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

The Playboy mansion was initiated by non-other than the legend, Hugh Hefner. The glory days may have passed this beautiful estate, but this deluxe house will forever go down as the most famous party-house in Hollywood. The 22,000-square-fοοt property has 29 bedrooms, 3 zoos, a wine cellar, game room, screening room, tennis and basketball courts, photography studios, and huge swimming pools. And if that wasn’t enough, we’re sure the home insurance for the property is certainly bigger than some of the guests’ annual income.