Tommy Hilfiger’s most expensive reported home sale was his Greenwich, Connecticut, estate at 30 John St., which sold for $45 million in 2021. Other high-value transactions tied to the fashion designer include a $41.4 million Palm Beach sale in 2023 and a $31.25 million sale of his Plaza Hotel penthouse in 2019. The available reporting does not verify a definitive ranking of eight homes, so the properties below are presented by reported transaction value—not as a confirmed top-eight list.
How to read the reported prices
These figures describe different stages in a property’s history: purchase prices, asking prices and completed sales. They are not appraisals made on the same date or a standardized comparison of current home values. Each amount below is identified by transaction type and year, and the homes are grouped by their strongest reported sale figures.
Homes with the highest reported sale prices
30 John St., Greenwich, Connecticut — reported sale: $45 million in 2021
The Hilfigers bought this 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 for $47.5 million before selling for $45 million in January 2021. The purchase and sale figures are reported by Greenwich Time; the listing and property details were also reported by Greenwich Time.
300 Clarke Avenue, Palm Beach, Florida — reported sale: $41.4 million in 2023
The Hilfigers reportedly bought this Palm Beach home for $36.9 million in 2023. The Real Deal reported that they sold it for $41.4 million after about five months. The purchase and sale were covered separately by Realtor.com and The Real Deal.
#1 Best Overall
Plaza Hotel penthouse, New York City — reported sale: $31.25 million in 2019
The couple reportedly bought two Plaza Hotel units for $25.5 million, combined them and renovated the resulting penthouse. Realtor.com reported the 2019 sale at $31.25 million. Those amounts are transaction reports, not an estimate of the penthouse’s current value. Realtor.com
Palm Beach Mediterranean-style mansion — reported sale: $35 million in 2017
Realtor.com reported that the Hilfigers sold this mansion for $35 million in 2017, roughly $1 million more than the reported purchase price a year earlier. The available coverage does not provide the same level of transaction-record detail as the Greenwich reporting. Realtor.com
Rank #2
Golden Beach, Florida, oceanfront home — reported sale: $24.5 million in 2020
The reported timeline distinguishes the asking prices from the completed sale: the Hilfigers bought the oceanfront home for $17.25 million in 2013, later asked $27.5 million and then $25.9 million, and sold it for $24.5 million in 2020. The listing amounts were not sale prices. Realtor.com
Other reported home transactions
Stone Hill, Round Hill Road, Greenwich — reported sale: $20 million in 2009
This was a separate Greenwich estate from 30 John St. Greenwich Time reported that Hilfiger bought the eight-bedroom, 20,000-square-foot Stone Hill property for $18 million in 2005. It was initially offered for $27.9 million and sold for $20 million in November 2009. Greenwich Time
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Rank #3
244 Fairview Road, Palm Beach — reported sale: $12 million in 2022
A Real Deal report says the Hilfigers sold this non-waterfront home to Bret Baier for $12 million in 2022, after paying $9 million the prior year. The report was circulated as a PDF copy, so the transaction is less firmly documented here than the locally reported Greenwich sales. The Real Deal
Palm Beach waterfront purchase in 2021 — reported purchase: $21 million
Realtor.com reported a $21 million purchase of a roughly 5,000-square-foot, three-bedroom Palm Beach home in 2021. Its coverage also mentions another Palm Beach purchase in March 2021 for $9 million, but does not fully identify that second property. Because no completed sale price is established for these purchases in the cited reporting, they should not be ranked alongside the completed sales above. Realtor.com
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Why this is not a verified eight-home ranking
Coverage mentions additional locations, including Aspen, Connecticut, New York and Mustique, but the available reports do not establish purchase or sale prices, ownership dates or current ownership for those properties. Architectural Digest and realestate.com.au mention locations, but do not supply enough verified transaction data to rank them. Nor should The Raleigh, a hotel Hilfiger reportedly bought in 2014, be counted as a home. realestate.com.au
On the evidence available, the clearest comparison is between documented or reported transactions: the $45 million Greenwich sale in 2021, the $41.4 million Palm Beach sale in 2023 and the $31.25 million Plaza penthouse sale in 2019. They are separate properties in different markets and years, not a like-for-like measure of present-day worth.
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