In 2010, Tommy Hilfiger and Dee Ocleppo Hilfiger paid $31.4 million for the 22‑acre, 13,300‑square‑foot French Normandy‑style mansion at 30 John St. on Greenwich’s Round Hill, a purchase that landed them on the highest point in the town and a property with sweeping Long Island Sound and Manhattan skyline views—source: Greenwich Time.
The Hilfigers’ three‑year restoration, detailed by Architectural Digest, replaced the original roof with handmade tiles, overhauled mechanical systems, and restored ceilings, moldings, and floors. The interior received a new chef’s kitchen, updated bathrooms, a theater room, and a wine cellar, while the outbuildings were upgraded and a new swimming pool and tennis court added—source: Architectural Digest.
After the extensive work, the estate was listed for $47.5 million, but buyers agreed on $45 million, a price that still exceeded the original purchase and reflected the restored luxury—source: Greenwich Time.
The property’s architectural pedigree stretches back to 1939, when architect Greville Rickard designed it for real‑estate magnate Charles Paterno. It later housed financier Joseph Hirshhorn, whose art collection was later donated to the Washington, D.C. museum that bears his name, adding historical cachet to the grounds.
The sale coincided with the Hilfigers’ planned relocation to Palm Beach, Florida. The pandemic accelerated their move, reshaping priorities for high‑end homeowners and boosting activity in luxury markets across the country.
With the transaction complete, the couple will transfer to their new Florida home, while Greenwich’s luxury market continues to attract buyers willing to pay premium prices for historic estates that blend heritage with modern amenities.