4. Wailea House
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.