204 S. Water Street, Chestertown, Maryland

About 204 S. Water Street

Life at 204 S. Water Street unfolds at the pace of the river. Begin the morning with boats leaving the marina across the street, wander through Wilmer Park along the Chester River, or walk one block to Chestertown’s shops, galleries, and restaurants. Behind its graceful 19th-century façade, the home reveals the enduring quality of historic craftsmanship, thoughtfully preserved and complemented by a carefully considered 2013 renovation. The interior feels warm, balanced, and remarkably livable, with each space flowing naturally into the next and ultimately to the screened porch. Upstairs, two bedrooms share a full bath, while a charming staircase rises to a private third-floor retreat with views of the Chester River. Outside, oyster-shell paths wind through lush gardens to a secluded dining area, creating a backyard sanctuary that feels worlds away from the heart of town. Rich in character yet easy to maintain, this is a home for those who value craftsmanship, walkability, and a life connected to the water.