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How Oprah Winfrey Made $17M on Her $10.5M Home By Dividing It — Selling Part to Jennifer Aniston for $14.8M and Another Piece for $2.3M to Trainer Bob Greene

Media mogul Oprah Winfrey has made an eight-figure real estate deal with one of Hollywood’s most elite A-listers. Usually celebrated for her work in television and publishing, with this sale the billionaire businesswoman shows her portfolio is quite diverse.

Oprah Winfrey’s Montecito home (Photo: Google)/Oprah Winfrey attends the “Sidney” Premiere during the 2022 Toronto International Film Festival at Roy Thomson Hall on September 10, 2022 in Toronto, Ontario. (Photo by Leon Bennett/WireImage)

In one year, Winfrey flipped the 4,320 square foot property in Montecito, California, for a massive profit.

She acquired the property for $10.5 million in 2021, Dirt reports, from hedge fund manager Fred Shuman and his wife Stephanie. However, after the purchase, Winfrey chopped the house up and sold the halves to two different buyers, Bob Greene and Jennifer Aniston.

Winfrey has a history with both of the new homeowners.

Greene, the OWN Network head honcho’s personal trainer and property manager, acquired his piece of the property for $2.3 million in the middle of August. The next week, the main house, created in a Mediterranean-styled home, was sold to the “Friends” actress for a whopping $14.8 million.

The property has increased in value over the last quarter century. Originally called the “Tuscan farmhouse,” it was built in 1998 and sold to the Shumans for $2.8 million. A decade after it was built, the couple renovated the house.

Now the home includes four bedrooms, three full bathrooms, and one powder room on its 2.1 acres.

The property has a detached guest house or standalone gym building, surrounded by mature oak trees and an acre of wooded areas. The motor court is large enough to easily accommodate 15 cars.

However, information about the house is limited as the house was never officially placed on the market and there are no photographs on the internet showing off its amenities and unique character. Aerial views of the home only capture a limited glimpse of the estate, but a decades-old listing mentions the house has “panoramic ocean and mountain views.”

According to Forbes, this almost $15 million will be added to her $2.5 billion, acquired from her media and business empire, which not only includes her OWN cable channel, where her current 25 percent stake is worth more than $64 million, but the productions she produces through her Harpo Productions like the Broadway version of “The Color Purple,” “Beloved,” and “Selma.”

Currently, the 10th richest self-made woman in America and the richest Black woman in the world, according to Afro Tech, her mind has been less set on the pursuit of success and more on the aspiration of greatness.

“Don’t worry about being ‘successful,’” Winfrey once shared. “Strive for the truest, highest expression of yourself … and then use that expression in service to the world. If the paradigm for which you see the world is, ‘How can I be of service with my talent? How can I be used in service?’ then I guarantee you, no matter what your talent or offer, you will be successful.”

And indeed, Winfrey has been successful in real estate, owning homes throughout the years in eight states, including California, Colorado, Florida, Hawaii, Indiana, Illinois, Tennessee, and Washington. The properties, in Tennessee and Indiana, Architectural Digest reports, are homes she purchased for family and friends.

She opened her real estate portfolio in 1985 with a condo in Chicago at Water Tower Place along the city’s Magnificent Mile. She later acquired three units around that one for $1.0625 million, $1.5 million, and $1 million, combining the four units to create a huge 9,625 square feet. She sold those properties in 2015 for $4.625 million. She either broke even or made a little profit after originally wanting $7.75 million.

A more successful flip was when she purchased $100,000 on a three-bedroom apartment at the Four Seasons Chicago in 1994. She sold that property for over 10 times the price in 2015 at $1.275 million.

The next year, she purchased a 6,170-square-feet penthouse condo on Fisher Island, an exclusive 216-acre man-made island situated just off the coast of Miami, for an undisclosed price. While people don’t know what she paid for the four-bedroom, six-bathroom home with an oceanfront terrace, she sold it in 2001 for $6.5 million to the former chairman of Campbell’s Soup.  

Around the same time as the sale, she purchased her original Montecito home, paying around $50 million for the mansion. She then bought herself a Colonial-style home in the Elmwood Park suburb outside Chicago for $298,000, selling that 17 years later for $375,000. This was the last property in Chicago.

She has two estates in Maui, both sitting on a total of 163 acres. She paid $5.3 million for those investments in 2003.

In 2014, after she purchased almost 60 acres of land near the Colorado Telluride Ski Resort for $10.85 million, she was sued by a retired nuclear physicist living in the area because he wanted access to a trail on her property. He later dropped the lawsuit. The next year, she bought another $14 million mansion in the same town.

Months later, she paid $28.85 million for a 23-acre estate in Montecito, one of the largest in the area and close to her first home in the town. This purchase, to be a part of her Promise Land ranch, was an equestrian property called Seamair Farm, proving her investments are not only business models, but for personal joys like horse riding.

Winfrey purchased her Pacific Northwest property, two adjoining parcels on Orcas Island, a part of the San Juan archipelago sitting between Seattle and Vancouver, for $8 million in 2018 and flipped it in 2021 for $14 million.

And her last purchase, before buying the property from the Shumans, was in 2019. She was able to acquire a four-acre complex from actor Jeff Bridges in Montecito for $6.685 million. This home is still in her holdings.

While people are focused on her gigs with “60 Minutes,” the deals with Tyler Perry, and her constant mentoring of women like Ava DuVernay, she has been quietly playing checkers in the real estate space and winning all the while.

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