Oprah Winfrey has taken a liking to one of Sydney’s icons.
Oprah Winfrey’s presence in Australia has already been felt as she arrived in Australia a couple of days ahead of her speaking tour — giving one Australian local business a massive shout out.
It comes as her $4.8 billion (US$3.2 billion) wealth has been exposed — and where she’s been hiding it after rising to fame from the late 1980s.
The now 71-year-old talk show queen, philanthropist and media mogul — who has come to Australia for her Oprah: In Conversation tour — unsurprisingly also happens to be a real estate tycoon.
Over the years the media queen has bought and sold many properties — and created a massive property portfolio.
This comes as Winfrey expressed her love of Australia — and its food scene — during a visit to Sydney’s iconic Bills cafe.
“It’s so great to be back in Sydney. It’s one of the most beautiful cities in the world,” she said in an Instagram post to her 22 million followers.
It was Hugh Jackman who tipped Winfrey off about their iconic ricotta pancakes.
“These hot cakes are much acclaimed and talked about by the one and only Hugh Jackman,” she said in a video as she sat at Bills in Bondi.
Oprah Winfrey at Bills in Sydney. Picture: oprahwinfrey/Instagram
“Hugh you were absolutely unbelievably right! This place, come here to Sydney you’ve got to stop in.
“We ate like we’ve never eaten before and those ricotta pancakes … mwa mwa mwa.”
Turns out they were so good, she went back for more.
When a Channel 7 reporter approached her and asked if she was back for lunch she answered saying:
“No, we are back for more ricotta pancakes. I hope they’re still serving them. If they’re not, we are going into the kitchen and see what we can do about that.”
Bills is owned by acclaimed restaurateur Bill Granger, who opened his first restaurant in Darlinghurst in 1993. Opening a second location in Surry Hills in 1996, Bills has then gone global across Japan, London and Seoul with different cafes and restaurants that focus on fresh, quality food.
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Hugh Jackman and Oprah Winfrey.
Winfrey’s wealth goes well beyond her career as she owns a myriad of sprawling mansions.
Here’s a breakdown of the list of homes she’s bought, sold, and currently holds.
‘The Promised Land’
Although she owns homes from coast to coast, Winfrey’s main residence can be found in Montecito, CA, a coastal community near Santa Barbara. It’s nearly two hours (with traffic) northwest of Hollywood.
In 2001, Winfrey moved into the neighbourhood with the $75 million (US$50 million) purchase of a place she’s dubbed ‘The Promised Land’. It is now estimated to be worth $150 million ($100 million).
The enormous neo-Georgian estate comprises six bedrooms, 14 bathrooms, and a 3136 sqm home on more than 40 acres.
One of Oprah’s many properties. Picture: Realtor
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Offering mountain and ocean views, the gorgeous grounds include a pool, stables, landscaped gardens, her bountiful vegetable gardens, as well as a pond.
Other features include a tea house, an “upscale outhouse”, plus more than 600 verdant rose bushes.
Winfrey continues to expand her Montecito masterpiece. She snapped up an additional 23.26 acres in 2015 for $40 million (US$28.85 million).
Most recently, she snagged her neighbour Jeff Bridges’ longtime retreat for $10 million ($US$6.85 million), bringing her total acreage in the area to nearly 70 acres.
Jeff Bridges sold his home to Oprah Winfrey. Picture: Elevated Horizon courtesy of Coldwell Banker
Aloha, Hawaii
Winfrey reportedly owns extensive plots of land in Hawaii, but the details are most clear for her farmhouse on the island of Maui.
Winfrey’s romance with Maui started back in 2003, when she purchased two properties in the Kula community on the Valley Isle, adding up to 23 acres for $8 million (US$5.3 million).
Each of those lots contain multiple buildings.
That purchase appears to have included a boutique bed and breakfast. So it seems she always expected to welcome guests to her tropical paradise.
Winfrey has continued snatching up properties in the area, for a total of over US$40 million and some 163 acres, according to O Magazine, which featured this video of Winfrey herself driving around her property on one of two all-terrain vehicles given to her by Ralph Lauren. She discovered the ATVs on his ranch.
She’s even rumoured 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 back in 2005.
Oprah is in Australia for a special speaking tour. Picture: Supplied
The Winfrey (Windy) City
The Oprah Winfrey Show was broadcast from Chicago from 1986 to 2011.
Along the way, Winfrey scored a few properties in Illinois. But with the end of her show’s long run in the Windy City, Winfrey appears to have also moved on from her real estate there.
In the 1990s, she bought four condos on the 56th and 57th floors of a luxury high-rise, with the idea of converting them into one duplex. The 900 sqm property sold in 2015 for $4.6 million.
She also shed a three-bedroom apartment over the Four Seasons Hotel that she had bought in 1994 for $100,000. The high-end home sold for US$1.275 million in 2015.
She also bid adieu to three units in a historic downtown building known as Acorn Lofts.
In 2013, she sold three of the live/work spaces, one for US$675,000, another for $507,000, and a third for US$875,000. For an idea of what the lofts look like, there’s a unit currently on the market (that’s not connected to Winfrey) for $1.6 million.
She also sold a modest colonial in Elmwood Park, IL, for US$375,000 in 2018.
She’s also been spotted picking up homes in Tennessee, Illinois, and Indiana, most of those houses are believed to be occupied by members of her family.
One of Oprah’s mountain escapes. Picture: Realtor.com
Mountain getaway
Oprah also has a cold-weather hideaway. She purchased 66 acres in coveted Mountain Village, Colorado in 2014, for US$10,850,000.
She apparently had a custom home constructed on the property, which sits above the ski town of Telluride.
But while it was being built, she reportedly bought a “temporary” home away from home to monitor the construction: a hi-tech mansion in Telluride for $13.7 million.
The contemporary construction offers complete privacy and direct trail access.
The grounds include a treetop observation tower, a fully functional funicular, and a glass and steel bridge over the great room.
Georgia on her mind
Some long-ago purchases have since been sold by the 71-year-old.
In Atlanta, Winfrey sold a 450 sqm, 39th-floor penthouse for US$1.8 million in 2008.
Reports were not clear on whether she ever made use of the place for herself. She made a small profit on the property, which she bought in 2003 for US$1,515,000.
The LA home that Oprah Winfrey bought from Jeff Bridges. Picture: Elevated Horizon courtesy of Coldwell Banker
She also had a 560 sqm house in Douglasville, GA, on 1.6 acres, which she had bought in 2005 for US$825,000. That suburban five-bedroom home was gifted to a lucky somebody in 2011.
Island living
Back in the late 1990s, Oprah had a fling with Florida life. She decamped to ultra-exclusive Fisher Island as a winter escape and snapped up multiple condos on the private island paradise, which is known as having one of the highest per capita incomes in the country.
However, she’s since let go of her Florida homes, which were all sold in the early 2000s. Many of them were smaller one-to-four bedroom apartments, and appeared to be for her entourage and friends.
Her 575 sqm penthouse sold in 2001 for $6.5 million. At the time, the sale price was considered “unheard of”. That seems quaint now — the same penthouse recently changed hands again for US$13.5 million.
Of course, after those sales, Oprah began buying up homes in Hawaii, a place that obviously held more appeal for the A-lister.
And the island life beckons closer to the mainland, too. The real estate maven reportedly picked up a 43-acre estate on Orcas Island, part of the San Juan Islands in Washington state, last May.
Oprah’s new digs, for which she paid US$8.2 million, include a four-bedroom, five-bathroom compound, plus a guesthouse.
Additional reporting by Brendan Casey
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