Welcome to this meticulously maintained legal four-family property located in the heart of New Haven's highly desirable East Rock neighborhood and within the sought-after Worthington Hooker School district. Combining strong investment potential with upscale owner-occupant living, 525 Whitney Avenue is a standout opportunity in one of the city's most prestigious areas. The spacious first-floor unit features 3 bedrooms and 2 bathrooms, soaring ceilings, newly refinished hardwood floors, and a cozy fireplace. One bedroom and bath include a private entrance, creating flexibility for a primary suite, in-law setup, or home office. The upper levels include two 1-bedroom apartments and a large 2-bedroom unit, all occupied by long-term tenants. Recent improvements include new flat roofs and renovated exterior stairs, making this a true turnkey property. Additional highlights include a 2-car garage, four off-street parking spaces, and direct access to the Yale Shuttle and bus lines. Conveniently located near Yale University, Downtown New Haven, parks, restaurants, and local amenities. Schedule your private showing today!