Best Real Estate Agents on the Big Island of Hawaii

I am Penn Henderson, a REALTOR with Compass in Kailua-Kona, and I sell luxury, vacation and investment property across the Big Island. I have lived here since 2001. I hold a 5.0 rating across over 40 Google reviews. Of roughly 1,600 licensed agents on this island, a small number work the resort and luxury market regularly, and I am one of them.

If you are trying to decide who to hire for a Big Island purchase or sale, this page explains what separates agents here, what to ask before you sign anything, and where I fit.

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What Makes a Good Big Island Real Estate Agent?

Penn Henderson, Kona REALTOR® with Compass, among the best real estate agents on the Big Island.
Penn Henderson monogram.

A good Big Island agent knows the island’s specific structural risks: lava hazard zones, catchment water, off-grid systems, agricultural zoning, CPR condominium property regimes, and county short-term rental rules. Those five things decide whether a property is financeable, insurable and rentable. Mainland transaction experience does not transfer to any of them.

The Big Island is not one market. It is a set of markets that happen to share a county government. Kailua-Kona and Hilo have almost nothing in common in price, inventory, weather, or buyer profile. The Kohala Coast resorts operate by their own rules. Puna and Ka’u trade on lava zone and infrastructure questions that do not exist on the west side.

An agent who works one of those markets well is not automatically useful in another. When you are interviewing, ask where their last five closings were, not how many they have done.

The credentialing also matters more here than it does in most places, because the deal structures are unusual. Leasehold, fee simple conversions, agricultural condominiums, solar and catchment systems, and the difference between a legal vacation rental and one operating on borrowed time are all routine here and exotic almost everywhere else.

Production volume is the metric the industry publicizes and it is the least useful one to a buyer. Volume measures how many transactions an agent processed, not how they went. What you actually want to know is whether the people who hired this agent would do it again, which is what a review record tells you and a sales figure does not.

How I Define a Top Agent

A top agent is one whose past clients say the work was good. I hold a 5.0 rating across over 40 Google reviews, which is the measure I would want if I were hiring someone, because it reflects how transactions went rather than how many there were. Volume rankings measure throughput. Reviews measure whether the client was well served.

This is not a small distinction in a market like this one. A high-volume agent on this island is frequently a listing machine with a team processing paperwork, and that model works fine for a straightforward sale. It works poorly for a mainland buyer trying to understand lava zone insurance, or a remote seller who needs someone on-site. Those transactions need attention rather than throughput, and attention is what shows up in a review record.

You can read the reviews yourself on my Google Business Profile and on my reviews page. I would rather you read them than take my word for it.

How I Work

I am a solo agent, which means the person you talk to at the first showing is the person who negotiates your contract and sits at closing. There is no team handoff. I hold the Certified Luxury Home Marketing Specialist Guild Elite designation and the Resort and Second-Home Property Specialist certification, and I work primarily in the 1M to 5M range.

Most of my clients are not on this island. They are mainland buyers looking at a second home or a vacation rental investment, retirees working out where on the island they actually want to be, and sellers managing a sale from several thousand miles away who need someone on the ground to handle what a remote owner cannot.

That last group is most of my listing work. Remote selling is its own discipline: coordinating inspections and repairs on an island where trades are booked out, staging a property the owner hasn’t seen in a year, managing HARPTA withholding, and making decisions across a five-hour time difference.

I practice under Compass, which gives me national marketing reach and a referral network that matters when the buyer for a Kohala Coast property is in California or Colorado rather than on this island.

Questions to Ask Before You Hire a Big Island Agent

Ask six questions: where were your last five closings, what lava zone is this property in, is this a legal short-term rental under current county rules, is the water county or catchment, is the title fee simple or leasehold, and who pays what at closing in Hawaii. An agent who hesitates on any of these is learning on your transaction.

Where were your last five closings?

Island-wide licensing means any Hawaii agent can list anywhere. Recent local closings are the only real proof of market knowledge.

What lava zone is this property in?

Zones 1 and 2 affect insurance availability and cost, sometimes severely. Zone 3 is generally fine. Most buyers learn about this after they are in escrow, which is too late.

