Penn Henderson Top real estate agent in Kailua Kona

Penn Henderson

NextHome Paradise Realty
4 Years of Experience
(32)
$21M
Total Sales Last Year
4
Years of Experience
26
Recent TransactionsTransactions from the last 3 years
$1.6M
Average Price Point
  • Service Areas
  • About
  • Credentials
  • Recent Sales
  • Contact Information
  • Social Media
  • Specialities

About Penn Henderson

Aloha from Hawai'i! The Big Island isn't just where I work, it's my home. Since moving to Kona in 2001, I've built my life, career, and family here, fully immersed in the island's unique culture and community. I know firsthand what it feels like to dream of living in Hawai'i and then take the leap to make that dream a reality. Today, I help others do the same. Whether you're searching for the perfect oceanfront escape, a quiet upcountry retreat, or a smart investment property, my role is to guide you through the details of Hawai'i real estate with local expertise, clear communication, and a client-first approach that makes the process seamless and stress-free. Specializing in Kona & Kohala Coast properties, including Waimea and Waikoloa Village.
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

Recent Sales

Showing 4 out of 19

We only display transactions from the last 3 years. To view transactions older than 3 years, please follow these steps:

  1. 1. Click the "View All Sales" button below.
  2. 2. Use the "Year" filter to select the desired past years.
Date
Address
Price
Represented
09/19/2025
68-3831 Lua Kula St #I208 Waikoloa, HI 96738
Sold For $380K
09/19/2025 Seller
06/24/2025
75-5919 Alii Dr APT AA3 Kailua Kona, HI 96740
Sold For $739.9K
06/24/2025 Buyer
06/24/2025
44-3895 Kukuipapa Rd Paauilo, HI 96776
Sold For $465K
06/24/2025 Seller
06/10/2025
75-5855 Walua Rd APT 20 Kailua Kona, HI 96740
Sold For $595K
06/10/2025 Seller

Penn Henderson's Reviews & Ratings

32 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

Joseph DeVito

Review for Member: Joseph DeVito
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 McManus

Review for Member: Sandra McManus
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 Ebenal

Review for Member: David Ebenal
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!

Ebenalb

Review for Member: Ebenalb
June 24, 2025
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
zillowZillowVERIFIED

Penn did a fantastic job helping us find and purchase our condo. He had information about all the condo projects in the area. He made a folder for me showing the condos, and we visited most of the complexes to get a feel of the different ones. A couple of months later, after we returned home off island, we found one online we thought we might like. I had Penn visited the unit. He made an extensive video showing the content of the unit, the location, and if the we could hear traffic noise or the ocean from the patio. Penn also helped us find loan agent who was familiar with Hawaii. Working with Penn was a great experience from start to finish. I cannot wait to use my condo!

Yosemiteheart0

Review for Member: Yosemiteheart0
May 10, 2025
Local Knowledge
Process Expertise
Responsiveness
Negotiation skills
zillowZillowVERIFIED

Penn is the very definition of going above and beyond, and I highly recommend him! I'm so lucky and grateful to have found him when it came time to sell my elderly mother's home in Kona Paradise. I didn't know where to start, so I researched online and read reviews for many different realtors. I knew that Penn was the right one for me after reading about how helpful and knowledgeable he is. Penn was communicative and professional and made what could have been a very stressful situation into a fairly easy one. I was sure that I'd have to travel to Hawaii from California during this process and didn't want to because of work and family commitments, but I didn't have to because Penn handled things there and I am so appreciative! Penn was there every step of the way providing guidance and support, and he got the best buyer and price for the house and the whole process went smoothly. Thank you so much Penn! Lindsey Jennings

FAQ

Contact Information

Location

75-175 Hualalai Rd #D118 Kailua Kona, HI, 96740

Social Media

More Agents Near You