West Shore, Big Island
While the Big Island is usually No. 1 -- or close to it -- on the Best Islands to Live On annual ranking, this $28 million 6,600-square-foot home on the west side of the Big Island is not the No. 1 most expensive house listed in the Hawaiian Islands. In fact, it's only No. 3. Still, if you can settle for five beds, six baths and views from your pool that will make you weep with joy, this house is worth it.