Oprah Winfrey Has Split Up Her $17 Million Montecito Estate and Sold It to 2 Famous Friends
Many know Oprah Winfrey as an award-winning TV host and actor. But away from the limelight, she’s a savvy businesswoman.
Along with running multiple companies, including The Oprah Winfrey Network and Harpo Productions, she boasts an impressive real estate portfolio. The 68-year-old billionaire recently split her $17 million Montecito, California property in two and sold it to her celebrity friends for a sizable profit.
Oprah Winfrey’s real estate portfolio is impressive
Winfrey is one of the biggest and most influential celebrities in the world. She’s a self-made media mogul and businesswoman. And her real estate portfolio reflects her successful 50-year career.
One of Winfrey’s first significant properties was a Chicago Water Tower Place condo. She purchased several apartments next to it and combined them into one large duplex that sold for $4.6 million in 2015. Another Chicago apartment the TV host snagged for $100,000 was flipped for $1.25 million the same year.
In 2001, Winfrey picked up the $50 million estate in Montecito, California, where she still resides. The 42-acre property features a 23,000-square-foot Georgian-style house and a massive 6,000-square-foot guest home.
Over the years, Winfrey began purchasing the homes and land surrounding her Montecito mansion. She also owns multi-million dollar properties in Hawaii, Colorado, and Washington.
Oprah Winfrey split and sold one of her neighboring Montecito properties to celebrity friends
In 2021, Winfrey purchased an estate near her Montecito home for $10.5 million. As reported by The Dirt, the 2.1-acre property included a large mansion and two cottages.
Nearly a year later, in 2022, Winfrey split the estate into two parcels and sold them. The Morning Show star Jennifer Aniston purchased the mansion half for $14.8 million. Winfrey’s property manager and trainer Bob Greene picked up the portion with two cottages for $2.3 million.
The sales proved to be highly profitable for Winfrey. Setting aside the costs of repairs or renovations, she likely pocketed about $6.5 million.
For Oprah Winfrey, there’s ‘no better investment’ than a home
Winfrey is quite private about her personal life and space. But in 2008, she wrote a piece for O at Home, and detailed what she looks for in a house.
“A home is a precious gift you give to yourself,” Winfrey wrote. “And it gives back daily. What can be more important than the space where you live and breathe and thrive, surrounded by memories and treasures that fill you up?”
“My home is my refuge and restoration,” she added. “For my money, there’s no better investment than in the place where you physically and emotionally reside.”
The icon also revealed how she enjoys having books and flowers around her home. And she gave her readers some great advice on what to do with their own space.
“That’s my greatest desire for you,” she suggested. “I hope you create something dreamy for yourself — a home that is an artistic expression of who you are in the world, what your family represents, the life you’ve lived, and what inspires you.”
