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 you're 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. It's 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.