Jessica Baker

My journey to Maui began at a very early age! Well before I could read I always wanted to look at picture books of tropical fish and marine life. Eventually, I would share with anyone who would listen, "When I grow up, I am going to swim with dolphins in Hawaii!" This was a very big dream for a kid in Michigan.

Fast forward to 2006. After graduating summa cum laude from the University of Michigan, I was fortunate enough to take my first (and only) vacation here to Maui with my parents. While we were having dinner that first night at the iconic Pioneer Inn in Lahaina Town, I just knew that the island was calling me. Armed with two suitcases and a bicycle, my next flight back to Maui two months later was as a brand new Lahaina resident.

Now I have happily lived on Maui for over nineteen years. As a child my parents couldn't keep me out of the water, I would spend as much time as possible in the chilly waters of Lake Superior, and I was a competitive swimmer in high school. Surfing was a natural progression, as well as snorkeling and open water swimming. I've completed both the Maui Channel Swim and the Waikiki Roughwater Swim. When I'm not in the ocean, I also enjoy hiking around the island, yoga, baking, reading a good book, and spending time with my dog Lucy.

I began my professional career here on Maui in Fine Art Sales then transitioned into Real Estate at the end of 2011. It was another natural progression based on my evolving interests and education. That first year I was awarded the Prudential Iwado Realty Rookie of The Year and worked almost exclusively in Commercial Sales and Leasing. Several years later I have now sold commercial properties, and even more single-family homes and condos, all across the island from Kapalua to Wailea, Wailuku to Kula, even Hana!

My mission is to help my clients achieve their goals, whether they're buying or selling, when the timing is right. I am strongly committed to providing clear, consistent communications and building long-term relationships, and have the diverse sales experience to back it up. I was named the 2021 Maui Realtor of the Year by the Realtors Association of Maui and first selected as a Hawaii Business Magazine Top Performer in 2021. I was also featured as one of Modern Luxury Hawaii's Dynamic Women in 2022. In 2023 I was recognized on the RealTrends America’s Best List Top 1.5% of all realtors in the U.S, and most recently in 2025 received that same RealTrends Verified recognition as the #56 Individual Agent in Hawaii.

I served on the Realtors Association of Maui Board of Directors from 2019 - 2022 and was chairperson of the RAM Technology Committee from 2019-2023. Within our exceptional Compass agent community, I'm a proud partner in the Private Client Network and the Compass Elite.
What are your Maui real estate goals and how can I help? Call, text, or email me anytime to talk story!

Oh! And did I ever swim with dolphins? Sure did. December 2007 was the first time of many. Life goal achieved.

Much Aloha from Maui,
Jessica