Penn Henderson

Hawaii, Big Island Luxury Professional

What do Clients Say?

I am a mortgage lender so I work with a lot of realtors in Hawaii. Penn is one of the absolute best on the Big Island. I recently chose him to handle my personal real estate transaction for several reasons: 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 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 who really cares about YOU and your wants and needs, pick Penn. You won’t be disappointed.

April Nelson

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, if everyone were like him the world would be a much better place.

Clay & Kelly Foster

Penn was amazing! He is a fantastic communicator, detail-oriented, and a very professional real estate agent. He was very considerate about the time difference to where we live and was super responsive with the many properties we had him check out! We feel like he went above and beyond for us! We don't feel like we could have purchased our amazing condo without him!!!

Lonnie & Ryan

Penn Henderson of NextHome Paradise Realty is our realtor. He just helped us close on a condo in Kona. Penn has our most enthusiastic recommendation. 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 on 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!

Michael & Ines Hanly

I worked with three realtors in Kona before landing a more long-term relationship with Penn and we ultimately closed on a home in Holualoa. Here are my reasons for recommending him: 1) He was extremely responsive throughout the whole process. Other realtors I've worked with took days to respond and sometimes missed messages completely. Penn rarely took more than an hour. 2) He wasn't pushy at all. In fact, in one of the homes we looked at early on, he actually warned me to proceed with great caution. He will look at comps and always be willing to advise me to walk if the price doesn't seem right -- during a huge seller's market. 3) He had Mike and NextHome backing him up. Whenever appropriate, he leveraged his broker for a second opinion and I felt this is much better than working with a single, more 'established' realtor that is spread way too thin in a busy market. Most importantly, he struck me as just a genuine, good man. He had empathy for his other clients who were struggling during this competitive market. He had empathy for me when I was having second thoughts multiple times throughout the process. He even had empathy for the sellers who seemed to be going through rough times. That might feel a little strange to mainlanders (like me) that envision successful realtors to be cutthroat and strategic, but Kona is a small town on an island. He's deeply rooted in the community, many of the triathletes around the island admire him, and now, so do I.

SJ Lee

About Penn

Penn Henderson is a distinguished luxury real estate professional specializing in the Hawaii market along the Kona & Kohala Coast on the Big Island. Regarded for his sophisticated work ethic and for consistently achieving results for his clients, Penn has a proven track record of success, featuring a portfolio of significant transactions ranging from beachfront estates to ultra-posh condos and investment properties.

Penn has acquired extensive insights & valuable expertise over the past two decades within the numerous exclusive luxury communities of West Hawaii such as Kukio, Hualalai, Kohanaiki, Hokulia, Mauna Kea, Mauna Lani, and others.

He takes a personalized approach to real estate, ensuring that each client receives the attention and commitment they deserve. His passion for helping others and his genuine aloha spirit make him an exceptional resource for those looking to buy or sell luxury property on the Big Island. As your real estate agent, he is your fiduciary, advocate, counselor, strategist, analyst, and chief negotiator, providing you unwavering integrity and fierce loyalty – and always with the utmost privacy & discretion.

Penn holds a Business Degree from the University of Colorado at Boulder and has received countless digital marketing certifications from Google, Meta, and Northwestern University. He is a member of the National Association of Realtors (NAR) and is certified as an E-PRO® Digital Professional, PSA® Pricing Strategy Advisor, RSPS® Resort & Second-Home Property Specialist, and an AHWD® At Home with Diversity certified agent.

Alongside his passion for real estate, Penn is an integral part of the local Big Island community, helping foster responsible economic programs and development. He has served on several key marketing committees that include the Kona-Kohala Chamber of Commerce, Keauhou Resort, and the Island of Hawaii Visitor's Bureau. He also regularly volunteers his time throughout the week as a youth soccer coach and is co-director of the Big Island's largest 5K running race, the Jingle Bell Beach Run, with proceeds from the event donated to various children's charities.