A rare opportunity to own one of the East End's most significant architectural homes-more than a house, it's a lifestyle. Commissioned by the Osofsky family and originally designed by Norman Jaffe in 1971, this waterfront estate was expanded by Jaffe himself in 1981-a rarity among his works. Recently renovated to preserve its architectural integrity while introducing modern comfort and luxury, the home offers a truly turn-key experience. Set on 1.7 acres with 175 feet of Gardiners Bay frontage, the property delivers sweeping views toward Orient and historic Gardiner's Island. Accessible only by ferry from the North and South Forks, Shelter Island ensures privacy and seclusion-just 2.5 hours from Manhattan yet worlds away. The 6,715 sq. ft. (incl. finished lower level) residence features 6 ensuite bedrooms, 8 full baths, and 2 half baths, plus a chef's kitchen, private gym, movie theater, and dedicated guest wing. Outdoor amenities include cantilevered decks, an extra-deep heated gunite pool, an entertaining pergola with kitchen and fireplace, and a tennis court with pickleball lines. Coastal-inspired landscaping and pollinator gardens complete the serene setting. An extraordinary waterfront retreat offering timeless design, privacy, and effortless luxury.