Oprah has sold a small piece of her expansive property portfolio to Jennifer Aniston, with the 53-year-old Friends star purchasing a stunning four-bedroom farmhouse in Montecito, California, from the talk show host for $14.8 million.
Oprah, 68, who has a reported net worth of $2.5 billion, owns numerous other homes in the area – and even more around the world – totaling $127 million, so it’s likely that Aniston’s new abode won’t be missed by the producer, actress, author, and philanthropist.
Her main base is a sprawling 23,000-square-foot mansion in Montecito, right next door to the home that she sold to Aniston – and just a stone’s throw from the $14.65 million home where Prince Harry and Meghan Markle live with their two children, Archie and Lilibet.
She first bought the luxurious home in 2001 for $52 million, and over the years, she has continued to expand the property by buying many of the neighboring estates.
She now owns a whopping 80 acres in the area – estimated to be worth around $90 million – and has nicknamed the property The Promised Land.
Oprah also forked out millions more on redesigning the stunning home in 2010, and it now boasts six bedrooms, 14 bathrooms, 10 fireplaces, a chef’s kitchen, expansive dining room, numerous living spaces – and a separate enclosed area called the ‘tearoom,’ where Oprah can sit and drink her tea.
And that’s not all. The TV personality also owns two vacation homes – a beachside house in Maui, Hawaii, which sits on an impressive 163 acres of land, and a mountainside mansion in Telluride, Colorado, which comes with its own observation tower, wine cellar designed to look like an old mine, and tram to the nearby ski slopes.
Over the years, Oprah has owned multiple properties, with her portfolio once boasting homes in Chicago, Florida, and Orcas Island, off the coast of Washington.
However in the past decade, the TV legend has sold off several of her sprawling houses, condos, and mansions, slimming down her property holdings to a much smaller – yet still very pricey – selection.
As she says goodbye to another small piece of her real estate empire, FEMAIL has taken a look into the many other homes that Oprah owns, from her Montecito base to her lavish Hawaii escape.
From the luxurious amenities – including saunas, movie theaters, gyms, and even a seven-person hot tub – in each home to the outdoor facilities – including tennis courts, pools, orchards, and ponds – take a look at Oprah’s impressive properties.
Oprah’s $90 million sprawling estate in Montecito, California
In 2001, Oprah purchased an enormous, 23,000-square-foot Georgian-style mansion for $52 million, which came with 42-acres of land and is located in Montecito, California – sitting between the Santa Ynez Mountains and the Pacific Ocean.
She bought the house from businessman Robert Veloz and his wife, Marlene, who had purchased it for $14 million three years earlier.
The Veloz’s were having the home revamped by Corinna Gordon Interior Design, and it was in the midst of construction when Oprah scooped it up.
It’s been said that the TV host used the home as the backdrop for a photoshoot for her magazine, O, and she quickly fell in love with it.
While the Veloz’s originally planned to keep the home for themselves after the renovations were complete – it wasn’t even on the market at the time – Oprah reportedly made them an offer they couldn’t resist; the deal earned headlines at the time, as it was the highest-priced sale for a private home in US history.
Of course, it’s no surprise that the stunning six-bedroom, 14-bathroom mansion came with a slew of lavish amenities, including a pool, tennis courts, its very own barn, herb and flower gardens, an orchard, two ponds, and a lake.
In 2010, Oprah revealed that she spent several more millions of dollars in remodeling the beachside home, after admitting that the ‘grand’ house didn’t feel ‘true to herself.’ She added that while it was ‘picture-perfect,’ it was ‘somewhat impersonal.’
‘The gilded mirrors, marble urns, the lavish carpets and sherbet palette – it was all very grand, but it wasn’t very true to myself,’ she explained in her magazine.
‘I can honestly tell you: Not once in ten years did I ever sit [in the dining room] – for fear of getting the fabric dirty. I don’t want to live in a grand space anymore. I want dinners to reflect my heart and spirit. I want people to feel free to ask for seconds.’
She enlisted designer Rose Tarlow to come in and help, and Oprah recalled Rose telling her, ‘I’ve never seen such a disconnect. The house has nothing to do with you. It’s like you created what you think a person of means should have.’
She had a fountain ‘the size of a lake,’ which ‘shoots water to the heavens,’ added to her yard, and planted a forest of ‘mature oaks,’ according to Vogue.
She also redid the dining room, kitchen, and many of the living areas, and had an entire second home built ‘for the sole purpose of reading the New York Times in the morning while drinking her tea’ – an open-air stone structure that she calls the ‘teahouse.’
After the renovations were complete, Oprah gushed that her home – which she nicknamed The Promised Land – now felt like a ‘womb,’ with her adding to O, ‘It’s cozy, it’s styled, it’s comfortable, it’s me.’
