For Tommy Hilfiger and wife Dee’s spectacular Connecticut manor house,
…we took inspiration from an English 19th-Century gentleman’s country estate. Filling the house with antiques and collectables from auction houses and dealers around the world, we gave the house layers of personality appropriate to an inherited home passed from generation to generation.
Originally designed by noted architect Greville Rickard in 1939, the sprawling property is situated at the summit of Round Hill, the highest point in Greenwich, and offers up unparalleled views of the Long Island Sound and the Manhattan skyline.
The main house measures an impressive 13,344 square feet with six bedrooms and seven full and three half bathrooms, six fireplaces, and a combination of hardwood and limestone floors throughout. When the couple first bought the home, it was “in disrepair,” Ocleppo told Architectural Digest in 2017, but they “knew that this would be [their] home.” They enlisted the help of architect Andre Tchelistcheff to oversee renovations on the main house, and called upon decorator Martyn Lawrence Bullard to spruce up the common living spaces.
“You can’t have a house like this and make it Americana,” Hilfiger told AD at the time, referencing his own signature aesthetic. “It’s an English manor with French details. And we wanted to preserve that feeling of being in a European country home with the carved-oak paneling and a patina that is authentic and a bit worn.” Outside the main house, the property includes sculptural hedges, water fountains, a topiary garden, and a tennis court, as well as other amenities all designed by Miranda Brooks.