Hugh Hefner | $113 Million | Holmby Hills

The founder and editor in chief of a famous men’s magazine, Hugh Hefner, certainly lived the life. He was a very vocal advocate of artistic freedom of expression, and, therefore, the First Amendment Rights. While Hefner lived a very liberal life, he actually hailed from a rather conservative family. He also served in the military from 1944 to 1946, writing for the military newspaper. He even took graduate courses in Sociology but never got the degree as he dropped out later on.

Hefner bought a mansion in Holmby Hills for $1 million back in 1974. Over the years and after many parties, renovation, and value appreciation, the house is now worth $113 million. The Tudor-styled house has 29 rooms, a fireworks permit, and, interestingly, a zoo license. With Hefner passing away, the ownership of the house changed hands and is now under the care of Daren Metropoulos, a billionaire.