Price: $47.5 million*
Location: Greenwish, Connecticut

Despite making a name for himself in the fashion world, Tommy Hilfiger is also well known in real estate as a house flipper. He’s invested millions from his world-famous fashion brand into restoring some of the country’s oldest homes and estates, and sells them on for very impressive profits.

He purchased this property, known as Round Hill, in 2010 with his wife Dee Ocleppo. After a year of total restoration, redecorating, and modification, the estate they originally purchased for a little over $31 million has now been sold for $45 million. His first wife, Susie Cirona, also lives in the area and sold her own Greenwich estate around the same time for $40 million.