These affluent residents bring new dynamics to Hawaii’s neighborhoods and towns, sparking ongoing conversations among residents and visitors. If you are curious about which celebrities have made Hawaii their home, you’ll also discover more in our article 37 Rich and Famous Who Call Hawaii Home.
When Beat of Hawaii editors swim at Hanalei Bay, we use the past homes of celebrities, including Julia Roberts (5204 Weke Road) and the late Michael Crichton (5438 Weke Road), as well as the one from the movie The Descendants (5031 Weke Road) as markers to determine the distance. Like many, these celebrities were drawn to Hawaii’s natural beauty and laid-back lifestyle, seeking privacy, seclusion, and a slice of paradise to call their own.
Hawaii’s Most Exclusive Neighborhoods Where the Rich and Famous Reside.
Certain Hawaiian communities are favored by high-profile figures for their remoteness, scenic beauty, and privacy. While you may not be able to get close to their homes, you may run into some of them while here. BOH editors remember talking with Charo at Long’s and also seeing Pierce Brosnan shopping at the Kukui Grove shopping center in Lihue.
Here’s a look at some of the most exclusive neighborhoods in Hawaii and the notable figures who live there.
Wailea, Makena and Upcountry, Maui. Known for stunning beaches and luxurious estates, Wailea and Makena attract celebrities seeking seclusion and ocean views. Oprah Winfrey owns a sprawling property upcountry, enjoying Maui’s quieter landscapes. Amazon founder Jeff Bezos purchased a $78 million estate at La Perouse Bay, adding to the attention this exclusive area receives. Other notable Maui residents include Clint Eastwood, Mick Fleetwood, Willie Nelson, Paul Simon, Steven Tyler, Woody Harrelson, Kris Kristofferson, Shep Gordon, Jim Carrey, and Alice Cooper.
The backlash against celebrity ownership on Maui.
During our recent visit to Maui, we noticed the “Hall of Fame” display at Kahului Airport. Featuring prominent celebrities like Oprah Winfrey, Clint Eastwood, and Jim Carrey as “Kamaaina Proud to Call Maui Home,” the display is intended to celebrate famous residents with ties to the island. However, it also serves as a reminder of the tension surrounding celebrity ownership on Maui and across Hawaii.
For many residents, this display highlights a growing disconnect between the affluent part-time residents and the local community, which faces rising property costs and a lack of affordable housing—a situation made even more pressing after the 2023 Lahaina fire. The question of who truly gets to call Maui home is part of an ongoing conversation as residents grapple with how high-profile ownership impacts the island’s cost of living, community identity, and housing accessibility.
This shift in Maui’s identity parallels trends seen in other popular destinations, like Florida, where an influx of affluent residents reshapes the local landscape. For Maui, balancing exclusivity with affordability has become a central issue, intensifying the need to preserve community values amid fast-shifting demographics.
Kukio, Big Island. Kukio is a gated community known for its privacy and beachfront properties, which appeal to major tech and business leaders. Michael Dell, CEO of Dell Technologies, and Charles Schwab are among those who have homes here.
As one commenter, Drew808, noted, “Homes sit empty most of the year, with AC and irrigation running 24/7.”
This focus on exclusivity has sparked conversations around resource use and its impact on local communities. The Big Island is also home to Roseanne Barr, Matthew McConaughey, and Marc Benioff.
Diamond Head and Kahala, Oahu. Situated near Honolulu, these neighborhoods combine convenience with exclusivity, appealing to celebrities and affluent individuals. Diamond Head’s prime beachfront properties have been home to figures like the late Jim Nabors and Duane Chapman (Dog the Bounty Hunter). With its oceanfront estates, Kahala draws those looking for prestige alongside Honolulu’s amenities. Oahu attracts high-profile residents like Jason Momoa, Barack Obama, Bruno Mars, Jack Johnson, Nicole Scherzinger, Kris Kristofferson, and Glenn Medeiros.
On an interesting note, Glenn Medeiros is now President of St. Louis School, and the former President of the United States, Barack Obama, lives in Waimanalo on the former estate used in the original Magnum, P.I. show.
For those who want to get a glimpse of the splendor of these homes, the Honolulu Art Museum has tours of the Shangri La Estate, which Doris Duke owned in the Kahala neighborhood. This popular attraction sells out months in advance, so book early if you decide to include it on your Oahu itinerary.
