Oprah Has a Private Road in Hawaii, but That’s Not the Extent of Her Real Estate There

When you’re someone like Oprah Winfrey, with a reported net worth of $4 billion, per Celebrity Net Worth, you enter a whole new tier of wealth. At that level, your money isn’t just going toward exotic cars, designer clothes, and fancy accessories. Instead, it goes to things like real estate, massive plots of land, and, yep, private roads.

For those that don’t know, Oprah actually owns a private road in Hawaii, which isn’t all that surprising given her fortune, but it does spark curiosity. Why does she need it, and what is it used for? Given that the road has reportedly been used during times of crisis, like evacuations during tsunamis or wildfires, we decided to dig into why exactly she has it.

Oprah owns property on the island of Maui in Upcountry areas like Kula and Hana, so it makes sense that her private road extends in that direction, likely connecting her homes or at least linking them to key routes, including the coast.

According to CNN, the road is located on her property and is near her ranch, if not passing directly by it. Beyond offering her the privacy she needs to travel between her properties, she doesn’t really need to give a reason for owning the private road in Hawaii. She’s Oprah, after all, and when you have her kind of money, a private road is just another luxury you can afford.

Since Oprah’s private road in Hawaii provides access to higher ground near Haleakalā, she has repeatedly opened it to local residents during emergencies. In 2019, when a brush fire broke out on Maui and other evacuation routes were overwhelmed, she confirmed on X (formerly Twitter) that she gave county officials access to her road as an alternate route to safety.

She did the same in 2023, and 2025 was no different. After an 8.8 magnitude earthquake struck Russia’s far east, triggering a tsunami warning for Hawaii and other U.S. states, Oprah opened her road to help residents reach higher ground, despite the false claims that suggested she didn’t.

Now that you know why Oprah has a private road, you’re probably wondering just how extensive her property in Hawaii is, and it’s pretty massive. According to Newsweek, Oprah reportedly owns over 2,000 acres of land on the island of Maui and has been living there on and off for more than 15 years.

She purchased her first piece of property in 2003, transforming what was once an “ordinary little gray ranch” into the “perfect 21st-century farmhouse,” according to her website. It was her personal trainer-turned-property manager, Bob Greene, who inspired her to plant roots in Hawaii after visiting various parts of the island for over a decade.

When he found an ideal plot, he worried developers might buy it and modernize it with condos, but Oprah bought it instead and now has a quaint farmhouse with a charming wrap-around porch.

Oprah went on to build a farm, and in 2013, she revealed, via her website, that she had dedicated 16 acres to farming. At that time, she was experimenting with “more than 100 species of fruits, vegetables, and herbs” to see which ones thrived. Presumably, her farm has expanded even more since then.