Tommy Hilfiger

January 19, 2021

Tommy Hilfiger sells lavish, chateau-style Connecticut estate for $45M

Fashion mogul Tommy Hilfiger has unloaded the last of his Greenwich, Connecticut properties for $45 million, Sotheby's International Realty tells 6sqft. The 22-acre estate was built in 1939 and resembles a French chateau from the outside, with an eclectic, European flair inside. It's located on the summit of Round Hill, the highest point in Greenwich, providing views of the Long Island Sound and Manhattan skyline. Other lavish amenities include a baronial Elizabethan-style spiral staircase, six fireplaces, a pool house, tennis court, and parterre gardens. According to the Post, he and his wife Dee Ocleppo bought the home for $31.37 million in 2010, after which they spent millions more on renovations.
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July 24, 2018

Tommy Hilfiger’s former reality TV-famous Connecticut mansion lists for $6.75M

This incredible Greenwich, Connecticut mansion looks like something out of a television show, and, in fact, it has made many an appearance in the reality tv world. Owned by Tommy Hilfiger until 2006, it was the setting for his CBS design show "The Cut" and his kids' MTV show "Rich Girls." Built in 1999 on nearly five acres, the residence, known as "Appleyard Estate," boasts stone walls and a cobblestone courtyard, a professional grade theater and music studio, a massive pool and hot tub, and tennis courts. And it's just hit the market for $6.75 million.
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September 11, 2017

Tommy Hilfiger again drops price of his Plaza Hotel penthouse to $50M

After making several attempts to sell his pad, fashion designer Tommy Hilfiger is relisting his lavish penthouse apartment in the Plaza for $50 million. Hilfiger and his wife, Dee Ocleepo, first listed the apartment at 1 Central Park South in 2013 for $80 million. After dropping to $75 million in March 2015 and then $69 million, the most recent relisting had the property on the market for $58.9 million in April (h/t Mansion Global). The couple paid roughly $20 million in renovations for the 5,600-square-foot duplex, which features marble-clad rooms, vintage limestone fireplaces from England and a domed room that features a custom-designed “Elouise” mural designed by the children book’s illustrator Hilary Knight.
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November 2, 2016

Tommy Hilfiger chops more than $20M off lavish Plaza penthouse

All-American fashion designer Tommy Hilfiger bought three separate condos in the Plaza in 2008 for a combined $25 million. He and his wife Dee Ocleppo then embarked on a very internationally influenced, $20 million renovation that combined the units into one opulent, 5,600-square-foot duplex, complete with marble-clad rooms, vintage limestone fireplaces from England, and a domed room inside one of the building's iconic turrets that features a custom-designed "Eloise" mural by the books' illustrator Hilary Knight. The couple listed the apartment in 2013 for $80 million, but despite its lavish interiors, it's been on and off the market since then, its price dropping to $75 million in March 2015 and to $69 million a few months ago. The Wall Street Journal now reports that it's reappeared with even sharper discount, dropping 26 percent to $58.9 million.
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August 28, 2014

Impeccably Finished Condo at the Plaza Asks $50 Million

Just weeks after Tommy Hilfiger put his Plaza Hotel estate up for sale, another one is following suit, asking an astronomical $49.5 million, nearly triple the amount it was purchased for back in 2008. However, as ambitious as the price may be, this three-bedroom condo is pretty spectacular. The 3,413-square-foot Art Deco residence has exquisite details, 13-foot ceilings, and stellar views of Central Park—including those of the pond and Gapstow Bridge—from every major room.
Take a look inside this impressive residence
July 30, 2014

Tour Tommy Hilfiger’s Lavish Plaza Penthouse

When we think of Tommy Hilfiger we might imagine him in an all-American, red-white-and-blue outfit, standing in a nautical seashore cottage, but his penthouse at the Plaza couldn't be any more the opposite than this vision. Instead of paintings of beach scenes there are Basquiats and Warhols (20 of the latter, to be exact); rather than white-washed walls there are entire rooms clad in marble; and instead of simple, shabby chic bedrooms there are opulent personal retreats that could fit entire NYC apartments within their footprint. In short, Mr. Hilfiger's city residence is nothing short of regal. He and his wife Dee Ocleppo purchased and combined three separate units in 2008, and they then embarked on a massive renovation of the duplex to emulate the old-world style of the landmarked building.
Take a tour through this magnificent home and see if the couple lived up to goal