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The 25 Most Expensive Homes in Hawaii


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Photo: David Croxford

NO. 3

$31.3 million

5 bedrooms • 7 full and 2 half bathrooms • 12,620-square-foot interior • 117,046-square-foot lot

This oceanfront Kukio property grabs the No. 3 spot even though it sits in the middle of acres of black lava rock in Kona; the luxury subdivision and golf course that will eventually surround it have yet to be built. It belongs to Carol Ann Bartz, the president and CEO of Internet service company Yahoo! Bartz has a long tech pedigree: When she purchased the property in 2006, she was working as president and CEO of Autodesk, a design software company, and has also worked at Sun Microsystems and Digital Equipment Corp. 

Photo: Ryan Siphers

NO. 4

$29.3 million

8 bedrooms • 8 full and 2 half bathrooms • 21,692-square-foot interior • 38,028-square-foot lot

This Wailea house,  the most expensive residential property on Maui, and one of three houses on our list within a 2-mile stretch of coastline, is owned by Thom Weisel, a financier who founded the San Francisco-based investment banking firm Thomas Weisel Partners Group. Weisel has been described by the San Francisco Chronicle as “the alpha male of Wall Street West” with an “uber-competitive streak.” It’s a drive that extends to athletic pursuits, as well. Weisel is a three-time world masters cycling champion.

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