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, separate utilities, and updated heating systems. Recent improvements include new replacement windows, fresh interior paint, 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!