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Penn Henderson
About Penn Henderson – Big Island REALTOR®
Aloha! I’m Penn Henderson, a full-time Hawaii REALTOR® with NextHome Paradise Realty, proudly serving the Kona and Kohala Coast communities. Hawaii’s Big Island has been my home since 2001, and I’m grateful to live and work in such an extraordinary place. My focus is helping clients achieve their real estate goals — whether that means finding the perfect oceanfront home, securing a high-performing investment property, or listing a cherished island residence for top value.
Over the years, I’ve earned a reputation as one of West Hawaii’s most trusted agents, consistently ranking in the top 3% of Big Island REALTORS®. I maintain over $20 million in annual sales and have represented clients in more than 50 successful transactions since 2022. My commitment to client success has been recognized through the NextHome President’s Circle Award (Top 1% sales nationwide) and the West Hawaii REALTOR® Rising Star Award.
With 24 years of island life experience and a professional background in marketing and finance, I bring both analytical precision and creative strategy to every transaction. Whether marketing a luxury estate in Kohala, guiding a relocation to Kailua-Kona, or analyzing the investment potential of Waikoloa Village properties, my goal is always the same: clear communication, honest advice, and results you can trust.
Above all, I believe real estate is about people — and Hawaii’s community spirit is what makes this work so meaningful. I’m proud to help clients turn their island dreams into reality, one home at a time.
Specialties: Luxury Homes • Oceanfront Properties • Residential Sales • Investment Real Estate
Markets Served: Kailua-Kona (96740), Kohala Coast (96743), Holualoa (96725), Keauhou (96739), Waimea (96743), Waikoloa Village (96738)
Brokerage: NextHome Paradise Realty
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Recommendations
1. He truly cares about people. Penn’s number one goal is to make sure his clients are satisfied, and it shows. I have seen him make extra trips to properties for client requests, and provide countless detailed videos for off-island buyers. He spends time with people to make sure they understand the process and are comfortable with the transaction. When you work with Penn, you are not just another sale; he treats you like an important client and a friend.
2. Penn is very detailed and writes up excellent, strategic offers. If you are buying and competing with other offers, he gives you the best chance of winning by being very thorough with his contracts. The way he delivers an offer is equally thorough. This is the same high quality of work you see on his website and marketing materials.
3. Speaking of marketing, if you are selling, Penn puts together beautiful websites and books and other extremely professional marketing materials to sell your home. I have not used Penn to sell a property for me, but I have seen his work for several other clients, and it is always extremely impressive.
4. He has built some amazing tools into his website. These are helpful if you are seriously hunting from afar or if you are just browsing the market for a possible future purchase. I use some of his web tools almost daily.
5. Penn has a very good handle on the market and watches new listings diligently with his clients in mind. I scour the market daily, and he still found a property for me that I had not seen yet. This property ended up being the perfect one for my needs, and Penn helped me win it in a multiple offer situation. He also ensured a smooth transaction despite some seller challenges.
Overall, realtors are NOT created equal. If you want someone that will work hard to get you the best deal possible and that really cares about YOU and your wants and needs, pick Penn. You won’t be disappointed.
He spent a lot of time explaining things step by step, and took all of our calls quickly.
It was a pleasure and a blessing to work with him.
I would highly recommend him and would use him again.
Like many buyers, we had to conduct all of our business from the mainland. Before we visited the big island in September, we scheduled a meeting with Penn. When we arrived in his office, he showed us a dossier full of properties matching our interests and price range. We spent the better part of an afternoon touring various areas in and around Kona. With the benefit of Penn’s expert knowledge of both the territory and the housing market, we were able to get a good idea of what kind of property we would be looking for, and where.
Once we returned home, Penn started sending us new listings in West Hawaii. In the fall it was still too early for us to buy, but we learned a great deal by checking these listings and asking questions. Penn was always ready to give us full and candid answers.
In January we got more serious about buying in Kona. When we asked about properties we were considering making an offer on, Penn would take the time to make thorough, informative videos for us. These weren’t always rave reviews; every now and then, he would essentially have to talk us out of making an offer based upon what we were seeing.
In the first two months of the year we made several offers, and missed out on the first properties we had bid upon. Although we would get discouraged at times, Penn just kept looking, assuring us that we’d eventually find the place we were seeking. He never gave up or got impatient; he just kept on working hard and writing well-crafted offers until we finally got one accepted at the beginning of March. Escrow just closed this week, and we owe it all to Penn.
Are you looking for a realtor to help you find a place in West Hawaii? You really can’t do better than Penn Henderson. He is simply the best there is. Mahalo, Penn!
All 900 agents in this market saw this property and saw the red flags, but Penn was the only one to do the work and see that those red flags were not really there! Truly an amazing job.
First day we met, we found our home and offered that night.
He was honest, professional, responsive, personable, and knowledgeable.
Everything went so smooth and fast. He accommodated our busy schedule and met us super early in the morning from Kona.
He went above and beyond for our sales and highly recommend this guy to anyone who wants to buy or sell houses.