Tucked away on Shelter Island's coveted southern peninsula, five 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 two thousand three hundred fifty-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 two hundred acres here in the late nineteenth 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 one thousand seven hundred fifty-square-foot main house features three bedrooms and two-and-a-half bathrooms, 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 one thousand three hundred ninety square feet of additional space. Designed for flexibility and privacy, the cottage offers one bedroom, two full bathrooms, 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 point seventy-eight 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 five Osprey Lane offers the rare chance to further customize and complete a truly exceptional Shelter Island retreat.Listing ID: 931125