OPRAH WINFREY

These days, Oprah Winfrey is considered to be one of the wealthiest self-made women in the world. She is also seen as the most influential figure in media, though some argue that her impact can be felt around the world. Winfrey has had many titles over the years, including being a host, actress, producer, and author. She was at the helm of The Oprah Winfrey Show for years and is the driving force behind its inimitable success.

Winfrey might be enjoying a lavish lifestyle currently, but before all that fame, fortune, and power, she lived in a modest home in Chicago. Located in the Elmwood Park neighborhood of the city, this cozy little abode is known to be the last property she owned in the Windy City. She made the investment in 2001 for $298,000, but eventually sold the property for $375,000 in 2018.