Hawaii Celebrity Real Estate Shake-Up: Who’s Buying, Who’s Selling

Hawaii’s rich and famous never seem to stay still. One year, it’s a new billionaire buying up hundreds or thousands of Hawaii acres, the next it’s a celebrity cashing out of paradise. From the postcard-perfect sands of Kailua Beach to the rolling pastures of the Big Island’s Hamakua Coast, the islands remain a strong magnet for fame and fortune. The roster of celebrity owners is always in motion.

This summer has brought another shake-up in Hawaii’s celebrity property market. Roseanne Barr just listed her 46-acre macadamia nut farm and ranch near Honokaa for about $1.95 million. On Oahu, singer Pat Benatar and Neil Giraldo have put their Kailua beachfront retreat on the market for around $5 million.

Mark Zuckerberg and Priscilla Chan have steadily grown their presence on Kauai’s north shore, where they now own well over fifteen hundred acres near Kilauea. Their acquisitions have sparked heated community debates over walls, fences, and restricted access, even as they have also made recent contributions to local causes, including a $2.3 million gift toward affordable rental housing in Hanalei.

Marc Benioff, the Salesforce founder, has also left his mark. His $150 million gift to Hawaii health care renamed Straub Benioff Medical Center, even as his growing land presence on the Big Island has drawn both praise and controversy.

Who’s selling includes Roseanne Barr’s macadamia nut farm.

Roseanne Barr’s ranch on the Hamakua Coast features 46 acres of land, a primary residence with over 2,700 square feet, and an orchard of macadamia nut trees. The region, once home to sugar plantations, is known for sweeping ocean views and lush green hillsides. While the $1.95 million price tag may seem like a steal, the cost of property upkeep will need to be factored into the decision by a potential buyer.

Barr has owned the property for years and even filmed parts of her reality series there, but she is now ready to sell, reportedly while living in Texas. The farm reflects Hawaii’s agricultural heritage, and its sale raises questions about whether it will remain a working property or be converted into a lifestyle estate for its next famous owner.

On Oahu, Pat Benatar and Neil Giraldo are parting ways with their home fronting Kailua Beach, one of the most recognizable stretches of sand in Hawaii. Kailua has become a magnet for celebrity buyers in recent years, with high-profile homes dotting its shoreline, and their departure fits into that larger trend.

Their exit also echoes other high-profile celebrity shifts, including those of longtime owners like Clint Eastwood, who maintains a property on Maui but has kept a lower profile in recent years. These changes remind us that even beloved celebrity owners eventually cash out.

Who’s buying in Hawaii?

While some are leaving, others are investing even more deeply. Mark Zuckerberg and Priscilla Chan have steadily expanded their presence on Kauai’s North Shore, where they now own well over a thousand acres near Kilauea. Their acquisitions have sparked heated community debates over walls, fences, and restricted access, making them one of Hawaii’s most controversial celebrity landholders.

Oprah Winfrey has assembled one of Maui’s most significant celebrity property portfolios, particularly in Kula, where she owns hundreds of acres.

Jeff Bezos and Lauren Sanchez made waves when they purchased a $78 million estate overlooking spectacular La Perouse Bay, a dramatic stretch of coastline known for rugged scenery. The record-breaking price then set a new benchmark for Maui real estate, underscoring how quickly Hawaii’s luxury market has escalated.

Larry Ellison, meanwhile, remains in a category of his own with his ownership of nearly the entire island of Lanai.

Why celebrities move on.

Celebrities sell in Hawaii for many reasons. For some, the challenge of maintaining large estates so far from their primary residences becomes too much. Others find the isolation and constant trans-Pacific travel to be exhausting. The spotlight of public scrutiny can also weigh heavily on individuals.

Roseanne Barr’s sale coincides with her move back to the mainland, while Pat Benatar and Neil Giraldo may be ready to downsize or spend more time closer to family.

Even for the rich and famous, Hawaii can be a challenging place to hold onto in the long term. Maintaining a property from thousands of miles away often proves difficult, and the romance of island life sometimes fades once the practical realities set in. That is why so many celebrity owners eventually leave, even as others arrive to take their place.

For every celebrity who exits, another one usually steps in. Hawaii continues to represent privacy, beauty, and the rarity of truly exceptional properties. That mix is irresistible for the wealthy, even if it proves fleeting for some.

What this means for Hawaii.

Celebrity real estate transactions are often treated like entertainment news, but in Hawaii, they also touch on larger issues of land, culture, and community. Each new purchase or sale sparks questions about how these transactions affect the islands.

A property like Barr’s mac nut farm highlights the tension between Hawaii’s agricultural heritage and the transformation of farmland into lifestyle estates.

While celebrity ownership can boost local economies through jobs, construction, and publicity, it also drives up property values in ways that make it harder for Hawaii families to afford homes. The fences and security measures that accompany many of these estates can limit access to beaches and trails, creating resentment among residents who feel shut out of places once shared freely.

Zuckerberg’s land acquisitions on Kauai have become a flashpoint for those concerns, while Ellison’s ownership of Lanai reshaped the entire island community.

A recent analysis by Beat of Hawaii found that just 37 wealthy individuals now control more than 218,000 acres statewide — over 10 percent of all privately owned land. Read more in, Who really owns Hawaii in 2025.

What do you think?

Does Hawaii’s celebrity churn make the islands feel more glamorous for visitors or less welcoming for both visitors and residents alike? We welcome your comments.