Buying a Home on the Big Island

Expert representation for what is likely one of the largest purchases of your life.

Honest assessment, real due diligence before you write, and a process built for buyers making the decision from three thousand miles away.

Hawai‘i License RS-83962

Contact Info Buyer’s Guide

How I Help Buyers

I represent buyers across West Hawaii, from Kailua-Kona and Holualoa to Waikoloa, Waimea, and the Kohala Coast resort communities. Every client gets properties vetted before they reach you, an offer built on research rather than instinct, and one point of contact from our first conversation through closing and beyond.

Every week, I watch buyers overpay, waive the wrong contingency, or discover a zoning, insurance, or tax issue after they are committed. Rushed diligence. Generic advice. Nobody on the ground. That is not how I operate.

Hawai‘i Resident

Client Video Tours

Big Island Sales

Google Rated

Penn Henderson, R(S)

Why Buyers Choose to Work With Me

Big Island Hawaii real estate, oceanfront property in Kona, luxury resort home with stunning views.

I run your search personally.

Previews, showings, due diligence, offer strategy, and the escrow timeline stay in my hands from our first conversation to the day you get the keys. Behind me is a bench I have built over 25 years on this island: experienced transaction coordinators, escrow and title officers, inspectors, lenders, and contractors. You get the focus of a solo agent with real depth behind it.

Trusted, Local Big Island expertise.

Full-time on the Big Island since 2001, and in West Hawaii business long before I sold my first home.

Straight Answers, Not Sales Pressure.

My clients say the recommendation to walk away is what earned their trust on the one to buy.

Research Before You Write.

Zoning, HOA financials, rental history, comps, and disclosures worked through before the offer.

Built For Remote Off-Island Buyers.

Narrated video walkthroughs, live FaceTime showings, and a rhythm set to your time zone.

Accredited At The Luxury Level.

A Certified Luxury Home Marketing Specialist (CLHMS), Pricing, and Resort Specialist.

Smart Negotiation on Your Behalf.

Price is one lever. Terms, timing, deep research, and information win properties at fair or better prices.

A CLEAR ADVANTAGE

What Compass Brings to Your Search

Compass Gives My Buyers a Platform Other Big Island Brokerages Cannot Match:

A national agent network, a client dashboard built for remote buyers, and for qualifying properties, a global luxury division. The platform extends the reach. I keep the experience personal.

A Home Search You Can Follow From Anywhere.

Compass One keeps your timeline, every document, our messages, and your entire team in one secure place, regardless of time zone.

Insight On Properties Before They Go Live.

Compass agents talk to each other about what is coming, and that network is one more channel I work while your search runs.

A National Network With Direct Listing Insights.

I reach the agent directly for any Compass listing in the country and learn what a listing sheet will never tell you.

Real Access At The Top Of The Island Market.

For the island’s highest tier, the Compass Luxury division connects me to the agents who handle property at this level.

Market Expertise

How I Make Sure You Do Not Overpay

The offer is not a number. It is a strategy.

Before we write, I research the seller’s motivation, the listing history, competing inventory, and documented comparable sales. You see the analysis and the reasoning behind every recommendation. You make the final call on price and terms.

Price is rarely the only lever that wins a property.

Earnest money, contingency timelines, closing date, and how the offer is presented can win a home at a lower number than a competing bid that simply paid more. Once we are under contract, the second negotiation begins, and inspection findings and credits get the same rigor as the offer itself.

offer strategy buyer graphic v3 outlines 01

The Full Due Diligence Process

My Approach

How I Search on Your BEHALF

Most buyers search the same three portals everyone else searches. That is a feed, not a search.

Real search is a process:

Criteria first, then daily monitoring, then pre-screening, then diligence, then an offer written with intent. I look at properties before you do and tell you which ones aren’t worth your time.

You are not sorting hundreds of listings wondering what you are missing. I have already done that work for you.

Criteria

We start with what you are actually trying to accomplish: use, budget, community, timeline, and whether rental income is part of the plan. Every recommendation after that flows from it, and it gets refined as you see more.

