California is home to hundreds of properties with an illustrious celebrity history—but it’s unlikely any dwelling can compete with the legacy of the dwelling that was just offloaded by TV mogul Oprah Winfrey for $17.27 million.
The 71-year-old media baron quietly sold off a Spanish-style dwelling that once made up part of her iconic Montecito estate to none other than Adam Levine and Behati Prinsloo—six years after she bought the home from Hollywood legend Jeff Bridges.
Oprah boasts one of the most enviable property portfolios of anyone in Hollywood; however, the jewel in that crown is undeniably her primary residence in Montecito, which is made up of multiple properties amassed over more than 20 years.
At the heart of that compound is an enormous mansion she renamed “The Promised Land” after purchasing it for $50 million in 2001. In the years since then, she has added several other surrounding parcels to the property, turning it into one of the most jaw-dropping estates in the tony Santa Barbara enclave.
However, over the past few years, Oprah has been downsizing, trimming back her Promised Land by estate selling off various properties that surround her main dwelling—most recently offloading a stunning Spanish-style mansion to Levine, 46, and Prinsloo, 37, who recently sold their own Montecito home for the sky-high price of $60 million.
When the A-list couple put their property on the market, their spokesperson said at the time that they had made the decision to move largely because they wanted to live in a dwelling closer to their kids’ school, but also because they came across a home that was “too special to resist.”
Now, Realtor.com® can exclusively reveal that the oh, so “special” home in question was sold to them by Oprah, who made quite the impressive profit on the deal, having bought the home from Bridges in 2019 for $6.85 million—less than half the price Levine and Prinsloo paid.
The sale of Oprah’s property was originally reported by Siteline Santa Barbara; however, the identity of the buyer was not revealed.
It’s understood that the couple plan to carry out some extensive renovations to the home, with their spokesperson previously revealing that they were viewing the dwelling as an “exciting opportunity,” adding that they were going to spend around a year “developing” the estate.
While they have not revealed where they will reside while work on the property is carried out, records show that the couple also purchased another nearby dwelling at the start of November for $12.5 million.
That property, which they purchased via the same trust as Oprah’s dwelling, boasts 7,300 square feet of living space, including five bedrooms and 6.5 bathrooms.
While their new home was never put on the MLS, instead changing hands in an off-market deal, a previous listing for the property described it as having been built in 1919, with the main residence on the sprawling parcel designed by architect James Osborne Craig.
At just 3,500 square feet, the main dwelling on the property is tiny when compared to the 13,300 square feet of living space the couple enjoyed at their former residence, which they sold Oct. 7, six weeks before closing on Oprah’s home.
The primary residence boasts just two bedrooms and four bathrooms, and features exposed-beam ceilings, hardwood floors, and five fireplaces.
While that might not seem like enough space for Levine and Prinsloo’s family of five, the property does feature several other structures on its 4-acre parcel, including a one-bedroom guesthouse, a carriage house with an office and “bonus rooms,” and an array of equestrian facilities, including a five-stall barn, a corral, and a tack room.
Other external amenities include a greenhouse, beautiful lawns and gardens, an orchard, and a pool and spa, according to a previous listing.
What’s more, Levine and Prinsloo’s new neighborhood boasts a very impressive number of celebrity residents, not least Oprah, whose enormous Promised Land estate backs up to the couple’s new dwelling.
Their property is also located just a few minutes’ drive from the $14.65 million mansion owned by Prince Harry and Meghan Markle.
While the dwelling was originally built more than 100 years ago, it has been “extensively renovated” over the years, including a significant transformation in 2016, while Bridges still owned it.
In 2018, the actor revealed that he and his wife had been helicoptered off the property amid the devastating mudslides that occurred in Southern California in January of that year—sharing in a post on X, then known as Twitter, that his home had been “severely damaged” in the floods.
When he listed the home for sale, his listing agent at the time told the Santa Barbara Independent, however, that all of the damage had been repaired, noting that the majority of it was contained to the carriage house and the gardens.
It’s unclear whether Oprah carried out any renovations to the home after she took ownership the following year.
According to property records, the media mogul’s portfolio in Montecito has dwindled to just a handful of homes, including her Promised Land estate, as well as another parcel of land adjacent to her primary estate.
Two years before selling Bridges’ former home to Levine and Prinsloo, Oprah had offloaded another nearby dwelling to “Friends” star Jennifer Aniston for $14.8 million, while two smaller cottages that were originally part of that same estate were sold to her longtime friend and trainer, Bob Greene, for $2.3 million.
While she has been downsizing in California, Oprah appears to be intent on growing her extraordinary estate in Hawaii, where she now owns about 1,000 acres in Maui.
Her love of the Valley Isle started in 2003, when she purchased two properties in the Kula community, before adding 23 more acres and multiple buildings to the estate for $5.3 million. She’s been a part-time resident ever since.
Multiple reports suggest that her Hawaii property purchase also included a boutique bed-and-breakfast, which is thought to be used by the TV legend to house any guests who visit her while she’s staying there.
Over the decades, she has picked up even more properties in the area, reportedly spending over $40 million on some 163 acres of prime Hawaiian land.
But she didn’t stop there. In March 2023, local news outlet KITV reported that Winfrey had picked up 870 “agriculturally zoned” acres in Kula for about $6.6 million.
She’s said to have built a secret road to her property, making access to the more populated parts of Maui that much easier.
In addition to her Kula holdings, she purchased over 60 acres in the Hana area in 2005.
Additionally, the TV legend owns a stunning 66-acre estate in Colorado, which she purchased for $10.85 million in 2014.
It has been reported that she had plans to build a custom home on the property, which sits above the ski town of Telluride, CO.
Clearly eager to ensure that she had somewhere to rest her head in the area, however, she chose to snap up a “temporary” home while work on her other resort property was completed, buying a high-tech Telluride mansion for $13.7 million in 2015.
