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 April 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, updated for April 2026. *
Wailea currently leans strongly toward buyers, with the market gauge at 85 and a clear Buyer’s Market label. With about 13.2 months of supply, plentiful choices and longer marketing times are giving purchasers more leverage in negotiations.
Prices, however, show notable strength, as the typical home value sits around $2,167,500 after rising 30.57% year over year and 5.86% month over month. In contrast, the median list price has dipped to $1,975,000, down 9.17% month over month, which suggests sellers are adjusting expectations to meet buyer demand.
Conditions on the ground reflect this push and pull, with 237 homes on the market, 35 new listings, and 28 pending sales, while homes spend a median of 99 days on market after dropping 20.8% from last month. Looking ahead to March 2026, typical values are projected to edge up to $2,227,500 even as projected list prices ease to $1,875,250 and inventory inches up to 240, and whether you are a buyer weighing options or a seller refining your strategy, Agent Pronto can connect you with a local agent who understands how to navigate Wailea’s shifting dynamics.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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.
“Adysyn was very helpful in our home purchase process. She was always available to answer any questions promptly and helped buy a house within a month of contact. Would definitely recommend her to friends and family and would use her services again in the future.”
“Working with Mae was honestly one of the best decisions we made during our home-buying process. From start to finish, she was knowledgeable, responsive, and truly had our best interests at heart. Mae took the time to explain every step, answered all of our questions (no matter how small), and made what could have been a stressful experience feel smooth and manageable. What really stood out was her dedication—she went above and beyond to make sure everything stayed on track and that we felt confident in every decision. We always felt supported and never pressured. We are so grateful for Mae's help in finding our home and would absolutely recommend her to anyone looking to buy or sell!”
“At the beginning of my searching I wasn't really sure on what I needed, he took a long time to have a very good discussion with me about, and we finally agreed on what I should look for. But the one we found was really good!! Recommend it for everyone”
“We were listed for SIX MONTHS with a"top tier" realtor and never even received an offer. We moved to Kevin Mills and we were under contract in SIX DAYS. We closed at 98.5% of asking. Highly recommended.”
“Lauren is the consumate professional and took care of everything down to the minute details. I would teccomend her to anyone looking to buy or sell a house.”
“Due to circumstances beyond anybody's control, Judy did an excellent job in getting the condo sold. I had HOA insurance problems and title problems when trying to sell my mom's condo. Judy was excellent during a rather long time period getting these problems fixed. She was able to find us a cash buyer and worked exceptionally with us during this process. Mind you, we live in Kentucky so much of what on was via email. We did all the paperwork over the internet, and she was outstanding in her help to us. On a scale of 1 to ten, she was way above that. My wife and I would highly recommend her to anyone. Side note. We had a title business in Kentucky, so we are very familiar with the whole process. She is excellent! Don and Paula Block.”
“I have worked with Kim multiple times. She is knowledgeable, thorough, communicates well, and has your best interest. She makes both the home buying and selling process easier by going above and beyond. She has become a friend and I would recommend her to anyone.”
“Amy was so responsive and handled an extremely complex sale with grace and professionalism.”
“The Blum Team was a pleasurable experience. Trustworthy, Professional, Transparent and very friendly. They handled our numerous requests and needs effectively and with enthusiasm. Our only issue was in communication, which at times, was less than stellar, but our overall experience was more than satisfying, and in the end, we were able to secure an effective Sale, and Purchase in our transition.”
“While I can promise in today's market that your property will sell in under 30 days, with Lauren Bishop's expertise ours did! We do not profess to be wise real estate tycoons, but thanks to Lauren's professional guidance we felt as much. She helped us make the right decisions regarding when to list, asking price, staging, open house presentation, etc... Then Lauren took over with her multi-marketing approach which included all the major listing platforms (MLS, Zillow, UtahRealEstate.com, Realtor.com and more), we even enjoyed a spot on a local TV program (https://youtu.be/aCJMSppNQVg?si=PJjI9okANGhEbcbn). Finally, her assistance during negotiations was invaluable, ultimately helping us through multiple offers. Thank you, Lauren, you made it the whole process an easy success!”
“Heather Bejda was a great help in our relocation from outside Philadelphia, PA to Oswego, IL. Ms. Bejda had great knowledge of the area and market. She provided excellent help, guidence and service. Would strongly recommend contacting Ms. Bejda if you are planning on relocating or purchasing property in the Naperville, IL area.”
“Christine was excellent to work with. She was knowlegeable, friendly and attentive. I would reccomend her to anyone looking or listing!”
“Maribel, nos brindo una ayuda única, porque más allá de la búsqueda de la propiedad, nos asesoro proactivamente acerca de todos los temas relacionados con el proceso de la compra y siempre estuvo atenta a todas nuestras dudas y consultas, que eran muchas porque era nuestra primera compra. Estamos muy agradecidos de todo su apoyo.”
“Our experience with Laura was excellent. From the moment we reached out to her everything moved forward quickly. As a first-time seller, I felt comfortable throughout the entire process thanks to Laura's knowledge, accessibility, and responsiveness. She also took the time to understand and cater towards our specific needs. I would highly recommend Laura.”
“Terri Jackson did a fantastic job selling my house. I had a full price contract in 4 days after the listing went up. She helped with minor repairs so I wouldn't have to make a 4 hour trip to handle minor issues, she referred us to a cleaning service who did an excellent job. Closing went smoothly. What more could you ask for? SOLD!”
“Randy was spot on every time we needed assistance from him, even on a short notice day went above and beyond our expectations”
“Excelente professional”
“Michelle was amazing. She constantly communicated with me and was very available whenever I reached out to her. I would definitely use her again and highly recommend her to anyone needing a realtor in that area.”
“Anyone using Crystal's services in the future is a lucky individual and will be well taken care of.”
“Bree was incredible to work with. She was consistent, reliable, and extremely knowledgeable throughout the entire process. Her communication and expertise ultimately helped us secure our home despite multiple competing offers. From the very beginning, she was always in our corner and advocated for us every step of the way until the finish line. She supported us through the entire journey and even attended our closing, which meant so much to us.”
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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