This Pastoral Town Is Home To Larry Fink, Georgina Bloomberg, David Letterman, Richard…

Jenn Gates recently walked the bridal path in the equestrian-friendly town of North Salem, New York. Inside the famously private, ultra-wealthy community.

By Luisa Kroll

When Jenn Gates married Nayel Nassar last month at her $34 million, 146-acre estate in North Salem, New York, it shone a spotlight on the bucolic Westchester town.

The area, which has its own “Billionaires’ Dirt Road,” is located just 55 miles north of New York City and home to more than half of the county’s agricultural land. Stretched out over roughly 23 square miles, it is just about the same size as the island of Manhattan but with a population of roughly 5,200—not counting all the horses and alpaca. 

That combination of wide-open spaces, few people, and North Salem’s decades-long status as an equestrian mecca—it boasts at least 56 horse facilities, including nationally renowned Old Salem Farm—has long attracted a mix of Wall Street tycoons and celebrities drawn to its rural character.

An accomplished show jumper, Jenn Gates set up an outpost of her Evergate Stables here. Her barn is three miles down the road from her fellow equestrian and wedding guest Georgina Bloomberg, the daughter of billionaire media mogul Michael Bloomberg. Other three-comma club residents include BlackRock CEO Larry Fink and Milwaukee Bucks co-owners Jamie Dinan and Wesley Edens and hedge fund billionaire Glenn Dubin. And in January, Richard Gere discreetly paid $9.8 million for the estate of a Woolworth heir, joining other famous neighbors, including late night legend David Letterman and Disney composer Alan Menken.

It helps that residents respect others’ privacy. “One of the nicest parts of North Salem is people don’t count other people’s money,” says the town’s deputy supervisor Peter Kamenstein. “If you want to be left alone, you are left alone.”

Residents have long sought to protect North Salem’s rural identity.  In 1974, a group of property owners created the North Salem Open Land Foundation, which has acquired 858 acres in town and holds conservation easements over another 500 acres. The foundation gets support from some of the town’s wealthy residents who are also board members—including McDonald’s franchise multimillionaire Bruce Colley and Target heir Duncan Dayton, who sold more than 140 acres to the Gates family. After philanthropist Ronald Stanton, founder of petrochemicals company Transammonia, died in 2016, two of his monied neighbors—Dinan and financier Steve Rattner—reportedly purchased his hundreds of acres to ensure that no one else developed the land. It also helps that nearly all of these wealthy landowners get tax benefits along with their huge parcels of land, either from putting acres into conservation easements or qualifying for agricultural exemptions.

“Everyone appreciates North Salem,” says longtime resident and head of the town planning board Cynthia Curtis, “and it wouldn’t be this way if not for the people who choose to live here and own the large parcels.”

*Note: I am a resident of Croton Falls, NY, a hamlet of North Salem. 

Meet some of the wealthiest property owners riding high in North Salem.

Jenn Gates

North Salem was a fitting setting for the glamorous October 2021 wedding of Jennifer Gates and Nayel Nassar, both professional show jumpers. The reception, where Coldplay, Paul McCartney and Alicia Keys all reportedly performed, took place on a giant field in three temporary glass structures across from her sprawling Evergates Stables. Through LLCs, Bill and Melinda Gates quietly spent at least $34 million buying up several properties on picturesque Mills Road in recent years and gifted it to their equestrian daughter. In 2018, they purchased a 124-acre farm from Target heir and race car driver Dayton Duncan for nearly $16 million. Months later, the Gateses bought their neighbors’ home for $2.5 million, paying three times the 2008 price to secure the unlisted property. Then in September 2020, the family paid Duncan another $15 million for 22 acres directly across the street (roughly 18 times what the property had sold for 12 years earlier), to further secure their privacy. It was on those fields that the wedding reception took place.