Oprah Winfrey – $50 Million, California

For becoming a successful figure in the entertainment industry, perhaps the most supportive fan Oprah Winfrey will ever have is her grandmother, who often said that she had quite a knack for talking. Throughout her childhood, Winfrey would often hold “interviews” with different objects she can find, like a doll or even a crow outside her home. Besides that, it was also her very own grandma, Hattie Mae, that encouraged the now-world-famous TV personality to be more confident with herself whenever she talks in public.

Other than becoming one of the most notable figures present in the entertainment industry, Winfrey has also made many investments in the real estate business over the years. However, among the many properties in her portfolio, her California home is arguably the biggest one. She paid about $50 million for an amazing 23,000 square-foot mansion. Without a doubt, that’s quite the price, but when her renovation expenses are taken into account, the property’s worth skyrockets to a whopping $165 million!