Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood floors, thoughtful built-ins, and charming fireplaces. Upstairs, three generously sized bedrooms await, including the primary bedroom with an en-suite bath. A second full bath is also located on the upper level between the other two bedrooms for ultimate convenience. On the main level, you'll find laundry and a powder room, as well as a bonus room that would make a great breakfast nook, office, or mud room. The family room and dining area are gorgeous and spacious, but if you need even more space, look no further! The cottage behind the home has its own address and offers nearly 350 more finished square feet (and was even used as an Airbnb in the past)! This adorable former summer kitchen offers endless possibilities - especially with the RB1 zoning (see attached documents). Behind the cottage, you will find a three-bay garage (a former blacksmith shop) and a shed. Brand-new garage were just installed on the garage on 2/3/2026! An off-street parking space is also available beside the shed, and if you want more green space, permission to remove the garage was previously granted to the current owners (please contact the Board of Architectural Review for more information). The most recent updates to the property include: siding repair in 2025 on the main house; new plumbing, flooring, and vanity in the cottage bathroom in 2023; and new toilets upstairs in the main house in 2024. A HOME WARRANTY ALSO CONVEYS with this property. The policy expires 4/24/2028 (see documents). This fabulous home awaits your imagination! Schedule your showing today!!