The Playboy Mansion – $100 Million, L.A.

Hugh Hefner was an American magazine publisher and life-stylist. He was the founder and editor-in-chief of the Playboy magazine. Unfortunately, he moved on to greener pastures in 2017 at age 91, leaving behind an abundance of wealth and investments for his children. During his heyday, Hefner was known for hosting lavish parties at his villa with socialites and celebrities in attendance.

His Playboy mansion boasts of round-the-clock staff as well as an underground cellar, screening room, game room, gym, spa, three zoos, photography studios, waterfall, and three fully grown forests. The thought of property insurance for an estate of this size would likely stun us, but its new owner, Dean Metropoulos, certainly would not bat an eyelash over the amount as he is also one rich guy. The billionaire investor also wanted to preserve the legacy of the mansion, so he applied for permanent protection, which would disallow the demolition of the house.