Rare opportunity to own an in-town retreat just steps from the historic Guilford Green. This unique and well maintained two-family home offers a combination of flexibility, charm, and outdoor space that is nearly impossible to find this close to town. Whether youre seeking multi-generational living, rental income, or a lifestyle property with room to spread out, this home delivers exceptional versatility. The true standout is the expansive, level backyard-an exceptional oasis featuring a rock garden, two professionally installed putting greens, and a large workshop with electricity. Its a space that invites relaxation, recreation, and creativity all in one, offering a sense of privacy and retreat rarely found in an in-town setting. Inside, the home offers 6 bedrooms and 4 full baths across two units, with a layout that provides defined living spaces and flexibility for a variety of living arrangements. The main residence spans two levels and lives like a single-family home, offering 4-5 bedrooms and 3 full baths, along with dining spaces, a wood burning fireplace, eat-in kitchen, walk in pantry with wet bar. The upper level has a cozy, cottage-like feel with lower ceilings heights, creating inviting intimate spaces ideal for bedrooms, quiet retreats or work from home offices. A separate-entry, second unit provides additional flexibility, with 1-2 bedrooms, full bath, eat-in kitchen-ideal for rental income, guests, or multi-generational living. The property has a strong history of successful multi-generational occupancy, tenancy and adaptable use. Recent updates include a new HDZ roof, 2 remodeled modern kitchens, 3 remodeled modern full baths, refreshed interiors, new updated lighting, new appliances, 4 new programmable thermostats, and select rooms with refinished original flooring that add warmth and character. Mechanical systems are well maintained, with two boilers and two updated Roth double walled oil tanks. The entire house was rewired in 2007 and brought up to current code this year. The location offers the best of both worlds-close enough to enjoy shops, dining, and the Green, yet set far enough away to maintain a peaceful residential feel. Nearby amenities include Jacobs Town Beach, Guilford Yacht Club, Westwoods Hiking Trails, Yale Shoreline Medical, Shoreline East Rail with connections to MetroNorth & Amtrak, and convenient to I-95. 96 miles to NYC or 150 miles to Boston, by car. Offered at 945,000 with a 10,000 credit at closing, this is an opportunity to personalize a property in one of Guilfords most desirable walk-to-town locations. For those who value location, outdoor living, and flexibility over cookie cutter design, this home presents something truly special.