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Oprah Winfrey Sells Home She Never Lived In, Takes Big Loss

Oprah Winfrey Sells Home She Never Lived In, Takes Big Loss

Such is the life of media mogul Oprah Winfrey, who last month closed on the sale of her fancy co-op on Chicago’s Lake Shore Drive, six years after she purchased it. Winfrey reportedly has never called the building “home.” She sold it for $2.75 million, far less than the $5.6 million she bought it for in 2006, demonstrating the new math of the hellish real estate market across the country, where nobody ever seems to sell any property for actual profit anymore.

According to, the fabulous life of Oprah extends far beyond a co-op in Chicago. For instance, when she’s in Chicago, she stays at a 15,000-square-foot duplex at Water Tower Place on Michigan Avenue. If she’s feeling in a West Coast mood, she might stay at her $52 million estate in Montecito, Calif., that she calls “The Promised Land.” If she wants to go even further then the West Coast, she can fly in her $42 million jet to her lovely farmhouse in Kula, Hawaii. Or she might want to head to the Caribbean, where she has a lavish vacation home on the shores of the laid-back Caribbean jewel. If none of these interest her, she could head to her homes in Telluride, Col., or Douglasvile, Ga., or Lavallete NJ.

The co-op home at 199 E. Lake Shore Drive, features 10-foot high ceilings, a library, solarium, terrace, gourmet custom eat-in kitchen, butler’s pantry, wine room and view of the lake. The unit is one of 13 housed in a Beaux-Arts style building, constructed in 1913 and designed by Benjamin Marshall. The late comedian John Candy lived in the building at one point, and actress Meg Ryan once stayed there while making a movie in Chicago.

Curbed National reported last November that Winfrey had sought to rent out the home for $15,000 a month but got no interest.

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