We analyze thousands of real estate agents in Windermere 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 October 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 Windermere real estate market. *
Jun 1, 2026 - Aug 31, 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 (Jun 2026 - Aug 2026).
Windermere’s rolling three-month data through August 2026 points to notable year-over-year growth. Typical home values are up a little over 6 percent from a year ago, and the median list price has climbed more than 14 percent. Sales activity has surged, with homes sold jumping around 131 percent compared with the same period last year.
In the latest rolling period, buyers are seeing a median sale price of about $1.29 million and a median list price near $1.43 million. Inventory remains relatively tight at 49 active listings and about 3.3 months of supply, reinforcing its seller’s market label.
Conditions have shifted over the past year, with the median days on market edging up to 51 days, yet almost one in five homes still goes off the market within two weeks. Only a small share of recent sales closed above list price and the average sale-to-list ratio sits around 95 percent, suggesting some room for negotiation. At the same time, new listings are up more than 30 percent year over year, providing more options for shoppers even as pending sales and supply indicate steady demand. Whether you are aiming to stand out as a seller or navigate prices and timing as a buyer, Agent Pronto can connect you with a Windermere agent who understands these trends.
Windermere offers residents a beautiful lakeside lifestyle with preserved natural spaces, abundant outdoor recreation, a tight-knit community atmosphere, excellent schools, and easy access to world-class amenities.
Windermere immediately feels different from nearby Orlando and Winter Garden. Centered around the Butler Chain of Lakes, it offers a quieter, lake-focused lifestyle while staying close to major employers and attractions. Tree-lined streets, water views, and golf course communities define many neighborhoods, giving residents a strong sense of place and privacy.
Local life often revolves around the water and small-town core. Residents gather at Fernwood Park, attend events in downtown Windermere, or enjoy boat days on the Butler Chain of Lakes. Families appreciate access to respected schools such as Windermere Elementary School and Windermere High School, along with nearby private options.
Daily conveniences are close, from coffee and dining along Main Street to shopping and entertainment in Dr. Phillips. Outdoor enthusiasts enjoy nearby R.D. Keene Park for sports fields, playgrounds, and lake access, while golf and country club amenities appeal to those seeking a resort-style routine.
Because Windermere is relatively small and in high demand, the timing of a move matters. Inventory can be tight and pricing varies widely by lake access, school zone, and neighborhood age. Partnering with a Windermere-focused real estate agent through Agent Pronto helps both buyers and sellers prepare strategically and act at the right moment.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Evelyn was the best. She was attentive to our needs and got to know us better before speaking with potential buyers. She was thorough in everything that we asked her to do, including working with vendors on repair projects after the inspection was done. We liked her recommendations on the appearance of our condo before it went on the market. We would definitely recommend her to others that are selling a condo in our neighborhood.”
“It's great to have Tony on your side, he is Knowledgeable, always thinking ahead. He will guide you in detail. You will have a stress-free experience. Tony, Keep up the great service, Thank You.”
“Deanna is very knowledgeable, patient, understanding, and trusthworthy. I believe that she is the best realtor out there, and when it comes to my realestate purchase/sell, she is the realtor.”
“I cannot say enough wonderful things about Deb. She seamlessly handled both the sale of my home and the purchase of my new one. Her dedication is unmatched—she answered every late-night text and early-morning call without hesitation. She truly goes above and beyond for her clients and feels like family by the end of the process. Thank you, Deb!”
“Crystal is not only my soror and friend, but she is also an exceptional real estate professional. While our relationship is personal, the sale of my home was strictly business—and highly professional. From start to finish, Crystal set and managed expectations, communicated consistently, and demonstrated an incredible depth of knowledge throughout the entire process. She treated the sale of my home as if she were selling her own home, and that level of care and attention was evident every step of the way. I was extremely pleased with the entire experience. Crystal made the process seamless and gave me complete confidence that my home would sell for the listed price. She not only works hard—she works SMART! I will absolutely refer Crystal to my friends and family. And when the time comes for me to purchase my next home, Crystal is the ONLY agent I will call! Thank you, Crystal, for making what could have been a stressful experience such a smooth and successful one!”
