5. Tommy Hilfiger’s Mansion – Greenwich, Connecticut

On the Market Since: 2020
Total Area: 13,344 square feet 
Initial Value: $48 million*

This is one of the newer list mega-mansions to hit the market. Fashion designer and millionaire Tommy Hilfiger is selling his Greenwich, Connecticut mansion for $47.5 million via Sotheby’s International. This continues the 2020 trend of affluent New Yorkers fleeing to nearby rural destinations and states, as opposed to staying in the city limits.

Hilfiger’s castle was originally called Chateau Paterno, and it was built for Charles Paterno in 1939. The real estate magnate hired Greville Rickard, a superstar graduate from Yale to build it. Twenty years later, Joseph Hirshhorn, an art collector, bought the property and used it to house 6,000 19th- and 20th-century sculptures and paintings. 

He decided to try to sell his mansion after hearing that the real estate market was “strong,” according to the Wall Street Journal. Hilfiger and his wife are relocating to Palm Beach, Florida. His residence measures 13,344 square feet and was built in 1939. It has water and rose gardens, as well as a four-bay garage, greenhouse, and guest cottage. The home has had no takers so far, which has surprised agents.