For a property that has already changed hands for tens of millions of dollars, this East Hampton estate is making an even bigger play the second time around. Once owned by Calvin Klein, the sprawling oceanfront compound returned to the market in the month of June with a $165 million price tag, putting it within striking distance of the Hamptons’ long-standing residential sales record. Scroll down to read the story of its trajectory.
A storied East Hampton address
More than a decade ago, hedge fund manager Barry Rosenstein set the benchmark for East Hampton real estate when he paid $147 million for an 18-acre property. That record has held ever since, but the latest listing could put it under pressure.According to a report by ELLE Decor, Klein sold his own East Hampton estate in 2021 in an off-market transaction reportedly valued at $85 million. The fashion designer had owned the property since 1987, when he purchased the roughly 8,900-square-foot home with his then-wife, Kelly Rector.The estate had already enjoyed a notable pedigree. Klein and Rector acquired it from the family of Juan Trippe, the former president of Pan American World Airways, and later brought in renowned architect Thierry Despont for an extensive renovation.
A 19th-century home with modern flair
Originally built in the 1890s, the main residence was designed by Joseph Greenleaf Thorp, the architect behind the famous Grey Gardens property. The Shingle Style home retains many of the period details that give it its character, including beamed ceilings, wide-plank floors, wainscoting and crown molding.Those traditional elements sit alongside decidedly contemporary touches. Inside, a mirrored catwalk stretches across the living room, while a dramatic two-story fireplace creates a striking focal point.The property also expanded beyond the main house during Klein’s ownership. A pool was added to the grounds, along with a boathouse on Georgica Pond. The boathouse is reportedly the only working one on the coastal lagoon.
A major new renovation
As per the ELLE Deco report, the current owner has undertaken another significant round of improvements, bringing the historic estate up to modern standards without stripping away its old-world appeal.Updates include impact-resistant windows and doors, energy-efficient heating and cooling systems, smart-home technology and advanced security. The result is a property that combines the architectural character of a centuries-old East Hampton retreat with the infrastructure expected of a contemporary luxury compound.Outside, the amenities are equally substantial. A red-clay tennis court, expansive entertaining spaces and 500 feet of ocean frontage give the estate an unmistakably resort-like feel.
Room to build even more
Perhaps one of the most significant details is the property’s development potential. The 8.22-acre compound can be divided into two parcels, with one parcel carrying its own building rights for an additional residence.That flexibility adds another layer of appeal to an already rare offering. Between its ocean frontage, architectural history, celebrity provenance and substantial acreage, the former Calvin Klein estate is now positioned as one of the most closely watched luxury listings in East Hampton.Images Courtesy: Instagram