The Barbarians at the Gilded Gate

Once home to the grand estates of titans like Frank Nelson Doubleday, Henry Phipps, Jr., C.W. Post, Harry Payne Whitney, and various Vanderbilts, Long Island’s Gold Coast, as the area is commonly called, is now besieged with a new breed of Gatsbys: tech billionaires, hedge fund sharks and celebrities like Adam Sandler (who nabbed a house on coveted Piping Rock Road) and Jimmy Fallon, who listed his Gramercy Park apartment for $15 million last March and bought Cedar Knolls, a 10,000-square-foot Georgian Manor in Laurel Hollow built for railroad magnate Frank Gould in 1929. The house, which has a private beach, ballroom, and underground speakeasy, is straight out of West Egg. Paging Daisy Buchanan. 

The gargantuan estates of yesteryear are swapping hands, fast. One real-estate agent has been showing the 1912 Palladian-style Vanderbilt Art Studio (now a 7,000-square-foot, five-bedroom home) in Old Westbury to internet billionaires and rap stars. The original owner, Gertrude Vanderbilt Whitney, a sculptor and founder of the Whitney Museum of American Art, liked to host wildly avant-garde parties on the property. She once emptied the swimming pool to make room for two kangaroos. The last of the Whitney family’s North Shore enclaves, the house on 6.59 acres, said swimming pool, and formal gardens is currently listed for $4.75 million. 

Whitney’s great-grandson, John LeBoutillier, a former congressman and the author of the bestselling Harvard Hates America put the art studio-turned-house on the market less than a year ago. “John is a throwback to what most people think about when they think of Locust Valley,” the broker explains. “He’s a Vanderbilt. But he knows things are changing. He didn’t blink about the people who wanted to see the studio. And [they’re] not people who are Rockefeller descendants. I think the old school WASP thing is dead, don’t you?” 

Even the most prominent of the lavish estates, the Phipps family’s Erchless,  a 1936 Colonial Revival mansion with 15 bedrooms, is up for grabs for a mere $29.995 million—with rumors that it might be—horrors!—subdivided. The 83-year-old Howard Phipps Jr. wants to, well, downsize. Erchless encompasses two greenhouses, three barns, a caretaker’s house and impeccable formal gardens. And nothing says: I’m really, really rich like your own horse stables, whether you ride or not. 

The new Gatsbys seem to want even more glamor and grandeur than their late 19th Century Gilded Age counterparts. Bigger-is-better defines much of the new construction. Water views (replete with big boy boats), Architectural Digest photo shoot–worthy gardens and staff quarters that would make Downton Abbey look puny are all par for the course. 

“I think people are trying to recreate the lost North Shore [through] the luxuriousness of the new homes,” suggests author-historian Gary Lawrance, who has an encyclopedic knowledge of the houses of Long Island and runs the Instagram account @MansionsoftheGildedAge (100K+ followers). “The vocabulary of the great estates is now seen in Belgian block-curbed subdivisions, lined with new formal rows of trees, entrances marked by gilded iron gates, lanterns, sometimes fountains on front lawns, and the main entrance featuring a double-height columned portico, large window and maybe a glimpse of a crystal chandelier,” he notes. “If one could compare vintage aerials to today’s Google Earth views the density change would be very dramatic.” 

The North Shore has plenty of famous residents, Fox News anchors Sean Hannity (who lives in a $9.5 million house in Oyster Bay) and girlfriend Ainsley Earhardt, Today host Jenna Bush Hager, and Deborah Norville among them. The latest generation of WASPs moving from Manhattan to the North Shore are far more fashionable than a pair of L.L. Bean duck boots and there isn’t a trace of “Locust Valley lockjaw” (lips tight, jaw clenched. Think Thurston Howell III) to be heard in town. 

Many attribute the very social, and highly successful fashion designer Veronica Swanson Beard with leading this new-prep migration, which counts New York society staples Jay and Allison Aston (weekenders), Jill Jervis, Beth Blake, jewelry designer Brent Neale (who bought decorator Jeffrey Bilhuber’s 17th century farmhouse “Hay Fever”) among the likes. 

“Veronica ended up buying a house out here and convinced all her friends to buy houses and they put all their kids in Green Vale, which is the private school,” observes one resident of over a decade, who has lived in Locust Valley for decades with her children and financier husband. 

