Welcome to a rare and meticulously maintained legal four-family residence in the heart of New Haven's most prestigious neighborhood. Situated within the highly coveted Worthington Hooker School district, 525 Whitney Avenue offers a lifestyle of sophisticated urban living combined with exceptional financial upside. Whether you are a savvy investor or an owner-occupant looking to live in luxury while your tenants help offset the mortgage, this East Rock gem is a standout opportunity. The crown jewel is the expansive first-floor owner's unit, featuring soaring ceilings, newly refinished hardwood floors, and a warm, inviting fireplace. This 3-bedroom, 2-bath suite is designed for flexibility; one bedroom and bath feature a private entrance, making it the perfect setup for a primary suite, an in-law unit, or a professional home office. The upper levels house two charming 1-bedroom apartments and a spacious 2-bedroom unit on the third floor, all occupied by stable, long-term tenants. With recent capital improvements including new flat roofs and renovated exterior stairs, this property is truly turn-key. Logistics are effortless with a 2-car garage and four additional off-street parking spots. Located directly on the Yale Shuttle and bus lines, you are just a short stroll from Yale University, Downtown New Haven, and local parks. Experience the best of East Rock living-schedule your private tour of this landmark property today!