“Turn your wounds into wisdom.” Overcoming a childhood marked by poverty, sexual abuse and teen pregnancy, Oprah Winfrey’s life was forever changed when she was sent to live with her father in Tennessee. There, the young girl with the gift of gab landed a job in radio and, before long, was anchoring the local news. Eventually moving to Chicago, Winfrey had already come a long way from her humble Mississippi roots when she debuted on The Oprah Winfrey Show and quickly earned the top spot in daytime television, a rank she kept from 1986 to 2011.
Known for promoting a culture of self-improvement rooted in intimate confessions, literature and spirituality, Winfrey has been praised as the “Queen of All Media” since launching numerous business ventures including O, the Oprah Magazine, Harpo Productions and the Oprah Winfrey Network. Along the way, she’s built a $3.1 billion empire as the most influential woman in the world who is also the greatest African American philanthropist in American history.
Determined to live out her rags to riches story alongside her partner of 30 years, Stedman Graham, Winfrey certainly doesn’t skimp when it comes to her homes. In the midst of her blossoming success, the billionaire media mogul spent $50 million in 2001 on a 47-acre estate in Montecito, California. Sharing the neighborhood with celebrities like Jeff Bridges, Robe Lowe, Drew Barrymore and Ellen DeGeneres, Winfrey was drawn to the seaside community and its gorgeous views of the Pacific Ocean and the Santa Ynez Mountains.
The estate, which is aptly nicknamed “The Promised Land,” was originally built in 1959 and has since been remodeled and refreshed numerous times by Winfrey and Rose Tarlow, the famed interior designer to the stars. Stretching across six bedrooms and 14 bathrooms, the residence has a stunning open floor plan that offers plenty of windows to maximize natural lighting in the earthy and ranch-style atmosphere. The perfect home for entertaining (and we all know how much Winfrey loves a good party), The Promised Land also includes 10 fireplaces, a gourmet kitchen and wine cellar as well as a ballroom, basketball court and home theater.
Moving outside, the exterior of Winfrey’s Promised Land has seen just as many renovations as the interior to ensure the Queen of All Media is comfortable and content with her exquisite and enchanted paradise. Nestled in the heart of California’s rich wine country and dotted with groves of citrus and avocado trees, the home features numerous terraces where guests can gather on cool evenings while taking in the scenery of the estate’s lush grounds complete with a barn, rose garden, orchards and koi ponds. Of course, a Montecito home wouldn’t be complete without a pool and Winfrey’s is definitely a grand affair situated between a massive guest house and an outdoor entertainment area.
Despite the luxury of having 47 acres to herself in California’s most affluent community just outside of Santa Barbara, Winfrey had her sights set on the neighboring equestrian ranch known as Seamair Farm and, by December 2015, expanded her Montecito property by purchasing the neighboring 23.26-acre estate for $28.85 million. Having obviously done her homework (or paying someone to do it for her) to add considerable value to her real estate portfolio, Winfrey now owns the largest estate in all of Montecito with over 60 acres and two breathtaking homes. So what does her second home include?
Designed by renowned architect Cliff May in 1955, Winfrey’s newest addition includes a 4,750 square-foot single story home with four bedrooms, four baths and the same panoramic views of the Pacific Ocean and Santa Ynez Mountains that her main estate offers. Considered an equestrian haven, the property also includes stables, a large barn and paddocks for horses to graze and cavort as well as a separate home for the horse trainer. After all, what self-respecting media queen wouldn’t have her own horse facility and show rings?
All horsing around aside, there’s absolutely no doubt that the 62-year-old Winfrey has left her mark on the world when it comes to media, philanthropy and even real estate. Proving that she certainly has enough money to live wherever she wants, California isn’t the Queen of Media’s only residence as she divides her time between her house in Lavallette, New Jersey, an estate on Fisher Island, Florida and a ski house in Telluride, Colorado. In addition to owning the Chicago apartment that served as her home in the early days of her budding television career, she also owns property on Maui, Hawaii and Antigua. What more could a woman want?
Embodying success and living by the motto “where there is no struggle, there is no strength,” Winfrey serves as an influential role model to people around the world, especially women, to follow their dreams and reach for the sky. After all, who better than a talk show queen and media mogul to stand as living proof that the “biggest adventure you can take is to live the life of your dreams”?