OPRAH WINFREY | $100 MILLION, MONTECITO

For Oprah Winfrey’s rise to celebrity stardom, it’s safe to say that a portion of the credit goes to her grandmother. Throughout her childhood, Oprah enjoyed interviewing her dolls, and seeing this, her grandmother greatly motivated her to take to the stage. Since then, she has made quite a name for herself in the entertainment industry, best known for her stint as host in the beloved show The Oprah Winfrey Show.

With all the fortune she’s earned through the years, Oprah accumulated more than enough to buy herself a few houses. One such property is so extravagant, so luxurious, that she even named it “The Promised Land.” Bought around 2001 for $52 million, Oprah’s 23,000-square-foot mansion sits on a massive 70-acre plot and is now reportedly worth approximately $100 million! With that said, this humble abode features a koi pond, a swimming pool, a pool house, and a separate 4,000-square-foot guest house.