Hawaii has long been a favorite escape for the rich and famous, whether as a vacation getaway or a permanent home. While Kauai, Maui and Hawaii Island boast the largest share of high-profile names (Meta’s Mark Zuckerberg, Amazon’s Jeff Bezos and Oprah Winfrey, to name a few), Oahu has its share of celebrity homeowners, too.
Read on to learn more about some of Oahu's most famous homeowners and the neighborhoods they call home.
Barack & Michelle Obama – Waimanalo
The former President of the United States grew up on Oahu and attended Punahou School. Today, Barack Obama and wife Michelle own a home in Waimanalo on the Windward coast. Located along Kalanianaole Highway, near Kainoa Beach Park, the Obama estate spans three acres of beachfront land. The homesite was once owned by the late actor Jim Nabors (best known for his role as Gomer Pyle on "The Andy Griffith Show") and famously appeared as Robin’s Nest in the original Magnum P.I. series. The home, which was sold in 2015 for $8.7M, has been under construction for nearly 10 years. The original mansion has been demolished, and the remodeled compound now includes 11 bedrooms, 14 bathrooms and multiple pools.
While luxury, beachfront estates like the Obama's can be found in Waimanalo, the neighborhood contains a mix of single-family home types. Sold prices in 2025 range from entry-level for older, plantation-style homes in need of repair, to $5 million for beachfront estates. With the dramatic backdrop of the the Ko'olau Mountains and the longest stretch of sandy shoreline on Oahu, Waimanalo's natural beauty and laidback lifestyle welcome those who seek peace and privacy.
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Jack Johnson – North Shore
Singer-songwriter Jack Johnson—best known for his hit song "Better Together," grew up on the North Shore of Oahu, where he still lives with his family. The son of a professional surfer, Jack learned to surf at young age, becoming the youngest invitee to make the finals of the Pipeline Masters at age 17. The Kahuku High School graduate gave up his professional surfing career after an accident, turning to his other passion—music. Jack and his family, including three children, have called Oahu's North Shore home for more than 20 years. Together with his wife, Kim, Jack runs the Kokua Hawaii Foundation, which supports environmental education in the community.
The Johnson's modest-sized home is located in the Pupukea neighborhood, an area popular with surfers, skateboarders, divers, snorkelers and tourists alike. Recent home sales in Pupukea ranged from around $1.5 million to $5 million.
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Pierre Omidyar – Kahala
Pierre Omidyar, the famously private tech entrepreneur and philanthropist, is one of only a handful of full-time billionaire residents of Hawaii. Like his fellow famous Oahu homeowner, Barack Obama, the Paris-born Pierre attended Punahou School; however, he graduated from another college preparatory school in Maryland. The eBay founder, along with his wife, Pam (also from Hawaii), and their three children, returned to Honolulu, settling in the upscale Kahala neighborhood. In 2010, he launched the online investigative reporting news outlet, Honolulu Civil Beat.
In 2006, the Omidyar family purchased a 5,800-square-foot beachfront estate on famed Kahala Avenue. Some of the most expensive homes on Oahu can be found in Kahala, which is sometimes refered to as the "Beverly Hills of Oahu." There are about 60 Kahala homes with beach frontage, like Omidyar's. These coveted properties easily command tens of millions of dollars. In 2025, a Kahala Avenue estate owned by another early tech entrepreneur sold for a record-breaking $65.75 million. Other notable past and present Kahala residents include actor Daniel Dae Kim, entertainer Don Ho, actress and singer Liza Minnelli, Olympian and surfing legend Duke Kahanamoku and comedian Carol Burnett.
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Glenn Medeiros – Hawaii Loa Ridge
Best known for his 1980s hit song "Nothing’s Gonna Change My Love for You," Kauai-born Glenn Medeiros has since built a career in education. After graduating from the University of Hawaii-West Oahu, he went on to earn a doctorate in educational leadership. He now serves as President and CEO of Saint Louis School, a Catholic private school for boys in Honolulu. Along with his family, Glenn resides in 2,200-square-foot home in the gated community of Hawaii Loa Ridge.
Situated on the foothills of the Ko'olaus in East Oahu, Hawaii Loa Ridge is one of the island’s most exclusive luxury neighborhoods. Prized for its ocean views, custom homes and quiet, private setting, the neighborhood is about a 20-minute drive from Honolulu. A gated entrance with 24-hour security adds peace of mind, while spacious lots—often over an acre—feature lush gardens and a mix of modern, Mediterranean and contemporary architecture. Recent home sales in Hawaii Loa Ridge range from $2 million to $7 million.
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Living Among Legends
From the Windward coast to the North Shore, Oahu attracts world-class musicians, actors, athletes, tech founders and even a former U.S. President. While celebrity homes may grab the headlines, the neighborhoods themselves remain vibrant communities that blend local culture, history and Hawaii’s natural beauty.
Thinking about finding your own dream home on Oahu? Explore our listings and discover the neighborhood that’s right for you!
