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If you’re a typical Maui homeowner thinking about selling in 2026, you’ve probably seen upbeat headlines: pending sales are rising, prices look strong, and luxury activity is surging again. But if you’re not selling a $4M Wailea estate, those numbers don’t tell the whole story. What most sellers are feeling on the ground is something different: more inventory, longer days on market, and buyers who are moving slower and scrutinizing value more carefully.

A lot of my clients ask me this question: Should I buy a second home in Maui?

I’ve lived on the island for 30 years and have sold real estate for 18 of them. On top of this, my company has a thriving property management company that takes care of a lot of second homes. Needless to say, I know the ins and outs of buying, owning, and managing Maui properties. It’s wonderful to own a second home, but before you make the big decision of doing so, keep these six things in mind:

We live in an era where technology is king, so when you’re choosing an agent to work with in your real estate transaction, you need to pick someone who is tech-savvy. This is especially true since we live on a little island in the center of the Pacific, where the time zone differs so much from the continental states. Technology will help bridge that gap.

People often ask me about how real estate agents make their money. The answer is a little more complicated than many might assume.

What’s the best way to make a great first impression when listing your home for sale?