The Hawaiian word for good fortune is pōmaikaʻi and most would say the exceptionally rare opportunity to purchase two side-by-side oceanfront homes in South Maui is good fortune indeed. A thousand years ago, Polynesian voyagers traveled by dugout canoe, guided by the stars, and that same sense of pōmaikaʻi landed them on the untouched shores of Mākena.

Today, this southwestern part of Maui is highly covetable, considerably lower in density than other areas of the island, with an inventory of only 80 or so oceanfront homes.

Two of those homes—4640 and 4650 Makena Road—are presently listed at $45 million as a single private compound, the two joined residences providing eight bedrooms sprawling across 7,500 square feet of living space set on 1.26 lush acres. More alluringly, the estate holds 200 feet of ocean frontage, and the homes are perched about 35 feet above a pearly crescent of golden sand beach, easily strolled down to by walking path. The lanai off one of the houses cantilevers over a black lava rock cliff, with Pacific Ocean views reaching to the Molokini crater, the volcanic island of Kahoʻolawe and the West Maui Mountains.

Beyond the tempting tropical-resort vibes at play, the considerable value here is the fact that Mākena’s coastal regulations no longer allow new residential builds of this kind. Current setback requirements state that structures must........

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