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In 2010, Tommy Hilfiger bought a 22-acre Greenwich estate for $31.4 million; after a three-year restoration of the 13,300-sq-ft mansion, new pool and renewed grounds, it sold for $45 million
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In 2010, Tommy Hilfiger bought a 22-acre Greenwich estate for $31.4 million; after a three-year restoration of the 13,300-sq-ft mansion, new pool and renewed grounds, it sold for $45 million

By WEB DESK TEAM
September 18, 2026 3 Min Read
Comments Off on In 2010, Tommy Hilfiger bought a 22-acre Greenwich estate for $31.4 million; after a three-year restoration of the 13,300-sq-ft mansion, new pool and renewed grounds, it sold for $45 million
In 2010, Tommy Hilfiger bought a 22-acre Greenwich estate for $31.4 million; after a three-year restoration of the 13,300-sq-ft mansion, new pool and renewed grounds, it sold for $45 million
The estate occupies the summit of Round Hill, the highest point in Greenwich, giving it sweeping views across Long Island Sound and toward the Manhattan skyline.

For Tommy Hilfiger, 2021 began with a substantial real estate deal. The fashion designer and his wife, Dee Ocleppo Hilfiger, sold their sprawling Greenwich, Connecticut, estate for $45 million, closing the chapter on a property they had spent years restoring and updating states online report by the Architectural Digest.The 22-acre estate, located at 30 John St. atop Round Hill, had been purchased by the couple in 2010 for $31.4 million. After an extensive renovation, the French Normandy-style property returned to the market with a $47.5 million asking price and ultimately changed hands for $45 million, adds the report.

A landmark at the top of Round Hill

According to Greenwich Time report, the estate occupies the summit of Round Hill, the highest point in Greenwich, giving it sweeping views across Long Island Sound and toward the Manhattan skyline. The main residence was designed by architect Greville Rickard and completed in 1939 for real estate magnate Charles Paterno.Its history also includes financier and art patron Joseph Hirshhorn, who lived at the property and used its grounds to showcase his art collection and sculpture garden. Hirshhorn later donated his collection to the museum that bears his name in Washington, D.C., adds the reportAnd by the time the Hilfigers acquired the estate, its architectural pedigree was well established. Their renovation sought to preserve that character while bringing the house up to modern standards.

Three years of restoration

The 13,300-square-foot mansion underwent a sweeping three-year restoration, explains the online report. This included replacing the roof with handmade tiles, updating the home’s mechanical systems and restoring original architectural details such as ceilings, moldings and floors. The interiors were also reworked with a new chef’s kitchen and updated bathrooms. Beyond the formal entertaining spaces, the house offers a theater room, family and game room, wine cellar and tasting room.A separate guest house adds another layer of space, with a living room, kitchen, two bedrooms, two bathrooms and a two-car garage.The Hilfigers extended the improvements beyond the main residence as well, refurbishing the property’s outbuildings, adding a new swimming pool and restoring the tennis court, adds the online report by Greenwich Time.

Gardens and grounds

The estate’s landscape is nearly as elaborate as the residence itself. Its grounds include a rose garden with a fountain, a boxwood knot garden, a water garden with a fountain and koi pond, and a topiary garden. Other structures include a detached four-car garage, a greenhouse and a former tea house that had been converted into a security pavilion. The combination of historic architecture, extensive grounds and modern upgrades helped place the property among Greenwich’s notable luxury home sales.

A move to Palm Beach

The sale came as the Hilfigers prepared for a long-planned move to Palm Beach, Florida. The relocation had been accelerated by the coronavirus pandemic, which reshaped residential priorities and helped fuel activity in several high-end markets. For the Hilfigers, the transaction marked more than the sale of another luxury home. It was the culmination of a three-year restoration that transformed a historic Greenwich estate while retaining the distinctive character that had made the property noteworthy long before the fashion designer arrived.Images Courtesy: Facebook and Greenwich Time

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13300sqft22acreboughtestateGreenwichgroundsHilfigermansionmillionPoolrenewedrestorationsoldthreeyearTommyus newsus top news
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