Once operated as a bed and breakfast, this distinctive property sits on 11.31 private acres, including 9.31 acres of open space and 2-acres of buildable space in one of Southold's most prestigious enclaves. Offering exceptional versatility and income potential, the property features a serving kitchen, dining room, library, five fireplaces, tile flooring throughout, and a four-car garage with a basement featuring 10-foot ceilings. An irrigation system and two-stall barn add to the appeal. A rare combination of privacy, space, and opportunity, ideal for horses, gardens, a potential income-producing venture, or future development.