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. I'm proud to be part of our Flem Family Team, where together we use our collective expertise and shared values as a family to enhance the service we provide.

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 325 transactions with a combined value of more than $250M. 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. Our daughter Laura has been around real estate for most of her life, attending open houses with us, putting mailing labels on postcards, and naturally being inducted into the world of real estate. It was only a matter of time before she wanted to join the “family business” and now we benefit from her deep knowledge and insight as someone who has grown up on the Big Island and knows it inside and out.

My personal 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 41 years, and we have two amazing kids and three wonderful grandkids. Our daughter is part of the Flem Family Real Estate Team and our son, daughter in-law and grandkids are in San Luis Obispo in CA, where my son has a landscape business called Avila Ridge Landscaping. 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.

For myself, wife Leanna, and our daughter Laura, real estate is a family endeavor. Together as a family and powerful real estate team, we’re ready to help you realize your real estate goals and dreams!

Please don’t hesitate to reach out to me for assistance:

808-895-3158 | DarylFlem@HawaiiLife.com