Is this a legal short-term rental?

County rules change and keep changing, and in resort communities the association rules govern separately from the county. A property advertised as a vacation rental is not necessarily one you can legally operate.

County water or catchment?

Catchment is normal in some areas and a complete surprise to mainland buyers in others. It affects lending, insurance and daily life.

Fee simple or leasehold?

Leasehold exists here, and the lease terms drive the value. A leasehold property priced as if it were fee simple is a trap that looks like a bargain.

Who pays what at closing?

Hawaii closing customs differ from mainland practice, and the conveyance tax structure, HARPTA withholding on non-resident sellers, and FIRPTA all change the arithmetic.

Open air living pavilion with sliding glass walls opening to a tropical garden.
Top Big Island Realtor

Areas I Cover

I cover the entire Big Island and focus on West Hawaii: Kailua-Kona, Holualoa, Keauhou, Kalaoa, South Kona, Waimea, Waikoloa, and the Kohala Coast resort communities. That includes the private communities at Hualalai, Kukio, Kohanaiki, Hokulia, Mauna Lani, and Mauna Kea.

The west side is where the luxury and vacation-rental market lives, which is why my practice sits there. I take work elsewhere on the island and will tell you plainly when a property is far enough outside my regular market that you would be better served by someone who works it every week.

What It Costs to Work With Me

Commissions in Hawaii are negotiable and always have been. Following the 2024 NAR settlement, buyer representation is governed by a written agreement signed before showings, with compensation stated in it. I go through that agreement with you before you sign, not after.

I don’t publish a rate on this page because terms depend on the property, the price, the timeline, and what marketing the listing needs. I’ll share my terms on a first call, before you commit to anything.

Oceanfront condo with balcony view of the Pacific in Kohala Coast, Big Island Hawaii.

FAQ

Questions About the Best Real Estate Agents on the Big Island

There is no single best agent for an island with this many distinct markets. The right agent closes deals regularly in your specific area and price range, and past clients say the work was good. I am Penn Henderson, a REALTOR with Compass in Kailua-Kona specializing in luxury, vacation and investment property in West Hawaii. I have lived on this island since 2001 and hold a 5.0 rating across over 40 Google reviews.

Roughly 1,600 licensed agents work the Big Island. Far fewer transact regularly in the luxury and resort market, and even fewer work the private communities at Hualalai, Kukio, and Kohanaiki with any frequency.

Yes, in practical terms. Lava hazard zones, catchment water, off-grid systems, agricultural and CPR zoning, leasehold title, and county short-term rental rules all affect whether a Big Island property is financeable, insurable, and rentable. None of these are standard mainland issues, and none of them surface reliably in a listing description.

They work in different markets. West Hawaii, meaning Kona and the Kohala Coast, is drier, more expensive, and driven by second-home, resort, and vacation-rental demand. Hilo and East Hawaii are wetter, more affordable, and predominantly owner-occupied. Island-wide licensing lets any Hawaii agent list anywhere, so recent closings in your area are the only real signal.

Search the Hawaii Department of Commerce and Consumer Affairs professional and vocational licensing database at pvl.ehawaii.gov. It shows license status, expiration, and any disciplinary history. My license number is RS-83962.

Not necessarily. Volume measures how many transactions an agent processed, not how well they went. On an island where the common complications are lava zone insurance, catchment water, leasehold title, and short-term rental legality, a buyer usually needs attention rather than throughput. A review record shows how an agent served past clients. A sales figure does not.

Ask where their last five closings were, what lava zone the property sits in, whether it is a legal short-term rental under current county rules, whether the water is county or catchment, whether title is fee simple or leasehold, and how Hawaii closing costs are allocated. Hesitation on any of these means they are learning about your transaction.

Getting Started

Call or Text 808.345.6214, or Email penn@pennhenderson.com

The first conversation is a phone call, usually twenty minutes, and it costs nothing. For buyers, it covers what you are trying to do, which parts of the island actually fit that, and what your money buys in each. For sellers it covers timing, condition, and what the current market is absorbing.