Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern comfort, and an enviable waterfront location. Filled with character and warmth, the home features beautiful hardwood floors, soaring ceilings, tall windows, built-ins, and a wonderful period gas fireplace that creates a welcoming focal point in the spacious living room. Two generously sized bedrooms and two beautifully appointed tiled bathrooms provide comfort and style, while an in-unit washer and dryer add everyday convenience. Generous room sizes and abundant natural light enhance the home's inviting atmosphere throughout. The heart of the home is the expansive kitchen and great room at the rear of the residence, overlooking the river. Designed for gathering, entertaining, and everyday living, this impressive space features gorgeous cabinetry, stainless steel appliances, gas cooking, abundant counter space, a farmhouse sink, sunny windows, and plenty of room for dining as well as additional living space. Whether hosting friends, enjoying a quiet morning coffee, or unwinding at the end of the day, it's a room you'll find yourself gravitating toward again and again. Just off the great room, the private balcony overlooks the Chester River and offers sweeping water views in a peaceful waterfront setting. Direct water access and a dedicated boat slip make it easy to enjoy the area's iconic Chester River and everything that life on the water has to offer. Chestertown is steeped in maritime tradition and widely admired for its extraordinary collection of Federal, Georgian, and Victorian architecture. One of the Eastern Shore's most desirable destinations, residents enjoy boutique shopping, fine dining, waterfront attractions, cultural events, and a thriving arts scene. Perfectly positioned along the Chester River, this residence is a historic treasure, a waterfront retreat, and an opportunity to experience the very best of life in one of the Eastern Shore's most cherished communities.