Offered for the first time in over 50 years, this rare side-by-side duplex presents an exceptional opportunity to own one of Rye Brook's most unique multifamily properties. Set on an expansive half-acre lot, the property offers the privacy and feel of two attached townhomes rather than a traditional up-and-down multifamily. An extensive driveway accommodates 8+ vehicles and leads to a detached two-car garage—an uncommon feature providing exceptional parking, storage, and versatility. Each residence enjoys its own private entrance, separate utilities, individual unfinished basement, and dedicated outdoor living space. Both units feature spacious living rooms, formal dining rooms, hardwood floors throughout, and kitchens with sliding glass doors leading to covered rear patios overlooking the beautifully landscaped, fully fenced backyard filled with mature plantings and established gardens. Unit 29 offers a spacious 2-bedroom, 1-bath layout with a walk-up attic providing abundant storage and future potential. Unit 31 features a desirable 2-bedroom, 2-bath layout with one full bathroom on each level, offering added convenience and flexibility. With separate gas service for cooking, individual 275-gallon oil tanks, and baseboard heating, the property is thoughtfully designed for practical ownership and efficient management. Whether you're an owner-occupant looking to offset your mortgage, seeking a multigenerational living arrangement, or an investor searching for a long-term addition to your portfolio, this meticulously maintained property offers exceptional versatility just minutes from shopping, dining, parks, Metro-North, and major highways.