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Century 21 BE 3
- Agent Pronto
- Florida
- Windermere
The best way to find top real estate agents in Windermere, FL
Skip the search. We analyze thousands of real estate agents in Windermere and nationwide to find you proven local pros, for free.
Compare top Windermere real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for April 2026. *
The Vastardis Team
Coldwell Banker
218 recent sales
$135K-$2.13M price range
$500K median price
Andy Neal
Maxim Realty Orlando
174 recent sales
$100K-$1.8M price range
$393K median price
* 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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Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
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Windermere real estate Market Report.
Information and statistics on the latest trends in the Windermere real estate market, updated for April 2026. *
Windermere’s housing costs sit far above the broader Orange County market, with a typical home value of $1,325,000 compared to $425,000 countywide. While county values have slipped by about 3.41% year over year, Windermere’s pricing is holding at a much higher tier. This gap highlights how homes here occupy a distinct luxury segment within the region.
In February 2026, sellers listed homes at a median price of $3,000,000, while the typical home value was much lower, suggesting some owners are testing higher price points. Homes spent a median of 116 days on the market, and with 30 active listings and 7.5 months of supply, buyers have room to compare options even in what is labeled a seller’s market.
Activity is steady, with 11 new listings and 8 pending sales in the latest month, and about 16.67% of listings seeing a price drop. Roughly 25% of homes sold above list price and the average sale-to-list ratio of 0.98 indicates many deals are closing slightly under asking. Looking ahead to March 2026, projections point to a higher typical home value of $1,525,000, a projected median list price of $3,502,500, and inventory nudging up to 31 homes. With these evolving conditions, both buyers and sellers in Windermere can benefit from Agent Pronto’s help in finding a real estate agent who understands this unique market.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Windermere has to offer.
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.
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“Paula was absolutely amazing to work with through the home buying process. Her attention to detail was incredible. She was always available to help answer any questions that we had and was continually looking to help us get the best possible deal. I would recommend her time and time again.”
Century 21 Affiliated
“What can I say about Cassandra, she was totally amazing during the entire home buying process. As first time home buyers, we were scared of the process and did not know what to expect but Cassandra made everything clear and easy to understand. She guided us expertly through some difficult situations and even fought for us and our interests. If I could give her ten stars or more I totally would. She is a total boss in real estate and I can't think of anyone better to help families find their forever home!”
Century 21 Wolfs Crossing Realty
“Anh Thắng là realtor người Việt tốt nhất ở Orlando! Anh làm việc chuyên nghiệp, tận tâm và rất hiểu nhu cầu của khách hàng Việt. Mình rất vui và tin tưởng anh khi làm việc cùng. Anh Thắng giải thích tận tình giúp mình hiểu hơn khi mua nhà lần đầu. Ai có nhu cầu cứ liên hệ anh Thắng nha!!!”
Alliance Real Estate Group
“Evelyn did such an incredible job leading the way in getting our home sold. We listed in a neighborhood where there were 10 listings, some of which had been sitting for several months. Everyone told us to be prepared to wait a long time, to be ready to drop our list price several times before we would get a bite. However, thanks to Evelyns understanding of the market, her connections with those looking for a house like ours and her dedication to make a sale we had an offer after only 2 WEEKS of listing. Our offer was everything we could have asked for, and we know there was no way this would have happened without Evelyn! I Highly recommend her to everyone!”
Southern Realty Enterprises Inc.
“This is the 2nd time I've utilized Debra's services. She is very good at her job. She is knowledgeable, efficient, always available and cares about the customer. I highly recommend her to anyone looking to buy or sell. Thanks, Debra!!”
CanZell Realty
“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.”
Exp Realty
“David is truly a professional and dedicated to his trade. Extremely strong communication and answered all concerns in a timely fashion. It is clear David has a great deal of experience in real estate and it shows! Would highly recommend David and 100% will utilize him again in the future if it is needed.”
