Known locally as the "Simonds House," this 1803 brick Federal offers a rare blend of historic charm, modern upgrades, and incredible versatility. The property sits back from Main Street, giving a wonderful sense of privacy while keeping everything Charlestown has to offer a short distance from the front door. Inside, a welcoming foyer with a sweeping staircase introduces a spacious, flexible layout. The main level features a comfortable living room with a fireplace insert and custom built-in bookcases, a large dining room with a sunny bay alcove, a convenient first-floor bedroom with full bath, large warm and inviting kitchen with exposed beams and brick, and a dedicated laundry room. Upstairs, find the primary suite with double closets and its own fireplace, two additional bedrooms, and a second full bath with double sink vanity. All the heavy lifting has been done here including Rinnai on-demand hot water, a newer roof, vinyl replacement windows, a Thermo Pride furnace, 200-Amp service, and public water/sewer. Beyond the main home exists massive value-add potential. A private 1-bedroom accessory apartment, equipped with its own Rinnai heater, washer/dryer, and screened in porch serves as a major financial asset - perfect for steady rental income, an in-law suite, short-term rental, or guest privacy. Additionally, a ground-level bonus space with its own exterior entrance may be used for a home business, an entertaining hub, or a second efficiency unit. Set on a level lot just under an acre, the grounds feature a private, fenced backyard oasis with a patio and pergola, plus a classic detached barn with upgraded electric, ideal for a workshop, hobbies and extra storage. Don't miss this rare opportunity to own a true piece of history with modern infrastructure and unmatched flexibility.