Tommy Hilfiger flipping eighth Connecticut home for $47.5M

If the jeans fit, buy them. But if Tommy Hilfiger’s Greenwich, Conn., estate suits your needs, prepare to reach deeper into those pockets. The fashion designer has put his palatial property in the posh county on the market for $47.5 million. The Wall Street Journal first reported the listing. Hilfiger is a serial house-flipper in …

If the jeans fit, buy them.

But if Tommy Hilfiger’s Greenwich, Conn., estate suits your needs, prepare to reach deeper into those pockets.

The fashion designer has put his palatial property in the posh county on the market for $47.5 million. The Wall Street Journal first reported the listing.

Hilfiger is a serial house-flipper in the affluent Manhattan suburb: the 69-year-old sartorial star has fixed up and sold a total of seven homes over the last 35 years, the Journal noted. This would be his eighth.

Hilfiger and his wife, 53-year-old former model Dee Ocleppo, are selling their French Normandy-style mansion, set on nearly 22 acres, at a time when many New Yorkers have set their sights on Connecticut, as work and schooling continue to happen at least partly virtually. In May, Connecticut saw a “tidal wave” of city residents who fled the then-pandemic-ravaged city. The coronavirus crisis led to a massive uptick in local markets that has lasted into the summer and fall.

“I hear from my friends in real estate that the market is very strong, and it hasn’t been this strong in years,” Hilfiger told the Journal, adding that he and Ocleppo will move to Palm Beach, Fla.

The couple is known for major real-estate moves. In the fall of 2019, Hilfiger and Ocleppo sold their Plaza Hotel penthouse for $31.25 million, a far cry from its highest $80 million ask in 2013. That four bedroom spent 11 years on and off the market, all the while undergoing price cuts. Hilfiger purchased the corner duplex for $25.5 million in 2008, then sought to flip it for $50 million several months later.

The pair bought this Greenwich estate, known as Round Hill, for $31.37 million in 2010. Dating to 1939, it previously belonged to the real-estate investor Charles Vincent Paterno and, later, the art collector Dr. Joseph Hirshhorn. After buying it in 2010, Hilfiger and Ocleppo spent millions of dollars renovating the home over three years — including redoing all the mechanicals, replacing the roof and tapping a company in Turkey to create replicas of the original terra-cotta tiles.

The residence spans a massive 13,344 square feet, with six bedrooms, seven full bathrooms and three powder rooms. Inside, a Turkish-inspired screening room has hand-painted fabric walls, while the family room has an 18th-century French fireplace. There’s also a lower-level wine cellar and tasting room. A guest house has a kitchen, two bedrooms and its own two-car garage.

Outdoor features include a fountained rose garden, a koi pond, a pool, a renovated tennis court and a lawn that looks out to the Long Island Sound.

Janet Milligan of Sotheby’s has this listing.