Penn Henderson

Your trusted guide to real estate on the Big Island, specializing in Kona and the Kohala Coast with Compass.

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About Penn Henderson - Kona Realtor, Big Island Real Estate
MY JOURNEY
Beautiful coastal property with ocean views and tropical landscape.
CLIENT REVIEWS
Recently Sold Properties by Penn Henderson - Big Island Hawaii Realtor
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Looking for a great real estate agent? Meet Penn.

A Top-Rated REALTOR® on the Big Island

Aloha. I am a full-time REALTOR® with Compass on the Big Island of Hawaiʻi and a Kona resident since 2001.

I represent buyers and sellers across Kailua-Kona, Holualoa, Keauhou, Waikoloa, and Waimea, along the Kohala Coast resort communities at Waikoloa Beach, Mauna Lani, and Mauna Kea, and inside the island’s private enclaves at Hualalai, Kukiʻo, Kohanaiki, Hokuliʻa, and Puako. My focus is luxury property, second homes, and investment real estate.

Top Kona Realtor - Penn Henderson - Big Island Hawaii Real Estate.

My Big Island Journey

I did not come here on vacation and decide to stay. I came here to live, and then spent the past twenty-five years learning what that actually means.

My first Big Island home was in Kona Highlands, up the hill from the airport, with a commute north to the Kohala Coast where I worked at Mauna Lani Resort. Then, fifteen years of tourism-related work at Keauhou Bay followed – wrapping up two decades in executive sales and marketing for West Hawaiʻi companies before my journey shifted to real estate.

That is where the useful knowledge comes from, and it is not the kind that shows up in a market report. It is knowing that Waikoloa Village catches wind Holualoa never sees. That the mauka clouds build around 2:00 PM most afternoons, and that a Kona oceanfront condo priced correctly may sell to someone in Newport Beach who has never walked through the door.

I became a full-time REALTOR® in 2021. The license was new. The island was not.

Penn Henderson, COMPASS

Twenty-Five Years, One Island

Yearly Sales Volume
Big Island Sales
Kona Resident
★★★★★

Big Island Real Estate

Why Clients Choose Me

1.

Rooted Big Island Local Perspective

Twenty-five years in Hawai‘i gives me more than market familiarity. I understand the lifestyle differences across areas, microclimates, schools, commutes, resorts, and rural areas, plus the small details that rarely show up in a listing.

2.

Honest Guidance Before the Deal

I will tell you when a property is wrong, when a price does not make sense, or when the risk is bigger than it looks. My role is not to push you into a transaction. It is to help you make a clear, confident decision.

3.

Research Before Recommendation

Before I give advice, I look at the data, comps, property history, zoning, HOA documents, rental rules, disclosures, and market context. You get recommendations grounded in evidence, not salesmanship dressed up as expertise.

4.

Real Marketing Experience, Applied

I spent over two decades in executive sales and marketing prior to real estate. That background shapes how I position a property, create photography and video, write the story, and build campaigns to reach the right buyers.

5.

A Smoother Process From The Mainland

Many of my clients are making decisions from off-island, whether buying or selling. I help make the process feel organized and manageable with steady communication, local coordination, and fewer surprises.

6.

Led Personally, Supported Fully

I remain your direct advisor throughout the transaction, overseeing the strategy, negotiations, communication, and critical details. A trusted support team helps keep everything moving, but the representation stays personal.
Big Island Hawaii oceanfront property in Kona with resort-style amenities and stunning ocean views.
Big Island Hawaii real estate, oceanfront property in Kona, luxury resort home with stunning views.
logo epro
Big Island Hawaii oceanfront property in Kona with resort-style amenities and stunning ocean views.
logo PSA

Real estate loves an acronym, and most of them are not worth much. These five I actually use. The luxury designation, CLHMS Guild Elite, came out of closed sales rather than a weekend class. RSPS is resort and second-home property, which is most of what my clients are buying. PSA is pricing and valuation. e-PRO is the digital side, and it matters more than it sounds like when your buyer is in Seattle, and the house is in Kona. At Home With Diversity is fair housing, which honestly should not need a certificate.

