Hawaii is not simply a place to live. It is a place that changes the way you live. A lanai that opens entirely to the ocean breeze. An infinity pool that mirrors the Pacific. The finest Hawaiian homes are not built despite their surroundings but entirely because of them. Here are four properties from our archive that prove that you really can live in paradise forever.
Wahi Lani, 5515 Weke Road, Hanalei, North Shore Kauai | Listed at $23M · Auction Ends August 25, 2026
Designed by Walker Warner Architects and completed in 2022, Wahi Lani sits steps from Hanalei Bay's white sand shore. A Heath ceramic infinity pool anchors a central courtyard wrapped in Shou Sugi Ban charred-cedar walls, with an integrated pizza oven on the lanai, surfboard storage, and a foot-washing station.
Casa En Maui, Keawakapu Beach, Maui | Sold at auction for $28.56M
Designed by Mexican master architect Ricardo Legorreta, Casa En Maui spans 21,692 square feet along over 100 linear feet of Keawakapu Beach oceanfront — eight bedrooms, dramatic interior volumes, and a dialogue with the Pacific that only Legorreta could have conceived. One of the most architecturally significant residential sales in Hawaii's history.
2620 Kauapea Road, Kilauea, North Shore Kauai | Sold at auction for $13.44M
Perched above Dolphin Bay at Secret Beach on one of North Kauai's most exclusive bluffs, this 4,721-square-foot estate features one of the largest continuous picture windows in Hawaii, framing Pacific panoramas where whales and dolphins regularly appear. Guest residence, pool, hot tub, and deeded trail access directly to Secret Beach.
4610 Makena Road, Wailea-Makena, Maui | Sold at auction for $20.16M
Formerly owned by Jerry Moss, co-founder of A&M Records, this trophy beachfront estate on Po'olenalena Beach spans 1.43 acres with 148 feet of direct ocean frontage. Four buildings, seven bedrooms, a chef's kitchen, three guest houses, and two private gated entrances. Sold in just 30 days.
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