North Shore, Kauai. The North Shore, particularly around Hanalei Bay, is known for its stunning scenery and laid-back vibe, making it a favorite for celebrities. Mark Zuckerberg’s extensive land purchases on Kauai have made headlines, sparking mixed reactions among locals. One reader, Marianne, remarked that “Zuckerberg is precisely the kind of tourist that the governor and mayor want,” referencing how some high-profile residents’ presence impacts affordability. Kauai is also home to Bette Midler, Pierce Brosnan, Owen Wilson, Ben Stiller, Natalie Merchant, and Bill Kreutzmann.
Other Celebrity Residents Across the Islands. Hawaii’s appeal spans all islands, with celebrities like Matthew McConaughey, Jack Johnson, Kelly Slater, Dwayne “The Rock” Johnson, and Eddie Vedder calling various parts of Hawaii home, each captivated by its unique blend of community, privacy, and natural beauty.
The balance between luxury and community.
Yet, as one reader, Erika, commented, “I always wondered how the ultra-rich contribute to the Hawaii local economy in a positive way…sure is a lot of land taken away and developed that will never be affordable for those who live full time in Hawaii.”
This sentiment captures a broader question of balance between privacy for the wealthy and accessibility for locals.
As affluent individuals acquire property across Hawaii, home prices in these areas continue to rise. Regions like Kahala, Makena, and Hanalei Bay have seen significant increases in property values, making it challenging for locals to achieve home ownership.
Long-time resident Ernie S. remarked, “How many properties could typical residents afford to buy? … People from many walks of life vie for space in Hawaii. That fact has driven property costs beyond what most find affordable.”
This trend reflects a growing divide between the luxury some enjoy and the struggles of the local population.
As one visitor observed, “Hawaii’s appeal is universal. It’s a paradise for everyone but also a place where people live, work, and grow up.”
Striking a balance between exclusivity for newcomers and maintaining accessibility for long-time residents is essential. Whether Hawaii’s most exclusive neighborhoods can coexist with the local community’s values remains an open question.
Photo Credit: Shangri La Estate, Doris Duke, courtesy of Honolulu Museum of Art.
Get Breaking Hawaii Travel News
The hotels are too expensive for normal day to day people to come there
Ernie S. I agree 100%. The first step in any recovery is to look in the mirror. Second step is to imagine you’ve traded places with those you bad-mouth. How would you feel in your new place if someone said what you just said? Would you want to help them? Probably not. Be honest.
JA, I am almost Always willing to Help those who are willing to Help Themselves. Even if I don’t agree, totally or in part, with the politics of the situation, I will offer my suggestions. I’ve done it previously and will, if approached properly, do it again. The only caveat, I will refuse to be involved with anyone or anything that involves Pearled Onions (gagging) or Communist/Fascist/Terroristic Beliefs! Toss in Satanism too.
The celebrities you site are just the tip of the iceberg when it comes to wealthy folks who own property in Hawaii. I think along with the display of the wealthy living on Maui there she also be facts about the poverty level and how many folks are either house or food insecure. This is the problem faced in American society as a whole in the amount of money concentrated in so few hands. It’s not just Hawaii.
In reality not much ….
Would love to see decent airfares !!
BOH your “…on an interesting note about Glenn Mederios…”. Does it make a difference if he was born & raised on Kauai & is able to enjoy his success living where the rich & famous transplants live?
Same with your knowledge about how Koloa’s history info may not have been complete without other well known local Koloa historians.
I’ve posted this elsewhere but I really get the feeling these folks are trying to turn the islands into their own private reserve… JMO.
Best Regards
Quit inviting or accepting tv shows like Magnum PI, Gilligan’s Island, Hawaii five O, Hawaii five O second series, Karate Kid, Movie Keiko, Point Break, and now Rescue High Surf. The only really celebrity was
Don Ho. Lived and performed in Hawaii for years. Quit buying things on Amazon, Microsoft, Tesla, and supporting all these people who take over your Islands. I suppose none of you ever purchased or sold an Oprah magazine also. How many Hawaiians own an Apple phone? Exactly.
d
The only celebrity is Don Ho? What about the surfboard riding Duke 🤔 and his Brothers? I’m Certain that there’s more. I’m just the occasional visitor and I know that!
