Luxury Guide
How is luxury is defined in Hawaii and should you buy or build?
When deciding which island to purchase a home, many might look to celebrities who reside in Hawaii. While many luxury Hawaii real estate purchases are done off-the-market to ensure privacy and confidentiality, it is known that many high-profile clientele and celebrities have purchased a luxury Hawaii house. Hawaii has always been a destination for affluent tourists to enjoy paradise, but many have also decided to also permanently dwell in paradise – often owning an additional residence in the islands.
Former U.S. President Barack Obama was born in Honolulu, Hawaii, on the island of Oahu, attending the prestigious Punahou School. Now, Barack and Michelle Obama own a 3-acre estate in the Windward Oahu community of Waimanalo (the town next to Kailua). The couple bought the oceanfront house, which was featured in Magnum P.I., in 2015 for $8.7 million. Over the past years, the Obama have completely remodeled the house, including upgrading its two swimming pools and three living structures.
In the Kailua community of Lanikai, rests a beachfront property that is more like a resort. Although the 1.3-acre property wasn’t completed before legendary hair stylist Paul Mitchell passed away, his son Angus now rents the property for celebrities and affluent clientele to vacation. Rihanna, Adam Sandler, Mariah Carey and Beyonce have all said to vacation on the property, which includes a main house, boat house, kitchen house, separate garage building, guest house, bath house and pool house for its saltwater pool and hot tub.
Nestled in the exclusive Kahala community of Black Point, Doris Duke, who was known “as the richest girl in the world” at the time, decided to build her house. It was 1935, and the tobacco heiress intentionally built her house on 4.1 acres of oceanfront land.
The home, which became known as Shangri La and now serves as a museum, showcasing art and architecture inspired by her travels throughout North Africa and Western, Central, South and Southeast Asia, and the landscapes of Hawaii. Because of the thousands of pieces of artwork, especially Islamic art, and Duke’s will, the public can now view this historic luxury Hawaii home.
Famous singer and songwriter – and former professional surfer – Jack Johnson calls Oahu’s North Shore home. Johnson grew up across from one of the world’s most famous waves, Pipeline, later becoming an internationally-acclaimed artist. Johnson now owns a somewhat “typical” Hawaii house near the town of Haleiwa with his wife Kim. It is said to have around five bedrooms and five bathrooms with around 2,000 square feet. Despite his success, he stays true to his roots and continues to enjoy surfing (with some of the world’s best like Kelly Slater) and living a simple, sustainable lifestyle on the North Shore. Johnson has also become a local philanthropic and environmental activist, founding the Johnson Ohana Charitable Foundation and Kokua Hawaii Foundation.
The famous talk show host, television producer, actress and author – and one of the world’s richest women – has been a Hawaii homeowner for over a decade. Oprah owns more than 1,000 acres on Maui, mostly in the upcountry Kula area and in Hana. In addition to the land, it is said that Oprah owns an 11-bedroom ranch home, which was meticulously remodeled and designed. Was Oprah’s home destroyed by the 2023 Maui fires? No, Oprah’s house was not burned in the fires, but it is said that part of her land might have burned. Oprah’s former fitness trainer and current property manager, Bob Greene, has also owned luxury Hawaii real estate on Maui.
One of the wealthiest people in the world owns a beachfront home in Maui. Jeff Bezos, who made many of his billions by leading Amazon, is a Maui celebrity homeowner that is said to have acquired 14 acres of land in La Perouse Bay. The isolated property has a main house consisting of about 4,500 square feet, including an outdoor kitchen and breathtaking ocean views. A 1,700-square-foot guest house and huge swimming pool along with lush landscaping complete the picturesque luxury Hawaii property.
The Facebook/Meta founder and his wife own around 1,500 acres on Kauai’s north shore, near the neighborhood of Kilauea. The Zuckerberg’s call their property Koolau Ranch and a portion of it was once the former sugar plantation called Kahuaina. The property includes a working ranch, farms, a water reservoir and a public beach (Pilaa Beach). Zuckerberg acquired the expansive property with multiple separate transactions, starting with a $100 million 750-acre purchase in late 2014. While the Zuckerberg’s initial purchases of property were somewhat controversial, including lawsuits with Native Hawaiians, some people and organizations in the Kauai community have now started to partner with them after witnessing their dedication to land conservation.
Oracle billionaire Larry Ellison owns 98% of the island of Lanai. One of the world’s richest people, in his Lanai property purchase, Ellison also acquired a resort, a golf course, the island’s main grocery store, the only gas station, the community newspaper and the only non-Four Seasons hotel. Ellison now is said to live full time on Lanai. And, his upscale Four Seasons resort has attracted top celebrities and affluent individuals from around the world, including Elon Musk and Tom Cruise. With parking areas for yachts and private jets, Lanai is an exclusive destination for the most affluent individuals. However, those looking to buy luxury Hawaii real estate will need to shop on another island since Ellison already bought almost all the property on Lanai.
For decades, luxury Hawaii real estate has attracted the world’s most exclusive clientele. Hawaii’s natural beauty, outdoor lifestyle, relationship-based culture, magnificent views and ideal climate along with the ability to live in a home with the latest amenities, highest quality finishes and ultimate privacy will continue to allure high-end buyers for many more decades to come. And, since luxury properties on Hawaii are rare and unique, the market is expected to continue to be competitive and have lasting appeal.
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