Top Five Most Expensive Properties on Shelter Island

It’s a dream to live on a beautiful island—and here on the East End, that opportunity is available on one of the most beautiful isles in America. Shelter Island provides a unique ownership opportunity because it is away from the glitz and glam of the Hamptons, and provides a more easy-going atmosphere and unpresedented beauty. This week our Top Five showcases the most expensive properties for sale on this wonderful island!

64 Burns Road, Shelter Island, $18.9 million

An extraordinary offering, this singular 24.81+/- acre waterfront property provides an unprecedented 1,500’+/- of pristine beach frontage and stunning vistas across Coecles Harbor on beautiful Shelter Island. Arguably the most unique and inspiring parcel of waterfront land currently available in the Hamptons, the remarkable property encompasses ten separate buildings, a long boat dock, swimming pool, tennis and basketball courts. Facilities include a 29-room guest house, renovated in 2000, two additional houses, garages, recreation and dining halls. The extensive shoreline provides the luxury of private deepwater dockage. This prime property provides a magnificent setting for an extensive range of sub-division possibilities. This is a once-in-a-lifetime opportunity to acquire such a large contiguous holding of buildable waterfront land on the East End of Long Island.

Bumble Bee Manor, Shelter Island, $14,995,000

Unquestionably one of the finest properties in the region, this luxurious waterfront estate is nothing short of majestic. Exquisitely positioned directly on the water, this extraordinary residential compound is sited on 3.25-acres +/- comprising lush gardens, rolling lawns, over 300′ of private beach frontage, and a long dock that can accommodate a large yacht,  helicopter and seaplane, as well as a deep water mooring. The estate boasts a 16-room mansion, guest house, a St. Barth’s-style pool house and a magnificent infinity-edge pool, all overlooking the water. The living space is designed for entertaining, as evidenced by an elegant living room, banquet-sized dining room and paneled library. The professional chef’s quality kitchen opens to a lovely garden room and the bluestone-floored dining terrace. There are seven custom fireplaces, six generously proportioned bedrooms, 6.5 baths, elevator, office, media room and private fitness room. The guesthouse has three bedrooms, a grand living area plus a three-car garage and garden room. The incredible pool house offers an expansive studio with balcony and glass cupola, summer living room, kitchen and bath. Truly an estate of unsurpassed grandeur.

64 Ram Island Drive, Shelter Island, $9,950,000

Located in the prime estate section of Little Ram Island on Coecles Harbor, this stunning traditional sited on two waterfront acres with sweeping sunsets is a rare find.  Embracing the purity of architectural detail, together with a refined simplicity, this waterfront manor offers a timeless elegance.  Eye-catching angles, a rich palette of pigments and thoughtful details provide constant visual interest, beginning with a double door entry reclaimed from a French estate.  A double height entry hall provides dramatic water views over a bluestone terrace and day-long natural sunlight. The living room has two water view verandas and a handsome fireplace.

23 Winthrop Road, Shelter Island, $6,495,000

Sited on 1.3 acres with elevated panoramic views and sunsets galore, this elegant and generously proportioned estate offers a true sailor’s paradise on one of the most coveted waterways in the Hamptons.

Private Address, Shelter Island, $5,950,000

Resort-style living on Shelter Island! This fabulous traditional is one of the few residences sited on the dunes on the Island. Southwest exposures and panoramic views toward Southampton provide a dramatic backdrop to this immaculate, recently built waterfront home. Built into a grade, while spacious, the residence strikes a proportionately elegant pose on the beach.