Rob Stephenson


As a Hawai’i Life agent on the island of Molokai, I bring a unique perspective, uncompromising commitment, and strong business skills to helping every client achieve their goals of buying and selling real estate. For over a decade I've worked in the field of land use planning and development on the island. During this time, I've learned to navigate the complexities of building and remodeling homes, developing and rehabilitating commercial and hotel properties, and working with agricultural land owners to fulfill their operational requirements. I attribute these experiences and a knowledge of Molokai that can only be gained from living here to my success in real estate.

Since becoming a licensed Real Estate Agent in 2017, I have helped my clients achieve their goals of buying and selling real estate. As a well-respected leader in the community, I have also served on the Board of the Molokai Community Federal Credit Union, Destination Molokai Visitors Bureau, the Molokai Community Plan Advisory Committee, and as the past Chair of the Molokai Planning Commission. I was appointed President and CEO of the Molokai Chamber of Commerce in 2009 and had the honor of being named a Pacific Century Fellow in 2012. Currently, I serve as the President of the Molokai Filipino Community Council and Vice President of the West Molokai Association.

A lifelong entrepreneur and small business owner, I have been involved with a number of successful businesses and developed trusted relationships throughout my career. I continue to nurture these relationships, which has given me a broad network of colleagues, musicians, friends, families, and neighbors on Molokai and throughout Hawai'i. I’m committed to bringing people together and forming collaborative partnerships, and this deep level of connection consistently benefits the buyers and sellers I represent.

When I moved to Molokai in 2007, I played in a jazz band at the Lodge in Maunaloa. It was there that I met my wife, Dawn, who was the lead singer of the band. We married in 2010 and continued performing on Molokai until the spring of 2020. When I’m not working towards my clients success, I enjoy playing the saxophone, spending quality time with my wife, our family, and most importantly, embracing my favorite job of being "Papa" to our three granddaughters.

Whether I am playing an active role in the legislative process, helping the local business community, or assisting a real estate client, I am dedicated to being an advocate for those I serve. I’m ready to put all of that to work for you, so feel free to email me anytime at, or text or call me at 808-658-0608.

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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.

— Jerry Legerton

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.

— Yuji & Robyn Hata