Maile Kessler


Licensed in Hawaii since 2003. Earned my broker’s license in 2006. Always learning, achieving numerous designations and accreditations along the way, to keep sharp.

Over the past 7 years, I started a family, while still working part-time for our beloved Broker-in-Charge, Cherie Tsukamoto. I am so thankful she allowed me to learn from her experience and borrow from her wisdom. Now that my children are daycare- and school-aged, I’m excited to get back to work full-time!

Professionally, satisfying clients and providing quality customer service is extremely important to me. Personally, I really enjoy creative problem solving, negotiating, and the finishing the unique puzzle that is part of every real estate transaction. It’s never boring!

Born and raised on Oahu, and I’ve lived almost exclusively in Hawaii Kai. I’ve been fortunate to take fantastic trips to Sweden, Bali, the UK, Canada, Mexico, Amsterdam, and all over the USA but I learned that I miss Hawaii madly when I’m away. I love my island home for that that it naturally offers.

I love the unique hiking and beaches here on Oahu. From Waimea to Kaimana, there is something for everyone. Portlock Beach is currently a personal favorite, as we frequently walk there from my family home and look for “treasures.” I am so looking forward to teaching my kids how to stand-up paddleboard and learning to surf with them when they are ready!

If you think I’d be a good agent for you call or text me at 808-781-8335 or email me anytime at



$9.6M | Honolulu | Learn More About this Property