Estate of Grace

An Orange County Tuscan mansion in distress gets a new lease on life as a luxurious country-house hotel



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glenmere mansionValley villa reborn: Designed by Carrere and Hastings, Glenmere’s 35,000 square feet include 35 rooms, a central courtyard, marble staircases, terraces, balconies, and myriad decorative details

Photographs by Sargent Photography/courtesy of Glenmere

“It was really our midlife crisis,” says Alan Stenberg, standing on the terrace of Glenmere, a once-rundown mansion in Chester, Orange County. “If we’d bought a sports car, it would have been over in 20 minutes, but instead...” He trails off, gesturing at what is now the Hudson Valley’s new (and possibly only) luxury boutique hotel — the result of a three-and-a-half-year, multimillion-dollar makeover. His partner, Daniel DeSimone, looks equally bemused. “It was kismet,” he adds.

Glenmere was built in 1911 for real-estate scion Robert Goelet, who commissioned the illustrious architectural firm Carrere and Hastings to design a country retreat for his vast property. The firm obliged with a 35,000-square-foot, 35-room Italianate villa enclosing a central courtyard, with sweeping marble staircases, columned porticos, terraces, balconies, and plenty of no-expense-spared decorative details like ornamental trim and hand-forged railings. When it was complete, Goelet hired Beatrix Farrand, one of America’s foremost landscape architects (and the first female one), to design the grounds. Farrand created a park-like setting framing views of Glenmere Lake (then part of the estate) as well as formal plantings, which included a 6,000-square-foot Italian walled garden with pools and statuary. Thanks to the racetrack in nearby Goshen, the area was a hotbed of high society in those days, and the Goelets put their lavish retreat to good use, entertaining homegrown elites as well as a sprinkling of British nobility. (In the fashion of American heiresses of the time, Goelet’s sister, May, had bagged a hard-up, titled Briton — the Duke of Roxburghe.)

Fast forward to 2005, when DeSimone — an orthopedic surgeon with a penchant for fixing up old houses — was driving through Chester’s winding, leafy lanes and spotted the neglected salmon-pink building on its hilltop. Intrigued, he called a real estate agent who happened to have the place secretly listed. The owner had purchased the mansion and 100 acres at auction from Orange County, which had seized it as a tax lien in the 1970s. (The county reserved 1,200 acres, including the lake, which serves as a reservoir.) Most locals knew it as a wedding location-for-hire, although the owner was still in residence and eager to sell.

DeSimone and Stenberg had recently finished a lengthy renovation of their home in Tuxedo Park, which Stenberg says was “a complete wreck” when DeSimone found it. “Same thing with a townhouse in Philadelphia,” recalls Stenberg, the more outgoing of the two. “A wreck. But he had to have it — he doesn’t think about whether it’s feasible.” DeSimone had to have Glenmere, too — although for months, Stenberg, who owned a P.R. company at the time, refused to go to see it. “An Italian mansion in Chester?” he says. “I thought he’d lost it.” Finally he relented, and was immediately won over. “One look, and I was in. Then we just had to think of what to do with it. We quickly realized it would be a great hotel.”

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