Raphael Wellerstein

Wailea Realty Corporation


A top producing agent on Maui since 2003 and acknowledged by Hawaii Business magazine as a "Top 100 Realtor for the State of Hawaii , Raphael Wellerstein specializes in both the purchase and sales of fine homes, luxury estates, condominiums, and land throughout the island of Maui. A Maui resident since 1992 and originally from Philadelphia, Pa., Raphael is a well respected member of the Maui community. Raphael has a passion to provide excellent customer service, with a commitment to work hard, listen, negotiate and follow through with each and every client. He provides quality service to build relationships with clients, and more importantly, maintain those relationships well beyond the completion of each and every transaction.

Consistently ranked as a top producer year after year, Raphael has been part of numerous sales records in residential homes and condominiums. Most recently, he has represented three Wailea and Makena sellers achieve record selling sales prices in their respective communities. With this proven track record of success, Raphael’s modern approach to real estate involves the utilization of both cutting- edge technology, personalized service and tactful negotiation skills.

In addition to being a Broker with Wailea Realty on Maui, Raphael is also a licensed Broker at Windermere real estate in Bellevue, Washington. “There are many Washington owners enjoying second homes and condos on Maui, and an increasing number of Hawaii residents looking towards Seattle for their secondary or new residence. I am excited to help both Maui residents discover the beauty and culture of the Pacific Northwest, as well as assisting Seattle residents locate and purchase their Hawaiian dream property.” Being a broker in both markets is extremely advantageous, and with all the resources necessary to assist buyers and sellers in both markets, Raphael is happily at your service.

When Raphael is not in the office or working on a transaction, you’ll most likely find him enjoying his family of three children, wife of 18 years and family dog, Makenna.

A forward thinking approach in an ever changing market climate is what separates Raphael from other Realtors, and makes him and the team at Windermere Real Estate a solid choice when it comes to your real estate needs.

Profile Details

Regent Territory
The Island of Maui

Service Areas

Wailea 96753, Makena 96753, Kihei 96753, Maui, Wailea.

Additional Resources

Recent Blog Posts

Modern Farmhouse on the Lower Slopes of Haleakala in Kula, Maui

Jun 15 - Raphael Wellerstein, Wailea Realty Corporation

My Listings

Wailea, HI, United States

$1,395,000 USD

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Raphael Wellerstein assisted us in buying our condo in Kihei, Maui. We could not have asked for a better realtor. He listened to our needs as a buyer and found us a place that we are very satisfied with. During closing we were in Seattle and could not be on site to see if the repairs we asked for had been done. He took the time to go to the condo and FaceTime with us so we could see first had the repairs and condition of the condo. He was very helpful during the entire process providing information and service that was beyond what we had experienced with realtors in the past. He is friendly, supportive and does a great job listening to the clients needs and responds accordingly.
Mary and Bob

Raphael Wellerstein

My Husband and I have used Raphael for the past 10years to purchase and sell properties 5 times. Every experience from the first to the last has been very professional and successful. Buying and selling can be a very stressful and confusing venture but Raphael has always gone above and beyond to alleviate any stresses and issues that arise during the process. His enthusiasm and knowledge have been invaluable. He was available at any and all times needed and remains a friend of the family always.

Jackie and Chris Foster

Raphael Wellerstein

We have been working Raphael since 2010 when he helped us purchase our first condo in Maui. Raphael took the time to meet with us initially for a coffee and we found that he carefully listened to our requirements and was able to answer our many questions about different condos and the different parts of Maui. After looking at numerous condos, we ultimately purchased a unit at the Polo Beach Club. During our search, it was clear that Raphael had extensive knowledge of the real estate market in Maui, and most importantly the Wailea market. Since we are non-residents, the process of buying a condo in Maui was very onerous and time consuming, but we found Raphael was always there to help. In spite of the process, the buying process was still a positive experience thanks to Raphael’s guidance and advice throughout the process.

 When we decided to look for a second condo in Wailea, Raph was the first person we contacted. Again, Raphael’s understanding of our needs, attentiveness, and extensive network resulted in him finding an off market listing at the Wailea Ekahi Village that was perfect for us. We were very happy with our purchase at the Polo Beach Club and Ekahi Village. Raph is responsive, transparent, and easy to deal with. He has demonstrated that he always advocates for our best interests and we look forward to working with him again on future real estate transactions in Wailea!

We have no issues in referring Raphael to our friends as we know they will be well represented. 

Sammi and I could not thank Raphael enough for all of his help over the years!

Kind regards,

Jason and Sammi

Raphael Wellerstein

Raphael has been my exclusive agent on Maui for the last 15 years. He’s always been very easy and enjoyable to work with. He always shows outstanding service and has never failed to act in my best interest – even when it’s meant that he would lose a sale.

Raphael has a deep knowledge of the Maui market as well as understanding to view properties from an investor’s perspective. He listens to his clients’ needs and melds that with a great ability to look creatively at a deal to make it work out with the best outcome for his client.

Raphael lives the Aloha spirit and always goes above and beyond my expectations before and after the purchase. He is wonderful to work with, and I cannot recommend him highly enough for anyone looking to buy or sell real estate on Maui.

Steve Tschudy – St. Louis, MO

Raphael Wellerstein

We met Raphael Wellerstein in November 2018 when we interviewed several realtors for our upcoming listing. We were most impressed by his detailed knowledge of the Wailea Ekahi property & keenness to represent us. We listed with Raphael in early January, ended up under contract by the end of April and closed by the end of May. Throughout that period Raphael was obviously very engaged in presenting our condo & advising us. What most impressed us was Raphael’s commitment to timely & detailed communications during the listing period & during the closing process. We have no hesitation in recommending Raphael Wellerstein as a true professional realtor that works diligently for his clients and knows how to assist in “getting the deal done”. Mahalo Raphael!

John & Lyn Thomson

Raphael Wellerstein


"We have worked with Raphael on three separate property purchases in Wailea. Raphael is knowledgeable, energetic, easy to work with, and focused on successfully completing transactions. We would be happy to recommend him.”


George G.

Raphael Wellerstein

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