The Most Expensive Celebrity Homes

Oprah Winfrey is one of the wealthiest women in entertainment, so it isn’t surprising she boasts one of the most impressive homes. In addition to other properties she owns around the country, she plopped down $50 million on her mansion in 2001.

Microsoft guru Bill Gates has amassed a fortune and isn’t afraid to spend it on a fortress! The internet legend built 'Xanadu' in Washington State, the largest private residence in the US, for a whopping $55 million in 1997.

Will Jada Pinkett Smith are one of Hollywood’s biggest power couples, so it isn’t shocking that they own a massive 25,000 square foot mansion in Calabasas that was featured in Architectural Digest in 2011.

Hugh Hefner’s Playboy Mansion is one of the most famous properties in the world and is said to be worth of $50 million.

Jerry Seinfeld’s East Hampton home is no joke! The Seinfeld star purchased the impressive property in 2005 for $32 million.

Arnold Schwarzenegger listed his stunning Brentwood property for $23 million in 2011.

Jennifer Aniston isn’t afraid of dropping money on homes! The Friends star is the proud owner of this $21 million Bel Air mansion.

Simon Cowell lives in luxury with his $25 million Beverly Hills mansion!

Matt Damon resides in the Pacific Palisades area of Los Angeles, in a stunning $16 million home.

Maria Shriver downgraded a little bit after moving out her Brentwood mansion, opting for this $12,220,000 property.

Petra Ecclestone dropped $85 million on the Spelling Mansion, which was a steal considering its’ initial $150 million pricetag.

Kim Kardashian and Kanye West recently dropped $11 million on their Bel Air love nest.

Tiger Woods is living it up in Jupiter, FL, where he owns a $60 million estate.

Gwyneth Paltrow and Chris Martin own homes all over, but their Brentwood pad ain’t too bad at $10,450,000!

Jessica Simpson and Eric Johnson recently plopped down $13 million on Ozzy and Sharon Osbourne’s Hidden Hills estate.

Ryan Seacrest is an American Idol when it comes to his Beverly Hills home, which cost him $37.5 million.

Rihanna isn’t exactly slumming it in her $12 million Pacific Palisades home!

Rod Stewart lives a rock star, with several impressive homes including this $12.5 million Palm Beach estate.

Ashton Kutcher’s $10.8 million Hollywood Hills home is no laughing matter!

It pays to be Conan O'Brien, who resides in a swanky $20 million Pacific Palisades pad.