Top Five Most Expensive Homes on Shelter Island

Believe it or not, the most expensive properties on Shelter Island aren’t above $20 million, but they’re pretty close. Check out this week’s top five homes that will knock your socks off.

Waterfront Compound, $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 accessory structure, renovated in 2000, two additional houses, garages, recreation and dining halls.

Bumble Bee Manor, $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.

Paard Hill, Shelter Island Equestrian Estate, $7,950,000

Sited on 36 magnificent rolling acres on one of the highest points on idyllic Shelter Island, NY, overlooking Gardiners Bay and Coecles Harbor, Paard Hill is a true equestrian estate, The sprawling compound is comprised of a state-of-the-art barn with 23 windowed stalls including one for foaling, two tack rooms, indoor and outdoor wash stalls, lunchroom and an office. The attached 70′ x150′ heated indoor riding arena has mirrors, viewing room, and arched windows with harbor views.

Shelter Island Estate Section, $5,125,000

If you dream of living by the sea, you can be at one with nature and salt breezes all around, as you take a winding drive down to this delightfully sequestered waterfront compound on 2.6 acres on desirable Ram Island.

Shelter Island Waterfront with Deep Water Dock and Pool, $4,950,000

Check virtual tour for more photos! Sleek, European style post and beam style home on nearly 1.25 acres is a sailor’s paradise, with 175 feet of bulkheaded waterfront, 118 foot deepwater dock with boardwalk and waterside meditation area, featuring pristine and unalterable views across Smith’s Cove to Mashomack Preserve.