Over the years, Oprah continued to expand her home by purchasing adjacent estates. She bought one neighboring 4,584-square-foot home for $4.3 million in 2004, which she reportedly used to house guests, and in 2005, she also purchased another 3,376-square-foot home nearby for $7 million.
Then, in 2015, the TV personally added a third 4,750-square-foot four-bedroom, four-and-a-half bathroom home to her collection – which is located next door and cost her $25 million – after reportedly eyeing the property for years.
The sale came with 23 acres of land and a miniature pony farm, and it resulted in her owning almost 80 acres of property in the prime Montecito real estate market at the time – which was estimated to be valued at around $90 million.
‘Oprah has been quietly but systematically buying up the properties around her estate. At this point she has only one neighbor to the west, it’s just the way she wants it,’ a neighbor told DailyMail.com exclusively at the time, adding that ‘it was only a matter of time until she swooped in’ and purchased the farm.
Oprah explained to Vogue in 2018 that she loved spending her free time doing ‘nothing’ in her California estate, explaining, ‘I live in a very beautiful space that I created, and every time I leave home and I’m driving out the back with the pond and the ducks, and I’m looking at the grass and I see the house on the hill, I have this moment where I think about when Dorothy says in The Wizard of Oz, “I learnt I didn’t have to look further than my own back yard.” Every time I think of that.
‘Most people don’t even know what makes them happy. But I can just sit on my porch and I’ll start reading a book and then realize, OK, I’m not reading any more. I can just take it all in. I can just be.’
In 2021, Oprah bought another two-acre estate in the area for $10.5 million, which she has now sold; she split it into two properties – the main home, a four-bedroom 4,320-square-foot farmhouse, was sold to Aniston for $14.8 million, and the accompanying two smaller cottages were sold to her longtime friend and personal trainer Bob Greene for $2.3 million.
Over the years, other residents of Montecito have included Gwyneth Paltrow, Jeff Bridges, Adam Levine, Julia Louis-Dreyfus, Rob Lowe, Larry David, George Lucas, Ellen DeGeneres, Ariana Grande, Kathy Ireland, Don Johnson, and Carol Burnett.
Prince Harry and Meghan Markle even chose the lavish area for their home when they moved from England to the states in 2020, purchasing an estate near Oprah’s for $14 million.
Oprah’s $23 million 163 acre house in Maui, Hawaii
Oprah also owns property in the stunning state of Hawaii, and the 68-year-old revealed on her website that it was her friend Bob who convinced her to purchase a home in the Aloha state.
‘Besotted with the weather, the mountains, and the ocean, Bob has been visiting Hawaii for 15 years,’ she explained, adding that he spent years looking for the ‘perfect spot’ for her.
‘He found it in a remote up-country region, where the houses that dot the moss-covered rock hillside face the ocean.
‘Bob convinced [me] to look at a nearby property for sale. He was worried that some developer might swoop up the land and build condos. Instead, [I] bought the land.’
She purchased two adjacent properties in Maui in 2003 for about $5.3 million, which contained a main house and a guest house, and sat on 23.7 acres of land.
She then enlisted designer Ellie Cullman to help build her the ‘ultimate Hawaii homestead.’ Ellie, along with architect Jeff Wooley, stripped the main house of its basic structure, raised the ceilings, installed French doors throughout, and wrapped the entire thing with a ‘wonderfully wide’ porch, which Oprah described as a ‘great place to sit and soak up the sweeping view.’
The ‘open and airy’ mansion is filled with ‘extraordinary’ antiques that are part of the American heritage, including custom curtains embroidered in India.
Like her Montecito home, Oprah has continued to expand her Hawaii property by purchasing nearby estates, and as of 2021, it was reported that she owned a whopping 163 acres in the state, totaling around $23.2 million.
Oprah’s $14 million mountainside mansion in Telluride, Colorado
Oprah splashed out $14 million in 2015 for a third residence – a mountainside mansion in Telluride, Colorado. Described as a ‘high-tech ski home,’ the five-bedroom, six-and-a-half bathroom house sits on three acres of land.
It comes with a 56-foot-long wine cellar – which can hold up to 1,600 bottles and looks like a mining tunnel – an at-home movie theater, a seven-person hot tub, multiple fireplaces, a sauna, a gym, an observation deck 34 feet in the air, and its very own tram ride that can bring you right to the ski slopes.
It also boasts a chef’s kitchen, a game room with a wet bar and pool table, and 8,700-square-feet of living space.
One of the other highlights is a glass fiber-optic bridge that connects the master bedroom to an office; elsewhere on the property is a guest house and a three-car garage; a ‘radiant heat system’ ensures that the driveway always stays snow-free at all times.
