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On the Anniversary of Hawaii's Statehood, Five Island Gems

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Hawaii turns 53 years old today—as a state anyway, descendants of native Hawaiians would remind us it's much older—and while the island's statehood has been contested and bemoaned by Hawaiian nationalists, there's no denying that the place has been a draw for vacationers ever since. Portions of America's tropical wonderland have been sold in bulk, like the recent purchase of the island of Lanai by the Oracle billionaire Larry Ellison for a reported $500M, parts have been held in trusts by the island's former royalty, but the ones we're interested in are the many homes that dot the paradise, which are some of the finest warm weather escapes in the country. This first one, a gated estate on Maui's unspoiled North Shore, includes 3.4 rare waterfront acres, a three-bedroom main house with soaring ceilings, and a lagoon-style swimming pool to rival any resort. This unique estate has a price tag befitting a self-contained resort of $12.4M.

? This waterfront estate on the Big Island comes with a bit of Hawaiian history attached. Members of the King family, descended from Hawaiian royalty and part of the inspiration for George Clooney's character in The Descendants, have owned this property for generations. Set behind a sea wall, the unassuming grey structure houses four bedrooms and four baths with exceedingly casual interiors. Glorious views and the waterfront rarity help to justify the $3.7M price tag.

? Formerly the grand center of the Baldwin sugar plantation at Haiku, on Maui, this sprawling traditional home was built to a high standard in the 1800s and seems to have stood the test of time well. Enjoying broad, downslope views of the jungle and Pacific, the 9,600-square-foot mansion boasts 10 bedrooms and 10.5 bathrooms on close to 40 acres. Priced at $11.9M, the compound also includes a one-bedroom guest house and a stone-lined swimming pool.

? Sometimes, feeling the waves crash beneath your feet costs more than a mountain of money. In this case, the price is $6.75M plus a serious headache from the gut-ready interiors. Located directly on the water, on lava rock with a private lanai jutting out over the ocean, this "Bali-inspired" mess of a mansion will probably require an interior redo to entice a buyer at this price point. That said, the location is positively brilliant, even if the Diamond Head hillside is crowded with other mansions.

? For some reason, in a land of so much rural gorgeousness, tiny waterfront plots attract some of the island chain's highest prices. This brand new mansion, built on spec and designed by architect Jeffrey Long, is asking a jaw-dropping $20.88M. That hefty price includes just 0.64-acres of land and a 6,600-square-foot house that, while spacious, is hardly the pinnacle of Hawaiian architecture.
· Larry Ellison Scoops Up 98 Percent of a Hawaiian Island [Curbed National]
· 473 Laulea Place [Sotheby's International Realty]
· 69-1886 Puako Beach Dr [Sotheby's International Realty]
· Haiku House [Sotheby's International Realty]
· Diamond Head [Sachi Hawaii]
· 3 Kapalua Place [Zillow]