The 25 Most Expensive Homes in Hawaii

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Photo: Ryan Siphers

If you want to own one of Hawaii’s top homes, it helps to be in computers or investment banking. Using public records collected by Title Guaranty Hawaii, we’ve compiled a list of Hawaii’s priciest homes—exclusive compounds filled with sprawling swimming pools, personal tennis courts and stunning oceanfront views, places for which the annual property-tax bill runs a cool half-million.

The Top-25 Club turns out to be a who’s who of tech CEOs, venture capitalists and other financial-service barons, almost all from out of state. These are people not only rich enough to afford one $20 million house, but several of them, in different parts of the world.

The distribution of these palatial properties is also illuminating. Oahu has some famously expensive neighborhoods, such as Kahala, Portlock and Lanikai, but they don’t appear in the top 10 spots on our list. In fact, there are only six Oahu properties on the entire list. When it comes to outrageous real estate, it’s all about the Big Island, where you’ll find nine of the 10 most expensive homes in Hawaii, all strung along the Kona Coast.

We assembled a similar list in 2005, limited to the City and County of Honolulu. Expanding the scope to all of Hawaii has raised the stakes considerably: While the top property in 2005 was assessed at $15.2 million, that number wouldn’t even get you on the bottom rung of this year’s list. The bar starts at $16 million and goes up from there.

The dollar amount listed for each house is the county’s most recent assessment of its value, for tax purposes. In most cases, the property details are also based on publicly available city and county data. One note: We restricted this list to single parcels as defined by the county tax offices. That kept things simple, but meant overlooking a few fabulous estates that comprise multiple parcels, such as the 174-acre Tara Plantation on Kauai, which sold in 2009 for $28 million.


Photo: David Croxford

NO. 1

$61.8 million

7 bedrooms • 7 full and 5 half bathrooms • 18,500-square-foot interior • 189,704-square-foot lot

It’s known as the Raptor Residence, but the man behind this luxurious oceanfront estate is Michael Dell, the founder and CEO of Dell Inc. This year, Forbes ranked Michael Dell as the 37th richest person in the world, with a net worth of $13.5 billion. Hawaii County assesses the house alone at $28.5 million, but the better part of the $61 million valuation of this property is the land itself. It’s lot 1A, the premier parcel in the private, luxury residential community of Kukio. (There are no lots 2 and 3—Dell combined three 1-acre parcels.) Kukio is a relatively recent development, an even more exclusive successor to the already spectacular Hualalai resort, next door, but it already figures prominently on this list. Seven of the 25 most expensive homes in the state are located within one of the three divisions of this Kona Coast oasis.



Photo: David Croxford

NO. 2

$39.4 million

11 bedrooms • 12 full and 3 half bathrooms • 16,023-square-foot interior • 220,414 square-foot lot

Property ownership  is public information, but many of the billionaires and millionaires on our list have set up walls of privacy between themselves and the tax records. The No. 2 most expensive house, for example, is officially owned by Kukio Limited. The Dallas address listed for the tax bill, however, is the same as for Kitano Capital, which was incorporated by financier Ellis Short in 2007. Short has been reported to be an extremely private person; he’s managed to stay largely out of the spotlight as the president of Lone Star Funds, a global investment firm that manages private equity funds worth $24 billion, but not as owner of Sunderland A.F.C., a soccer team in England.

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