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The 25 Most Expensive Homes in Hawaii


(page 11 of 13)

Photo: Ryan Siphers

NO. 21

$17.1 million 

5 bedrooms • 5 full and 1 half bathrooms • 5,914-square-foot interior

It would be hard to find a more spectacular location for a dream home. Michael G. McCaffery’s $3-million house sits alone out on a point in Makena, surrounded on three sides by ocean. The Maui retreat has obviously inspired McCaffery—the investment management firm of which he is the CEO is called Makena Capital Management.

Photo: Ryan Siphers

NO. 22

$16.7 million 

9 bedrooms • 9 full and 2 half bathrooms • 19,000-square-foot interior • 22,902-square-foot lot

This Wailea property, known as sandy surf, isn’t used as a full-time residence. Owners Charles and Elizabeth Thieriot frequently rent the place out for extravagant vacationers. Guests have included everyone from Prince to Michael Jackson and Mel Gibson. Charles “Kip” Thieriot, now retired, is a member of the prestigious family that founded and ran the San Francisco Chronicle, and was himself the president of Western Communications.

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