St. Michaels, Maryland, blends historic waterfront charm with an active Eastern Shore community. Homes throughout the town and surrounding area range from historic cottages and traditional single-family residences to newer coastal homes, condominiums, townhomes, and expansive waterfront estates. Talbot Street offers independent shops and restaurants, while boating, kayaking, waterfront parks, and the Chesapeake Bay Maritime Museum provide plenty to explore. Local schools, a seasonal farmers market, and community events round out everyday life in this distinctive Chesapeake Bay town.