Daryl Flem


As one of Hawaii’s most dedicated real estate professionals, I combine my people-oriented perspective, positive attitude, and hard work ethic with solid business skills and extensive knowledge of Hawai’i Island’s real estate market to help my clients realize their goals and dreams.

Born in Bakersfield, CA, I moved to Oahu in 1975, straight out of high school. While there, I got my start in sales, bartending in Waikiki. I also successfully ran a multi-line insurance brokerage for years that my father had started. It was this experience that truly taught me how business operates. My wife Leanna and I have also owned a few restaurants which were incredibly successful and a ton of fun. To this day, I’m still a big time foodie!

In 2000, we moved the family to the Big Island of Hawai’i and my real estate career began when I obtained my license in 2001. In 2003, my wife Leanna obtained her real estate license and in 2005, I obtained my broker’s license.

Throughout my 20+ year career, I have received numerous sales awards including: Top Producer, Top Sales, the President's Circle Award, and several President Elite Awards. I was also recognized as one of the Top 100 Hawai’i Realtors by Hawai’i Business Magazine in 2017.

Before joining Hawai’i Life, I held the role of Principal Broker and Director of Sales at Kohanaiki, Principal Broker for Coldwell Banker and Windermere Real Estate, and I was a Broker in Charge for Century 21.

Why Hawai’i Life? To me, Hawai’i Life just feels like ‘ohana. The marketing team is amazing, and it’s a 100% locally owned and operated brokerage that’s only in Hawai’i, which I really love.

Looking for experience? You found the right team. Leanna and I have closed over 293 transactions with a combined value of more than $221M. Two of the most significant sales were an oceanfront home in Kolea for $7.5M and a Shay Zak golf course home at Kohanaiki for $7.5M.

My knowledge of the Big Island real estate market spans from private golf course communities to beachfront homes, from vacation resort properties to year-round estates. Today, my real estate focus is on condos, homes in private communities, and the luxury resort market. I especially enjoy putting the hard to fit transactions together.

I’ve been married to Leanna for 39 years, and we have two amazing kids and three wonderful grandkids. We love calling Kailua-Kona on Hawai’i Island home. And in our free time, we golf, body surf in the beautiful waters off the Kona Coast, and entertain family and friends with our cooking.

Let's stay connected! Follow me on Instagram for fun news about Hawai’i Island and up to date real estate market news.

Please don’t hesitate to reach out to me for assistance:
808-895-3158 | DarylFlem@hawaiilife.com

My Blog Posts
latest news
West Hawai’i Luxury Market Update: Q3 2022 Sales & Trends
Hawai’i Life recently released our Q3 2022 Luxury Market Report and as we take a look back at the third …
Wednesdays @ Willies! 
Wednesdays @ Willies!  What started as something to do mid-week, Wednesdays @ Willies is now a family (and client) tradition. We’re …
big island
Big Island Market Update – Q2 2022
One question I am often asked is “how is the market doing right now ?”, referring to the Real Estate …