O‘ahu’s 10 Most Expensive Homes

Each of these is a striking opportunity—if you can afford it.
O‘ahu’s 10 Most Expensive Homes
Photo: Augie Salbosa


The real estate market continues to hold strong on O‘ahu, with the number of home sales and prices rising steadily and homes only staying on the market for an average of less than two weeks. This week, we take a look at what it looks like at the very top of the market—the most expensive homes on the island currently available for sale.


10. 4577 Kāhala Avenue

It’s no surprise that Kāhala Avenue makes the list. This resortlike property, located on a private and quiet stretch of Kāhala beach, has five bedrooms and five-and-a-half baths spread out over more than 6,000 square feet. Situated on nearly half an acre of land, the home’s contemporary Island style makes you feel like you’re in your own private Four Seasons. The large master suite on the second floor has gorgeous views of the ocean and beyond to Koko Head. Listed for $15 million.


9. 1105 Kaimoku Place


1105 Kaimoku Place
Photo: Choi Group


Located on the rarely available Kaimoku Place, this estate has two homes on nearly an acre of beach just east of Wai‘alae Golf Course. The oceanfront single-level home has five bedrooms and a pool overlooking 118 linear feet of beach; the second home on the property is a four-bedroom guest house that was built in 2000. All in all, it’s more than 8,000 square feet of living area. Listed for $15 million.


8. 41-543 Kalaniana‘ole Highway


41-543 Kalaniana'o Highway


Just steps away from where Magnum P.I. (the original) famously helped ladies learn to snorkel, this beautiful home overlooks some of the clearest waters on O‘ahu. The property has a total of nine bedrooms and seven-and-a-half baths, and underwent a multimillion-dollar remodel in 2017 that includes custom hand-carved wood finishes, a modern chef’s kitchen with Viking appliances, and remodeled baths that feature stunning glasswork. This estate is an entertainer’s dream with 360-degree views, a resort-style pool and spa, and extraordinary outdoor living spaces for hosting events. Listed for $16.9 million.


7. 280 Po‘ipū Drive


280 Po'ipu Drive
Photo: David Tonnes


This home is being sold with the neighboring property for a total of more than 60,000 square feet of ocean-view lot on the slopes of Koko Head. With stunning views from Maunalua Bay to Diamond Head, the six-bedroom, seven-bath home was built in 2010. Listed for $17,750,000.


6. 5403 Kalaniana‘ole Highway


5403 Kalaniana'ole Highway


Originally built in 1989 and remodeled in 2015, this Niu Beach modern estate is sophisticated, warm and welcoming. The 1.43-acre oceanfront estate has 185 linear feet of beach frontage, a tennis court and pavilion, Jacuzzi and pool pavilion, and lush tropical landscaping. The seven bedrooms include three master suites, three additional bedrooms and a caretaker suite. Listed for $17,950,000.


5. 3639 Diamond Head Road

This Diamond Head beach home was rebuilt in 2004 in a classic kama‘āina style, complete with board-and-batten siding, hardwood floors and glass doors that slide away to reveal 85 linear feet of beach. The three-bedroom, four-and-a-half-bath home was originally built in 1941. This one’s not as large as some of the others on this list, but who needs interior space when you have a large grassy yard and direct ocean access? Listed for $18.8 million.


4. 68-407 Farrington Highway

This vacant lot, located on the beach in Mokulē‘ia, is all about location and wide-open space. With 1,393,900 square feet (that’s 32 acres) of land, it’s one of the last large oceanfront properties on O‘ahu. It’s actually four separate parcels, with enough space for up to eight homes. While other properties in this price range usually offer around 100 linear feet of beach frontage, this property has 1,000. Walk to polo games and North Shore fishing, surfing and diving spots. Listed for $20 million.


3. 202 Kaikū‘ono Place


202 Kaiku'ono Place
Photo: Chris Schmauch

With neighbors like Doris Duke’s Shangri La, this contemporary home has a gracious interior that opens onto terraces overlooking Diamond Head Beach. Steps from great South Shore surf, the 4,829-square-foot, four-bedroom, four-and-a-half-bath home was featured in Forbes Magazine and Architectural Digest. Private deeded beach access is included. Listed for $22 million.


2. 51 Kaikea Place                

Built in 2008 on more than 2 acres of Kailua Beach, this 7,851-square-foot home has seven bedrooms, five full baths and two half baths. With vaulted open-beam ceilings and a lava rock fireplace, it has all the charm of an old Hawai‘i estate without the pitfalls of an older building. Listed for $26 million.


1. 145 Kailuana Loop


145 Kailuana Loop
Photo: 360 Property Photos


Kai Moena, “House of the Resting Sea,” listed for $30 million, is the most expensive home currently available on O‘ahu. The 60,000-square-foot property is situated on more than 250 linear feet of Kailua Beach. Kai Moena comprises two main residences that include a total of 10 bedrooms, eight full bathrooms and three half baths. Rich tropical hardwood accents, vaulted ceilings, and doors that slide away blur the lines between indoor and outdoor living. Luxury amenities include two fully appointed kitchens, a tennis court, a sauna, fitness and media rooms, and a lagoon pool.