Jeff Simon


I am the Broker-In-Charge (Maui) for Hawaii Life Real Estate Brokers, which enables me to both represent Buyers and Sellers in the purchase and sale of their own properties, and to assist the many great Hawaii Life agents we have on Maui with their contracts and transactions. We have a really great crew on Maui, and I am very happy to be here.

While growing up in Southern California, my family always enjoyed vacations to Maui. We would come once or twice a year, and every one of those vacations felt too short. I never imagined that I would wind up living on Maui, and my past provided me with no hints that this would ever be the case.

I graduated from the University of San Diego in 1987, where I also played on the U.S.D. Men's golf team for four years. After graduating with a degree in accounting, I worked as a C.P.A. for Coopers & Lybrand, in Newport Beach, California. In 1993, I graduated from Boston College Law School, after which I practiced law in Southern California with the law firm of Keesal, Young & Logan. I specialized in business litigation, and later switched to corporate law. After practicing law for eight years, I was ready for a change of pace. I wanted to be able to spend more time with my kids, William and Katie, and to do things like coach their teams, attend their school functions, and have more family time. A few years earlier, my parents had moved to Maui to start a real estate brokerage, Simon Properties, LLC, and in 2001, we decided to join my folks on Maui, where a couple of years later I became the principal broker at Simon Properties. In 2012, my Dad and I decided to join Hawaii Life Real Estate Brokers, where it has been a perfect fit. I specialize in South Maui real estate sales, with my primary focus in Wailea, Makena, and South Kihei, while helping the other Hawaii Life agents in my role as broker-in-charge of Maui.

My kids are a bit older now -- William attended Seattle University and is now living in Los Angeles, and Katie graduated from Santa Clara University and is now living in San Francisco -- but they always love coming home to Maui. I can't imagine ever living anyplace else.

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My Blog Posts
for sale
Makena Surf Condo Overlooking Po’olenalena Beach
Enjoy breathtaking unobstructed ocean, outer island, and sunset views from this extra-large, elegantly renovated, 2 bedroom 2 bathroom Makena Surf …
Spectacular Views From This Beautiful Mana Kai Unit Overlooking Keawakapu Beach
Enjoy spectacular ocean, Molokini, Kahoolawe and Upcountry views from this beautifully and thoughtfully renovated two-bedroom, two-bath Mana Kai unit, o...
Spectacular Ocean, Beach, Molokini, Kahoolawe, and Upcountry Views from this Beautiful Mana Kai Unit
Enjoy spectacular ocean, beach, Molokini, Kahoolawe, and Upcountry views from this beautiful two-bedroom, two-bath Mana Kai unit, overlooking Keawakapu ...

What my clients are saying...

Jeff came highly recommended, but I have to say he exceeded my already high expectations. No detail was too small for his attention and he was very responsive to every situation. Time was of the essence in this transaction, and Jeff kept the process moving along smoothly. I was not on island at the time of the sale; everything was done remotely. That made Jeff's organizational skills and follow through even more important. He certainly has my highest recommendation.

— Bill K., Oregon

We met Jeff many years ago at an open house and were immediately impressed with his interest in finding what WE wanted, not just trying to sell us that condominium. Since then Jeff represented us in the purchase of three properties on Maui, as well as the sale of another. Jeff is honest, works hard on behalf of his clients, and is easy to talk to . . . he actually listens to what you are saying. We appreciate that Jeff always takes the time needed to select and preview properties to make sure they meet our requirements prior to showing them to us. He has always made our transactions easy by negotiating our offers and counter offers with sellers, handles all of the details such as arranging and being present for property inspections, requesting needed documents, and assisting with changes to documents.
We trust Jeff and value his opinions. We highly recommend Jeff to our closest friends without hesitation.

— Brian & Beth C., Washington