Tommy Hilfiger’s highest reported home sale in the available coverage was his Greenwich, Connecticut, estate at 30 John St., which sold for $45 million in 2021. Other notable transactions include a Palm Beach home reported sold for $41.4 million in 2023 and the couple’s Plaza Hotel penthouse, reported sold for $31.25 million in 2019. The available reporting does not substantiate a definitive ranking of eight homes, so the properties below are presented as documented deals—not as a verified top-eight countdown.
How to read the reported prices
These figures refer to different stages of ownership: a purchase price is what the Hilfigers reportedly paid, an asking price is a seller’s proposed amount, and a sale price is the reported amount at closing. They are not comparable appraisals. The strongest local reporting here concerns the two Greenwich transactions; several Florida and New York figures come from secondary coverage.
Highest reported completed sales
30 John St., Greenwich, Connecticut — $45 million sale in 2021
The Hilfigers bought the 22-acre property in 2010 for $31 million, according to property records cited by Greenwich Time. The six-bedroom French Normandy-style estate was listed at $47.5 million before its reported $45 million sale in January 2021. Greenwich Time and its listing report cover the transaction and property details.
300 Clarke Avenue, Palm Beach — $41.4 million sale in 2023
Realtor.com reported that Hilfiger bought this Palm Beach home for $36.9 million in 2023. The Real Deal later reported a $41.4 million sale after about five months. These are two stages of the same property’s short ownership period, not two separate homes. Realtor.com; The Real Deal.
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Plaza Hotel penthouse, New York City — $31.25 million sale in 2019
Realtor.com reported that the couple sold their Plaza Hotel penthouse for $31.25 million in 2019. The Hilfigers had reportedly bought two units for $25.5 million, then combined and renovated them. Realtor.com.
Palm Beach Mediterranean-style mansion — $35 million sale in 2017
Realtor.com reported a $35 million sale in 2017, approximately $1 million above the reported purchase price a year earlier. The coverage does not provide the same transaction-record detail available for the Greenwich estate, so treat the figure as a reported sale rather than a directly verified public-record amount. Realtor.com.
Golden Beach, Florida — $24.5 million sale in 2020
The Hilfigers reportedly bought this oceanfront home for $17.25 million in 2013. It was later offered at $27.5 million and then $25.9 million before a reported $24.5 million sale in 2020. The asking prices were not sale prices. Realtor.com.
Stone Hill, Round Hill Road, Greenwich — $20 million sale in 2009
This earlier Greenwich estate was a separate property from 30 John St. Greenwich Time reported that Hilfiger bought the eight-bedroom, 20,000-square-foot home in 2005 for $18 million. It was originally offered for $27.9 million and sold for $20 million in November 2009. Greenwich Time.
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Waterfront home bought in 2021 — $21 million
Realtor.com reported a $21 million purchase for a roughly 5,000-square-foot, three-bedroom Palm Beach home. The amount is a reported purchase price, not a later sale figure. Realtor.com.
Another Palm Beach purchase reported in March 2021 — $9 million
The same Realtor.com coverage mentions a separate $9 million Palm Beach purchase in March 2021, but the available description does not fully identify that property. It should not be conflated with the roughly 5,000-square-foot waterfront home or with the later 300 Clarke Avenue transaction. Realtor.com.
Rank #4
Why this is not a verified eight-home ranking
Coverage also mentions homes in Aspen, Connecticut, New York, and Mustique, but the available reports do not establish purchase prices, sale prices, or ownership dates for Aspen or Mustique. Architectural Digest’s broader account names Aspen, Connecticut, and New York without supplying the missing transaction details; another report mentions Mustique. Those references are not enough to place the properties in a price ranking. Architectural Digest; realestate.com.au.
The Raleigh is a hotel, not a residence. Although a 2017 report says Hilfiger bought it in 2014, it does not belong in a homes list without a separate reason for including hospitality properties. Architectural Digest.
Best Value
A 2022 Real Deal PDF report also says the Hilfigers sold 244 Fairview Road, a non-waterfront Palm Beach home, to Bret Baier for $12 million after paying $9 million the prior year. Because the report surfaced as a PDF copy rather than a confirmed original article, it is weaker evidence than the transactions above and is not used to bolster a definitive ranking. The Real Deal PDF.
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