WITH PENN, YOU GET

Local Expertise + National Accreditation

Where I Live. Where I Work.

West Hawai‘i

I work on one island, mostly the West side (Kona & Kohala Coast).

West Hawaiʻi is the leeward stretch from Honaunau up to Kohala Ranch. Nine inches of rain a year down on the Kohala Coast. Afternoon cloud over the Kona coffee belt. Ranch country at 2,600 feet in Waimea. An hour from my front door covers everything I sell, and I have spent decades learning the difference between one end of it and the other.

Luxury oceanfront homes in Kohala Coast, Big Island Hawaii with resort-style amenities.

Kona is Home

I loved my life in Colorado, but after twenty-nine winters, the explorer in me was ready. Within six weeks, I sold my townhouse, bought a home in Kona, packed a twenty-foot container, and landed here in October 2001.

I have never looked back. Three IRONMAN® World Championships on the Queen K. Fifteen years working at Keauhou Bay. A holiday 5K my wife and I started in 2005 that still runs every December, and enough Saturdays on Big Island soccer fields to lose count. You do not learn a place like this from a listing feed. You learn it by showing up, year after year.

Community Commitment

Kona and Kohala Coast active lifestyle, diverse properties, scenic views, and luxury homes on Big Is.

Jingle Bell Beach Run

FOUNDERS / ORGANIZERS

My wife, Rani, founded Kona’s largest 5K event in 2005. It draws hundreds every December and funds a Special Recognition Award for a local nonprofit each year.

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Big Island Hawaii soccer team under a tent, representing local sports and community lifestyle.

City SC Hawai‘i

BOARD PRESIDENT

President and volunteer coach for West Hawaii’s largest youth soccer club, where countless players have gone on to compete collegiately and professionally.

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Family & Island Life

My wife Rani, a third-generation Big Islander and a Kona elementary school teacher, and I are raising our two boys amid the sunshine, the saltwater, and the soccer fields. We were once regulars in Hawaii’s triathlon scene. These days the endurance test is keeping up with them.

Family enjoying outdoor living in a Big Island Hawaii luxury home near Kona and Kohala Coast.

“He provided above-and-beyond service, making this sight-unseen mainland transaction a breeze.”

Pat & Pam Kemp | Kona Oceanfront Condo

“I have a background in real estate, and can honestly say Penn was as good as they get. 10/10!!!”

Jeni Winegarner | Alii‘i Drive Condo

“He was forthright if he did not think a home was right for us. I would highly recommend Penn.”

SJ Lee | Holualoa 5-Acre Home

FAQ

Common Questions I Get Asked About My Journey to the Big Island

I came out in early September 2001 to scope out a change of scenery from Colorado. Northern California and Oregon were on the list too, but Hawaii was the one that resonated. The tropical environment, the lack of malls, the warm climate, and a sense that my work ethic would find a place here. Halfway through the trip, while staying at a bed-and-breakfast in South Kona, my mom called at 4:30 in the morning and told me to turn on the television. It was September 11th. Watching it unfold from where I was standing cemented the decision rather than shaking it. Finding peace amid chaos is not a bad reason to choose a place.

A week after I got back to Colorado, my company shut down amid the economic fallout. I had severance, unemployment, and a decision already made. Within six weeks, I listed my townhouse in Golden, bought a house in Kona Highlands that I had walked through on that trip, packed a twenty-foot container, and drove to Long Beach with my two big dogs, Tiki and Paulo, in crates that barely fit in the car. Tiki had to lose four pounds to meet the airline weight restriction, and she was not happy about the diet. I shipped a beater Volkswagen Fox that was worth less than the cost of shipping it. All of this was before Zillow, before you could research a neighborhood from your couch. I closed on Kona Highlands October 30th, six weeks after the trip.

I arrived with no job in a tourism economy that had just been hit as hard as any in the country. Five months later, right as my savings ran out, Mauna Lani Resort hired me as Sales Manager. Six interviews to get there, which I am told was not typical. They wanted someone with an outside perspective, and then they taught me everything there was to know about Hawaii’s tourism industry. That job changed the trajectory of my entire life here.

