Rare opportunity to own two side-by-side residences on a beautifully landscaped 0.45-acre property in the highly sought-after Chappaqua School District. 52 Orchard Ridge features a renovated 3-bedroom, 1.5-bath home with hardwood floors, stainless steel appliances, updated cabinetry and countertops, and in-unit laundry. This residence will be delivered vacant at closing, offering immediate occupancy for an owner-user. 54 Orchard Ridge offers 4 bedrooms, 1 bath, in-unit laundry, ample basement storage, and is currently leased, providing immediate rental income. The property also features attractive landscaping, a large driveway, generous outdoor space, and an approximately 800-square-foot accessory cottage attached to the main residence, offering flexibility for a home office, studio, recreation space, or other permitted uses. Ideally located within walking distance to downtown Chappaqua, shops, restaurants, parks, and everyday amenities, this property combines convenience, charm, and exceptional lifestyle appeal. Whether you're seeking a multigenerational living arrangement, an investment opportunity, or the ability to live in one residence while generating rental income from the other, this unique property offers versatility, strong income potential, and long-term value in one of Westchester County's most desirable communities and top-rated school districts.