This classic Queen Anne-style two-family home offers historic charm and modern flexibility all within walking distance of Wesleyan University and just minutes from Middletown's vibrant Main Street dining scene. Conveniently located near major highways, it's a commuter's dream. The first-floor unit features 2 spacious bedrooms, a large kitchen with a center island and stainless steel appliances, and beautiful hardwood floors throughout. The second-floor unit offers 2 bedrooms plus an office space, with two additional finished rooms in the attic perfect for extra bedrooms, a rec room, or flexible living space. Enjoy original hardwood flooring throughout both units, and take advantage of the rare bonus of two separate garages, each accommodating two cars. The backyard provides the perfect setting for entertaining or relaxing outdoors. Whether you're looking for owner-occupancy with rental income, a pure investment property, or multi-generational living, this property delivers space, location, and opportunity.