10 Questions to Ask a Seasoned Hawaii Agent

Before You Buy on Oahu

Buying property in Hawaii is different from buying almost anywhere else in the country. Between leasehold land, unique insurance and tax rules, and a market that moves differently block by block, the questions that protect you here aren't always the ones you'd think to ask. This guide walks through the ten questions I most want every buyer to bring to their agent — mine or anyone else's — before making an offer.

Question 1: Is this property fee simple or leasehold — and if leasehold, when does the lease expire and what happens then?

In most of the U.S., when you buy a home you own the land underneath it. In Hawaii, that's not always true. Some properties are “leasehold,” meaning you own the structure but lease the land beneath it for a set term — often decades. When the lease ends, ownership of the land (and sometimes the structure) can revert to the landowner unless the lease is renewed or renegotiated. This dramatically affects long-term value, financing options, and resale.

Why ask this: Buyers who don't ask this can end up owning a home that becomes far harder to sell, finance, or pass on as the lease term shortens.

It's easy to fall in love with an ocean view and forget to ask what it costs to insure a home in that flood or wind zone. Flood zone designation and hurricane/windstorm insurance requirements vary block by block in Hawaii, and premiums can add hundreds of dollars a month to your real housing cost.

Why ask this: The view sells the home; the insurance bill is what you'll actually be paying every month for as long as you own it.

Question 3: Has this property or building had any special assessments, and are more likely?

If you're buying a condo, ask directly about the building's special assessment history — one-time fees charged to owners for major repairs (roofing, plumbing, elevators) that aren't covered by regular HOA dues. Also ask whether the reserve fund is healthy enough to avoid another one soon.

Why ask this: A move-in-ready unit can come with a five-figure surprise bill within the first year if the building's reserves are underfunded. During the escrow period, you have the right to review the Condo Association Documents. There are companies that you can hire to review the condo documentation, including the Reserve Study.

A mortgage quote only tells part of the story. Ask your agent to walk through the full monthly picture: HOA or condo fees, property tax, homeowner's and flood/hurricane insurance, and any maintenance fees specific to the property.

Why ask this: Buyers who budget only for the mortgage payment are often caught off guard by how much higher the true monthly cost is in Hawaii.  Typically the HOA or AOAO fees go up every year as costs to maintain and also future costs (reserves for future repairs) go up. The Associations try to manage the increase but also do not want to have to charge special assessments later for repairs or upgrades. It is not uncommon to see condo projects that are lower density to have association fees higher. This is because the higher density projects can spread the monthly maintenance fee across a larger number of owners.

Inventory and competition vary significantly by neighborhood and price point across Oahu. A seasoned agent can tell you honestly whether the specific area and price range you're looking at is moving quickly with multiple offers, or slower with more room to negotiate.

Why ask this: Knowing the real pace of the market you're in — not the market in general — shapes how you should approach your offer strategy.

Question 6: What would make this property harder to resell later?

Every property has something that could make a future sale more difficult: an unusual layout, a busy road, a leasehold with a shortening term, a building with a poor reserve fund, or a location dependent on a single access road. Ask directly what that factor might be for this specific property.

Why ask this: Thinking about resale on day one protects you from buying into a property that's hard to sell when your life circumstances change. As the saying goes, “location, location, location.” 

Question 7: Is there anything about this area's history — zoning changes, development plans — I should know before buying?

Local zoning changes, planned developments, or shifts in an area's character can affect both quality of life and long-term value. A seasoned local agent should be able to speak to what's changed in an area recently and what's realistically on the horizon.

Why ask this: This is the kind of context that rarely shows up in a listing but can matter enormously five or ten years down the road.

Question 8: What financing quirks apply to non-resident or out-of-state buyers here that wouldn't apply on the mainland?

Financing a Hawaii property as an out-of-state or non-resident buyer can involve different lender requirements, appraisal considerations, and timelines than a typical mainland purchase. Ask your agent to walk you through what's different so your financing doesn't stall your closing.

Why ask this: Buyers who assume their mainland financing experience will translate directly sometimes face avoidable delays. A lender must be licensed in the State of Hawaii to process a loan. If you are using a mortgage broker from the mainland, you want to verify that they are licensed in the State of Hawaii. Most Listing Agents and Sellers prefer and its highly recommended that a buyer use an on-island mortgage company. Many loans and closings are delayed or are not closed due to the mainland lender not being familiar with our requirements. Sometimes mainland lenders ask for documentation that we don’t have. Many times Buyers will lose the “property of their dreams” because of the loan processing delay.

Question 9: Who actually pays my agent — and do I need to negotiate that myself?

Real estate commission rules changed nationwide in 2024. Buyer-agent compensation is no longer advertised through the MLS, and buyers are required to sign a written buyer-broker agreement specifying their agent's fee before touring homes. Sellers can still choose to offer to pay buyer-agent compensation as part of a negotiated deal, but it's no longer automatic — it has to be discussed and agreed upon directly.

Note: Commission structures and rules can change and vary by transaction. Confirm current terms directly with your agent in writing before touring homes.

Why ask this: Many buyers assume, out of habit, that the seller always covers this. In today's market, that has to be confirmed and negotiated, not assumed.

Question 10: If I'm not a Hawaii resident, what will I owe in withholding taxes when I eventually sell this property?

Hawaii law (HARPTA) requires a withholding of a percentage of the sales price when a non-Hawaii-resident seller disposes of Hawaii real property — this is separate from, and similar to, the federal FIRPTA law that applies to foreign sellers. This withholding is not a final tax bill; it's collected in advance against whatever capital gains tax is actually owed, and some or all of it may be refundable depending on your situation. Knowing this now, as a buyer, helps you plan for the day you eventually sell.

Note: HARPTA and FIRPTA rules, rates, and exemptions are subject to change and depend on your specific circumstances. Always confirm current rules with a qualified CPA or tax attorney before you sell.

Why ask this: This surprises almost every out-of-state seller who didn't know it existed — planning for it from the start avoids an unpleasant shock at your future closing.

Ready to Talk Through Your Own Situation?

These ten questions are a starting point — every property and every buyer's situation is a little different. If you're thinking about buying on Oahu, I'm happy to walk through your specific questions directly.

Karla Casey - REALTOR  |  Coldwell Banker Realty  |  www.KarlaCasey.com