Penn Henderson Top real estate agent in Kailua Kona

Penn Henderson

NextHome Paradise Realty
4 Years of Experience
(34)
$21M
Total Sales Last Year
4
Years of Experience
29
Recent TransactionsTransactions from the last 3 years
$1.6M
Average Price Point

    About Penn Henderson

    As a REALTOR® with NextHome Paradise Realty, Penn Henderson ranks among the top 3% of agents on Hawaii's Big Island. A full-time Kona resident since 2001, Penn is recognized for consistent $20M+ annual sales, strong market insight, and genuine local connection. He specializes in luxury homes, oceanfront estates, and investment properties throughout Kona, the Kohala Coast, Waimea, and Waikoloa. With professional certifications including CLHMS, REALM®, and PSA, Penn combines data-driven strategy with a personalized, aloha-centered approach. Clients value his integrity, communication, and proven ability to deliver exceptional results in Hawaii's dynamic real estate market.
    OTHER LANGUAGES
    English
    Community Involvement
    I am proud to be actively engaged in the Kona community. I currently serve as President of City SC Hawai'i Youth Soccer Academy and am the co-owner and organizer of the Kona Jingle Bell Beach Run, one of the island's most recognized holiday events. I also volunteer with the Hawai'i Island Humane Society and have contributed my time over the years to government and marketing committees for both Kailua-Kona and Keauhou. In addition, I served for many years on the marketing committee of the Big Island Visitors Bureau, helping promote Hawai'i Island's culture, lifestyle, and unique sense of place.
    HOBBIES/INTEREST
    Outside of real estate, I enjoy an active lifestyle with my two boys, supporting them in their competitive soccer journey and spending time together outdoors. I'm passionate about mountain biking, hiking, and swimming, and I still make time to train and explore the island's natural beauty whenever possible. Earlier in life, I competed as an elite cyclist and triathlete, racing in the Ironman World Championship in Kailua-Kona three times--a foundation that continues to fuel my love for fitness, discipline, and the Big Island's vibrant outdoor lifestyle.
    FAMILY
    My wife, Rani, is a third-generation Big Islander and an elementary school teacher in Kona, dedicated to her students and the community. Together with our two boys, we stay active through youth soccer, which has become a big part of our family life. While Rani and I once competed in Hawai'i's triathlon and cycling scene, these days our greatest joy is cheering from the sidelines and enjoying the everyday adventures of island living.
    Read More About Penn

    Credentials

    LICENSE
    Real Estate - Hawaii - # RS-83962
    Designation

    REALM® Luxury Certified

    At Home with Diversity

    PSA (Pricing Strategy Advisor)

    CLHMS (Certified Luxury Home Marketing Specialist)

    Top Producer

    Licensed Realtor

    ePro

    REALTOR

    Specialties

    • Sellers
    • Buyers
    • Residential Property

    Loading recent sales...

    Penn Henderson's Reviews & Ratings

    34 Reviews
    (5/5)
    Note: Reviews may include other agents on their team
    What clients say about this agent....
    • Professional
    • Responsive
    • Communicative
    • Knowledgeable
    • Outstanding
    • Trustworthy
    • Attentive
    • Hard working
    • Excellent negotiator

    April N.

    Review for Member: Penn Henderson
    December 1, 2025

    Penn is one of the absolute best agents on Big Island. I know many local Realtors and recently chose Penn 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. 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. 3. Penn has excellent marketing abilities which not only help your offer get accepted, but also means he puts together 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 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. 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.

    Carolyn H.

    Review for Member: Penn Henderson
    October 18, 2025
    Local Knowledge
    Process Expertise
    Responsiveness
    Negotiation skills
    zillowZillowVERIFIED

    Penn was very knowledgeable about all areas in the Kona, Kohala district. He truly made our experience of purchasing our new home enjoyable. We appreciate his support and prompt responses to our inquiries and felt he supported us through the entire process.

    Joseph D.

    Review for Member: Penn Henderson
    September 23, 2025
    Local Knowledge
    Process Expertise
    Responsiveness
    Negotiation skills
    zillowZillowVERIFIED

    What can one say? We sold our unit on the big island at a very challenging time in that market And I dont think we could have without Penn Hendersons help and expertise. There were twists and turns throughout the process aEUR|. Mostly on the buyers side aEUR|. And Penn was able to navigate them all . Its a difficult thing to sell a property when you live 3500 miles away from it It requires trust and Penn earned our trust in every way possible. He also went above and beyond his job description by handling issues like turning in our cable boxes and emptying a storage locker and donating the items it contained . This is a person who knows the real estate market and has great experience,but so is kind, thoughtful and very professional We cant say thank you enough Penn!

    Sandra M.

    Review for Member: Penn Henderson
    June 28, 2025

    Penn is an excellent Realtor who went above and beyond to get our property visible and on the market right away. He is the best agent I have ever worked with. His calm demeanor and willingness to listen was evident when issues came up during the process of showing the property. He always kept me informed and made himself available. Do not hesitate to use Penn ! You will not regret it!

    David E.

    Review for Member: Penn Henderson
    June 25, 2025
    Local Knowledge
    Process Expertise
    Responsiveness
    Negotiation skills
    zillowZillowVERIFIED

    It is sincere respect and appreciation that we recommend Penn Henderson as your real estate professional. He is a polished professional, with expertise in the Kona community, his personal touch create a stress free environment in which to buy or sell your home. We are very fortunate to find Penn!

    FAQ