Price: $88 million*
Location: Montecito, CA

Oprah is the perfect example of what can be done when you set your mind to it. Winfrey didn’t have the greatest start in life, but she managed to create one of the biggest media empires in the world. Now worth over $1 billion, Oprah has spent a large portion of that on her sprawling Montecito home, named “Promised Land.” 

Sitting on 42 acres near Santa Barbara, the idyllic home was actually snapped up by Winfrey after she attended a party there in 2001. Initially, the owners didn’t want to sell, but they soon changed their minds once the TV personality pulled out her checkbook and offered them a reported  $52 million.