Not long after popular fashion designer Tommy Hilfiger sold his Greenwich estate, his ex-wife listed one for $40 million.

Married between 1980 and 2000, the Hilfigers have called the affluent Connecticut town home for decades, but both are now planning to leave. Mr. Hilfiger sold the 22-acre estate where he lived with his new wife Dee Ocleppo for $45 million, as first reported by the Wall Street Journal.

The main house is built in a French Normandy-style and sits at the highest point of Greenwich. The home is filled with elaborate wood work and intricate coffered ceilings, and has multiple fireplaces and extensive closets, as well as a screening room. The manicured grounds, designed by renowned landscape architect Miranda Brooks, include a swimming pool and tennis court.

Famed architect Greville Rickard built the property in 1939. Mr. Hilfiger and Ocleppo bought it in 2010 for $31.375 million and undertook a massive restoration and modernization — from redoing all the plumbing to hiring a company in Turkey to reproduce the terra-cotta tiles that were part of the house’s exterior.

Ms. Hilfiger, meanwhile, listed a summer estate known as Denbigh Farm for $40 million this week. Bought during their marriage in 1995 for $8.5 million, the 20-acre estate has been around since the 1700s. Allan Greenberg, an architect well-known for his classic style, renovated the property. The landscaped grounds include spacious lawns, formal English gardens, as well as a playhouse modeled after the residence of George and Martha Washington.

At over 14,000 square feet, the main house is decked out in luxury — a flower-arranging room, hand-painted Chinese wallpaper, a ballroom with a marble mantle imported from Hotel Particulier Montmartre, a 17th-century hotel once home to the Hermès family. Decorations include fine art and antiques such as furniture once belonging to the Duke and Duchess of Windsor.

Janet Milligan of Sotheby’s International Realty was the agent who represented both Mr. and Ms. Hilfiger. The buyer of the $45-million estate, whose identity is being kept anonymous, was represented by Sally Slater of Douglas Elliman.

“They both get along very well,” Milligan said of the former couple to the Wall Street Journal. “They are both creative people with excellent taste.”

Mr. Hilfiger’s preppy, all-American style at affordable prices has kept his clothing consistently popular since the 1980s. The fashion designer is worth an estimated $450 million.

Much like the Hamptons, Greenwich has been a popular place for some of the country’s wealthiest people to wait out the pandemic — local agent Chris Finlay told us this summer that both rentals and sales were being snapped up after just a few days on the market.

But it seems like the Hilfigers, who have four grown children together, may have outgrown the town. While Ms. Hilfiger is selling to be closer to her children on the West Coast, Mr. Hilfiger has made a habit of buying and later flipping homes. He and Ocleppo sold a Mediterranean-style mansion in Palm Beach for $35 million in 2018 and listed his pop-art-style mansion in Miami for $24.5 million earlier this year.

Email Veronika Bondarenko

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