Oprah Winfrey Sells Chicago Condo For $2.75M Talk show host Oprah Winfrey's former apartment in this 1913 Beaux-Arts building on the Gold Coast, in Chicago. She sold the eight-room, 4,607-square-foot condo July 18, 2012 for $2.75 million, after paying $5,6 milliion for it in 2006. Raymond Boyd/Michael Ochs Archives/Getty Images