Oprah Winfrey loves one of Sydney’s icons.
Oprah Winfrey’s presence in Australia was already felt when she arrived in Australia just days before her speaking tour, causing a huge shout-out from a local Australian company.
It comes as her US$4.8 million ($3.2 billion) wealth has been exposed – and where she hid it after rising to fame in 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 – is unsurprisingly also a property mogul.
Over the years, the media queen has bought and sold many properties – and built up a huge real estate portfolio.
Winfrey expressed her love for Australia and its food culture while visiting the iconic Bills cafe in Sydney.
“It’s so great to be back in Sydney. It’s one of the most beautiful cities in the world,” she told her 22 million followers in an Instagram post.
It was Hugh Jackman who tipped Winfrey about their iconic ricotta pancakes.
“These hotcakes are much praised and talked about by the one and only Hugh Jackman,” she said in a video while sitting at Bills in Bondi.
Oprah Winfrey at Bills in Sydney. Image: oprahwinfrey/Instagram
“Hugh, you were absolutely incredibly right! This place, come here to Sydney, you have to stop by.”
“We ate like we had never eaten before and those ricotta pancakes… meh meh meh.”
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 replied:
“No, we’re back for more ricotta pancakes. I hope they still serve them. If not, we’ll go into the kitchen and see what we can do about it.”
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 subsequently gone global in Japan, London and Seoul with several cafes and restaurants focusing on fresh, quality food.
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Hugh Jackman and Oprah Winfrey.
Winfrey’s wealth extends far beyond her career, as she owns numerous sprawling mansions.
Here is a look at the list of homes she has bought, sold and currently owns.
‘The promised land’
Although she owns homes from coast to coast, Winfrey’s primary residence can be found in Montecito, CA, a coastal community near Santa Barbara. It’s almost two hours (with traffic) northwest of Hollywood.
In 2001, Winfrey moved to the neighborhood with the purchase of a place she called ‘The Promised Land’ for $75 million (US$50 million). Its value is now estimated at US$150 million ($100 million).
The enormous neo-Georgian estate consists of six bedrooms, fourteen bathrooms and a 3,136 m² house on over 40 hectares.
One of Oprah’s many properties. Image: real estate agent
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The beautiful grounds offer mountain and ocean views and include a swimming pool, stables, landscaped gardens, bountiful vegetable gardens and a pond.
Other features include a tea house, a ‘luxury outbuilding’ and more than 600 green rose bushes.
Winfrey continues to expand on her Montecito masterpiece. She bought another 23.26 hectares in 2015 for $40 million (US$28.85 million).
She recently secured her neighbor Jeff Bridges’ old retreat for US$10 million ($6.85 million), bringing her total acreage in the area to almost 70 hectares.
Jeff Bridges sold his house to Oprah Winfrey. Photo: Elevated Horizon courtesy of Coldwell Banker
Aloha, Hawaii Nokia
Winfrey reportedly owns vast tracts of land in Hawaii, but the details are clearest for her ranch on the island of Maui.
Winfrey’s romance with Maui began in 2003, when she bought two properties in the Kula community on Valley Isle, covering 23 hectares for $8 million (US$5.3 million).
Each of these plots contains several buildings.
That purchase appears to include a boutique bed and breakfast. So it seems she always expected to welcome guests to her tropical paradise.
Winfrey has continued to grab properties in the area, totaling more than $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.
There are even rumors that she built a secret road to her property, making access to the more populated parts of Maui much easier.
In addition to her Kula property, she purchased more than 60 acres in the Hana area in 2005.
Oprah is in Australia for a special speaking tour. Image: supplied
The Winfrey (windy) city
The Oprah Winfrey Show aired from Chicago from 1986 to 2011.
Along the way, Winfrey scored a few properties in Illinois. But at the end of her show’s long run in the Windy City, Winfrey also appears to have left her real estate there.
In the 1990s, she bought four apartments on the 56th and 57th floors of a luxury high-rise, with the idea of converting them into one duplex. The 9,000-square-foot property sold in 2015 for $4.6 million.
She also sanded a three-bedroom apartment above the Four Seasons Hotel that she bought for $100,000 in 1994. The luxury home was sold in 2015 for $1.275 million.
She also said goodbye to three units in a historic downtown building known as Acorn Lofts.
In 2013, she sold three of the live/work spaces, one for $675,000, another for $507,000 and a third for $875,000. To get an idea of what the lofts look like, there’s a unit currently on the market (not affiliated with Winfrey) for $1.6 million.
She also sold a modest colonial home in Elmwood Park, Illinois, in 2018 for $375,000.
She has also been seen picking up homes in Tennessee, Illinois and Indiana, most of which are believed to be occupied by members of her family.
One of Oprah’s mountain escapes. Image: Realtor.com
Getaway in the mountains
Oprah also has a cold weather shelter. She purchased 66 acres in coveted Mountain Village, Colorado, in 2014 for $10,850,000.
She apparently had a custom home built on the property, which sits above the Telluride Ski Resort.
But while it was being built, she reportedly bought a “temporary” home away from home to monitor construction: a hi-tech mansion in Telluride for $13.7 million.
The modern construction offers complete privacy and direct access to the path.
The grounds include a treetop observation tower, a fully functional cable car and a glass and steel bridge over the main hall.
Georgia in her mind
Some purchases from long ago have now been sold by the 71-year-old.
In Atlanta, Winfrey sold a 4,500-square-foot, 39th-floor penthouse for $1.8 million in 2008.
Reports were unclear whether she had ever used the place for herself. She made a small profit on the property, which she bought in 2003 for $1,515,000.
The LA house that Oprah Winfrey bought from Jeff Bridges. Photo: Elevated Horizon courtesy of Coldwell Banker
She also had a 5,600-square-foot home in Douglasville, Georgia, on 1.6 acres, which she bought in 2005 for $825,000. That five-bedroom house in the suburbs was given to someone lucky in 2011.
Island life
In the late 1990s, Oprah had a fling with living in Florida. She headed to the ultra-exclusive Fisher Island as a winter escape and bought several condos on the private island paradise, which is known for having one of the highest per capita incomes in the country.
However, she has since let go of her Florida homes, all of which were sold in the early 2000s. Many of them were smaller apartments with one to four bedrooms, and appeared to be for her entourage and friends.
Her 5,750-square-foot penthouse sold in 2001 for $6.5 million. At the time, the sale price was considered ‘unheard of’. That seems strange now: the same penthouse recently changed hands again for $13.5 million.
Of course, after those sales, Oprah started buying up homes in Hawaii, a place that clearly had more appeal to the A-lister.
And island life also beckons closer to the mainland. The real estate expert reportedly purchased a 43-acre estate on Orcas Island, part of Washington state’s San Juan Islands, last May.
Oprah’s new home, for which she paid $8.2 million, includes a four-bedroom, five-bathroom complex, plus a guesthouse.
Additional reporting by Brendan Casey
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