Barrons’ Twenty Best Places to Buy a Second Home: Maui, Hawaii

Maui Second HomeFor second homes in America’s most affluent locations, the past year was ugly. No way else to describe it. Median home prices were down 50% in North Lake Tahoe, and 44% on Martha’s Vineyard, to cite two examples.

Last year was brutal for second homes in the nation’s most affluent areas. But the market is firming up again. Here’s our list, expanded to 20 sites, for those seeking top-tier refuges.

6. MAUI, HAWAII: While Michael Dell and Charles Schwab gravitate to the land-rich Big Island (Hawaii), Maui has Oprah and her 100-plus-acre estate in the isolated upcountry coastal town of Hana. There, she transformed a modest rancher into an oceanfront farmhouse. Critics sniff that the wraparound porch is more Deep South than tropical plantation. Country music star Willie Nelson hangs with locals at Charley’s Western saloon and eatery on the north shore in Paia, where he is known to pick and strum. The outdoor bar at the Four Seasons Hotel in Wailea is for tuna poke (poe-kee), an indigenous “pupu” of raw fish. Five sales last year were over $10 million, with the finest going for $14.5 million.

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