Aloha Guys! A similar situation is occuring at Lake Tahoe’s North shore. Larry Ellison has bought the Hyatt Regency property there and is dismantling the cottages to build a luxury resort that only the uber rich will be able to afford. Tahoe is becoming more and more exclusive as well.
~ Debi
Debi, Lake Tahoe has been a Destination, as well as Residence, for the Wealthy, Rich, and Famous for 60 plus years. I don’t envy them. Ellison’s purchase and transformation simply follows that pattern and evolution. I would counter your worries with this thought, we all now know where they will be. It’s like they are all behind a protective glass enclosure, akin to a Zoo, our interactions only occur when They are docile and restrained! Not much comfort, but there’s some.
A small 2 bedroom condo in Kihei with a price tag of $1.5 million is just as unaffordable for the average Maui resident as the mansions and acreage owned by celebrities. Being famous doesn’t make it wrong to spend your money on a slice of paradise. Be honest and admit that you would do the same. Being unable to afford to buy local real estate is not a problem unique to Hawaii,and chasing all the big money spenders out will not solve anything. The sense of entitlement displayed by some Hawaii residents is astounding. Home ownership is a privilege,not a right and there are lots of places besides Hawaii where this is an unattainable dream. So don’t blame the rich and famous for your problems.
In summary:
1. Affordable housing in resort areas is a universal problem.
2. It’s been improved in areas where Private investors and Public officials have worked together. It’s called PPP. This also includes investing in non-tourism industries and infrastructure.
3. The root cause is Hawaiian (state and country) Public officials that follow a tax & spend strategy and demonized investors and wealthy individuals (that pay astronomical taxes) while pandering to the voters that demand handouts and reparations while leaving their junk along the roads.
4. The solution should be obvious.
Wow, Your posting deserves a Billboard, actually Many, on Every Island and in prominent places. Along with that, Your Reply Deserves a Huge and Loud “Amen!”
Ernie, I’m not willing to give up on the Hawaiian people. They have the wheel. All they have to do is vote out the corrupt current batch of politicians. What do they have loose?
I wasn’t surprised at Kahala making the list, quite a few people of wealth have shoreline homes. Johnny Depp lives there, part time, and his Pirate Flag flying is supposed to indicate that he is at home. Most of the Celebrities that own homes in Hawaii are part time residents. Of course they have Security of some kinds to ensure their privacy is respected, they assuredly have it at their full time homes, elsewhere, as well. Whether full or part time residents they definitely contribute to the community. They support local businesses and eateries, hire local companies and people to fulfill their needs. Are they good stewards of the land? With the money they spent on their properties, how often do you see them, or the land, in despair or decline! Friendly? I’ve never heard accounts of them being anything but. Good neighbors? More than likely, how would anyone really know, exclusivity has its privileges!
aloha – It’s hard to understand, they’re all over the map on what they want. i do know the housing affordability is a challenge all over the United States and not just Hawaii.
Instead of being frustrated with celebrities who own small parcels of land on Kauai, people should be frustrated with the Locals who several years ago stopped the planning for a development of 135 affordable homes near the Lihue airport on vacant sugar cane fields because it would “take away scenic open spaces”.
You sound like one of those ‘celebrities’
It’s not surprising, the populace working against what is best for itself over something like that. Imagine if it had gone through, how many people, Families, would have had Affordable Housing. The Dreams and Desires of so many, gone because of a view. How many times will something like this play out before the Government builds what’s needed for the people, disregarding public input. Are they going to Refuse to live there? That’s highly Doubtful! Just build it and they will come.
If the property tax levy on these properties is proportional to what we pay for our Maui STR, the county is receiving millions of dollars in property tax’s from them every year. I’d ask the journalists that run this site to investigate and publish what these properties are paying. If they are paying the equivalent to us (based on selling price) they are contributing a huge $ amount to the county and consuming very few of the services.
Those that are complaining IMHO just suggesting the old socialist “distribution of wealth” process.
In the end I’m guessing if all these people left Hawaii and their properties were worthless, there would be a huge shortfall in property taxes that the regular citizens would have to make up.
With all of the property taxes from the Wealthy, if that were to disappear I believe that many Services for Residents would too. I know that our in-law bought, and significantly improved, his part-time residence in Kahala, and the upkeep is not cheap. His home is in an area of working people, despite being in Kahala the residents of that area are very friendly and down to earth. The mostly exclusive portion is along the stretch that is basically on the beach, that’s where most people couldn’t afford to live.
