Tommy Hilfiger | $47.5 Million | Greenwich, Connecticut

You probably see the name Tommy Hilfiger on perfumes and just think of it as a brand. He is, however, a very real person and is the founder of his namesake corporation. Building a fashion empire in upstate New York backin the ‘70s was what kept him busy then. Primarily focused on men’s clothing, he decided to expand it to cater to women’s fashion as well. His fashion directions are usually influenced by music, so it can change rather significantly.

Hilfiger likes his garden, so his 22-acre estate in Greenwich has a number of them spread all around the massive land. There is also a water garden, which could make those engaged in plumbing services a bit dizzy due to its size. This is in addition to a massive swimming pool and tennis court. It is only expected that when stressed out in New York, the entrepreneur would travel the distance to relax in his palatial home.