Penn Henderson, Real Estate Agent

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Penn's Concierge Page

Specialties

Practice Areas

Luxury and resort property
Relocation and second-home buyers
Remote and off-island sellers
Short-term vacation rental and investment property
Vacant land and new construction
Off-grid property
First-time buyers and foreclosure acquisition

Areas Served

Kailua-Kona, Holualoa, Keauhou, Kalaoa, Kealakekua, Captain Cook, Waikoloa, Waimea, North Kohala, and the Kohala Coast

Private communities: Hualalai, Kukio, Kohanaiki, Hokulia, Mauna Lani, Mauna Kea

Certifications

Certified Luxury Home Marketing SpecialistGuild Elite · CLHMS

Resort and Second-Home Property SpecialistRSPS

Pricing Strategy AdvisorPSA

At Home With DiversityAHWD

e-PRODigital and remote transaction certification

Hawaii REALTOR® license RS-83962
Compass, Kailua-Kona

Education

University of Colorado Boulder
BS Finance, Leeds School of Business

Client Testimonials

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SJ Lee · Relocation Buyer, Holualoa

★★★★★

I worked with three Realtors in Kona before landing a more long-term relationship with Penn. He was extremely responsive throughout the whole process. He wasn't pushy at all. Most importantly, he struck me as just a genuine, good man. He had empathy for me when I was having second thoughts multiple times throughout the process. He's deeply rooted in the community, and now I admire him too.

Srikanth R. · Bayview Estates Buyers, 1031 Exchange

★★★★★

We were introduced to Penn through a trusted realtor recommendation, and even though we began working with him remotely from the mainland, the distance was never a factor. He made himself incredibly available through phone and Zoom, and he took the time to truly understand our unique needs. If you want an agent who is thorough and genuinely listens, we cannot recommend Penn highly enough.

Steve & Jennifer Spelshaus · Sold Their Iolani Estates Home in Kona

★★★★★

Penn helped sell our home in Iolani. He was extremely detail-oriented and knew everything that was going on in the market. He was on top of scheduling showings and open houses. He was always communicating with us and there were never any surprises. He kept us informed 100 percent through the entire process. He did a great job and we'd recommend him to anyone buying or selling on the Big Island.

Jeff Jensen · Keauhou Estates, Second-Home Buyer

★★★★★

We just moved into our awesome Kona home. Penn was extraordinarily patient and his process, understanding goals and video tours, for off-island buyers works spectacularly. He was honest and when showing us many properties, was forthright if he didn't think a home was right for us. I would unconditionally recommend Penn to anyone looking for something special in Kona.

Mila Krueger · Kona Palisades, Relocation Buyers

★★★★★

We visited the Big Island from Atlanta to scope out home ownership. I searched online since we didn't know any realtor and Penn was the most responsive and accommodating during our short visit. 15 months later, we were ready to purchase. Penn knew exactly what we were looking for. In this competitive housing market, he was able to close the deal in record time.

Clay & Kelly Foster · Kailua-Kona, Buyers

★★★★★

Penn went above and beyond what we ever expected of a realtor. He helped pick up my pets at the airport because our rental car wasn't big enough for their crates. He lent us his generator when our power was out so our groceries wouldn't go bad. Excellent service doesn't even begin to cover what he provided for us, truly an amazing human being.

Christina De Vito · Condo Buyer, Waikoloa Village

★★★★★

He listened to all our needs and was with us every step of the way, from the beginning to the end of the process. He sent us a video of our complex and the specifications, and was so knowledgeable and professional. He went above and beyond and exceeded our expectations, giving us information about the area and contractors for our unit. We couldn't have navigated this journey without him.

Charity

City SC Hawaii
Board President and volunteer coach. The largest youth soccer club in West Hawaii.

Jingle Bell Beach Run
Co-producer since 2005 alongside my wife Rani, who founded the event. It is now the largest 5K on the Big Island.

About Penn

I moved from Colorado to Kona in 2001 and never found a reason to leave. Twenty-five years later I have built a family, a career, and a life here, and the island knowledge behind my real estate practice comes from actually living it rather than studying it. I came to real estate the long way around. I hold a finance degree from the University of Colorado Boulder and spent more than twenty years in executive sales and marketing, including senior roles at Mauna Lani Resort and Keauhou Bay, before earning my license and going full time in 2021. That background shapes how I work. I read a market through numbers, I price with data, and I negotiate like someone who has done it professionally for a long time.

How I Work

Most of my clients are buying or selling from thousands of miles away, so I built my practice around that reality. I have produced more than 450 narrated property tour videos, run live FaceTime showings, coordinate remote signings, and set my schedule to my client's time zone rather than mine. Relocation buyers almost always start with a week on island, where we work through which parts of the Big Island fit how they want to live before we ever talk about specific properties. Many find the house on that first trip. More often they fly home, we keep the search running, and they buy remotely with confidence because they have already done the groundwork.

I stay hands-on across pricing, marketing, showings, negotiation, and escrow, and I am the point person on every transaction I take. Around me is a network built up over 25 years on this island: transaction coordinators, escrow and title officers, inspectors, lenders, and contractors I trust. My clients always know who is accountable for their deal, and I make sure the details are handled from the first conversation through closing and long after.

What I Sell

Luxury, resort, and residential property along the Kona and Kohala Coast, including Hualalai, Kukio, Kohanaiki, Hokulia, Mauna Lani, and Mauna Kea, along with Kailua-Kona, Holualoa, Keauhou, Waikoloa, and Waimea. I work across single-family homes, condos, vacant land, and second homes, with depth in short-term vacation rental investment, where zoning rules and association restrictions vary considerably and have changed in recent years.

Island Life

My wife Rani is a third-generation Big Islander and a Kona elementary school teacher. She started the Jingle Bell Beach Run in 2005, and we put it on together every year. It is now the largest 5K on the Big Island.

I have competed in the IRONMAN™ World Championship in Kona on numerous occasions, ridden more than 100,000 miles on these roads, and currently serve as Board President and volunteer coach for City SC Hawaii, the largest youth soccer club in West Hawaii. The lifestyle my clients are hoping to find here is the one I have been living for twenty-five years, and that is the perspective I bring to every transaction.