Tucked away on Shelter Island's coveted southern peninsula, 5 Osprey Lane presents a rare opportunity to own a private Hamptons compound featuring two distinct residences, beautifully landscaped grounds, and room to add a pool. Located within the sought-after Shorewood Farm enclave, this exceptional property blends historic character, modern comfort, and an unmatched connection to the surrounding natural landscape. Set along a narrow stretch of land surrounded by Peconic Bay, Shorewood Farm offers a lifestyle centered around waterfront living and outdoor recreation. Residents enjoy access to a private association beach, community tennis courts, nearby boat ramps at Wade's Beach, and close proximity to the South Ferry. Just moments away, the protected 2,350-acre Mashomack Preserve provides miles of unspoiled tidal creeks, trails, and old-growth forest, ensuring privacy and tranquility for generations to come. Rich in Shelter Island history, the property traces its origins to the famed Shorewood estate of advertising pioneer Artemas Ward, who assembled over 200 acres here in the late 19th century. The main residence a Shepherd's Cottage, remains one of the original homes from the estate and has been thoughtfully renovated to preserve its historic charm while introducing modern functionality. The approximately 1,750-square-foot main house features three bedrooms and two-and-a-half baths, highlighted by a renovated kitchen, updated primary suite, and warm architectural details that reflect the home's timeless character. The downstairs flex room can easily be used as an additional guest room. Complementing the main residence is a separately built guest cottage, offering approximately 1,390 square feet of additional space. Designed for flexibility and privacy, the cottage offers one bedroom, two full baths, and a light-filled third-floor mezzanine with seasonal views toward the ferry crossing-ideal for a home office, or creative studio space. Situated on approximately .78 acres, the property is surrounded by mature landscaping and curated outdoor living areas, including a wraparound bluestone patio that seamlessly connects the homes to the natural setting. With ample room to add a pool, 5 Osprey Lane offers the rare chance to further customize and complete a truly exceptional Shelter Island retreat.Listing ID: 931125