The best way to find top real estate agents in Windermere, FL

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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 June 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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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, FL real estate

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.

“David Dorman has sold my husband all of his previous homes and sold them as he moved and upgraded as well. Even so I wanted David to map out his strategy for selling my rental property home. He valued it correctly, promoted it quickly, got significant views and offers and held on until he negotiated the right deal. He knew how to not spend time off market with buyers who wouldn't complete the deal and steered me in the right directions. The home sold much faster than expected for what I was hoping to get. David gives each client the same world class service whether you Home range is $200K or Millions. Thank you David and Century 21 for making this process stress free.”

Moe Merkel · Orlando, FL

Photo of David Dorman
Century 21 Carioti
“We had a great experience working with Cassandra Kelly. She was professional, responsive, and did an outstanding job marketing our home. Thanks to her hard work and expertise, our home sold quickly. I highly recommend Cassandra to anyone looking to buy or sell a home!”

Christian · St Cloud, FL

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

Shauna Kelley · Weeki Wachee, FL

Photo of Rich Noto
Dalton Wade Real Estate Group
“Paula was absolutely wonderful to work with. She was always available to answer questions and helped me through the whole process. I highly recommend her!”

Claudia Deliteris · Apollo Beach, FL

Photo of Paula McConahay
Century 21 Affiliated
“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”

Alex Paganucci · Vero Beach, FL

Photo of The Greenberg Group
Coastal Real Estate Professionals LLC
“Used before and will use again!”

Amy Van De Pol · Altamonte Springs, FL

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

Hy · Orlando, FL

Photo of Duc Thang Nguyen
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!”

Kevin Schmitz · Altamonte Springs, FL

Photo of Evelyn Hartnett
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!!”

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
“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.
“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

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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
“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.
“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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