Classic Colonial charm meets strong income potential in the heart of the sought-after East Rock neighborhood. Built in 1904, this well-maintained four-unit property includes three apartments in the main house plus a separate single-family carriage house, offering flexible rental income or owner-occupant options. The main home features beautiful hardwood floors, ornate architectural details, crown molding, and classic fireplace mantles. Large windows bring in abundant natural light, while the spacious living areas create an open and inviting feel. Updated kitchens offer modern cabinets, countertops, and appliances. Residents enjoy second and third floor balconies, on-site laundry, basement storage, and separate utilities. Recent updates include kitchens, electrical panels, hot water heaters, roof, and exterior paint. The property offers five off-street parking spaces and sits on a 0.17-acre lot. Ideally located near East Rock Park, local markets, restaurants, and neighborhood shops, with easy access to public transit and the Yale shuttle. Just minutes to downtown New Haven, parks, and recreation. A rare opportunity in a prime location.