Oprah Winfrey opened her private Maui road after a tsunami warning. Here's her history with Hawaii, where she owns 1,000 acres of land.

Winfrey owns an estate in Montecito, California, which she bought for $52 million in 2001, as well as a duplex in Chicago, a home in Antigua, a ski chalet in Telluride, Colorado, and more.

But her biggest real-estate investments in terms of acreage have been in Hawaii. She owns around 1,000 acres across two towns in Maui, Hāna and Kula, local news outlets KITV4 and Maui Now reported.

Maui's upcountry is a region of Maui that includes the volcano, Mount Haleakalā. According to Hawaii Guide, it's set across the upper slopes of Haleakalā and away from the shore.

"'Upcountry' is as much a lifestyle as it is a place. Many people who live Upcountry consider themselves to be quite different from those fancy 'city-slickers' who live in places like Kahului, Wailuku, Kihei or West Maui," according to Maui Guidebook.

The biggest towns in upcountry are Pukalani, Makawao, Kula, and Haiku.

Winfrey chatted with her magazine O about her first Hawaiian purchase in 2006.

She bought the Kula land — which included these two buildings, pictured — at the recommendation of her property manager (and former personal trainer) Bob Greene.

Greene mentioned to her that he had found the perfect spot in upcountry, but was "worried that some developer might swoop up the land and build condos," according to Winfrey.

Instead, she purchased the land and "has no plan to build any condos," according to the magazine.

"The original plan was to do a quick job on the house then think about building the ultimate Hawaii homestead," Winfrey's decorator Ellie Cullman told O in 2006.

Instead, it became a much larger renovation of the existing house. Architectural designer Jeff Wooley, of John B. Murray Architect, changed the floor plan, stripped down the house, moved the staircase, and added a huge veranda so every part of the house would have a view, O reported.

"She liked [the home's] small scale," Cullman said. "She already has a large home in Santa Barbara — this seems to go back to something real and personal."

"I love, love, love my house," she is quoted saying in the article, calling it "a real, normal" home that "feels like a nice blanket."

In 2010, Hawaii News Now reported that Winfrey was planning on turning the 12-bedroom inn into "a high-end bed-and-breakfast" for her friends and other wealthy customers.

The next year, Real Estate Maui Hawaii reported that Maui's County Council had approved her request for a "a 10-year extension on her permit to operate the vacation rental."

However, it's unclear if she ever opened the business. Winfrey did not respond to a request for comment from Business Insider.

Maui Now reported that Winfrey purchased a 3-acre property that was adjacent to her other properties in Kula, adding to her almost 100 acres at the time.

The property, which is zoned for agriculture, also came with a 1,139-square-foot building, according to Maui Now.

Also according to Maui Now, Winfrey's properties were all owned through her companies, OW Ranch LLC, Oprah's Farm LLC, and Yellow Brick Road LLC.

In March 2023, Maui Now reported that Winfrey spent $6.6 million on 870 acres of land in Kula.

First, two parcels of 10 acres each were sold in December 2022 to Winfrey's Los Angeles-based company Harpo Inc. for $100,000 each.

Two more parcels were sold in February 2023 by ʻUlupalakua Ranch to Harpo Inc: 520 acres for $3.89 million and 330 acres for $2.47 million.

For now, it seems that Winfrey intends to keep this land undeveloped. She did not respond to Business Insider's request for comment.

According to Maui Now, Winfrey bought "more than 200 acres of coastal land in Hāna" through 2005. It is unclear what the land is used for, and she did not respond to Business Insider's request for comment about its status.

As well as Winfrey, Hawaii's billionaire landowners include Jeff Bezos, Peter Thiel, and Mark Zuckerberg, Forbes reported.

Billionaires have previously faced criticism from locals for making big land purchases in Hawaii, saying they are pushing up the cost of property and pricing out locals, Forbes reported.

According to the National Alliance to End Homelessness, Native Hawaiians and Pacific Islanders have the highest rates of homelessness, and the number of Native Hawaiians or Pacific Islanders experiencing homelessness increased by 19% between 2020 and 2022 — before wildfires began in 2023 and wiped out even more homes.

As ProPublica reported in 2020, legislation to begin giving land reparations to Native Hawaiians passed in 1995, with a directive to return land seized by the US government.

However, the US still owes Native Hawaiians 1,300 acres across the state, ProPublica reported.

Maui council member Yuki Lei Sugimura told local outlet KITV4 in 2023 that she appreciated what Winfrey was doing with the land, calling agricultural land "treasured," and also praised Winfrey for hiring local residents.

"She's always been a great steward of our land, to preserve it," said Maui senator Lynn DeCoite, adding that she "wish[ed] we had more people like her," according to KITV4. DeCoite also noted that "much of the land" Winfrey has purchased has remained undeveloped.

On August 31, 2023, Winfrey and Dwayne "The Rock" Johnson, who is of Samoan descent and partially grew up in Hawaii, launched the People's Fund of Maui with a post on Instagram.

Its stated goal was to help the people of Maui rebuild after the wildfires that left more than 100 people dead and thousands of structures damaged or destroyed. The damage was valued at as high as $5.5 billion by the National Centers for Environmental Information.

All money donated to their fund would go directly to the residents of Lāhainā, a town in Maui that was severely affected, they said.

Some fans took issue with Winfrey, who is worth $3.2 billion, per Forbes, and Johnson, who was worth $270 million in February 2022, asking people for financial help.

However, a Facebook post published by Business Insider received thousands of comments, with some fans coming to the defense of the duo.

"They donated $10 million! I don't understand why there is such negative reaction to this, but I must emphasize that being wealthy and accomplished doesn't obligate someone to distribute their wealth," one Facebook user wrote.

In the wake of the backlash, Winfrey said she'd experienced "an onslaught of being terrorized and vilified online" in an interview with CBS Mornings. She called any criticism "attacks, lies, conspiracy theories."

Johnson and Winfrey did not respond to Business Insider's requests for comment.

Maui experienced "a very active fire season" in 2019, Fire Services Chief Rylan Yatsushiro told The Maui News in December that year. Throughout the year, 25,000 acres burned, according to The Maui News, compared to the 3,900 burned acres in 2018.

Winfrey shared on X that she had opened her private road to help citizens evacuate on July 12, 2019.

"Access to the road was given to county officials immediately. This was many hours ago. Hoping for the safety of all," she wrote.

The official account of the governor of Hawaii reposted her message on X, writing, "A big mahalo to @Oprah for giving @mauicounty access to your private road for use to assist in the #Mauifire."

In July 2025, there was some confusion regarding her private road when a tsunami warning was issued after an earthquake off the coast of Russia. Her spokesperson told People that she was in contact with authorities immediately to open her road for any evacuees.

"As soon as we heard the tsunami warnings, we contacted local law enforcement and FEMA to ensure the road was opened. Any other reports are otherwise false," the spokesperson said.

A local police bulletin also said Winfrey's road is open.

"The road will remain open as long as necessary," said Winfrey's rep.