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Resort-Style Living and Small-Town Values in the Hudson Valley

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On a recent afternoon at Silo Ridge Field Club, a gated resort community in the Hudson Valley, two men abandoned a round of golf on account of inclement weather and ducked into a “comfort station” overlooking the 16th green. Silo Ridge occupies some 800 acres that hold hiking trails, a produce garden, boating facilities, equestrian pastures, and an 18-hole course designed by Tom Fazio. It was the first offering in the Northeast from Discovery Land Company, a development firm run by the real estate and liquor tycoon Mike Meldman, who has had extraordinary success creating a formula to please clients who—almost literally—have everything. When it broke ground in 2016, Silo Ridge became the latest of some two dozen ultrahigh-end communities that Discovery has been planting across the globe since 1994: from Cabo San Lucas to the Rockies, Nashville to the Dominican Republic.

All Discovery buyers already own one, if not two or three, other homes, and the golfers at the comfort station exuded the breezy confidence of prosperous middle age. One had recently purchased one of Silo Ridge’s condos, which start at $2.5 million, while the other had sprung for a plot of land beside a small lake on the back nine. Using one of the development’s seven design templates, which yield residences that can cost more than $10 million, he’d built a handsome, rustic-luxe home. His lakeside neighbors include Tom Brady and Gisele Bündchen, who also own property at Discovery’s Yellowstone Club, in Montana, and at Baker’s Bay, in the Bahamas. The Silo Ridge membership includes many New York City financiers, some of whom were wooed by the development’s proximity to the elite boarding schools—Kent, Hotchkiss, Millbrook—that their children attend. Discovery’s motto is “Life Celebrated.”

But the weather wasn’t cooperating. Rain beat audibly on the comfort station’s tin roof. A signature of Discovery properties, all but one of which feature a golf course, Meldman’s comfort stations belie their humble name. An elegant slate board offered duck charcuterie. Local produce, arranged on a tiered server, made up an attractive still life. Homemade cookies filled glass jars on a marble countertop. Outside, a grill awaited sunnier conditions. Two staffers were on hand to address member needs. Margaritas made with Casamigos—the tequila brand Meldman founded with George Clooney and Rande Gerber, who once owned adjacent Discovery properties in Mexico— were available, but the rain-flecked golfers drank juice and crunched on tortilla chips.

Discovery emphasizes the sense of community that develops among members. “Like-minded people are attracted to the environment, people who appreciate the same things,” said Mindy Grossman, the CEO of WW International (née Weight Watchers) and a Silo Ridge member. “Once we bought, we found that a number of people we knew were also members, and none of the people surprised me.”

Among the things that Discovery members appreciate are private ski lifts (18 of them, servicing more than 100 alsoprivate trails in Montana); Pebble Beach–quality waterfront golf (the Dominican Republic); and the opportunity to create their own wine label, using grapes harvested from their own vineyard (Austin). “These aren’t vacation homes,” Richard Bressler, the president of iHeartMedia, told me. Bressler and his wife, Lisa Gersh—a former CEO of Alexander Wang and Gwyneth Paltrow’s Goop—have places at both Baker’s Bay and Silo Ridge. “Mike’s a genius at building communities,” he continued. “Places people want to call home, where they want to raise kids, make new friends, improve their way of life.”

This is not one of Discovery’s largest properties—the Yellowstone Club boasts more than 15,000 acres—but it will still take years to fully realize. At Silo Ridge, only about 35 percent of the planned 245 residences have been completed—a third of them spoken for—and the golfers were still getting to know one another, trading stories about travel and business. One of the men had visited Iron Horse, another Discovery community in Montana, as a guest. “That’s how we ended up here,” he said. The other man had recently completed a three-week golf tour, including stops in Scottsdale and the Bahamas. His companion recalled a stay at the Ritz-Carlton residences in Puerto Rico. “My buddy at D. E. Shaw owned it,” he said.

It’s lifestyles like these and the resources to support them that make Discovery’s customers such a coveted consumer class. But they also make them difficult to please. And planned communities—especially extravagant ones requiring enormous front-end investment—are inevitably characterized by uniformity, choreographed by constrained choice. But Meldman has mastered the contours of his craft, making the limits of the form seem, to Discovery members, like means of transcendence. “These projects are hard,” Meldman told me. “You gotta spend a lot of money up front and spend it the right way. If you don’t know how it’s gonna be received, it’s scary and risky. We’ve derisked it, because we’ve done it 30 times now.”

In recent years, big-investment planned communities have popped up with some frequency: Las Catalinas, MindSpring founder Charles Brewer’s beach town experiment in Costa Rica; Serenbe, outside Atlanta; Hudson Woods, in the Catskills. Many have a utopian bent, catering to a yen for old-world “authenticity” that has gripped wealthy urbanites. Hudson Woods’ Dwell magazine modernism tends to draw a Brooklyn crowd, while Serenbe appeals especially to wellness seekers. The communities’ founders often emphasize the kind of serendipitous, faceto-face interaction—what Jane Jacobs famously called a ballet of the sidewalk—in combination with back-to-the-land idealism.

