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.

The listing describes the home’s historic roots:

Designed by noted architect Greville Rickard and built in 1939 for real estate magnate Charles V. Paterno, this Great Estate later became the home of famed financier and art patron Joseph H. Hirshhorn, who displayed his eminent art collection and sculpture garden here before gifting it to the Hirshhorn Museum in Washington.

The renovations were done by Andre Tchelistcheff Architects, Xhema Industries, interior designers Martyn Lawrence Bullard and Cindy Rinfret of Rinfret, Ltd., and landscape designer Miranda Brooks.

Immaculate gardens, a mix of French and English styles, greet you upon arrival and lead to the turreted entrance. The home is made more majestic thanks to mature, climbing ivy.

Upon entering is the “great hall,” perhaps the grandest room of all. There are painted beamed ceilings, incredible carved millwork, an 18th-century French fireplace, and a baronial Elizabethan-style staircase that spirals upward inside the leaded-glass bay.

The Hilfigers took care in the renovation to preserve the home’s many historic elements, including tons of elaborately carved wood-paneling, intricate plasterwork, six fireplaces, and wide-board and limestone floors.

In the kitchen, old-world style mixes with modern conveniences. An adjacent breakfast room is beyond cozy.

Other entertaining spaces include a family/game room, a lower-level wine cellar/tasting room, and a home gym.

There’s also a media room that was inspired by Ms. Ocleppo’s Turkish heritage, according to the Post. “It has a candy machine, popcorn, sofas, and different levels of chairs,” listing agent Janet Milligan told the paper.

In total, there are six bedroom suites. The main suite has two bathrooms, two dressing rooms, and an office/study.

As the listing notes, “most first-floor rooms open to engaging outdoor living spaces.”

The landscaping includes a fountained rose garden, boxwood knot garden, water garden with fountained koi pond, a topiary garden, and a great lawn facing the Long Island Sound.

There’s also a gorgeous pool, tennis court, greenhouse, four-car garage, and guest house with its own two-car garage.

The Hilfigers are not strangers to the Greenwich, Connecticut real estate market. The Post says “this is the eighth house the couple has renovated and sold over the last 35 years.” And Mr. Hilfiger is not the only one unloading homes. His ex-wife Susie Hilfiger, with whom he is still very close, is selling her own Greenwich estate. According to Mansion Global, the then-couple bought the property known as Denbigh Farm in 1995 for $8.5 million. Some of the lavish, personalized amenities include a playhouse built to scale of Mount Vernon, a meat locker, a marble mantle imported from the Hermès family’s former Paris home, sunken English gardens, and a special room to house Ms. Hilfiger’s vase collection. She told Mansion Global that she is selling to move to the west coast where her children live.

In 2019, Mr. Hilfiger sold his famous penthouse at The Plaza for $33.25 million. He and Ms. Ocleppo first listed the apartment in 2013 for $80 million but chopped the price several times.

Mr. Hilfiger and Ms. Ocelppo decided to sell Round Hill because they are relocating to Palm Beach, Florida. Sally Slater of Douglas Elliman represented the buyer.

[Listing: 30 John Street by Janet Milligan of Sotheby’s International Realty]

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All listing photos by Samuel Rodriguez & Steve Rossi for Sotheby’s International Realty