Oprah Winfrey – Estimated $165 Million, California

Oprah Winfrey was living very close to bankruptcy growing up so it was really an achievement for her to be able to build a billion-dollar fortune. She lives in an immense 40-acre estate in California which reportedly cost $165 million. The 23,000-square-foot mega-mansion is so big that we bet it’s easy to get lost inside the place.

The estate apparently has rose bushes to add that fresh, garden ambiance. We’re not sure if Oprah should be proud of her massive house, or if the house should be proud of hosting Oprah; after all, she’s one of the most powerful women alive and one of the most universally beloved celebrities ever.