This remarkable 4BR/3.5BA waterfront home boasts historic elegance and beautiful water views! The best of both worlds, this property is located on the Chester River, offering the relaxing water-oriented lifestyle while also being walkable to all the great restaurants and shops that downtown Chestertown has to offer! This historic gem, built in 1900, sits on a .22-acre lot, offering you space and privacy in the heart of Chestertown. Step inside and be awestruck by the expansive foyer leading to the great room with its soaring ceilings, creating an open and inviting atmosphere. Stained glass doors and windows, 2 fireplaces with Quimper and Delft tiled surrounds, and original hardwood flooring are some of notable details throughout this special home. With over 5,400 square feet of living space, there's room for everyone to enjoy and endless potential! An unexpected treat, the home has an indoor pool for year-round relaxation and entertainment. Additionally there is an attached 2-car garage, a very rare find in downtown. The large covered brick patio is ideal for outdoor entertaining overlooking the lawn and Chester River.