Classic East Rock two-family offering timeless character, flexible living space, and a deep private backyard in one of New Haven's most sought-after neighborhoods. This well-built residence features approximately 1,660 square feet with 4 bedrooms, 2 full bathrooms, and 8 total rooms across two thoughtfully laid out units. Traditional architectural details, hardwood flooring, and oversized windows fill the home with warmth and natural light, while well-maintained systems provide modern comfort and convenience. The second-floor owners unit features an eat-in kitchen, large primary bedroom, second bedroom or den, living room, and a large wooden deck overlooking a surprisingly peaceful backyard with mature landscaping tucked into one of New Haven's most vibrant residential neighborhoods. Additional features include low-maintenance vinyl siding, central air, forced hot air heat, energy-efficient blown-in insulation, in-unit laundry's, and unfinished attic and basement space ideal for storage or workshop use. Perfectly situated moments from Yale, Science Hill, East Rock Park, East Rock Brewery, neighborhood cafes, restaurants, coffee shops, and downtown New Haven amenities. A rare opportunity to own a versatile multi-family property blending classic East Rock charm with modern updates and exceptional location. *Eligible for the Yale Home Purchase Program.