31 Manhanset Road, Dering Harbor, New York 11964

Tucked within the storybook charm of Dering Harbor-New York’s smallest incorporated village and one of the most exclusive enclaves on the East End, 31 Manhanset Road presents an extraordinary opportunity to create a significant Shelter Island estate. Encompassing approximately 8.1 acres, this remarkable parcel offers a combination of scale, privacy, history and development potential rarely available within this coveted seaside village. Once part of the legendary Oriole Farm, the celebrated private arboretum and cultivated gardens of noted horticulturist Alice Fisk, the property carries with it a rich legacy of landscape and place. Today, its expansive grounds offer the next owner the opportunity to reimagine that heritage for a new generation. With approximately 2.17 acres as a designated development area, surrounded by nearly six acres of preserved open space-an unusual configuration that allows the residence and amenities to be concentrated within an elegant estate compound while the surrounding acreage provides a magnificent natural backdrop of lawns, specimen plantings, woodland and potential walking paths. The property allows for a principal residence of up to approximately 10,000 square feet of total interior space which incorporate approximately 7,000 square feet across the first and second floors with an additional 3,000-square-foot finished lower level, creating a substantial residence while maintaining a gracious, appropriately scaled above-grade presence. Beyond the main residence, the property’s size creates the potential for an exceptional array of amenities as a thoughtfully conceived estate could include a heated pool and spa, pool house, tennis court, expansive lawns and gardens, and a detached carriage house/garage incorporating up to approximately 1,000 SF guest or staff accommodations with 2 bedrooms and bathroom. Discreet secondary access further enhances the property’s privacy and functionality. The result could be something increasingly difficult to replicate in Dering Harbor, a complete country estate set within more than eight acres, yet with the majority of the property remaining open and beautifully landscaped. Imagine arriving through mature plantings to a sweeping motor court, with the residence opening toward terraces, pool and gardens, tennis beyond, and acres of meadow, specimen trees and woodland surrounding the entire compound. Dering Harbor itself makes the offering even more compelling. Unlike many areas of Shelter Island, the Village maintains its own municipal water system, an important advantage for both the residence and extensive landscaping. Directly across Manhanset Road are the verdant fairways of Gardiner’s Bay Country Club, while nearby beaches, boating, waterfront dining and the relaxed pleasures of Shelter Island are all within easy reach. Convenient access to both the North and South Forks allows the property to feel wonderfully removed without being isolated. Yet once inside Dering Harbor, the pace changes entirely with quiet roads, historic homes, mature landscapes and the water seemingly never far away. 31 Manhanset Road is more than an exceptional building parcel. It is an opportunity to create a legacy 8+ acre estate in one of the Hamptons’ most intimate and difficult-to-replicate settings-where architecture, gardens, recreation and preserved open space can come together as one extraordinary private domain. Come walk the land, breathe in the salt air, and imagine what could be created here.