The ‘Finest’ House in Dering Harbor Sits Perched Atop a Bluff

An aerial look at the historic property at 44 Manhanset Road in Dering Harbor.
Brian Bailey for Gary DePersia

A recognizable historic waterfront mansion in Shelter Island’s Dering Harbor is available for the first time in 20 years. With a rare 150-foot dock and an even rarer 300-foot sandy beach, plus a rich history, the home is one of the most coveted on the island.

New to the market, the 2.7-acre property at 44 Manhanset Road is listed at $11.95 million. Gary DePersia of the Corcoran Group is representing the property exclusively.

“Combine a historic mansion, a prominent location in Dering Harbor, 300 feet of private beach, expansive views, sunsets, a boathouse servicing a deep-water dock and you just might begin to imagine this nearly three-acre estate perched on high overlooking broad swaths of bayfront that has rarely come to market since it was built at the turn of the last century,” DePersia says.

The Mediterranean-style home with its distinctive red clay tile roof and stucco facade was first built in 1913 on property that had been home to the Manhanset House, a 19th century hotel situated on the bluff just east of Locust Point. There were rooms for 500 guests across the two buildings, one four stories high and one five stories, with a dance hall pavilion in between.

The Mediterranean-style home has a distinctive red clay tile roof.Brian Bailey for Gary DePersia

In 1885, The New York Times wrote that the Manhanset House was “the largest and finest” in the seaside summer resort town. New York City residents could escape the heat and malaria in the city for the island, a 2-hour and 20-minute ride on the Long Island Rail Road or a cruise on the steamer Frances.

The current home on the property served as the clubhouse for the Gardiner’s Bay Golf Club, established under a different name in 1896 (the original nine-hole golf course was among the first on Long Island; Shinnecock Hills in Southampton was founded in 1891). “It was the brainchild of the manager of The Manhanset House Hotel, H.D.W. Lawson. His vision was combining the game of golf and the natural beauty of Dering Harbor and Hay Beach,” according to an article in The Shelter Island Reporter.

The property at 44 Manhanset Road has a 150-foot dock that extends into Shelter Island Sound.Brian Bailey for Gary DePersia

Just weeks before the 1910 summer season, the hotel was struck by lightning and burned to the ground. Other buildings survived, including the private clubhouse and a casino the club owned, as well as Victorian gingerbread “cottages” that would pave the way for the incorporation of Dering Harbor Village.The 100-year-old village remains the least populous village in New York State; in fact, the 2020 Census recorded just 11 residents living there.

After several years of financial struggles, the club separated from the casino and the clubhouse was relocated to its current site nearby.

Today, the 8,000-square-foot house sits 30 feet above Peconic Bay and enjoys some of the most spectacular unobstructed views of the North Fork and blazing sunsets.

The ferry boats going back and forth to Greenport and the luxury yachts and fishing boats traversing the calm bay waters are the only traffic to be found here.

The home boasts three levels of living space with eight bedrooms and seven bathrooms.

“Dramatic beams enhance the great room,” says Gary DePersia of The Corcoran Group, who is representing the listing exclusively.Brian Bailey for Gary DePersia

“Dramatic beams enhance the great room with vaulted ceilings and an imposing fireplace while a more intimate living room, warmed by its own fireplace, will become a favored haunt of those looking to read, watch TV, or quiet reflection,” DePersia says.

In addition, there is a bar room with an original soda fountain, billiard and game rooms, a gym, and hot tub located up on the bluff.

The 24-foot-by-60-foot heated pool, which has, DePersia says, “a decided Slim Aarons feel,” overlooks the water. A cement switchback path leads to a private beach. The dock can be found just beyond the sand, extending out 150 feet into the water with several amenities; electric, dual hydraulic boat lifts and even its own boathouse.

A separate cottage on the property, perfect for private guest quarters, could be repurposed as that coveted artist studio. There is also an outdoor shower.

The home’s unique character certainly harkens back to a simpler, yet opulent time on Shelter Island. Now one of the most recognizable properties in all of Dering Harbor’s 200 acres, it is primed for someone else to enjoy in the 21st century.

This article appeared in the October 2021 issue of Behind The Hedges. 

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