Search

Daily monitoring of new MLS listings, a custom search for your criteria with instant alerts, plus off-market opportunities through long-standing agent relationships and direct outreach to owners in the areas you are targeting.

Preview

I see properties before you do. Narrated video walkthroughs, live FaceTime showings you direct in real time, and an honest read on layout, condition, road noise, neighbors, and everything the listing photos and description left out.

Diligence

Zoning and short-term rental eligibility, lava zone, HOA financials and rules, condo warrantability, rental history, comparable sales, and a thorough disclosure package, all worked through before we write rather than after.

Every Property We Take Seriously Gets a Narrated Video Walkthrough

Listing photos are curated. Video shows the truth: the neighbor’s roof, the road noise, the view from the kitchen, what the lanai actually feels like at four in the afternoon. I have made more than 450 property tour videos for clients, and I will make one for any listing you want to see.

Property Tour Videos Filmed For Clients

95%

Of Buyers Begin Their Search Online

Of Clients Have Said My Video Tours Were Key to Finding Their Home

*My video tours are included on every property we seriously consider. No limit. We don’t stop until we find your perfect home in Hawaii.

Every step, every cost, and every Hawaii-specific detail is covered in my buyer’s guide.

Big Island Buyer’s Guide

Buying a Home on the Big Island From the Mainland

I MANAGE THE DETAILS, SO YOU CAN FOCUS ON the decision.

You do not need to be in Hawaii to buy a home in Hawaii. Most of my buyers run the entire purchase from the mainland. I preview every property in person and attend every inspection; documents are signed electronically or by mobile notary at your location, and your funds are wired directly to escrow.

No Worries

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

Video Tours

Narrated tours of every property we take seriously, showing what listing photos leave out.

Remote Signing

Electronic signature where permitted, mobile notary where original documents are required.

Live Showings

FaceTime tours you direct in real time, with your questions answered as we walk the property.

Client Dashboard

Compass One gives you real-time visibility into your timeline, documents, and full team from anywhere.

Inspections

I walk every inspection personally and coordinate timely communication with the inspector.

One Contact

I keep it simple with a single point of communication. You call me. Not an assistant, not a coordinator.

Spacious Kona and Kohala Coast home featuring indoor-outdoor living and modern design.

Big Island Luxury Homes

Luxury Buyers

The Big Island’s highest-value inventory does not behave like the rest of the market. Owners at this level often prefer not to advertise. Some test quietly before a public launch. Others sell to the right buyer and never list at all. A search built on portal alerts misses it all.

Finding those properties comes down to relationships, and mine go back 25 years here. I represent buyers in Hualalai, Kukio, Kohanaiki, Hokulia, Mauna Lani, and Mauna Kea, as well as the Kohala Coast resort communities.

West Hawaii’s luxury tier begins around $3.2M. At that level, I also work within the Compass Luxury division, and I hold the Certified Luxury Home Marketing Specialist designation at the Guild Elite tier.

Explore Luxury Properties

Success Stories

Penn provided above-and-beyond service, making this sight-unseen mainland transaction a breeze. He provided detailed videos showing every aspect of the condo, including one of an evening sunset.

— Pat & Pam, Oceanfront Condo Buyers, Kona

Read All Reviews

Luxury oceanfront condos in Kohala Coast with resort amenities and stunning coastline views.

We truly cannot express how grateful we are for Penn’s professionalism and care throughout the home-buying process. What could have been incredibly stressful felt manageable thanks to his expertise.

— Brooke & Nick, First-Time Buyers, Kailua-Kona
He sent us a video of our complex and the specifications, and was so knowledgeable and professional. He went above and beyond our expectations. We could not have navigated this journey without him.

— Christina De Vito, Condo Buyer, Waikoloa Village
For over a year, we viewed homes online from Atlanta. When we were ready, Penn knew exactly what we were looking for and closed the deal quickly. Even after we closed, he made sure everything was fine.

