$2,950 - 4 Bed, 2 Bath Historic Home in Heart of Chestertown

This charming 1916 home in Chestertowns historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes a kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, you’ll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom, spacious closet, and bonus room, perfect for a playroom, office, or workout room. The beautiful mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an additional fenced garden area. The driveway has off-street parking for two vehicles. Additional home updates include a tankless hot water heater, high-efficiency 3-zone boiler, whole-house surge protector, upgraded panel, and Kenmore gas range. In summer 2025, the current owners invested in over $60,000 in major renovations hoping to stay for many years. They replaced the roof, updated the electrical wiring, and painted the interior. All upgrades were intended to be enjoyed by current homeowners. Unfortunately, they found that they had to move out of state to be closer to a new job. All utilities and lawn care assumed by tenant. Pet friendly on case-by-case basis. Available July 1, 2026. $2,950 per month, plus $2,950 security deposit required. Please submit the form on this page or contact Erin at [Use CALL button] to learn more. This property is managed by a responsible landlord using Avail landlord software.