The new Gatsbys are all vying to join the club. The “club” is Locust Valley’s super-exclusive Piping Rock on the Long Island Sound, directly across from another preppy beacon: Greenwich, CT. The other must-joins: The Creek, popular among the full-time residents; and Seawanhaka Corinthian Yacht Club on Oyster Bay’s ultra-secluded Centre Island in Oyster Bay, where the sailing and Southside sipping set congregate. 

One recent Locust Valley transplant lured by Veronica Beard is Christin Rueger, who moved with her family from Greenwich Village pre-pandemic. “Veronica gets the credit for pulling us out here,” Rueger confesses. “We had no itch to get out of the city. Our kids were at Grace Church School. We were surrounded by good friends.” But after renting for a year, the family was hooked and decided to make it permanent. 

“The people who want to be here don’t want to be in a typical suburb,” notes Rueger. “It’s a small town, but it’s also very social so you don’t feel suffocated like [you] need to bust out.” The area, she adds, has an eclectic mix of people for a historically very WASP-y area. “It’s broken out of that mold a little bit,” she says, citing friends who’ve bought quaint cottages near town and others who purchased huge historic estates. “The mood is very democratic,” adds one resident. “My friends in Greenwich—it’s a little more competitive there; a little more ‘keeping up with the Jones’– but here everyone socializes together.” 

Maybe not everyone. One well-connected New Yorker whose name we won’t mention, famously moved to Locust Valley, bought the right house on the right street, and got his kids into the right schools, only to be rejected by the insular Piping Rock membership committee. Within a year, the family was back in Manhattan.

Last April, Rueger opened the first franchise of Knockout Beauty (which was founded by her friend Cayli Cavaco Reck) in Locust Valley. “This town is such a great blank canvas. Since I opened my store, three new stores have opened in town,” she says. “People are really starting to pick up on the retail opportunity here.” Where the new Gatsbys go, fancy stores and eateries follow. A top broker declares that Oyster Bay could be—believe it or not—the new Williamsburg. “Oyster Bay is so hot,” she gushes. “It’s on fire right now.” 

The village definitely drips with charm with turn of the century commercial buildings and tin ceilings. But now the beloved, slightly run-down circa 1884 drug store/soda fountain Snouders is rumored to soon become an upscale gourmet market. Award-winning Italian chef Fabrizio Facchini is opening the much-anticipated Stellina Ristorante on a corner of South Street. And the hipoisie can always be found at the be-seen coffee shop, Southdown. “There are a lot of people from Brooklyn moving out. They want a small home on not a lot of property. They want to be able to walk to the train and have a vibrant village, which is what Oyster Bay is. I used to see it as their getaway. But now they are ditching Brooklyn, downtown, whatever and coming to Oyster Bay and Locust Valley.” 

Interior designer Meg Braff, one of North Shore’s go-to decorators, who also owns a design store in Locust Valley, welcomes the boom. “There is a whole new group in town which has been wonderful,” she enthuses. “In the past few years there has been a noticeable influx of young families. Locust Valley had gotten a touch sleepy, but it feels fresh again. Covid really made people consider moving to Long Island from New York.” 

The pandemic certainly accelerated the real-estate boom—and prices keep soaring. The North Shore’s undisputed grand dame of real estate, Christy Porter, grew up in Locust Valley and runs Sotheby’s International Realty Porter Teagle Team with daughter Tina Teagle. She phones in from a showing of a $10 million dollar home to report: “Our inventory is very low. We are seeing people bidding over the asking price because they want to be in the area.” 

Just two years ago, luxury listings were not trading. Today, Gatsby-era houses with a fancy provenance have become the hottest ticket, she notes: “A lot of people who are buying like to know the history of the house—who built it, who owned it, the architect, who designed the gardens—that’s all part of the process now.”

As with pricey real estate elsewhere, rumors of plutocrats from China buying mega-million dollar houses as shell companies make for constant dinner party chatter. “A couple from China bought the property next to us,” one well-heeled Locust Valley resident laments. “It’s been three years and no one has moved in. It’s disturbing.” There’s plenty of ire for the mega-moneyed who do actually move in. Zach L (he prefers to remain somewhat anonymous), who runs the Instagram account @oldlongisland (23.5K+ followers) quips: “[The area] has been completely developed; open land has been replaced with generic suburbia and a ton of hideous McMansions.” 

The flashy nouveau Gatsbys will always attract haters, but “the North Shore is still the place to have a primary home or country place,” concludes author Lawrance. And the buying boom shows absolutely no signs of slowing down. As Fitzgerald wrote in The Great Gatsby: “Those who pursue the American Dream believe that no matter how much they accomplish, there is always something better to strive for.”