Not directly, and the detour is most of what makes me useful now. Mauna Lani moved me up to Director of Marketing, which was a great few years. Then my parents decided to follow me out here after their Florida retirement turned out not to be what they had pictured. We bought five acres off Alii Drive together and built a family compound during the 2004 to 2006 building frenzy, when reliable contractors were nearly impossible to get. I ended up managing the project myself and doing whatever I could by hand. It was probably the hardest year and a half of my life, and I was driving an hour each way to Mauna Lani on top of it.

Then I saw an ad in the newspaper, an actual newspaper, for a Director of Marketing position at a snorkel company in Keauhou, five minutes from the house. Better pay, half the hours, no commute, and we finally finished the place. Fair Wind is a local family-run operation, and the owners took me under their wing and made life good for a long time. Sixteen years, as it turned out.

Covid. Sixteen years in, the work was still good, but the shutdown gave me pause to consider what I actually wanted next. My boys were five and seven, and I knew I wanted a life with more financial upside and more flexibility to be around for theirs. Real estate offered both. Rather than walk out, I worked out an arrangement with the Fair Wind owners: I would stay on for a year while phasing into real estate. That gave me a softer landing against the startup costs, and it gave them time to find the right replacement. It says something about those owners that the conversation went that way, and I am still grateful for it.

Absolutely nuts. I started in 2021, right in the middle of the frenzy, running Google ads to generate buyer leads and then walking those clients into bidding wars with ten and fifteen offers on every property. I was not scared about whether it would work. I had the Big Island knowledge, the local connections, a finance background, and real marketing experience, which are the actual ingredients for this business. What I did not have was reps, so I got them fast. I learned to write a clean contract quickly, and then I started winning them. Three months in, I had four escrows open. That year, I was named Rookie of the Year by the West Hawaii Association of Realtors, and I have been selling around $20 million a year fairly consistently since then. I learned this business on the fly in the hardest market anyone had seen in a decade, which is not the easiest way to start, but it is a good way to get good.

Three things. Valuation is the first, on both sides of a transaction. I came to this with a finance degree, and I build my own analytics rather than pulling a template comp report and calling it a number. I am confident in what the data says, and I will tell you plainly when it does not support what you want to hear. Clients do not always want that conversation. It is still the most valuable thing I do.

The second is that I have not spent twenty-five years on a couch. I have been out exploring this island the whole time, hiking it, riding it, swimming it, driving roads most agents have never been down. That means I know areas very few people in this business know, and I have a big-picture read on the island that almost nobody has. When someone is considering relocating here, it turns into a real conversation rather than a sales pitch.

The third is the one that actually matters. I follow through. I do not let people down, and if a deal needs me for twenty hours in a day, that is what it gets. Every client, not just the expensive ones. That is not something anyone can prove on a website, but it is the thing my past clients would tell you first.

Part of why I left Colorado was burnout from the cold. I grew up ski racing in the mountains and spent years on the US junior national development team, with cycling and soccer as off-season training. The funny part is that the off-season work made me a better cyclist than I ever was a ski racer, though I never raced bikes in Colorado. I just rode. One semester I commuted forty miles a day to college on a mountain bike. By the end of my twenties, I had four ACL surgeries behind me and figured my athletic life was over.

Then we finished building the Kona house, and I was mentally wiped out and completely out of shape. I signed up for Lavaman, the local triathlon at Waikoloa I had been reading about in the paper for years. The problem was that I could not actually swim. I could keep from drowning, but proper freestyle was something I had to learn from scratch with the Kona Masters group, and I hired a local coach four months out just to finish respectably. Turns out all that ski racing base was still in there.

