Tommy Hilfiger’s Former Connecticut Castle

521 Round Hill Road, Greenwich, CT 06831


Greenwich Connecticut is home to so many beautiful historic homes, this one is Tommy Hilfiger’s new home with bride Dee Ocleppo. Ocleppo is an up and coming luxury fashion designer whose teamed up with the Tomster to bring the world hand bags most people can only afford with a second mortgage. Tommy likes his homes unique to fit his eccentric style and this one is no different.

From the listing: “Magnificently sited on one of the highest elevations (570’) near the ocean along the entire Atlantic coast, this Pre-War French Normandy estate with breathtaking architecture has unparalleled 180 degree views of New York City skyline & LI Sound. Two double-gated driveways lead to magnificent courtyards beautifully designed in cut stone and framed by velvety lawns, boxwood gardens, flowering trees and bushes, rose and flower gardens. The grounds offer complete privacy with many terraces for entertaining. Classically scaled rooms showcase leaded windows, French doors, incredible quality floors, a dazzling display of intricately carved motifs including a carved circular stairway. Luxury Master Suite w/dual Bedrooms, Baths and Dressing Rooms. Gourmet Kitchen w/Breakfast Room, Butler’s and Service Pantries. Billiard/Exercise/Media Rooms, Guest Suite, In/Outdoor Pools, Gazebos, Greenhouse w/fireplace. Totally updated to exceptional standards –A must see for anyone who wants the best!”

Photo credit: Sotheby’s and Kelly Stuart of Elle Decor

Location is approximate

Estimated value

$33,000,000 (for sale status unknown)


521 Round Hill Road, Greenwich, CT 06831
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