Tucked into the highly desirable East Jackson neighborhood, this truly one-of-a-kind property offers a rare blend of versatility, charm, and income potential all within steps of May Park, hiking trails and the amenities of downtown. Set on a single parcel with duplex zoning, the property offers incredible flexibility with two fully independent homes plus a studio apartment--perfect for multi-generational living, rental income, or hosting guests with comfort and privacy. The first residence is a charming chalet-style home featuring approximately 1,500 square feet, with 3 bedrooms and 2 bathrooms. The home showcases thoughtful craftsmanship, vaulted ceilings, Carrera marble countertops, and gas range and fireplaces, creating a warm and inviting atmosphere... A fenced front yard provides the perfect space for relaxing, entertaining, or enjoying Snow King views. The second home, built in 2015, brings a modern touch with 2 bedrooms and 2 bathrooms across a spacious 1,600 square feet, perched above a heated, oversized two-car garage. This thoughtfully designed residence captures peekaboo views of the Tetons, adding a special sense of place to everyday living. Additionally, the property features a studio apartment, providing even more flexibility--whether utilized as a guest suite, rental, office, or creative space. Located just steps from May Park, residents enjoy year-round amenities including summer food trucks, open green space, and groomed cross-country ski trails in the winter. With its unbeatable location, unique layout, and multiple living options, this property is a rare opportunity in one of Jackson's most sought-after neighborhoods.