Nestled on approximately 2.1 acres with an impressive 186 feet of natural beachfront, 33 Dinah Rock Road is a rare west facing waterfront estate on Shelter Island. This elevated property, rising about 26 feet above sea level, delivers uninterrupted sunset views, refreshing southwest summer breezes, and sweeping vistas across the water. Its defining feature is the expansive private shoreline, complemented by a private dock with 4+ feet of depth at low tide plus a deep water mooring accommodating a variety of vessels. The thoughtfully expanded and meticulously maintained residence features 6 bedrooms and 4 full bathrooms, while a separate accessory building offers additional garage space, an art studio, and wood shop with clear potential for guest house conversion, bringing the total to three garage bays. Mature grounds, multiple outdoor living spaces, and proximity to Gardiner's Bay Country Club create a perfect blend of seclusion, natural beauty, and long term potential, ideal as a timeless Shelter Island country retreat or a premier site for future reimagination.