“Professional, responsive, and knwoledgeable. Paula was always responsive, always pointing out great ideas and assisted us with navigating the new Florida laws as they differ by State. She brought her A game to the table and was super.”
“Thắng làm việc rất chuyên nghiệp, phản hồi nhanh và đặc biệt là tư vấn rất có tâm, sẽ liên lạc lại Thắng nếu cần”
“David Dorman was outstanding to work with. From the very beginning, he was personable, easy to talk to, and genuinely listened to what we wanted in a home. With his 27 years of real estate experience, he quickly narrowed down our options, combining his expertise with the homes my wife had already found. Thanks to his guidance, we found the right house and had an offer submitted within just two days of looking. Our closing turned out to be far more difficult than expected, but David remained calm, patient, and reassuring throughout the entire process. Whenever challenges came up, he helped us work through them without adding stress. His steady guidance and professionalism made a huge difference and ultimately helped us close successfully on our new home. If you’re looking for an experienced, knowledgeable Realtor who truly cares about his clients and keeps a level head when things get complicated, I highly recommend David Dorman.”
“Shelby went above and beyond for my family and I throughout the entire process. I was a first time home buyer and she answered all my questions without hesitation. I would highly recommend her to anyone I know looking for a new home.”
“Since we worked with Gary previously, he knew us personally. Through some time spent in looking in different areas Gary found us the ideal home close where we needed it to be. Without a doubt Gary is extremely patient and diligently works to provide exactly what we wanted and needed. We cannot think of another broker that we would want to work with as Gary is a true “Professional”. All we can say is “Gary, Thank You for providing exactly what we wanted and we will recommend you to everyone we know!””
“This is my second transaction with Charles, buying an investment property Charles and Lynn are amazing. I recommend them to everyone.”
“There were issues going into buying our first home but Chandra made the process smooth, fast and was with us every step of the way. She got us the best possible deal & made sure on closing day we were taken care of. Absolutely love her!!”
“Danny is great real estate agent you can trust and rely on”
“She listened and understood what was needed/wanted. She was aggressive with offers and getting compensations. Would use her again.”
“10/10 realtor for new construction! We built a home with KB Home over in Weeki Wachee Florida, and we had heard how important it was to have a realtor who understood inspections. We hired Rich because this is where he specializes, and he did not disappoint. He was truly with us every step of the way and guided us not only through hiring inspectors, but educated us on what to look for when noticing potential problems. Rich is a wealth of knowledge and won’t ever leave you hanging. In fact, I don’t think I have ever seen a realtor as passionate and invested in the process. This guy will look out for you. Another great part, as a buyer, his services are free to you because the builder pays him all of his commission. It is honestly just silly not to have him by your side for guidance and support. He may also make you laugh from time to time. 😅 Thank you for everything you did for us and helping us build our dream new construction home in the Tampa Bay area!”
“Al Spry can assist you whether you're planning to purchase or sell a property. He has a deep knowledge of the area and offers great ideas and recommendations. He's a great listener which proved valuable while narrowing down the many options and decisions faced. I highly recommend Al Spry for all your real estate transactions.”
“Zachary Greenberg was the correct choice. He was knowledgeable, he communicated as the process evoleved. His whole staff was as well. I felt my interests were being met. Alex Paganucci”
“Cory did an excellent job from start to finish. He was professional, responsive, and made the entire process smooth and stress-free. I really appreciated his attention to detail and clear communication. Highly recommend working with him.”
“I would recommend Kimberly to anyone trying to sell a high-priced home. She is knowledgeable about the market and was able to sell our house in 2 weeks, even though it had previously sat on the market for 9 months pre-COVID. Her customer service is excellent, and she is helpful with questions and contacts throughout the selling process.”
“Thank you for selling my house! It was a pleasure having you as my realtor!”
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 Windermere. 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 Windermere Realtor® or real estate agent today.
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