“When you walk out of your door, you’re in this beautiful, rather lively, but also peaceful environment,” Brewer said of Las Catalinas, which, like Silo Ridge, dramatically limits car traffic. “It’s safe for your kids. There’s a sense of freedom. Everyone gets the benefit of this natural sociability that happens in that kind of setting. It’s hard to come by in today’s world.”

No other new planned community operates anywhere near Discovery’s scale or price point. If he ever had any direct competitors, Meldman said, they disappeared with the 2008 downturn. “We have bought projects where people had invested hundreds of millions of dollars, but it was not worth anything to us because they didn’t know how to spend the money,” he said. “What to do, when to bring in the amenities.” The logistics of maintaining the pristine, blindingly emerald golf courses that are central to the Discovery brand make the company’s occasional paeans to sustainability difficult to accept as anything other than savvy marketing.

From Manhattan, the roughly 80-mile trip to Silo Ridge takes about two hours by train—a pleasant passage through an increasingly bucolic landscape dotted with quaint towns. The property practically abuts the train depot in Wassaic, a hamlet in the town of Amenia, but most members drive from the city (or arrive by helicopter). “I think our members prefer not to be on someone else’s schedule,” Dan O’Callaghan, Discovery’s New York sales director, explained.

Having worked for Discovery for 14 years, O’Callaghan, a slim man with graying straw-colored hair, is in a position to know. Dressed in khakis and hiking sneakers when we met, he was piloting one of the forest-green golf carts that members and staff use to navigate the community’s network of smooth asphalt paths. We passed construction workers putting late-stage touches on new houses, condos, and communal buildings. Negotiating a ramp of lumber, we walked into the shell of the Family Barn. A soaring structure of 11,000 square feet, it will contain an art studio, a bowling alley, a game room, a movie theater, and a kid-friendly diner. For more mature patrons, it will also house a restaurant whose cuisine and aesthetic, O’Callaghan said, might suggest Blue Hill at Stone Barns, Dan Barber’s celebrated locavore temple in Pocantico Hills, New York

O’Callaghan, who previously worked at Baker’s Bay, was surprised by the demand at Silo Ridge for condos, which has been roughly the same as for single-family homes. “I thought people would want a yard,” he said. “But increasingly, people just want finished, turnkey properties.” Indeed, convenience accounts for much of Discovery’s appeal. Describing the company’s genius, one Baker’s Bay member told me, “You don’t have to think about anything.” O’Callaghan added, “I’m selling a lifestyle, not real estate. You could buy 100 acres in this area for the price of a condo here, but it won’t have the amenities, $200 million worth of infrastructure, 800 acres that you don’t have to maintain. We have everything you could possibly want in the Hudson Valley right in our gated community.”

Mike Meldman’s Silo Ridge condo—3,600 square feet, double-height great room, plenty of marble, hardwood, and televisions—had recently been visited by the member services team, which provisions homes in advance of members’ arrival. Meldman has described Discovery residences as “frat houses for families,” and his kitchen contained seven kinds of beer, eight kinds of ice cream, and enough liquor to sink a pirate ship. Discovery members like to entertain.

O’Callaghan motored next toward the southwestern corner of Silo Ridge, where Richard Bressler and Lisa Gersh have a custom-built home. En route, he pointed to a small wooden building that looked plucked from a Wild West diorama: Silo Ridge Bait Shop. It contains mechanicals. “But if you make it look like an old Western store,” O’Callaghan said, “someone will buy real estate right across from it and not realize it’s a pumphouse.”

Ultimately Silo Ridge’s hub will be a 30,000-square-foot clubhouse with a spa, fitness center, and swimming pool. But it remains unbuilt, and for now, life largely revolves around the Ridge House, a cozy clubhouse and “terrain-to-table” restaurant with a stone fireplace, timbered ceilings, and an overall rustic vibe. A patio commands views of the golf course, which is enfolded by forested hills.

On a bright, breezy afternoon, I had lunch there, having spent the morning visiting some golf-free attractions: the garden, where everything from artichokes to heirloom tomatoes are grown; a chicken run, aflutter with some 50 spirited birds; a hutch containing three very soft Flemish giant rabbits much beloved by Silo Ridge youngsters; a pixie-sized Wiffle Ball field. On a dirt promontory overlooking the lake, an employee was installing a wooden platform to make jumping safer. Nearby, a clearing has been furnished with a tepee for overnight stays. Bressler likes to say that Discovery excels at infusing its communities with “indigenous” elements from just beyond the gates, and at Silo Ridge, the Outdoor Pursuits program—a Discovery staple—will organize camping, hunting, fishing, archery, and kayaking.

“A lot of people in our demographic are type A,” Meldman told me. “They’ve worked very hard.” What they value most now is time—to enjoy family and friends and, on occasion, to visit an idealized version of the past. If there is a secret to Meldman’s success, it is perhaps persuading the most discriminating consumers that a certain kind of innocence is what they’ve been seeking all along. “With these projects—Silo, Iron Horse, Yellowstone—you feel like you’ve escaped to simpler times,” he continued. “I wanted to bring back good memories, childhood memories. No matter who you are as an adult, life’s simpler as a kid.”


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