Celebrity Real EstateTommy Hilfiger Sells Contemporary Aspen Ski Home for $50 MillionThe fashion designer and his wife only owned the place for three months—and turned a $19 million profit

By Rachel Davies

March 24, 2022

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PROJECT RUNWAY -- "Finale" Episode 1914 -- Pictured: Tommy Hilfiger -- (Photo by: Greg Endries/Bravo/NBCU Photo Bank via Getty Images)Bravo

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If there’s one thing Tommy Hilfiger and his wife, Dee Ocleppo, know just as well as fashion it must be real estate. Last year they earned their spot on the list of top celebrity real estate transactions with the $45 million sale of their Connecticut home, and now, according to the Wall Street Journal, they’ve broken their own record with the sale of an Aspen ski home for $50 million.

Hilfiger and Ocleppo bought the 7,150 square foot property just three months ago in December of last year. At the time they paid $31 million, leaving them with a rather seamless $19 million profit. According to the Wall Street Journal, Compass agent Stephen Shane represented both buyers in the off-market deal, and though Hilfiger himself declined to comment, Shane was able to provide insight. “It was never their intention to buy it and sell it," Shane told WSJ. “It's difficult to pry a property like this one away, but I think everything has a price.”

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Conveniently located on the trendy Little Nell Ski Trail on Aspen Mountain, the contemporary space contains four bedrooms and nine bathrooms. Sloped ceilings combined with the sleek wood paneled interiors to create a chic take on the traditional coziness of a lodge, with rooms spread between four natural-toned levels.

For now Hilfiger and Ocleppo are left to enjoy a much more balmy springtime in one of the two Palm Beach, Florida properties they purchased last year for $9 million and $21 million, respectively, or perhaps someplace even warmer on their Americana-inspired yacht, which is aptly known as Flag. In recent years, Hilfiger and Ocleppo have parted ways with other massive properties including an apartment at the Plaza hotel and a castle-like dwelling in Connecticut.  

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