For as long as comfortable commercial flights have connected the West Coast to Hawaii, celebrities and wealthy mainlanders have flocked to the islands to recharge and relax. Some fall so deeply in love with Hawaii that they buy property. The list of celebrities who have bought estates in Hawaii is very long. Jeff Bezos, Pierce Brosnan, Bette Midler, Willie Nelson, Carlos Santana, Anthony Kiedis, Nick and Vanessa Lachey, Woody Harrelson, Owen Wilson, Clint Eastwood, and Mick Fleetwood are just a small sample of the celebrities who own homes or property on one of the islands.

But when it comes to Hawaii's most famous private landowners, three names arguably stand above the rest.

Larry Ellison owns nearly the entire island of Lānaʻi. Facebook honcho and zinc sunscreen aficionado Mark Zuckerberg has assembled nearly 1,000 acres on Kauaʻi. And then there is Oprah Winfrey.

Oprah Winfrey's net worth today is $5 billion. Oprah made her first Hawaiian real estate purchase in 2002. A year earlier, she cracked billionaire status for the first time. With a $1 billion fortune, Oprah easily could have purchased any available lavish estate on Maui and called it a life. Instead, over the last few decades, she has slowly built what has become a sprawling, 2,100-acre, Maui real estate empire…

Oprah's longtime personal trainer and friend Bob Greene helped introduce her to Upcountry Maui, a rural region of farms and ranches located high above the island's beachfront resorts.

Greene reportedly found a modest ranch house surrounded by open countryside and ocean views. The house itself was not the problem. The concern was that neighboring land could eventually be developed with homes or condominiums that would destroy the property's privacy and scenery.

So Oprah began buying the surrounding parcels.

During her first two years on Maui, she reportedly spent more than $25 million acquiring roughly 166 acres across several transactions. Some parcels contained homes, while others were empty agricultural land.

Rather than demolishing the existing ranch house and building a giant resort-style mansion, Oprah renovated it into a Hawaiian farmhouse. The project added higher ceilings, French doors, and a wraparound porch overlooking the surrounding countryside.

The house became the residential center of her Upcountry holdings, but most of Oprah's land remained undeveloped.

Oprah also acquired property near Hāna, a remote town on Maui's eastern coast that is reached by the famously winding Hāna Highway.

In 2002, Oprah and Greene acquired approximately 102 acres of coastal pastureland in the area. The largely undeveloped property is several hours from Oprah's Upcountry home and should be thought of as a separate holding, not an extension of the same estate.

The Hāna property sits beside Hāna Ranch, one of Maui's largest privately owned properties.

In 2022, Hāna Ranch was placed on the market for $75 million. The offering included approximately 3,600 acres, agricultural land, horse facilities, a working cattle operation, and extensive ocean frontage. As we explained at the time, the listing gave a very wealthy buyer the chance to become Oprah's neighbor on a 3,600-acre Maui ranch.

Oprah did not buy Hāna Ranch. Her next major land acquisition occurred on the opposite side of Maui.

Oprah eventually turned part of her Upcountry property into a working farm.

The farm sits nearly 4,000 feet above sea level on the slopes of Haleakalā, where volcanic soil, regular rainfall, and abundant sunlight create excellent growing conditions.

Oprah and Greene designated 16 acres for agriculture. They initially planted a single acre with approximately 100 varieties of fruits, vegetables, and herbs, and added chickens to produce eggs.

The farm was developed with help from Bio-Logical Capital, a natural-resource management company that used regenerative agricultural practices to improve soil quality and conserve water.

By 2013, that single cultivated acre was producing approximately 145 pounds of food per week. The harvest exceeded what Oprah and her guests could consume, so produce was distributed to neighbors, local restaurants, and charitable organizations.

The farm became nationally known after Oprah and Greene posed among the crops for the June 2013 cover of "O, The Oprah Magazine."

Oprah dramatically expanded her Maui holdings through four transactions completed between December 2022 and February 2023.

Her company, Harpo Inc., first purchased two parcels of approximately 10 acres each for $100,000 apiece.

Two months later, Harpo purchased approximately 520 acres from ʻUlupalakua Ranch for $3.89 million and another 330 acres for $2.47 million.

In total, Oprah acquired approximately 870 acres for $6.6 million. That works out to an average price of roughly $7,600 per acre.

The new parcels were located in Kula, close to Oprah's existing Upcountry holdings.

Before the transaction, Oprah reportedly owned approximately 1,280 acres on Maui. The expansion pushed her total holdings to roughly 2,100 acres.

Oprah's original motivation appears to have been privacy and control of the landscape surrounding her home. Buying neighboring land reduced the risk of subdivisions or large developments appearing beside her property.

Agriculture and conservation later became important parts of the project. Much of the acreage remains undeveloped and is used for farming, cattle grazing, and environmental restoration.

Oprah's Maui holdings are a significant part of the at least $200 million worth of real estate she owns across the United States. Her wider portfolio has also included major properties in Montecito, Telluride, Chicago, and Washington state.

But nowhere else has she accumulated this much land.

What began with a Hawaiian farmhouse and a desire for privacy eventually became a roughly 2,100-acre Maui real estate empire assembled one parcel at a time.