With a conversation, not a listing search. Before we look at specific properties, we should talk about what you want out of your Maui home — second home, primary residence, or investment — which part of the island fits your lifestyle, your timeline, and the full cost of ownership (not just the sticker price). From there, I’ll set up a tailored search and we’ll start looking at the right properties instead of scrolling through everything on Zillow. Reach out any time and we’ll set up a short intro call.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

More than anything, this depends on lifestyle rather than budget. The island has six real estate regions: West Maui (resort coast — Ka’anapali, Kapalua, Napili), Central Maui (primary-residence value — Wailuku, Kahului), North Shore (surf-town character — Paia, Spreckelsville, Haiku), Upcountry (cooler climate and acreage — Makawao, Kula, Pukalani), South Maui (sunshine and beaches — Kihei, Wailea, Makena), and East Maui (remote Hana). Take a look at my Maui Neighborhoods guide for the full breakdown, map, and links to each area’s in-depth guide. Most buyers end up choosing between two or three regions, and a short conversation usually narrows it down quickly.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

Maui County assesses property taxes based on your property’s classification — owner-occupied (with a homeowner exemption), non-owner-occupied, long-term rental, short-term rental / TVR, commercial, and a few others. Each classification has its own rate, and the rates are adjusted annually for the July-to-June fiscal year. Because the classification dramatically affects your annual bill — sometimes by thousands of dollars — and because rates change, I prefer to quote current numbers for your specific property situation rather than post a figure that goes stale. Reach out and I’ll send the current rate sheet along with an estimate for what you’re considering.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

Maui County uses four main property-use classifications: owner-occupied, non-owner-occupied, long-term rental, and TVR-STRH (short-term rental). Each carries its own property tax tier, has its own qualifying criteria, and changes what you can legally do with the property — including whether you can list it on AirBnB or VRBO.

The biggest mistake mainland buyers make is assuming the classification is locked in or that it follows the listing description. It doesn’t. Classification follows your actual use, and Maui County actively reviews. A property listed as a “vacation rental” that you don’t actively rent can land in a different category at a different rate. A “primary residence” you only spend six months a year at may not qualify the way you think it does.

Picking the right classification before you offer changes the math meaningfully — and sometimes changes which buildings are even worth looking at. Tell me how you’d actually use the property and I’ll walk you through which classification fits and what each one means for your annual carry.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

Sometimes — it depends on the building and the area. Maui County’s short-term rental regulations are evolving, and zoning varies by property. Some buildings are legally permitted for nightly rentals, others are limited to long-term (30+ day) rentals only. If vacation rental income is part of your plan, please reach out before you offer on any property. I track the current status and will walk you through whether the specific property you’re considering supports the rental model you want.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

Bill 9 is Maui County legislation, signed into law December 15, 2025, that phases out short-term rental use in roughly 7,000 apartment-zoned condominium units across the island. The phase-out timeline is January 1, 2029 for West Maui and January 1, 2031 for the rest of Maui.

The honest answer to “does it affect me?” is it depends on the specific building. Some Maui condos are hotel-zoned and unaffected. Others are on the Minatoya List and losing their STR rights on the dates above. A third group never had legal STR rights to begin with — though listings don’t always say so.

The rules continue to evolve as legal challenges and county clarifications work their way through. Before offering on any condo where rental income is part of your plan, the zoning and current legal status need to be verified building-by-building.

I keep a working reference of every Maui condo with its Bill 9 status, zoning, and any known HOA red flags. If you’re considering a specific building, send me the name and I’ll tell you what I have on it.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

For short-term rentals, almost always yes — running a vacation rental remotely is a full-time operation that a good manager handles for you (cleaning, guest communication, maintenance, bookings, taxes). For long-term rentals, it depends on your comfort with remote management. Most of my out-of-state and foreign owners use a local property manager, and I can recommend several I trust.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

FIRPTA — the Foreign Investment in Real Property Tax Act — is a federal law requiring 15% of the gross sale price of US real estate to be withheld at closing when the seller is a non-US person. It’s a withholding, not a final tax — the seller recovers any overpaid portion by filing a US tax return. As a buyer, this affects you only if you’re purchasing from a foreign seller (the withholding happens through escrow). As a future seller, if you’re a foreign national, you’ll want to plan for this.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

HARPTA — the Hawaii Real Property Tax Act — is the state-level equivalent of FIRPTA. 7.25% of the gross sale price is withheld at closing if the seller is a non-Hawaii resident. It applies to mainland US residents selling Hawaii property as well as to foreign sellers. As with FIRPTA, it’s a withholding, not a final tax — you recover the overpaid portion by filing a Hawaii state tax return after closing.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.

Yes, and in almost every case, nothing out of pocket. In Maui residential transactions, the seller typically compensates both their listing agent and the buyer’s agent through the sale. Having your own agent means someone represents your interests, walks properties with you, checks the building financials and HOA health, flags red flags, and negotiates on your behalf. Going directly to a listing agent means that agent represents the seller — not you.

Last updated: May 9, 2026. This is general educational information, not legal, tax, or financial advice. Maui real estate rules — particularly property tax tiers, short-term rental regulations, and county ordinances — change. Always verify current details with the County of Maui, a qualified Hawaii-licensed CPA or attorney, and a Hawaii escrow officer for your specific situation. I’m happy to refer you to my trusted Maui partners — just ask.