Tommy Hilfiger Lists His Regal Connecticut Estate for $47.5 Million

Jeff Vasishta for Dirt
·4 min read

SELLER: Tommy Hilfiger, Dee Ocleppo

LOCATION: Greenwich, Connecticut

PRICE: $47.5 million

SIZE: 13,344 square feet, 6 bedrooms, 8.5 bathrooms

Mere days after recently re-listing his vibrantly colorful, pop-art-filled waterfront spread in Miami for $24.5 million, American retail fashion tycoon Tommy Hilfiger has also hoisted his European-inspired estate in exclusive Greenwich, Conn. onto the market with a publicity-assuring $47.5 million asking price.

The turreted manor house appears transported from a Disney movie set in the French countryside, and is perched on the highest piece of land in Greenwich, in an exclusive area known as Round Hill. With six ensuite bedrooms, seven bathrooms and three powder rooms in 13,344 square feet, the regal, ivy-clad manor house has almost as much wood within — ceiling beams, floors, doors, wall paneling, staircases, wainscoting, ceilings, mantelpieces, moldings and more — as there are verdant acres of forest outside.

Adding to the estate’s storybook vibe are terracotta roof tiles, Holland brick walls and miles of privet hedges that define the estate’s many gardens: a fountain rose garden, a boxwood knot garden, a water garden with koi pond and a fanciful topiary garden. Amongst all that carefully maintained greenery is a bean-shaped pool and a grass tennis court. The estate’s high, castle-like perch allows for panoramic vistas that stretch to the Long Island Sound and the Manhattan skyline.

But the house didn’t, however, always look this way. Designed by architect Greville Rickard and built in 1939 for real estate magnate Charles V. Paterno, the 22-acre spread has a rich history of being passed down from one financial aristocrat to another. It was once owned by financier and art patron Joseph H. Hirshhorn, namesake of the Hirshhorn Museum in Washington, D.C., and business development attorney John V. Holten sold it a decade ago for $31.4 million to Hilfiger and his wife of twelve years, Dee Ocleppo, a fashion model turned commodities broker and handbag designer.

Many rooms have been totally redesigned to reflect Hilfiger and Ocleppo’s stylishly eccentric taste. There’s a technicolor red carpet in the Turkish-inspired screening room that resembles a boudin tent, and a ground floor dressing room takes its cue from a high-end boutiques with shimmery floral paper, chenille-like carpets and a chandelier. Along with the six antique fireplaces, original wide-plank floorboards were kept in the main entrance and dining room, while elsewhere is a mix of newer wood floors, as in the kitchen, and limestone tile with wood inlays, as is showcased in the billiards lounge.

Other luxuries include a compact fitness room, a wood-clad massage room and master suite with two bathrooms, two dressing rooms and a private study. A separate two-bed/two-bath guesthouse is fully equipped with living room and kitchen, and the property additionally includes a greenhouse and a charming teahouse converted to a security pavilion.

The Hilfigers, who previously owned another Round Hill estate they sold in 2009 for $20 million, are in the midst of culling their property portfolio. Their current Miami listing follows the sale of Miami Beach’s Raleigh Hotel for $103 million, almost double the $56.5 million they originally paid. After years on and off the market, their quirky Plaza Hotel penthouse sold last year for a reported $31.25 million. Also cut loose from their portfolio was an 11,000 square-foot Mediterranean-style Palm Beach mansion that sold for $35 million, a million bucks more than they paid for it the year before. One property they seem determined to hang on to, at least for the moment, is a plush beachfront mansion in the Hamptons — that one acquired in 2007 for $25.7 million.

Janet Milligan of Sotheby’s International Realty is the listing agent for the Round Hill estate.

See more photos of the home below:

Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home
Tommy Hilfiger Greenwich home

More from Robb Report

Best of Robb Report

Sign up for Robb Report's Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.