Oprah Winfrey
Price: $88 million*
Location: Montecito, CA
Oprah is the epitome of what can be accomplished when you put your mind to it. Winfrey didn’t have the best start in life, yet she went on to build one of the world’s largest media empires. Oprah is now worth more than $1 billion, much of which she has spent on her vast Montecito estate, dubbed “Promised Land.” The lovely estate, which sits on 42 acres in Santa Barbara, was purchased by Winfrey after she attended a party there in 2001. The owners first refused to sell, but they quickly changed their minds once the TV star brought out her checkbook and offered them an estimated $52 million.