Century 21 Carioti
“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.”
Orlando Regional Realty, Inc.
“A Heartfelt Recommendation for Tony Fuentes, Realtor in Kissimmee, Florida! I recently had the pleasure of working with Tony Fuentes, and I can't express enough how remarkable my experience was! From the moment I reached out, Tony was quick to respond, returning my call in less than 30 minutes. His knowledge of the real estate market is awe-inspiring, and his enthusiasm for helping me get everything in order made the process feel effortless. What stood out most was that Tony never pressured me to sign anything. Instead, he provided valuable referrals to help get my villa ready for sale. In less than thirty days, my house was beautifully painted, thoroughly cleaned, and all those little fixes were taken care of. I was amazed at how smoothly everything went, especially considering I didn’t even live in the state! Thanks to Tony’s expertise, I was able to sign my paperwork remotely with a notary, making the entire experience incredibly convenient. He truly goes above and beyond!”
eXp Realty
“Thank you for selling my house! It was a pleasure having you as my realtor!”
CENTURY 21 Alton Clark
“I had never worked with a realtor. And I continuously kept getting advice not to get a Realtor... because everyone put a money value on Realtors job. I am so glad I did Not listen to all those people!!! Getting a Realtor like Chasandra was the best decision I made when purchasing a home... I didn't feel any presure to choose the first home I saw... she is honest. Helpful, professional and above all she is looking out for your best interest in purchasing a home...she walks you threw the entire process....I was a pleasure having chasandra as my realtor and I will never forget her impact on my life ...”
Oliver Mosley Realty
“We absolutely loved working with Madeleine! From day one, she was so friendly and easy to talk to. She was always available to answer our questions or set up a showing, no matter how many houses we wanted to see. Her knowledge and guidance made the whole process so much easier and less stressful. We always felt like she genuinely cared about helping us find the right home. Couldn’t have asked for a better realtor — highly recommend!”
Coldwell Banker Realty
“Erika was the key to getting this house sold. Without her help and experience the wonderful outome would not have been achieved. Erika was knowledgeable, professional, friendly and went above and beyond to help with this property sale. You would benefit from Erika's help on any property purchase or sale!”
CENTURY 21 Professional Group, Inc.
“Zach has been nothing but 100% professional. He answers all correspondence quickly and effectively. I must also say that his ability to get a deal finished is unparalleled. He truly has a gift with working in real estate.”
Coastal Real Estate Professionals LLC
“I highly recommend Rich Noto for new home construction. He was a fantastic advocate throughout my build, especially since I was relocating from Pennsylvania to Florida. Living states away, he sent detailed videos of construction progress and found defects during various inspections. His communication and availability far exceeded my expectations. Rich has a keen eye for potential issues and a deep understanding of building codes that many other agents, and even some inspectors, might miss. He truly knows the critical phases of construction, from the foundation on, and when to schedule inspections. He understands the tricks builders use to hide problems and is a fierce advocate for his clients. I have no doubt he saved me from future headaches. He is an invaluable resource who ensured I ended up with a high-quality home.”
Dalton Wade Real Estate Group
“Excellent experience”
Eluxe Realty
“I had the pleasure of working with Claudia Garzón as my realtor, and I couldn't be more satisfied with her work. From the very beginning, she showed a high level of professionalism, responsibility, and an inspiring motivation that made the entire process much smoother and more manageable. Claudia has an exceptional ability to solve any issues that may arise, always finding quick and effective solutions. Her experience and dedication made a real difference at every stage of the transaction. I highly recommend her with complete confidence. Thank you, Claudia, for your outstanding work!”
Worth Clark Realty
“Charles listened to all of our wants, showed us an amazing house that we instantly loved and was more helpful then we could have imagined”
Century 21 Professional Group
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”
Sheen Real Estate Professionals
Frequently Asked Questions
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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.
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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.
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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.
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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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