Was stealing land from Kanaka Maoli a “socialist distribution of wealth process” or just criminal theft? We still live with this legacy and mindset today.
For long timers forced to move to the mainland because of rising rents due to outsiders moving in, I’m all for a little socialist redistribution of wealth fund to keep locals here.
“…For long timers forced to move to the mainland because of rising rents due to outsiders moving in, I’m all for a little socialist redistribution of wealth fund to keep locals here.”
1. Who is an “outsider” and how long would you have to live in HI to be considered a “local”? (I was born in HI before it was a state)
2. And who decides how much “little socialist distribution” is the right amount?
3. And how much money do you have to have to be considered one of the people the money is taken from?
Excellent questions. Difficult questions. And important ones worthy of discussion.
Patrick, You’re really out of touch with the truth and realities of life!
I fell in love with Hawaii and it’s wonderful people on my first visit to the islands as a teenager in 1965. So much in Hawaii has changed over these decades, and unfortunately not all of it has been good. We visit every year, and some years multiple times a year.
It’s getting more expensive and some day we won’t be able to come. But the thing that troubles me most, and makes our heart’s ache, is what these changes and economic pressures have done to the people of Hawaii. It’s beyond disgusting. Hard working people having to juggle three jobs to make ends meet! This is terrible and should not be happening anywhere in America.
Aloha to all.
The richest 130,000 American families now own nearly as much wealth as the bottom 90 percent — 117 million families — combined.
The three richest Americans own as much as the entire bottom half of the population.
The only other country with similarly high levels of wealth concentration is Russia.
This has been accompanied by a dramatic increase in the political power of the super-wealthy and an equally dramatic decline in the political influence of everyone else.
We see this in Hawaii, as native Hawaiians and local families are forced to move to the mainland, replaced by wealthier people and corporations.
Here’s a novel concept, instead of trying to ban STR’s maybe they should ban celebrities and non U.S. Citizens from owning property in Hawaii. I’ve never understood this infatuation our culture has with celebrities and athletes. People look up to them as if they are deities but in reality the vast majority of them are pompous and arrogant jerks who wouldn’t urinate on you if you were on fire. They come to the islands and throw their money around, purchase houses built on sacred land and spend less than 30 days there the entire year. Meanwhile you have natives who can’t even afford groceries let alone a place to call home. Something needs to change otherwise there will be no more Hawaii.
Well said. Agree completely!
Aloha.
Who sold them the property? Don’t they have some culpability in this?
A couple of things here that come to mind…
1. “If you are curious about which celebrities have made Hawaii their home…” I think it might be more appropriately be titled “Which celebrities have bought a house in Hawaii..” Have any of them really made it a home?
2. As far as affordability goes.. it’s not any different than any other place in the U.S or the world for that matter, the more desirable, the more expensive. just the facts of life. I grew up in CA but could never afford to by on the coast.
I am a resident of Kauai’s North Shore and I shudder with dread every time I read about another big shot buying property up here. Because as soon as the deal closes the no trespassing signs go up blocking off access to beaches, waterfalls and hiking trails. And it’s not just no trespassing signs, it’s security cameras and security guards. Aloha for me but not for thee.
100% Correct! Hawaii is for the people not for the Uber Wealthy. If they really want to solve the problem then they need to enact a law that states if you want to purchase property on the islands you must be a resident for a minimum of 183 days per year and the purchaser themselves must occupy the residence not one of their lackeys. That will quickly fix the vast majority of issues natives have with investors coming in buying everything up. If you want to take it a step further then the state can stipulate for every new luxury house being built, an equivalent of 3 low income houses must be built for natives. I’m generally not in favor of these policies on the mainland but the islands are a completely different case. So many are being forced out in large part due to the cost of living. I’ve said this dozens of times but you cannot have Hawaii without Hawaiians…
Remember, when people purchase expensive homes, someone made money selling it. The local realtor, broker company, loan office, etc. These homes create a wealth for the county and residents through taxes. Yet they are only here part time. They provide jobs year round.
the realtor makes money in a feast or famine environment. the other “jobs provided” are mostly low paying jobs service jobs maintaining the properties and desires of the wealthy–these are the people most at risk for having to move to the mainland. if these homes were replaced by multiple homes for natives with decent paying jobs, the tax base would be fine. job creation is another issue, as we are too dependent on tourism.
