$8,500,000

Set along the quiet shoreline of Pipers Cove Bay in Shelter Island Heights, this west-facing waterfront retreat is tucked at the end of a private drive and has been thoughtfully reimagined by Heiberg Cummings, whose signature approach to layered design transforms the home into something both sophisticated and deeply connected to its surroundings. Every room on both levels is oriented toward the water, creating a constant dialogue between the interiors and the landscape beyond. Natural textures, a restrained palette, and carefully considered details allow the landscape to remain the focal point. The house unfolds around the view with a central wood-burning fireplace anchoring the open living room, kitchen and dining space. Glass doors open onto a series of waterfront decks, blurring the line between indoors and out and offering a front-row seat to the island's spectacular western sunsets. The primary suite occupies the main level, complete with an en-suite bath and private waterfront terrace. Downstairs, two bedrooms and a full bath are complemented by a generous waterfront den and library, creating an inviting second living space with uninterrupted views across the cove. On the opposite side of the den, a shaded terrace offers another quiet place to read, relax, or escape the afternoon sun. Outside, the property reveals itself one destination at a time. Multiple outdoor living spaces, perfect for hosting summer dinners on the terrace overlooking the water, or sunset cocktails in the private beach garden with two fire pits and a lantern lit dining area. Fully equipped beach bar , integrated outdoor sound system disappears into the landscape. Mooring rights for a vessel up to 40 feet make it easy to explore the surrounding waters before returning home for sunset. Private, thoughtfully designed, and deeply connected to the water, this is a home that captures the quieter side of the East End, where mornings begin on the beach, afternoons are spent on the water, and each day ends with the sun setting over Pipers Cove Bay. Residents also enjoy access to the Shelter Island Heights community tennis courts, while the Ferry, Marie Eiffel Market, Leon 1909, and the Heights' shops and waterfront are all just a short distance away, placing some of the island's favorite destinations within close proximity.