St. Michaels, MD homes for sale & real estate

St. Michaels, MD Homes for Sale

Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, seasonal farmer's market, museums and more. This home has received a fresh interior painting and is "move in ready" It is a 4 bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2 car attached garage. The main part of the home is both comfortable and casual while at

St. Michaels, MD Homes for Sale

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low mai

St. Michaels, MD Homes for Sale

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—pe

St. Michaels, MD Homes for Sale

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportun