Featured Properties

Somewhere in Time on the Shores of Shelter Island

44 Manhanset Road, Shelter Island

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 3-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 century. Poised 30’ above the Peconic, on a site to where, for almost 40 years, steamers would deposit the rich and famous from New York, Boston and beyond to the venerable Manhanset House, an enormous 500 guest hotel opened in 1874 which would eventually, in 1896, anchor a new golf course.

The current house and its once connected neighbor built in the early years of the 20th century would serve as the clubhouse for what would become Gardiners Bay Golf Club after the original hotel had burned to the ground. Today a fortunate new owner would enjoy blazing sunsets and unobstructed views to the North Fork as the nearby ferries carry travelers between Shelter Island and Greenport while luxury yachts and fishing boats pass back and forth out to sea. The 8,000 SF Mediterranean style manse offers 8 bedrooms, serviced by 7 baths on three levels of living space. 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. Additional amenities include a bar room with an original soda fountain, billiard and game rooms, gym, and bluff top hot tub. The 24’ X 60’ pool, with a decided Slim Aarons feel, looks out past 300’ of a private, sandy beaches to the 150’ dock with water, electric, dual hydraulic boat lifts, and its own boathouse.

A separate cottage on the property could be repurposed as that coveted artist studio. Dubbed the Smallest Village in New York State, Dering Harbor occupies an enviable 200 acres within the approximately 8,000 acres that comprise the roughly 7-mile-long township of Shelter Island. Well known to many who frequently ply these waters, this imposing seaside estate awaits your private tour.

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