Discover this rare multi-family gem in a highly desirable Winchester neighborhood, offering endless possibilities for savvy investors, owner-occupants, or multi-generational living. Situated on a large, flat, private lot with a detached two-car garage and ample off-street parking, this home perfectly balances charm, function, and convenience. The first-floor unit includes two bedrooms, a bright kitchen, living room, and full bath, while the second unit spans two levels, showcasing three bedrooms, two full baths, an open kitchen with pantry, an office, and a spacious living room. Both units feature high ceilings, hardwood floors and separate utilities. Recent improvements include: fresh interior paint, a new heating system and beautifully landscaped grounds complete with a new back fence and plantings. With easy access to downtown Winchester, top-rated schools, the commuter rail, and major highways, this is an opportunity you don’t want to miss!