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Windermere, FL real estate

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 March 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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Windermere real estate Market Report.

Information and statistics on the latest trends in the Windermere real estate market, updated for March 2026. *

Windermere had 11 new listings and 8 listings that went under contract in February, increasing the area’s total available inventory to 30—up 11.11% from the previous month. Inventory is projected to have further increased in March.

Of those 30 active listings, 16.67% reduced their price in the month of February. The median listing price for homes in Windermere grew 50.38% from January to February, bringing the current median listing price to $3,000,000. Based on projected data for March, listing prices may continue to grow.

Windermere, FL real estate
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Seller’s Market
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Buyer’s 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.

* Data provided by Redfin, a national real estate brokerage.

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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See why so many people rely on Agent Pronto to make their real estate journey a success.

“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!”

Kevin Schmitz · Altamonte Springs, FL

Photo of Evelyn Hartnett
Southern Realty Enterprises Inc.
“Mình rất hài lòng khi làm việc với Thắng. Em rất nhiệt tình, trung thực và luôn phản hồi nhanh mỗi khi tôi cần hỗ trợ. Highly recommended!!!”

Jason · Orlando, FL

Photo of Duc Thang Nguyen
Alliance Real Estate Group
“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!!”

Paul · Spring Hill, FL

Photo of Debra & Jacob Myers
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.”

Matt · Tampa, FL

Photo of Cory McMillan
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.”

Nate Jasmin · Saint Cloud, FL

Photo of David Dorman
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.”

Randi Bergman · St. Cloud, FL

Photo of Kimberley Beaudry
Orlando Regional Realty, Inc.
“Great expreience start to finish. I threw some challenging cureballs and she dealt with them professionally and quickly. I would definatlely use her again for any selling or buyiong I had to do in the area. 5 star experience.”

Greg Langham · Seffner, FL

Photo of Paula McConahay
Century 21 Affiliated
“My name is Kenneth Martin my family and I had a really bad experience with a different real estate agent while trying to find a house and we stumbled upon Cassandra through days of research and reading every review on every realtor on the Internet and it was a blessing we closed on a house in two weeks and Cassandra was one of the best thing that happened to my family.”

Kenneth Martin · Ocala, FL

Photo of Cassandra Kelly
Century 21 Wolfs Crossing Realty
“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!”

Bridgette · Buena Ventura Lakes, FL

Photo of The Fuentes Team
eXp Realty
“Thank you for selling my house! It was a pleasure having you as my realtor!”

Teresa · Deltona, FL

Photo of C21 Alton Clark
CENTURY 21 Alton Clark
“Ms. Crystal is greatly knowledgeable in the industry of real estate. She is great at her craft, with resources that benefits her clients, at her fingertips. She strives to provide an experience that reflects integrity & realistic outcomes. Ms. Crystal is an integral asset in your home buying journey.”

Alicia Hatchett · Ocoee, FL

Photo of Crystal Washington Booth
Century 21 BE 3
“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 ...”

Sylvia Pagan · Orlando, FL

Photo of Chandra  Mosley
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!”

Zach S · Orlando, FL

Photo of Madeleine Haughwout
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!”

The Shaw · St Cloud, FL

Photo of Erika Garcia
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.”

Christopher · Jupiter, FL

Photo of The Greenberg Group
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.”

Jimmy S Luciano · Minneola, FL

Photo of Rich Noto
Dalton Wade Real Estate Group
“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!”

Jose Triana · Pembroke Pines, FL

Photo of Claudia Garzon Pernia
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”

lily · Spring Hill, FL

Photo of Charles Thomasson
Century 21 Professional Group
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”

Laurie W. · Dade City, FL

Photo of Sam Sheen
Sheen Real Estate Professionals

Frequently Asked Questions

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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