will appreciate the abundance of recreational activities available, including kayaking, paddleboarding, and biking along scenic trails.

Saint Michaels is also home to several annual events and festivals that bring the community together, such as the renowned Saint Michaels Wine Festival and the charming Christmas in Saint Michaels celebration. With its small-town charm and welcoming atmosphere, Saint Michaels is not just a destination; it’s a place to call home.

Explore the unique real estate opportunities in this idyllic town, where you can find everything from historic homes to modern waterfront properties, and experience the enchanting lifestyle that Saint Michaels has to offer. Your dream home awaits!

Newest Listings in Saint Michaels

Lot 16A Meadow, Saint Michaels
$799,000
4 Beds ⋅ 3 Baths
Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe. Time to make your personal selections. Make this home your personal statement. Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more. Make this your dream home.

Lot 16A Meadow, Saint Michaels

Listing courtesy of Keller Williams Flagship. Contact:

24580 Deepwater Point Dr Unit 3, Saint Michaels
$375,000
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:

7963 Pond Haven Ct, Saint Michaels
$630,000
3 Beds ⋅ 3 Baths
BIG REDUCTION -GREAT VALUE DO NOT MISS OUT ! 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:

23820 Mount Pleasant Lndg, Saint Michaels
$2,800,000
4 Beds ⋅ 3 Baths
FALL IN LOVE WITH LIFE IN ST. MICHAELS! The Eastern Shore becomes even more captivating as the seasons change. Just one mile from vibrant downtown St. Michaels with on-going seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities. The meticulously renovated home provides comfortable & effortless one-level living, Thoughtful design in boutique resort-like setting. The westerly orientation provides expansive water views and truly spectacular sunsets. Offered completely turnkey EVERYTHING SHOWN INCLUDED THE OFFERING: all furnishings, linens, a fully equipped kitchen ... even the firewood! Notable features include a newly renovated saltwater pool with pool house, a three-car garage and a separate, fenced “tiny house” for the dogs! Enjoy the changing seasons, exceptional waterfront comfort & design, excellent dining & charming boutiques and year-round activities of Maryland's Eastern Shore. Whether for a weekend, an extended stay, or year-round enjoyment, everything is ready for your arrival.

23820 Mount Pleasant Lndg, Saint Michaels

Listing courtesy of Engel & Volkers Annapolis. Contact:

202 E Chestnut St, Saint Michaels
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

202 E Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

111 Chesapeake Ave, Saint Michaels
$949,000
4 Beds ⋅ 3 Baths
Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a first‑floor primary suite with an ensuite spa bath, custom shower, and generous walk‑in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1‑car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you’ll enjoy easy access to charming shops, restaurants, waterfront activities, and year‑round festivals.

111 Chesapeake Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

214 Madison Ave, Saint Michaels
$375,000
4 Beds ⋅ 2 Baths
Discover the potential of this 4-bedroom, 2-full-bath home in the desirable Rio Vista community of St. Michaels! Offering a spacious two-level layout, this property presents a fantastic opportunity for buyers looking to make a home their own or investors searching for their next project. Inside, you'll find hardwood floors, a separate dining room, a galley kitchen, and comfortable living spaces with plenty of possibilities. The flexible floor plan provides room to reimagine, update, and create a space that fits your needs. Step outside to enjoy a generously sized yard with plenty of space for entertaining, gardening, or simply relaxing outdoors. A storage shed adds convenience and additional storage. Located in the established Rio Vista community, residents enjoy access to wonderful neighborhood amenities, including a community boat ramp, kayak launch, and marina, making it easy to embrace the Eastern Shore lifestyle. Enjoy all the charm, shopping, and dining of historic St. Michaels while benefiting from a location outside the town limits. This home is ready for some TLC, but the opportunity is undeniable! Whether you're an investor, renovator, or buyer with a vision, this property offers the chance to create something special in a sought-after waterfront community. Bring your ideas and discover the possibilities!

214 Madison Ave, Saint Michaels

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

104 Mulberry St, Saint Michaels
$1,399,000
3 Beds ⋅ 3 Baths
This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! Come by boat or by car. Buy in time to enjoy Saint Michaels wonderful holiday festivities. ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact:

9020 Bozman Neavitt Rd, Saint Michaels
$1,995,000
4 Beds ⋅ 3 Baths
Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

9020 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

204 E Marengo St, Saint Michaels
$525,000
2 Beds ⋅ 1 Baths
Just reduced to $525,000—affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investments—a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows—mean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact:

109 W Marengo St, Saint Michaels
$995,000
4 Beds ⋅ 3 Baths
This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family room—perfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street—a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.

109 W Marengo St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

24700 Deep Water 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 Deep Water Pt Unit 20, Saint Michaels

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

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