We analyze thousands of real estate agents in Wailea and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for August 2026. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
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Information and statistics on the latest trends in the Wailea real estate market. *
Apr 1, 2026 - Jun 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Apr 2026 - Jun 2026).
Wailea currently shows a neutral market balance, with conditions not clearly favoring either buyers or sellers in this rolling three-month view through June 2026. Inventory is relatively high at 10.4 months of supply, giving buyers more options even as overall activity remains steady.
Prices have shifted down notably compared with a year ago, with the typical home value lower by about a third and median list prices also declining year over year. At the same time, more homes are changing hands, as homes sold are up roughly 29% and pending sales have surged more than 40% from last year, pointing to renewed buyer engagement despite softer prices.
Time on market has lengthened significantly, with the median days on market jumping compared with a year earlier, indicating that properties generally take longer to find the right buyer. Only about 8% of homes sold above list price and the average sale-to-list ratio sits just under 95%, suggesting buyers often have room to negotiate. In this kind of evolving, data-heavy environment, both buyers seeking value and sellers aiming to price strategically can benefit from Agent Pronto helping them find an agent who understands Wailea’s dynamics.
Wailea offers residents a serene, upscale coastal lifestyle with year‑round sunshine, safe, walkable neighborhoods, access to pristine beaches and outdoor recreation, and a vibrant mix of dining, wellness amenities, and a close‑knit community.
Wailea offers resort level amenities with practical, everyday livability. Located along Maui’s sunny south shore, it features master planned neighborhoods, golf course communities, and condo resorts that appeal to full time residents and second home owners who value convenience and coastal access.
Daily life centers on outdoor recreation and easy services. Residents enjoy beach walks at Wailea Beach and snorkeling at Ulua Beach Park, along with three renowned courses at Wailea Golf Club. Upscale shopping, dining, and basic errands are handled at The Shops at Wailea, while nearby Kihei offers additional grocery options, schools, and medical services. Families and professionals also appreciate access to Kihei Charter School and community programs at Kalama Park.
Traffic is lighter than in central Kahului, yet the airport and big box shopping remain within a reasonable drive. Weekend outings might include a short trip to Makena Beach State Park or dining in Lahaina when conditions allow.
Choosing a home in Wailea means balancing resort style surroundings with commute times, association rules, and varying microclimates. A local real estate agent who understands Wailea’s neighborhoods, view corridors, and building histories can simplify each decision, reduce stress throughout the process, and help both buyers and sellers move forward with confidence through Agent Pronto’s matching service.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Kathy was so patient and amazing. She was the first person to guarantee me things regarding a property I was looking to buy. She came through with the guarantee plus more. She is very honest and upfront too. She's easy to work with and will always have your best interest at heart. I would 100% refer everyone to her and I'm looking forward to working with her even more.”
“We've known Brittany for many years and we have had experience working with her in the past. We chose to work with her once more because of our wonderful experience In the past. I would highly recommend her because of her professional approach and her genuine interest to provide the best to her customers.”
“Augustina is a honest go getter. She has her clients back through the while buying process. When I say amazing, I mean AMAZING!”
“Debra Morris was instrumental in getting all the complications ironed out and seeing us into our forever home on time and under budget. The only regret is we do not plan on moving again and so we will not be needing an agent soon! I would definitely recommend Debra Morris to anyone buying or listing their home!”
“Brooke helped me navigate a difficult market. We actually sold our home in about a week for cash. You can't ask for more than that. I would recommend this agent.”
“Fantastic realtor. He was extremely responsive and proactive. He was appropriate knowledge to locate and negotiate real estate deals. I will definitely use Pat Gaumond for all future real estate deals in this area.”
“Darrell was very helpful and responsive through every step of the way. Would highly recommend.”
“Was very responsive and was happy to break stuff down to make it easier to understand. Very Straight forward, isn't gonna sell you something she herself wouldn't purchase.”
“Very focus and dedicated agent. It was a pleasure working with her.”
“Tim and team, Thanks for your service and attention to detail making our transaction efficient and easy!”
“Very helpful whether in answering your questions or communicating. Was very honest and solid advice moving forward.”
“From the first conversation with Peggy all the way to closing day and after she was not just my realtor but someone who truly cared about me and what I was going through. Thank you Peggy, you certainly were a voice of reason and an excellent choice in choosing you as my realtor. Thanks for getting me through such an emotional and challenging time.”
“Having used Tom and Karan's services twice now, I can confidently say they deliver exceptional service at every stage. They were always available whenever I needed them, guided us through each step with ease, and made the whole transaction feel seamless. Best of all, their strategies paid off and got me top dollar on my home sale. A huge thank you for the incredible work—five stars all the way!”
“Diana was very professional and extremely helpful throughout the entire process. We had a great experience working with her and would highly recommend her as an agent for anyone looking to buy or sell a property. Thank you Diana!”
“Paula was fantastic! She was knowledgeable, very responsive, and was able to walk me through the process step-by-step as a first-time seller. Would highly recommend to anyone and everyone!”
“Hello Gabriela, Thank you for helping make this milestone possible. I'm so grateful for all your support and professionalism I will gladly recommend you to anyone looking for an outstanding realtor! Thank you Rosemarie Rodarte”
“He is very professional, he is always there to answer and solve any questions and he is very kind to make you feel a lot of satisfaction with the purchase because he explains the whole process”
“I've known and worked with Lauralyn Lambert for 19 years. Her enthusiasm, can do spirit, years of real estate knowledgeable, and integrity are some of the reasons she is my real agent and the one I recommend in the greater Oroville area. She has helped friends of mine with some complicated real estate needs and has always come through. She will come through for you too.”
“Liked him almost immediately. If I did,, others will also. He assessed my situation and treated it accordingly. He already knew how to proceed. I didn't have a clue. Excellent knowledge of the market and process. Experience. Drive. Availabllity. He literally took over and handeled the entire project. He works well at all levels of the project. Strongly recommend him.”
“Tracy was great to work with. Very responsive to phone calls and emails. If she didn't know the answer she found out quickly. Would definitely recommend. Thnx”
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Wailea. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Wailea Realtor® or real estate agent today.
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