This historically designated home, situated on High Street with a refreshing gaze of the Chester River as you enter, receives many a pause by passers-by as they meander the brick sidewalks of downtown Chestertown. The 1790 residence was completely renovated and expanded in 2004 with an eye for both formal entertainment and comfortable living. The gracious foyer with front staircase and ample coat closet leads to a large parlor with original crown moldings and a fireplace. The generously sized dining room has an adjacent wet bar, powder room and storage closet. A rear staircase leads to the primary suite on the second floor. An open floorplan emerges beyond with large island kitchen, a second dining space and sun-soaked living room with built-in cabinets and bookshelves. A wall of paned windows and French doors overlook a beautiful garden with brick pathways and mature plantings. While this beautiful property is recorded as a four-bedroom house, it currently features the entire middle to rear second floor as a primary suite with office, graciously accessed by a back staircase. The south-facing bedroom, with large walk-in closet, has a pair of French-doors leading to a nicely sized roof with wood railings and copper-topped pilasters waiting for a deck and perhaps pergola. A marbled bath includes soaking tub, glass enclosed shower, pair of sinks and full-sized washer and dryer. The office (or 4th bedroom) completes the primary suite. The front staircase leads to a nicely proportioned bedroom with fireplace and ensuite bath. Finally, another paneled door sparks curiosity until it is opened and a solidly built staircase with landing is revealed. An enchanting bedroom with two built-in beds, gabled roof, walk-in closet and ensuite bath awaits. This floor makes a perfect hideaway. The basement is 2/3 concrete slab and 1/3 wood planked lighted crawl space offering plenty of storage. A hobby/workshop room has a laundry sink. All mechanicals are easily accessed and well labeled.