Winfrey currently lives on “The Promised Land”, her 42-acre (170,000 m²) estate with ocean and mountain views in Montecito, California, outside of Santa Barbara. Winfrey also owns a house in Lavallette, New Jersey, an apartment in Chicago, an estate on Fisher Island off the coast of Miami, a ski house in Telluride, Colorado, and property on the island of Maui, Hawaii. She also owns Read more...

Winfrey and her partner Stedman Graham have been together since 1986. They were engaged to be married in November 1992, but the ceremony never took place. Winfrey believes that the reason she never had children was because her students at South Africa’s Oprah Winfrey Leadership Academy for Girls were meant to be her daughters:

“When I watched Oprah with those girls,” observed Read more...

Winfrey once dated movie critic Roger Ebert, whom she credits with advising her to take her show into syndication. The relationship of Winfrey and Graham has been documented through the years with numerous romantic tabloid articles often accompanied by color spreads of the couple at home and on lavish vacations. Prior to meeting Graham, Winfrey's love life was a lot less stable. A self-described Read more...