Oprah Winfrey –  $50 Million, California

Media mogul Oprah Winfrey is one of the most successful TV personalities of all time with an estimated net worth of close to $3 billion. Aside from her generosity, Oprah likewise possesses the savvy mind of a real-estate investor. Her biggest one to date is her 23,000-square-foot mansion. It sits on over 40 acres of plantation and is estimated to be around $50 million. However, due to Winfrey’s lavish taste, and a bank account to support it, the overall price of the house, together with the luxuries and amenities, can be listed at around $165 million.