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. *
Jul 1, 2026 - Sep 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 (Jul 2026 - Sep 2026).
Over the latest rolling three-month period ending in September 2026, Windermere’s home values are down sharply compared with a year ago. The typical home value has fallen more than 25 percent year over year, while the median list price is down about 24 percent. Despite lower prices, more homes are changing hands, with homes sold up nearly 29 percent from the same time last year.
Conditions on the ground show a market that is active but not overheated. There were 39 active listings and 19 homes sold in this latest three-month window, with about 3.9 months of supply, consistent with a moderate seller’s market. Homes are taking time to move, sitting a median of 80 days on the market, yet the share of properties selling above list has risen to just over 10 percent.
Demand indicators are firming, with pending sales up almost 44 percent year over year even as new listings are only slightly higher than last year. Buyers are paying closer to asking price, as the average sale-to-list ratio has inched up to about 95.5 percent, and nearly one in five homes goes off-market within two weeks. With these shifting dynamics between pricing, inventory, and speed of sale, both buyers and sellers in Windermere can benefit from Agent Pronto’s help connecting them with the right local real estate agent.
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.
“⭐⭐⭐⭐⭐ I’m incredibly grateful to Natalia for helping me through my home-buying journey! She was professional, patient, knowledgeable, and always willing to go the extra mile. Even when the process became stressful, she made sure I felt informed and supported every step of the way. Her dedication and genuine care made a huge difference. Thank you, Natalia, for helping me find the perfect home for my family! Highly recommended! 🏡❤️”
“David Dorman is an exceptional realtor, and we cannot recommend him highly enough! From start to finish, his professionalism, market knowledge, and dedication were outstanding. His team’s marketing exceeded our expectations, from the beautifully produced video showcasing our home to the impressive listing presentation. Every detail was handled with care and expertise. What truly set David apart, however, was his remarkable negotiating ability. His skill in communicating and working with the other agent, advocating for our best interests, and navigating the process was invaluable. He demonstrated confidence, experience, and genuine commitment every step of the way. Selling a home can be stressful, but having David on our side made all the difference. We are incredibly grateful for his hard work and the exceptional service we received. If you’re looking for a realtor who truly knows his business and delivers results, David Dorman is the one!”
“I can't say enough great things about Jackie and the incredible job she did helping me purchase my property in Kissimmee. From start to finish, she went above and beyond to make sure everything went smoothly. Jackie was extremely responsive, knowledgeable, and proactive throughout the entire process. She was always available to answer questions, help navigate challenges, and make sure my interests were protected. What really stood out was her attention to detail, willingness to go the extra mile, and genuine commitment to making sure I was happy with the purchase. Even after closing, Jackie continued to be helpful and supportive, which speaks volumes about the level of service she provides. I would absolutely recommend Jackie to anyone buying or selling a home in the Orlando/Kissimmee area. She truly cares about her clients and delivers an exceptional experience. I wouldn't hesitate to work with her again!”
“Zack from the first time we met in 2024 worked in my best interest and help our family get what we needed and as our family grew we called him again to help us find a house that better fit our needs he and Arnold worked to find exactly what we were looking for they listen and found it . In the first week grateful for them and will let anyone I know to give him a call , If you are looking for a home or rental him and his team are who you need to go with they did a outstanding job”
“Had the pleasure of working with Caleb. Great communicator that works relentlessly to get his deals closed. Caleb has grown up in the area and has a deep knowledge of the local Real Estate Market. I highly recommend working with Caleb.”
“Duc is not only my Realtor but also a great friend. He helped us find an amazing investment property in downtown Orlando at an unbeatable price. He answered all our questions upfront and guided us confidently throughout the entire process. We had such a great experience that we’re already working with him to purchase another property!”
“Rich Noto is fantastic! He’s hardworking, dedicated, and extremely knowledgeable. We’re based in New York, and he has helped us tremendously with getting our new home ready in Orlando, Florida. Having someone we trust looking out for us while we’re out of state has made such a difference. He truly cares about his clients and their best interests. We’re grateful for all his help and highly recommend him!”
“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.”
“Working with August to buy our beach house was such a wonderful experience. From the very beginning, she was incredibly communicative, helpful, and genuinely supportive throughout the entire process. She always kept us updated, answered our questions promptly, and made everything feel so much less stressful. What really stood out was how much she truly cared about helping us find the right home, not just any home. Her guidance, patience, and attention to detail meant so much to us. We’re so grateful to August for helping us find our beach house, and we would wholeheartedly recommend her to anyone looking to buy a home.”
“As first time home buyers Lily and Brian went above and beyond helping us with buying our new tonwhouse! Best service we could expect, they both guided us through everysetp ! Thank you so much Lily and Brian.”
“Exceptional Realtor & Even Better Person Cassie is truly one of a kind. Although we ultimately did not purchase a home in Florida because our family ended up relocating elsewhere, I cannot say enough wonderful things about our experience with her. She spent so much time helping us, showed us several homes, answered countless questions, and was incredibly patient and knowledgeable throughout the entire process. What impressed me even more was that her support didn’t stop with buying a home. Cassie also gave me valuable advice about selling my own home and was always willing to share her knowledge and expertise, even when there was nothing in it for her. Over time, Cassie became much more than our real estate agent—she became a lifelong friend. I was going through an extremely difficult time at work, and she became someone I could talk to and a genuine shoulder to cry on. That speaks volumes about the kind of person she is. She truly cares about the people she works with, not just the transaction. Cassie is an amazing person inside and out. She is professional, knowledgeable, responsive, compassionate, and genuinely dedicated to her clients. If you are looking for a real estate agent in Florida, I would recommend Cassie without hesitation. She is absolutely top-notch, and if I ever needed an agent in her area again, I wouldn’t hire anyone else.”
“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.”
“She’s the best!! Adry went above and beyond helping us every step of the way to find the place we now call home. Thanks so much to you and your team!! Don’t doubt to contact her if you are looking to get your new home. Blessings”
“Working with Alexa was an absolute game-changer! From start to finish, she went above and beyond to make my home-buying journey in Florida as smooth and stress-free as possible. Y Habla Español! What sets Alexa apart is her incredible communication, market knowledge, and negotiation skills. She negotiated seller credits, making my closing costs and out-of-pocket expenses far better than I could have imagined. On top of that, she locked in fantastic overall terms and guided me step-by-step through every detail of the loan process, inspection, and closing disclosures. Whenever I had questions, Alexa was always responsive, patient, and proactive. Her dedication to protecting my interests and ensuring every detail was handled correctly was top-tier. If you are looking for a reliable, hardworking, and sharp real estate agent who truly fights for her clients, I cannot recommend her highly enough!”
“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!”
“Livia is by far the best realtor I have worked with and I have purchased many houses. She goes over and above her realtor duties and makes herself available to respond to your needs. In addition she is very personable and makes you feel at ease when difficult situations present themselves. I highly recommend her!!!!”
“Andrew is by far one of the most individuals to work with. From start to finish he always ensures that he is doing all he can do to make you experience wonderful. From helping us move back to Florida from North Carolina last year to helping us find our forever home. He always checks in even if it’s just to say hi and see how you’re doing. I would recommend Andrew for all your home needs. Working with Andrew you’re not just his client, you become family!”
“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.”
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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