An Extraordinary Opportunity To Craft A Private Shelter Island Retreat With Sweeping Views And Timeless Appeal
In the heart of one of Shelter Island’s most exclusive villages, Dering Harbor, is a remarkable 8.2- acre estate parcel that was once part of the storied “Oriole Farm” is available for the first time in generations. Framed by cultivated gardens, views of Gardiner’s Bay Country Club, and the natural beauty of Shelter Island, this legacy property offers the rare chance to create a private sanctuary of scale and sophistication. We sat down with veteran broker Gary DePersia of The Corcoran Group to learn more about this extraordinary offering and the unique lifestyle that Dering Harbor affords.
Gary, what makes this estate parcel in Dering Harbor such a unique opportunity?
This is truly a once-in-a-lifetime offering. You’re looking at 8.2 acres in Dering Harbor, Shelter Island New York’s smallest and arguably most exclusive village. With only 35 homes in this 200-acre enclave, the chance to own such a significant, pristine piece of land is incredibly rare.
Can you tell us more about the property’s history?
Absolutely. This parcel was once part of the famed “Oriole Farm,” the private arboretum and cultivated gardens of Alice Fisk, a legendary horticulturist. The land carries with it a legacy of beauty, heritage, and tranquility. It’s steeped in history and has remained untouched for many generations, until now.
What kind of potential does this property offer to a prospective buyer?
The scale and serenity of this parcel give you room to create something truly special. There’s space for a grand manor, a pool, a pool house, tennis court, and even a carriage house with legal living quarters above. It’s a blank canvas for someone looking to make a lasting mark in this exclusive area.
How does the location enhance the appeal of this estate?
It’s ideally positioned directly across from Gardiner’s Bay Country Club, offering peaceful views and a refined atmosphere.
Plus, it’s just a short walk to Dering Harbor’s village center, sandy beaches, charming boutiques, and fine waterfront dining. It’s island living at its best.
Are there any practical benefits of owning in Dering Harbor compared to other Shelter Island locations?
Yes, and that’s an important point. Dering Harbor has its own municipal water supply, which means reliable, high-quality water year-round—critical for both your home and landscaping. It also offers a discreet service entrance on the west side of the property, enhancing privacy and accessibility.
What kind of buyer is this property ideal for?
This is for anyone looking to build a timeless legacy in a setting that’s as private as it is prestigious. If you’re drawn to history, nature, and elegance—and want the freedom to create your dream estate then this property is calling.
Any final thoughts for potential buyers?
Come walk the land, feel the breeze, breathe in the salt air. It’s not just a property, it’s an invitation to craft something extraordinary. This is your chance to build a sanctuary that will stand the test of time and become your legacy.
