hash-mark1. Oprah Winfrey
With an empire spanning media, entertainment, and philanthropy, Oprah Winfrey needs no introduction. The media mogul made headlines when she purchased a staggering 870 acres of land in Kula, located in the Upcountry region of Maui.
Renowned for her talk show “The Oprah Winfrey Show,” which became one of the highest-rated television programs of its kind, Winfrey is not only a cultural icon but also a powerful advocate for causes such as education and women’s rights.
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hash-mark2. Steven Tyler
As the frontman of the iconic rock band Aerosmith, Steven Tyler has rocked stages around the world. In 2012, Tyler decided to plant his roots in Maui, purchasing a $4.8 million home on the island.
Tyler’s musical career spans over five decades, with hits like “Dream On” and “Sweet Emotion” solidifying Aerosmith’s place in rock history. Beyond his musical endeavors, Tyler also served as a judge on the hit TV show “American Idol.”
hash-mark3. Clint Eastwood
Known for his stoic demeanor and iconic roles in Westerns, Clint Eastwood chose Maui as the location for his oceanfront retreat. With a career spanning over six decades, Eastwood has left an indelible mark on the world of cinema as both an actor and director.
From classics like “The Good, the Bad and the Ugly” to modern masterpieces like “Million Dollar Baby,” Eastwood’s influence is felt far and wide.
hash-mark4. Chris Berman
The legendary sportscaster and ESPN anchor, Chris Berman, is another famous celebrity that has found his slice of paradise in Maui. Known for his iconic catchphrases and unparalleled enthusiasm, Berman has been a fixture in the sports broadcasting world for decades.
Beyond his career in broadcasting, Berman is also a six-time winner of the National Sportscaster of the Year award, cementing his status as one of the most respected figures in sports media.
hash-mark5. Kris Kristofferson
A singer-songwriter, actor, and musician, Kris Kristofferson’s career has been nothing short of legendary. Nestled in the lush surroundings of Hana, Maui, Kristofferson’s home is a testament to his love for island life.
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With hits like “Me and Bobby McGee” and “Sunday Mornin’ Comin’ Down,” Kristofferson’s music has resonated with audiences for generations, earning him multiple awards, including three Grammy Awards.
hash-mark6. Woody Harrelson
Best known for his roles in “Cheers,” “True Detective,” and “The Hunger Games” franchise, Woody Harrelson has also found solace on the shores of Maui.
His property in Huelo serves as a peaceful retreat from the demands of Hollywood. Harrelson’s versatility as an actor has earned him critical acclaim, with nominations for Academy Awards, Golden Globes, and Primetime Emmy Awards.
hash-mark7. Paul Simon
In 2019, music icon Paul Simon graced Maui with two unforgettable concerts in Wailuku, benefiting the Auwahi Forest Restoration Project.
The Grammy-winning artist, known for his work as one half of the duo Simon & Garfunkel, has captivated audiences with timeless hits like “Bridge Over Troubled Water” and “Graceland.” Simon’s contributions to music have earned him numerous accolades, including 16 Grammy Awards.
hash-mark8. Owen Wilson
The laid-back charm of Maui’s Paia Town is the perfect fit for actor Owen Wilson. Known for his roles in comedies such as “Wedding Crashers” and “Zoolander,” Wilson’s relaxed demeanor mirrors the island lifestyle. With his trademark wit and comedic timing, Wilson has become a beloved figure in Hollywood, starring in a multitude of box office hits.
hash-mark9. Alice Cooper
While best known for his theatrical stage presence and shock-rock persona, Alice Cooper has also endeared himself to the Maui community through his philanthropic efforts.
Cooper’s participation in the Maui Food Bank New Year’s Eve concerts has helped raise awareness and support for those in need on the island. Beyond his music career, Cooper is also an avid golfer and has appeared in numerous films and television shows.
hash-mark10. Willie Nelson
The legendary country music icon Willie Nelson has made Maui his home, residing in a sprawling 6,038-square-foot property on the island. With a career spanning over six decades, Nelson’s influence on country music is unparalleled.
Hits like “On the Road Again” and “Always on My Mind” have solidified his place in music history, earning him countless awards, including multiple Grammy Awards and a Kennedy Center Honor.
hash-mark11. Jeff Bezos
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As the founder of Amazon and one of the wealthiest individuals on the planet, Jeff Bezos spared no expense when he purchased a $78 million compound on La Perouse Bay. Setting a record for the priciest home on Maui, Bezos’ retreat offers unparalleled luxury and privacy, allowing him to escape the demands of his high-profile career.
hash-mark12. Jim Carrey
Known for his dynamic performances in comedy classics like “Ace Ventura: Pet Detective” and “Dumb and Dumber,” Jim Carrey finds solace on the North Shore of Maui. Beyond his comedic talents, Carrey is also an accomplished artist and philanthropist, using his platform to advocate for various social causes.
hash-mark13. Shane Victorino
Dubbed “the Flyin’ Hawaiian” for his remarkable athleticism on the baseball field, Shane Victorino has deep roots in Maui. As the son of former Maui County Mayor Mike Victorino, Shane has maintained strong ties to the island community while enjoying the serene surroundings of his home on Maui’s shores.
hash-mark14. Mick Fleetwood
As the co-founder and drummer of the legendary rock band Fleetwood Mac, Mick Fleetwood is no stranger to the spotlight. However, when he’s not touring the world, Fleetwood can often be found in Maui, where he actively participates in charity events and supports the local community through philanthropic endeavors.
hash-mark15. Stevie Nicks
With her enchanting voice and poetic lyrics, Stevie Nicks has captured the hearts of audiences around the globe. Nestled near the town of Lahaina, Nicks’ Maui residence provides the perfect backdrop for her creative endeavors, allowing her to draw inspiration from the island’s natural beauty.
hash-mark16. Lars Ulrich
Rumored to reside in Launiupoko on Maui’s west side, Lars Ulrich, the drummer for the iconic heavy metal band Metallica, enjoys the tranquility and seclusion that the island offers. Beyond his musical pursuits, Ulrich is also an avid art collector and philanthropist, contributing to various charitable causes.
hash-mark17. Helen Hunt
Although details about her Maui residence are scarce, Academy Award-winning actress Helen Hunt is known to spend time on the island, soaking in its laid-back atmosphere and stunning vistas. With a career spanning film, television, and theater, Hunt’s versatility as an actress has earned her widespread acclaim.
hash-mark18. Larry Ellison
In 2012, tech mogul Larry Ellison made headlines when he purchased 98% of the island of Lanai in Maui County. As the co-founder of Oracle Corporation, Ellison’s investment in Lanai has brought renewed attention to the island, with plans for sustainable development and eco-tourism initiatives underway.
hash-mark19. Sammy Hagar
Known for his rock ‘n’ roll persona and hits like “I Can’t Drive 55,” Sammy Hagar has also made a name for himself in the culinary world with his chain of Sammy’s Beach Bar & Grill restaurants. Hagar’s presence extends to Maui, where he owns the Kahului Airport location of his popular eatery.
hash-mark20. Matthew McConaughey
The Oscar-winning actor and heartthrob Matthew McConaughey frequently visits Maui with his wife, Camila Alves, indulging in the island’s natural wonders and laid-back lifestyle. With acclaimed performances in films like “Dallas Buyers Club” and “Interstellar,” McConaughey’s star continues to shine bright in Hollywood and beyond.
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