The Real Deal New York

A look at the enormous mansions hidden behind the Hamptons’ famously high hedges

By Business Insider | August 06, 2017 10:22AM

Jeff Cully/EEFAS

Beyond its beautiful beaches, bays, and lagoons is another type of eye candy native to the Hamptons: gorgeous, hidden real estate.

At the end of snaking driveways, with huge shrubs blocking any roadside view, some of the East End’s most breathtaking homes are rarely seen — at least until now.

Jeff Cully, an aerial photographer with East End Fine Arts Services, captured the area’s most exclusive enclaves and the mansions hidden within.

Our tour of the Hamptons starts in Southampton Village, at the western edge of the South Fork of Long Island.

Jeff Cully/EEFAS

One of the most prestigious communities on Long Island, Southampton is also the most residential, with tons of bars, restaurants, and luxury boutiques. Tree cover is dense, hiding the celebrity summer homes of celebrities like Rachael Ray, Howard Stern, George Soros, Kelly Ripa, and Tory Burch.

Jeff Cully/EEFAS

To the east of Southampton is Bridgehampton, a smaller hamlet. It’s a bit more low-key but no less ritzy. The Hampton Classic Horse Show is held here every year.

Jeff Cully/EEFAS

Heading east over Sagaponack Pond, we land in Sagaponack, New York, which was named the most expensive small town in the country in 2012.

Jeff Cully/EEFAS

The East End’s long heritage of family farming lives on in Sagaponack at the Foster Farm, which grows potatoes.

Jeff Cully/EEFAS

A tour of Sagaponack wouldn’t be complete without a look at the junk-bond king Ira Rennert’s gigantic house on the waterfront. An 110,000-square-foot home on 63 acres, Rennert’s Hamptons mansion is considered one of the largest occupied pieces of residential real estate in the US. The house has an assessed value of $250 million.

Jeff Cully/EEFAS