The Complete Guide to Buying a Second Home on Maui

buying a second home on maui

Buying a second home on Maui can be one of the most exciting and life-changing decisions a person can make. I've worked with a lot of second-home buyers over the years, and what I've found is that most of them have been thinking about this for a long time.

Maybe they started coming to Maui as kids, and as adults, they want to share that with their children. Maybe they fell in love with the island on a honeymoon and have always felt a connection. Maybe they've been renting for longer periods each year and have finally decided it makes more sense to own than to keep renting.

Whatever has you thinking about buying a second home on Maui, I want to share my experience and help you navigate this…

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What Bill 88 Means for Kihei Condo Buyers and Sellers

Bill 88 and Kihei Condo Market

If you own a condo in Kihei, or you've been thinking about buying one and have been waiting on the sidelines while the Bill 9 situation played out, here is an update on how things are developing.

On June 19, 2026, the Maui County Council passed Bill 88 on second and final reading by a 7-2 vote. It now heads to Mayor Bissen for his signature, which is widely expected, given that he authored Bill 9 and testified in support of Bill 88 himself earlier this spring.

Once signed, it becomes law. This is a big deal for anyone with a stake in the Kihei condo market, as owners in several complexes are likely to be able to put this stress behind them while others will be looking to either appeal for…

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Upcountry Maui Real Estate: Your Guide to Kula, Makawao & Haiku

Upcountry Maui Real Estate

When most people think about buying real estate on Maui, their minds immediately jump to the ocean. They imagine beachfront condos in Kihei, luxury estates in Wailea, or resort living in Ka'anapali. And I get it. The coast is spectacular. But after 16 years of living and working on this island, I can tell you that some of the most unique, sought-after, and frankly underappreciated real estate on Maui is found somewhere else entirely — higher on the slopes of Haleakala.

Upcountry Maui is a world unto itself. The moment you start climbing Haleakalā Highway and the temperature drops a few degrees, the air gets a little crisp, and the landscape shifts from dry coastal scrub to lush…

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