Real estate on Molokai isn’t like anywhere else, and that’s exactly why I’m here.
Since 2009, I’ve worked in planning, permitting, and development across the island and throughout Maui County, helping people navigate everything from new home construction and remodels to agricultural land use, commercial and hotel projects, and SMA (Special Management Area) and building permit approvals. That experience gives my clients a real advantage when buying, selling, or building on Molokai — because here, local knowledge matters.
Licensed since 2017 and with Hawai‘i Life since 2023, I’ve helped clients from all walks of life make confident real estate decisions. I also oversee Hawai‘i Life’s Long-Term Rental Property Management Division on Molokai, providing full-service support to both property owners and tenants. Whether you’re buying or selling, investing in a rental, managing an inherited home, or just trying to figure out your next step, I’m here to help you move forward with clarity and confidence.
More than anything, I believe in being useful, not flashy — just helpful, consistent, and honest.
I currently serve as President of the Molokai Chamber of Commerce and President of the West Molokai Association. Over the years, I’ve held a range of leadership roles across the island and throughout the state, including appointments to the State of Hawai‘i Reapportionment Commission Advisory Council, Chair of the Molokai Planning Commission, member of the Molokai Community Plan Advisory Committee, and board positions with the Molokai Community Federal Credit Union and Destination Molokai Visitors Bureau. In 2012, I was honored to be named a Pacific Century Fellow.
In 2007, I moved to Molokai and met my wife, Dawn, while playing saxophone in the Molokai Jazz band at the Lodge in Maunaloa. She was the lead singer. We married in 2010, continue to raise our family here, and today we’re fortunate to have four generations living on the island. I’m proud to call this place home, and even prouder to be “Papa” to our three granddaughters.
If you’re thinking about real estate on Molokai — buying, selling, renting, or simply trying to understand your options — I’d be glad to help. Email me at RobStephenson@HawaiiLife.com or call/text 808-658-0608.
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- Rob Stephenson
- Nov 25, 2025
- Rob Stephenson
- Nov 23, 2025
- Rob Stephenson
- Oct 20, 2025
What my clients are saying...
I've worked with a large number of professionals for a variety of services over a lifetime. My experience with Robert Stephenson (Rob) falls in the category of most enjoyable, efficient and effective, and well-executed service of all of my transactions spanning six decades. Rob is a consummate professional and precise communicator. He manifests total dedication to his client even though he is busy with family, civic and community service activities. Rob was referred to me by Zillow when I was searching for a home in Maui County. The referral was seamless and meeting him has been joy by surprise. I am very grateful.
Rob also referred me to a continuum of other professionals including insurance agents, inspectors, contractors, and various agents and support people. All of them have been exemplary. Rob clearly has a great network of people like him. His network is a reflection of his values, ethical manner, and care for his fellow man. Rob and his network of folks made this long-distance purchase with the its anticipated challenges happen.
Rob did a great job selling our house. He knows the Molokai market and knows how to negotiate for his client. We were so lucky to have him as our agent. Thank you for listing and selling our house at the reasonable price.