Top 5 Waterfront Homes for Sale on Shelter Island

Resting between the Hamptons and the North Fork, Shelter Island has long been the place to be for those truly private people who want to enjoy the region’s beauty without the seasonal scene. Here we present our top five waterfront homes for sale on this special island.

Exquisite Dering Harbor Estate

A superb waterfront location with panoramic views and a unique historic pedigree, this is an unrivaled opportunity to own in Dering Harbor. The exquisite 4-acre property, featuring a main residence and a fully appointed guest cottage, offers understated elegance, stellar views and unparalleled sunsets. The spacious living room has wooden beams, a fireplace and wide-plank floors. French doors lead to a screened porch and extensive brick terraces. The renovated kitchen with designer appliances leads to a formal dining room. And 2 en-suite bedrooms and a rustic pine-clad library complete the first floor, while a second-story master suite offers a cathedral ceiling, fireplace, two bathrooms and a classic New England deck overlooking the pool and the bay beyond. The 1,200-square-foot guest cottage includes 4 bedrooms and a 3-car garage—all with more than 430 feet of waterfront and a deepwater dock. Sotheby’s IR

4 Little Ram Island Drive view
Waterfront on Ram Island, Photo: Courtesy Brown Harris Stevens

Stunning Waterfront on Ram Island

This grand, 5.4-acre waterfront estate features a bulkhead-protected, 8,000-square-foot home overlooking Gardiner’s Bay. A two-story entrance foyer leads to the large living room with fireplace and French doors. In addition to the formal dining room, a family room offers a great place to relax and enjoy the majestic view. The ground floor master bedroom is a luxurious suite with fireplace and sitting room. Upstairs has 3 additional bedrooms, 4 full baths and 4 half-baths. The grounds are open and manicured with waterside pool and large pool house with changing room and bath. Brown Harris Stevens

Shelter Island Crown Jewel SusanCincottaDanielGale
Shelter Island Crown Jewel, Photo: Courtesy Susan Cincotta, Daniel Gale Sotheby’s IR

Shelter Island Crown Jewel
Price Upon Request

Classically modern, this gem has stunning, panoramic views of Shelter Island Sound, Orient Harbor and Long Island Sound to Connecticut. Take in the bay throughout elegant, formal entertaining rooms, along with 7 bedrooms, 8 bathrooms, chef’s kitchen and covered waterside porch. A 50-foot St. Barth’s waterside pool and cabana add to the inviting grounds. This 4-floor, turn-key house was built in 1883 and fully renovated in 2010 with new foundation and systems while restoring the magnificent original floors, staircases, fireplaces, mantles and framing. The sunset water views are truly breathtaking and your own sandy beach is just nearby. Daniel Gale Sotheby’s IR

4 Little Ram Island Drive

Located on prestigious Little Ram Island, this spacious, light-filled, 4–5-bedroom, 5.5-bath waterfront home includes 1.5 beautiful acres. A boater’s dream with unobstructed harbor vistas toward Reel Point and Gardiners Bay, the property has a 125-foot dock with electric and water. The house is surrounded by mature evergreens and carefully selected shrubs and perennials, and it sits atop a gently sloping lawn that beautifully accents the pool and water. An elegant entry opens into a dramatic living and dining room with more fabulous views. The home also features a raised hearth, wet bar, cathedral ceilings accented with bead board, perimeter lighting and more. Douglas Elliman

29 Winthrop Road

This one of a kind, light-filled home features 600 feet of private beach and a 166-foot deepwater dock. Each of the 6 en-suite bedrooms, including a ground floor master, has a private deck with water views. The 9,230-square-foot home features a outstanding grand foyer, full service professional bar with teak flooring and private wine cellar, along with a home movie theater, library and 4-car garage on 1.7 acres with room for a full-size pool. Douglas Elliman

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