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About Penn Henderson
As a REALTOR(R) 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(R), 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.
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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
Awards
2026
TOP AGENT
Kailua Kona, HI
2026
TOP AGENT
Kamuela, HI
2026
TOP AGENT
Waikoloa, HI
Other Awards
2022 West Hawaii REALTOR(R) Rising Star Award - 2023 NextHome President's Circle Award - 2024 NextHome President's Circle Award
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FAQ
Take the time to understand the nuances of Hawai‘i’s real estate market. Every neighborhood, from oceanfront communities to upcountry retreats, has its own unique character, microclimate, and lifestyle. I encourage buyers to clarify their priorities, whether that’s ocean views, investment potential, or proximity to schools, and then rely on a trusted local agent like myself who can help navigate zoning, land use, lava zones, and other details unique to the Big Island. Patience and preparation make the process much smoother. For more detailed information about the buying process in Hawaii, visit: https://pennhenderson.com/buying
Presentation and pricing are everything. A property should tell a story that resonates with buyers, and it’s my job to showcase that story through professional marketing, strong local exposure, and targeted online reach. I advise sellers to view their home through a buyer’s eyes, addressing small details that make a big difference—and to trust their agent’s pricing strategy to attract the right audience. With a proven process, and done right, the results follow. For more detailed information about the selling process in Hawaii, visit: https://pennhenderson.com/selling
I’ve had the privilege of working with a wide range of clients, including first-time buyers, families relocating to Hawai‘i, luxury second-home owners, and investors seeking rental income properties. Many of my clients are from the mainland or abroad, and I specialize in helping them understand the local market and feel confident in their decisions. View some of my "success stories" here: https://pennhenderson.com/reviews
One that stands out was helping a local family I’ve known for years, who had been caught in the difficult rent cycle here in Kona. With a lot of hard work, creativity, and persistence, we were able to secure a home of their own—just in time for Christmas. Handing them the keys during the holidays was incredibly rewarding and a reminder of why I do what I do. View some of my "success stories" here: https://pennhenderson.com/reviews
After moving to Kona in 2001 from Colorado, I was fortunate to be hired by Mauna Lani Resort as their Director of Marketing, which provided me with unique insights into the Island's business and economic environment. Over the years, my background in marketing and community involvement further strengthened my reputation in Hawaii, and real estate has become a natural extension of both. My success as one of Hawaii's Top Realtors has genuinely been built on relationships, integrity, and a commitment to helping people achieve their dreams in one of the most beautiful places on earth. For more about me, visit: https://pennhenderson.com/about
Contact Information
Location
75-175 Hualalai Rd #D118 Kailua Kona, HI, 96740
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Available Listings View All
Active
$75,000
bds | 0ba Acres
Road 9 Koloa Maoli Lot 5437 Kurtistown, HI 96760,USA
Active
$1,625,000
3bds | 2ba 1934 Acres
75-5545 Hahai St Holualoa, HI 96725,USA
Active
$1,050,000
2bds | 2ba 806
76-6246 Alii Dr #411 Kailua Kona, HI 96740,USA
Active
$1,410,000
3bds | 2ba 1528 sqft
73-4368 Kapuahi St Kailua Kona, HI 96740,USA
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