Hmmmm… let’s say “..these homes were replaced by multiple homes..” Say 30 or 40? right on the coast / beachfront? then they would be affordable by the natives as you put it?
no, more assistance is needed because the gulf is so wide. an affordable housing program would be needed to subsidize loans or to buy, build, and rent these units out at below market rates.
Kaleo, all of this things that you seek probably sounds good to you and your friends, in the Real World it’s quite ridiculous. Why are you attacking honest, hard working, professionals who chose to have a piece of paradise? It’s their own money that they used, not some State Subsidy. Wanting to portray yourself, and others, as the typically poor and downtrodden doesn’t help. Why don’t You get together with others who feel this way and attempt to force the building of the homes and condos paid for by the State of Hawaii? Better yet, forcefully speed up the Hawaiian Council that is giving away lands to the Indigenous to build houses upon? Stalking, and Gawking, the Wealthy isn’t Healthy.
the “real world” is what we make it to be. I’m attacking the system in which the word “billionaire” even exists, not the people themselves.
The three richest Americans “own” as much as the entire bottom half of the population. In a wealthy nation with millions of homeless, this is obscene.
The only other country with similarly high levels of wealth concentration is Russia.
This has been accompanied by a dramatic increase in the political power of the super-wealthy and an equally dramatic decline in the political influence of everyone else.
In other words “You’ve decided they have to much too much money. They have to give it to…?”
Residents like this might be okay, but maybe Hawaii should have its own approach to such high-profilers, with guidelines on how they can contribute to community. That would show respect for the islands and the people here beyond just taking.
You can add one more name to your list of the super-wealthy who have bought Hawaii’s land. Larry Ellison, one of the richest men in the world, bought about 98% Lanai Island. His neighborhood is a whole Hawaiian Island.
It disgusts me that this was even possible and is still possible. What next, Elon Musk “purchasing” Molokai? This is not pono, it is not Hawaiian.
He bought it from someone. Ask them why they sold it?
I’m indicting the system that allows for this to happen, regardless of who the “buyers” and “sellers” are. no one person should have control of Lanai, the people should. we have modern day kings and queens that we call billionaires, because of the system.
Naomi, “Taking” would assume that they had walked into an office and forced someone to give the land to them, that’s Not how it happened. They have Spent Their Money to Purchase the Property. Even more Money was Spent on Building a Home, as well as Everything Else to Improve and Secure the Property. It happens pretty much Everywhere, except some Communist Countries!
Thanks for this. This has been a concern for more than a while. We need to shed light on how residents feel and what’s at stake in the bigger picture.
Mixed feelings here. The attention might bring more jobs and growth, but I worry about losing the Hawaii that I grew up in.
That is why do many kama’aina have moved to the mainland, myself included. The only property I could afford is my plot at the graveyard, where generations of my family are!
Hi Eric – Unfortunately, I think you’ve already lost that Hawaii. The Aloha is gone, and Hawaiians have made it clear that visitors are not welcome, so they need to figure out a way to revive their economy with non-tourism industries in order to survive. It may take a generation or two making sacrifices, but I believe they can do it because of their strong spirit of determination.
These neighborhoods are all amazing looking, but aren’t there ways for celebrity residents to support local communities more directly? That’s what I’m hoping to see more of from these folk.
So many homes sit empty most of the year, while other long time residents cannot afford rent, and are forced to move away from Hawaii. This is especially true for Kanaka Maoli.
How about a heavy tax each day a home sits empty beyond 45 days a year? Use the money to help Kanaka Maoli stay in Hawaii.
Celebrities or not, people are always going to want to be here. Maybe it’s more about how we balance tourism and local needs, which is tricky but important.
Living on Maui my whole life, I’ve seen how celebrity interest raises housing costs. I’m all for sharing our beautiful islands, but it’s tough to watch locals struggle to afford homes.
Aloha Lani –
I really appreciate what you had to say, and just want you to know I empathize with you regarding locals not being able to afford housing. It is the same here in the SF Bay Area, and we see dozens of homes bought up by corporations that turn around and sell the homes at a huge profit, and foreign nationals that buy the homes and let them sit empty for years, waiting for them to gain equity. I know in California there is legislation being proposed that will limit any buyer to purchasing only two homes. Maybe Hawaii will consider the same. Much Aloha to you.