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

3 Beds ⋅ 2 Baths

Coming soon in St. Michaels! 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: 4432741900

4 Beds ⋅ 4 Baths

7964 Pond Haven Court, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

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 Court, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

4 Beds ⋅ 3 Baths

Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its westerly orientation delivers spectacular sunsets every evening, complemented by expansive water views and abundant wildlife. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs convey. Additional features include a saltwater pool, pool house, three-car garage and even a separate, fenced “tiny house” for the dogs! The property fronts Broad Creek, a tidal tributary of the Choptank River and Chesapeake Bay, and is not located within a FEMA-designated flood zone

23820 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

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: (410) 745-0415

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: 4108226272

4 Beds ⋅ 2 Baths

Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future improvements. This home is in need of some TLC and is priced accordingly, making it an excellent opportunity for investors, renovators, or buyers looking to add their own personal touches and build equity. With great bones and endless possibilities, this property is ready to be transformed into something special.

214 Madison Ave, Saint Michaels

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

2 Beds ⋅ 2 Baths

All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered by peaceful woods,an ideal setting for relaxing or entertaining. Upstairs, two spacious ensuite bedrooms are thoughtfully positioned at opposite ends of the home, providing added privacy for owners and guests alike. Newly installed flooring adds warmth and a fresh, stylish appeal throughout the home. Beautifully cared for and move-in ready, this charming Widgeon Place townhome is a wonderful opportunity to enjoy low-maintenance living in a serene setting.

24362 Widgeon Pl Unit #5, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

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! ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact: 4102244400

3 Beds ⋅ 3 Baths

Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive landscaping with full irrigation and so much more!

101 Seymour, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

Commercial Opportunity– Positioned along S. Talbot Street (Route 33) at the entrance to St. Michaels, this General Commercial (GC) property offers exceptional visibility, convenient access, ample parking, and a flexible three-unit configuration suitable for a variety of commercial uses. The property provides a strong location for an owner-user or investment opportunity with easy access to St. Michaels, Easton, and surrounding Talbot County communities. Three Condominium Units A-C. Unit A– 248' of Road frontage / Showroom Approximately 4,044± SF One-story block construction with storage attic Large display windows Showroom space Office and planning areas Shop and storage areas Central air conditioning 2-zones 10'x8' door Unit B– Warehouse / Flex Space (Heated) Approximately 4,148± SF Metal building Warehouse/light industrial configuration Two 12' × 12' drive-in doors Flexible warehouse and storage space 2nd Floor storage space added Loading and service access Unit C– Workshop / Storage Additional detached commercial unit offering workshop and storage flexibility. Potential Uses– The property's General Commercial zoning and flexible layout make it well suited for a variety of commercial applications, including: Retail Professional office Showroom Automotive/service business Warehouse Marine Businesses Distribution Flex commercial Contractor headquarters Storage Light industrial Investment opportunity Owner-user occupancy

1007 S Talbot St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

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: (410) 745-0415

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