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
Wonderfully Positioned Mana Kai 607
Mana Kai 607 offers spectacular ocean views from both sides of this wonderfully positioned unit! From the living area, main …
Mana Kai Unit With Spectacular Ocean Views
Enjoy spectacular ocean views from both sides of this wonderful 2 bedroom, 2 bath condominium unit! From the living area, …
Wailea Ekahi Condo, With Direct Access to Keawakapu Beach
Enjoy spectacular ocean views from the living area, bedroom, and extra large lanai of this beautifully and completely renovated 1 …

What my clients are saying...

We first met Jeff at an open house, and subsequently purchased two Maui properties and later sold one of them with Jeff's assistance. Jeff is very knowledgeable about the market, has a low-pressure approach, and was very patient in helping us narrow our search to our price range and lifestyle. He always gave us his honest opinion about properties, both positive and negative, and steered us away from less desirable properties and toward properties that had better features. He gave us excellent advice about making offers and counter offers to ensure we got the property we wanted and the price we wanted to pay.

— Mary Ellen & Jim D., Nevada

I immediately felt in good hands with Jeff. His prior experience as an attorney and CPA, and his clear, calm way of answering my questions put me at ease. He helped us navigate the marketplace and the options extremely well. I am very happy with the results. I would definitely use Jeff again!

— Dr. Kevin R., Wailea, Maui