Over the next seven or eight years, my wife Rani and I raced constantly. We met at my very first running race in Kona in 2008, which tells you something about how this community works. She is a local legend on the run here, a third-grade teacher, and she has written a weekly sports column for West Hawaii Today called Running with Rani for the past fifteen years. Between us, we did countless Ironman events, three World Championships for me, and a long list of 70.3s. We have both won races outright, including Lavaman as overall winners rather than age group. We were flown to Japan five times to compete representing Kona. I was fine in the water and decent on the run, but the bike is where I belonged, usually posting one of the fastest splits in the field, and I still hold course records on the bike here in Hawaii.

Then our second son was born in 2015, and dad life kicked into overdrive. A few years later, the boys got into soccer, and real estate got busy. That athletic chapter is on hold for reasons I am grateful for. I am honestly out of shape right now, and I stay connected to the endurance community anyway. I will be back. Hopefully sooner than later.

By accident, the way most of the good things here happened. In 2022, just after COVID, my older son came home from school at age 8 and said he wanted to try soccer. He joined City SC Hawaii, developed fast, and I got roped in as a parent coach. Before long, both boys were in it completely, and we were traveling to Japan, the Netherlands, Oahu, and all over the mainland for tournaments, camps, and training.

In 2024, the club’s president stepped back after his thirteen-year-old, a Kona kid, was scouted and signed by San Diego FC’s MLS professional academy. I took over as Board President. It is more work than anyone assumes, and it has given me a front-row view of how this community shows up for its kids. Being able to say a boy from Kona went straight into an MLS academy still means something around here.

This year my own son signed with the Barca Residency USA Academy in Arizona, part of the Spanish FC Barcelona system. He is boarding there now, school and soccer full-time. None of that was on the plan when he came home asking to try a sport. It is also the honest answer to why I got into real estate in the first place: I wanted a career with the flexibility and the resources to be there for my kids and to back them when something like this comes along. That part worked exactly as I hoped it would.

Building our family home. I went into it thinking I could manage a construction project alongside a full-time job, and it turned out to be a far bigger endeavor than I could have imagined. There were no reliable contractors to be had during that stretch; prices were being gouged, budgets needed constant monitoring, and, on top of all that, we were balancing multiple family members, each with their own ideas about the design. It was taxing in a way I did not anticipate, and honestly, it took a chunk out of my enthusiasm for building. We got there. If I could do it again, I would do a lot of it differently.

What I got out of it is firsthand knowledge that very few agents here have. I know what county codes, zoning, permitting, and construction costs will actually do to you on this island, because they did it to me. So when a client tells me about the house they want to build or the fixer they want to take on, I take their plan seriously and scrutinize it. Upkeep, uncertainties, risk, what happens when a contractor disappears for two months. I have talked people out of buying a house and out of building one more times than you would expect an agent to admit. That is not me being negative. That is me having lived the version of the dream that does not appear in the listing photos, and thinking you deserve to hear about it before you commit rather than after.

I have watched countless people come and go over twenty-five years, including friends I expected to be here forever. There is no single reason people leave. Family pulls them back. Affordability catches up with them. Some get tired of the limited career ceiling, though technology and remote work are changing that faster than anything else has.

The ones who stay have something in common, though, and it is not money or timing. They get involved. They volunteer at the festivals and local events; they show up and embrace the way of life here rather than resisting it. The ones who fight it, who try to reshape this place into the mainland with better weather, do not last. I understand the impulse, because I came close to that level of frustration myself. Roads that would take six months to build somewhere else take ten years here. Government moves at a pace that will test you. The infrastructure and the parks are not what you left behind.

My advice is to accept that not everything is perfect and to embrace the unique way of life here. You can absolutely still be who you are. Just do not expect everyone to fall in line behind you. Once you get into the local current instead of swimming against it, you will be fine, and it will carry you toward an enjoyable and fulfilling life here. That is a conversation I would rather have with you before you buy than watch you learn on your own three years in.

Talk Story

Every Big Island move starts with a conversation. Tell me what you are looking for, and we will take it from there.

Compass Real Estate in Kona, Hawaii - Penn Henderson, Big Island Real Estate
Penn Henderson of Compass

75-1029 Henry St., Suite 301
Kailua-Kona, HI 96740

Phone: (808) 345-6214
Email: penn@pennhenderson.com