1. Oprah Winfrey

Price: $88 million*
Location: Montecito, CA

Oprah Winfrey’s story is inspiring. Despite a tough start, she built a massive media empire, now worth over $1 billion. She invested a big chunk in her grand Montecito home, “Promised Land.” It’s on 42 acres near Santa Barbara, which she bought after a party in 2001. The owners initially hesitated but sold it for around $52 million when Oprah made the offer.