These are the Most Expensive Homes in Hawai‘i Right Now

An estate in a sleepy north shore town beats out even the priciest penthouse.
Ala Moana home
Waiea’s grand penthouse.
Photos: Courtesy of Property Shark


Living in a state where the median home price is $762,000 (as of March 2017), it’s easy to get numb to home-price sticker shock. Hawai‘i is a beautiful, healthy and happy state to live in, and space for homes is limited, so high prices are just a fact of life. It’s basic supply and demand.


That said, we think some of these top 10 most expensive homes in Hawai‘i might surprise you anyway.

  Weke Road home



The most expensive home currently on the market right now isn’t a shiny new penthouse in urban Kaka‘ako. Instead, it’s a $45 million oceanfront estate in Hanalei. 5418 Weke Road is a 2.5-acre slice of paradise on Hanalei’s sandy beach. The estate has multiple properties that total more than 14,000 square feet of living space with nine bedrooms. The home is for sale in two parts—for $35 million, you get the five-bedroom main home, a two-bedroom beachfront home and a studio. The separate two-bedroom pool house, whose 2,387-square-foot deck is larger than the cottage itself, costs an additional $10 million.


Waiea’s long-anticipated, often-guestimated grand penthouse is second on the list. Located on the 36th floor of the new Kaka‘ako building, it’s priced accordingly at $36 million. It comes complete with its own infinity pool and palm trees. The five-bedroom residence has stunning views of the ocean, Diamond Head and the mountains of O‘ahu, and is located in Ward Village, where residents have easy access to dining, shopping and other activities.

  Puako Home

The Puakō home.


The remaining eight properties include another Waiea penthouse, more of Kaua‘i’s north shore at the very private Kalihiwai and at Kīlauea, oceanfront homes in Maui’s Kīhei and Mākena, one on O‘ahu’s coveted Kailua Beach, and a 10-parcel property at Puakō on the Big Island. The Puakō home, number nine on the list at $27.5 million, includes a 10,000-square-foot home that is as private and quiet as can be along the Big Island’s beautiful Kohala coast. Remember the tag line, “You’re going to like the way you look. I guarantee it”? The home’s owner is George Zimmer, founder and CEO of Men’s Wearhouse.


To see them all, click here.