— Mila Krueger, Relocation Buyer, Kona

FAQ

Common Questions About Buying Real Estate on The Big Island.

Yes. There are no citizenship or residency requirements to own real estate in Hawaii, and that applies to homes, condos, and land alike. What changes for out-of-state and international buyers is the mechanics: financing options narrow, notarization takes more planning, and non-resident sellers face withholding at closing under HARPTA or FIRPTA when they eventually sell. None of it is difficult. It just needs to be handled by people who do it regularly.

Fee simple means you own the land and the improvements outright, permanently. Leasehold means you own the structure but lease the land beneath it, typically for a fixed term, with monthly lease rent on top of your other carrying costs. Nearly everything I sell in West Hawaii is fee simple. Leasehold shows up occasionally in older condo projects and can make sense for a short-horizon buyer, but the remaining lease term, the rent escalation schedule, and the lender’s willingness to finance it all need review before you go under contract.

Buyers do it regularly, and I have closed transactions for clients who did not see the property in person until they picked up the keys. I preview the home on video, walk the neighborhood, note road noise, afternoon sun, and the things photos never show, and attend every inspection on your behalf. Documents are handled electronically, and escrow can arrange remote notarization. That said, if you are relocating rather than investing, I would rather you spend a few days on the island first. Choosing the wrong side of the island is a more expensive mistake than choosing the wrong house.

Sometimes, and the answer is property-specific. Short-term vacation rentals on the Big Island are defined as stays under 30 days and are regulated by the County of Hawaii. Properties in resort and certain commercial zoning districts are generally eligible. Properties outside those districts require a Nonconforming Use Certificate, which must be renewed annually and kept in good standing. Zoning is only half the question, since the AOAO or HOA can restrict or prohibit rentals regardless of what the county allows. Before you write an offer on an income property, I verify zoning, permit status and renewal history, house rules, and actual rental performance. Assumptions are expensive here.

The USGS divides the island into nine lava hazard zones, with Zone 1 carrying the highest risk and Zone 9 the lowest. The West Hawaii markets I work in fall well down that scale. Zones matter primarily for insurance and financing. Most national carriers decline coverage in Zones 1 and 2, which pushes owners toward the Hawaii Property Insurance Association and can complicate a loan. People live happily in those zones, but the cost and resale picture deserve an honest evaluation before you buy.

Not required, but usually worth it. Local lenders understand lava zone classifications, leasehold structures, condotel rules, and CPR ownership, all of which routinely stall mainland underwriters who have never seen them. They also share a time zone with your escrow officer. If you already have a lender you trust, keep them and get a second quote from a Hawaii lender for comparison. I am happy to make introductions either way.

Thirty to forty-five days is typical from accepted offer to recording. Cash can close in as little as two weeks. Hawaii contracts are date-driven rather than contingency-driven, so every milestone has a fixed deadline, and closing occurs when the deed records at the Bureau of Conveyances in Honolulu rather than at the signing table. Condos and leasehold properties can add review time for association documents.

Since August 2025, buyer-side compensation is negotiated directly between you and me in a Buyer’s Representation Agreement rather than assumed to come from the seller. In most of my transactions, the seller still covers it, and that request is written into the purchase contract. The difference is that the terms are spelled out in advance instead of surfacing at closing. I walk through the agreement with you before you sign anything and before I show you a property.

Because the details that decide whether a Big Island purchase works out are local ones. Which condo projects allow vacation rentals. Which subdivisions have water meter issues. Which coastline gets vog and which gets trade winds. Which inspector actually understands post-and-pier construction. I have lived in Kona since 2001 and sold here full time, and when you are buying from the mainland, you are hiring eyes and judgment on the ground, not just MLS access.

Let’s Talk

Ready to find your big island home?

Whether you are ready to buy now, planning a move a few years out, or just starting to learn the island, I would welcome a conversation. No pressure and no obligation.

When we talk, you can expect a focused conversation about what you are trying to accomplish, an honest read on the communities and price points that actually fit, a walkthrough of how the process works here, and straight answers to every question you ask.