Located in heart of beloved Historic Wooster Square; where timeless charm, vibrant city living, and smart investment potential beautifully align. This tastefully renovated two-family offers both lifestyle and opportunity. Set on a picturesque tree lined street just around the corner from WSQ Park, world-famous Wooster Street pizza, eateries & Farmer's Market, and just minutes to Yale University, Downtown New Haven and more. Thoughtfully updated with modern finishes while preserving its classic character, this special home features new kitchens, beautiful hardwood floors, and bright, inviting living spaces designed for both comfort and style. The first-floor unit offers a warm open layout perfect for owner occupancy or rental income with 2 spacious bedrooms, a dedicated office (or dressing room!), 1 full tile bath with tub, and private laundry. The second-floor unit creates excellent flexibility for investors or multi-generational living with 3 bedrooms, 2 full baths, living room and a sunny eat in tile kitchen. This special home also features a rare find, a spacious & private backyard with a fetching brick wall, plenty of parking parking, and Lenzi Park right out your front door! Whether you're seeking a soulful place to come home, an income-producing investment, or the perfect blend of both, this Wooster Square gem offers more than real estate, it offers possibility, connection, and to be part of one of New Haven's most iconic neighborhoods.