31 Manhanset Rd, Shelter Island, NY 11964

Tucked within the storybook charm of Dering Harbor—New York's smallest and arguably most exclusive village—lies a majestic 8.2-acre estate parcel waiting to be reimagined. With only 35 homes dotting this picturesque 200-acre seaside haven, the opportunity to claim such a vast and pristine canvas is nothing short of extraordinary. Once part of the legendary “Oriole Farm,†the private arboretum and cultivated gardens of famed horticulturist Alice Fisk, this land is steeped in heritage and beauty. Now, for the first time in generations, this treasured property emerges from its quiet slumber to invite a visionary buyer to shape their own legacy in an unmatched setting. Surrounded by whispers of nature and the tranquility of the sea, the gently cleared land offers a rare combination of serenity and scale—with ample room to design a grand manor, shimmering pool, elegant pool house, tennis court, and even a bespoke carriage house with legal living quarters above. A discreet service entrance on the west side adds both convenience and privacy, and shortens your stroll to the village center. Unlike other areas on Shelter Island, Dering Harbor benefits from its own municipal water supply—ensuring both crystal-clear drinking water and a thriving landscape nourished year-round. Directly across from the verdant fairways of Gardiner's Bay Country Club, with views of the iconic 4th hole, the estate is perfectly positioned for those who appreciate refined leisure. Within a leisurely walk, you'll discover sandy beaches, charming shops, and fine dining tucked along the waterfront—each moment here infused with the idyllic pace of island life. With easy access to both the North and South Forks and the freedom to shape your vision while finalizing architectural plans, this singular offering invites you to craft something timeless—a sanctuary where nature, history, and elegance converge. Come walk the land, breathe in the salt air, and imagine the extraordinary life that awaits.