29. Hawaii Ranch House
This small gray ranch house in Maui, Hawaii, is the talk show queen’s other property. Oprah once considered tearing it down, and fortunately, she didn’t. Winfrey’s property manager Bob Greene advised her to purchase land in Hawaii. She also called in a designer and architect to renovate the home. As a result, the property becomes a beautiful 21st-century farmhouse.
30. $8 Million Washington Compound
This $8 million Washington property of Oprah’s is a private luxury compound on Orcas Island, in the northwest of Washington state. Constructed in 2007, the estate sits on over 40 acres of land. Its three-story main house includes four bedrooms, three baths, and a powder room. Here, Oprah can enjoy the sunset along the 3,000 feet of west-facing shoreline.
31. Chicago Real Estates
Formerly based in Chicago, Oprah used to have several real estate in the city. In 2018, Oprah sold off her last Chicago property, a 2,250-square-foot Colonial-style house in Elmwood Park, for $375,000. Oprah’s other Chicago properties include a duplex in Water Tower Place, which was sold for $4.6 million, and a co-op unit in the Gold Coast, swhich old for $2.8 million.
32. Fisher Island Condo
The TV screen queen once owned a condo on Fisher Island, in Florida, a place described by the Sun-Sentinel as such: such: “Peacocks roam free here. So do millionaires, movie stars, and moguls.” The condo covers 1,838 square feet of land and has 2 bedrooms and 2 baths. However, Oprah listed it for a whopping $2 million in 2008.
