Connecticut Manor
"In The Hilfiger's Manor, we drew inspiration from a 19th-century English gentleman's country estate."
Originally designed by renowned architect Greville Rickard in 1939, this sprawling property sits at the summit of Round Hill, the highest point in Greenwich, offering unparalleled views of Long Island Sound and the Manhattan skyline.
The main house spans an impressive 13,344 square feet, featuring six bedrooms, seven full and three half bathrooms, and six fireplaces, with a blend of hardwood and limestone floors throughout. When the couple first purchased the home, it was “in disrepair,” as Ocleppo shared with Architectural Digest in 2017, but they “knew that this would be [their] home.” They enlisted architect Andre Tchelistcheff to oversee renovations and called upon decorator Martyn Lawrence Bullard to enhance the common living spaces.
“You can’t have a house like this and make it Americana,” Hilfiger told *AD* at the time, referencing his signature aesthetic. “It’s an English manor with French details. We wanted to preserve the feeling of being in a European country home, complete with carved-oak paneling and a patina that is authentic and a bit worn.” Outside the main house, the property features sculptural hedges, water fountains, a topiary garden, a tennis court, and other amenities designed by Miranda Brooks.
