Oprah Winfrey | Montecito, California, 100 Million

Oprah Gail Winfrey is an American talk show host, TV show producer, actress, writer and philanthropist. The media mogul Oprah Winfrey is one of the finest self-made women in the industry and she single-handedly lifted her family from the poverty line, making billions of dollars throughout her career. Money issues and bankruptcy will never be an issue for this lady right here and she proves this with her extravagant yet humble home in Montecito, California, which was dubbed “The Promised Land.”

It covers 42 acres of land with a straight upshot of the ocean and mountains. She bought it for $50 million in 2001 and it has a current value of around $100 million. Her house in The Maui estate now spans a colossal 163 acres and in 2010 she was granted permission to run a bed and breakfast on the site. Oprah has made use of the fertile ground and amazing climate and now grows fruit, vegetables and flowers on the site.