A rare opportunity in New Canaan! This impeccably maintained two-family home features a unique back-to-back configuration, giving each residence exceptional privacy, its own outdoor space, garage, central air, separate parking and utilities. The property also benefits from a New roof and ideal location close to the train, shops, restaurants and highly regarded schools. Unit A offers the space and feel of a single-family home. Updated kitchen with granite counters, stainless appliances and sliders to a private deck. Stunning living room with hardwood floors, Palladian windows, soaring ceilings, skylights and exposed brick. A separate dining room with fireplace and terrace enhance the layout. Primary bedroom features a newly renovated en-suite bath, plus 2 additional spacious bedrooms and 3 full baths total. The finished walk-out lower level includes a family room, bonus space ideal for an office or guest area, full bath and a private entrance. Unit B features a kitchen updated with stainless appliances, open-concept dining and oversized living room, newer hardwood floors, 2 spacious bedrooms, 1.5 updated baths and in-unit laundry. Private patio and large backyard add to it's appeal. Ideal for investors looking to capitalize on the income potential or an owner-occupant seeking the benefit of rental income. Live in one and generate income from the other!