Oprah Winfrey has built an enviable empire. With an estimated net worth of $3.5 billion (yes, billion!), the beloved businesswoman has created a network of endeavors tied to philanthropy, media production and distribution (she recently produced the movie The Color Purple), and so much more. Considering how well-traveled Winfrey is, with personal and business connections all over the country, it’s no surprise the former talk show host has put down roots in multiple locations. For the past two decades, Montecito, California, has remained her main hub. But the multi-hyphenate has also owned homes in nearly every region of the United States, with properties in Illinois, Florida, Hawaii, Colorado, and Washington state. We’ve gathered the highlights of her vast real estate portfolio below.
1985: Winfrey Buys a Chicago Condo
A year before Winfrey’s iconic talk show, The Oprah Winfrey Show, first aired nationally in 1986, the media mogul made one of her first big real estate moves by purchasing a condo in Chicago’s Water Tower Place for an undisclosed amount. Located along the Magnificent Mile, the city’s bustling commercial district, the condo was the first of many she’d own in the building. According to the Chicago Tribune, she bought three other units surrounding the original one: a roughly $1.06 million unit in 1992; a $1.5 million unit in 1993; and a $1 million unit in 1994. She combined the four units into one massive duplex that totaled 9,625 square feet and consisted of four bedrooms, five full bathrooms, and two half bathrooms. In January 2014, Winfrey listed the duplex for $7.75 million. It sold for nearly $4.63 million in 2015.
1995: Winfrey Secures a Home on an Exclusive Florida Island
Winfrey stepped up her real estate game in
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