St Michaels Homes for Sale

St Michaels Homes for Sale

Welcome to St. Michaels, Maryland – a picturesque gem nestled on the Eastern Shore! This charming town, located in Talbot County, is renowned for its rich maritime history, stunning waterfront views, and vibrant community spirit. With roots dating back to the early 17th century, St. Michaels offers a delightful blend of historic charm and modern amenities, making it a perfect place to call home.

St. Michaels boasts a thriving arts scene, with galleries, boutiques, and delightful eateries lining its quaint streets. Whether you’re strolling along the waterfront or exploring the charming shops, you’ll find a warm, welcoming atmosphere that embodies the essence of small-town living. Outdoor enthusiasts will love the abundance of recreational activities, from boating and fishing to biking along scenic trails.

For those looking to make St. Michaels their home, the real estate market offers a diverse array of homes for sale. From historic waterfront properties with breathtaking views to cozy cottages tucked away in serene neighborhoods, there’s something for everyone. Whether you’re a first-time buyer, looking for a vacation retreat, or seeking a permanent residence, St. Michaels has a variety of options to suit your lifestyle and budget.

Experience the best of Eastern Shore living in St. Michaels, where community, culture, and natural beauty come together. Explore the homes for sale and discover your dream home in this enchanting town – your new adventure awaits!

Newest St Michaels Homes for Sale

4 Beds ⋅ 4 Baths

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants, grocery stores, museums, and downtown shops. A wonderful place to settle in and enjoy the lifestyle that makes St. Michaels so special.

407 Seymour Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

3 Beds ⋅ 1 Baths

INVESTOR SPECIAL – PRIME IN-TOWN ST. MICHAELS OPPORTUNITY! Bring your contractor, vision, and renovation plans to 105 W Marengo St. This circa-1890 home offers approximately 1,656 square feet and presents an excellent value-add opportunity for an investor, renovator, or buyer looking for a substantial project in highly desirable St. Michaels. The property is ready for renovation, providing an opportunity to restore its character while updating the home for today's buyer. Whether your strategy is renovate and resell, hold as an investment, or create a distinctive personal residence, the location makes this one worth a serious look. Enjoy an in-town St. Michaels location convenient to downtown shops, restaurants, attractions, and the waterfront. Properties with renovation potential in established Eastern Shore destinations can be difficult to duplicate—here's an opportunity to improve the property from the ground up and make it your own. SOLD AS-IS. Seller will make no repairs. Cash, renovation financing, or other appropriate financing may be best suited for the property. Buyer to independently verify property condition, square footage, permits, zoning, and intended use.

105 Marengo St, St Michaels

Listing courtesy of Witz Realty, LLC. Contact:

4 Beds ⋅ 4 Baths

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

114 W Chestnut St, St Michaels

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

3 Beds ⋅ 2 Baths

NEW PRICE!! 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 chef’s kitchen, three well-proportioned bedrooms, and two elegantly finished full baths—all 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, creating a tranquil setting for outdoor dining, entertaining, or quiet relaxation. Ideally located in the heart of St. Michaels, the home is just moments from the town’s renowned boutiques, acclaimed restaurants, waterfront parks along the Miles River, the community pool, and the YMCA. Offering the rare combination of like-new construction and one of Maryland’s most desirable small-town settings, 803 New Lane presents an exceptional opportunity to enjoy Eastern Shore living at its finest.

803 New Ln, St Michaels

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

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