St. Michaels, MD homes for sale & real estate

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

St. Michaels, MD Homes for Sale

Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace

St. Michaels, MD Homes for Sale

St. Michaels Charmer! Welcome Home to this Cozy Cottage perfectly situated in the desirable, walkable Historic Town of St. Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. Spacious . 25 acre lot with mature trees and flower gardens. Step inside to find a welcoming living room with real hardwood floors and a wood-burning brick fireplace, ideal for relaxing evenings. A light filled Sunroom provides the perfect spot for a home office, reading nook, or studio. The updated bathroom features new ceramic tiled floors, a new toilet and sink and a beautifully tiled shower. Peace of mind comes with having all new Anderson Windows

St. Michaels, MD Homes for Sale

Welcome to * * Back Creek Landing * * — one of Saint Michaels’ most desirable neighborhoods, known for its peaceful setting, friendly community, and easy access to town. Just a few minutes by bike or golf cart from downtown, this neighborhood offers the best of both worlds: close to everything, yet surrounded by nature. This beautifully maintained home invites you in with a wide front porch — perfect for a swing, morning coffee, or simply watching the world go by. Step inside to find a cozy living room with pocket doors to the left, ideal for a den or home office. To the right, a versatile dining room (currently used as a sitting room) connects directly to the kitchen,