Celebrities With Homes on Maui

There are a number of celebrities who have called Maui their home and some who continue to live (either some or part of the time) on the island. You may spot one of them, or some of them, all together.

Oprah Winfrey

Oprah Winfrey speaks at “Live Your Best Life” on Maui. PC: Wendy Osher / Maui Now

Oprah Winfrey, the $2.8 billion media executive, talk show host and former actress is arguably the most eminent celebrity who calls Maui home at least part of the time. Oprah owns an American-farmhouse style property in Upcountry Maui and an estimated 200 acres of land in the East Maui town of Hāna.

For much of her initial time on Maui, Oprah shied from involvement with the Maui public. However, her public appearances in recent years have marked a shift towards more engagement in Maui’s public affairs.

In July of 2019, Oprah stopped by the Maui Humane Society following a wildfire to check on the animals. She snapped a photo and shared it to her Instagram. According to the shelter, Winfrey thanked staff and volunteers for their hard work and made a donation during the visit.

In 2017, Oprah hosted a public event sponsored by the Hawai‘i Medical Service Association entitled “Live Your Best Life,” promoting healthy lifestyle conversations with Maui and Hawai‘i residents.

Oprah said, “They wanted me to come here to talk about living your best life and being healthier… and I go, how do you tell [that to] the people who already live in the best place in the world?”.

In 2012, Oprah became involved in the organic food business, using some of her properties to cultivate and distribute organic produce throughout Maui and the Hawaiian Islands.

Paul Simon

Paul Simon Maui concert 8.3.9. File photo by Wendy Osher. Exclusively for Maui Now.

Legendary singer and songwriter Paul Simon. is one of the more recent celebs to make Maui his home.

Simon held two concerts in August 2019 at the Maui Arts & Cultural Center, marking the first Hawaiʻi shows since Simon & Garfunkel appeared at the Blaisdell Arena more than 50 years prior.

Simon undertook the concerts with the goal of devoting his net earnings to designated local environmental organizations: the Auwahi Forest Restoration Project on Maui, led by his friend, biologist Dr. Art Medeiros; as well as Kua‘āina Ulu ‘Auamo (KUA) which works to advance community-based natural resources management across the Hawaiian archipelago.

Mick Fleetwood

Tony Takitani, Lani Correa, Mick Fleetwood, Saedene Ota and Wesley Lo. (Left to Rt). Courtesy file photo.

Mick Fleetwood, legendary drummer and co-founding member of the iconic band, Fleetwood Mac is pictured above in 2010 when he served as a member of the Maui Memorial Medical Center Foundation Board of Directors.

The muti-Grammy Award winning artist and inductee of to the Rock n’ roll Hall of Fame is no stranger to the island music scene here on Maui.  His Mick Fleetwood Island Rumours Band was developed in collaboration with island musicians, creating a unique blend of rock and Hawaiian music.  Fleetwood opened a restaurant, bar and night club in Lahaina, Maui on Front Street, in the Summer of 2011.

Fleetwood’s on Front Street transitioned to a temporary closure amid the COVID-19 pandemic, but managed to drum up a virtual concert that raised money for the Maui Food Bank.

Steven Tyler

File photo courtesy: Katarina Benzonva

Aerosmith lead singer Steven Tyler is also a part-time Maui resident.

Back in 2012, Tyler purchased a $4.8 million home in Wailea.

Tyler’s presence in the islands has also influenced a particularly unusual piece of Hawaiʻi legislation.

In 2013, the State of Hawaiʻi passed a bill titled the Steven Tyler Act which protects celebrities on their privately owned properties from paparazzi.

Tyler also appeared alongside Willie Nelson at the 2018 Maui student-led rally and concert to end gun violence in schools.

Owen Wilson

Actor, producer, screenwriter, and Academy Award nominee Owen Wilson purchased an $8 million home in Pāʻia on Maui’s north shore back in 2009.

Wilson has been known to visit north shore beaches or frequent shops and restaurants in Pāʻia Town.

His acting roles have notably been alongside Kauaʻi home owner and Emmy Award-winning actor Ben Stiller, who have both appeared in such films as Zoolander, Tropic Thunder, Night at the Museum and Meet the Fockers.

In 2001, Wilson faced off with then Maui Mayor Alan Arakawa in a $50,000 charity chess match where Arakawa beat Wilson 2 to 3 and donated the proceeds towards relief efforts for the 2011 Japan earthquake, tsunami, and nuclear crisis.

Wilson has also made regular appearances at the annual Maui Film Festival.

Willie Nelson

The country music legend, songwriter, poet and activist Willie Nelson has been a long-time Maui resident and performs regularly all over the island.

Nelson is known to frequent the Pāʻia landmark, Charley’s Restaurant and Saloon where he has been known to perform live with his son Lukas Nelson.

In March 2018, Nelson appeared alongside other celebrated artists in a Maui student-led rally and concert to end gun violence in schools.

Clint Eastwood 

Academy Award winning actor, director, and star of films Dirty Harry, Gran Torino, and The Good, the Bad, and The Ugly has been a long-time resident of Maui, owning a home on Maui’s south side in Wailea.

Eastwood has regularly attended the Maui Film Festival, claiming that it’s just 5 minutes from his house.

In 2010, Clint Eastwood used a portion of Front Street in Lahaina to film his Romance/Thriller Hereafter.

“I love Maui, what’s not to love?” said Eastwood.

What makes Maui unique is that whether born and raised, “flown and grown,” full or part-time residents, Maui’s host of celebrities come together for the community they call home. Whether its hosting a benefit concert in support of high school students, supporting Maui’s organic farming community, or even Owen Wilson and former Mayor Alan Arakawa duking it out in chess for charity, these celebrities e hui pū, come together.