We analyze top real estate agents in Windermere and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for October 2025. *
* 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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“Chandra Mosley is a phenomenal Realtor! She helped sell 3 of my properties in Orlando and helped me to find my " forever home!" Through the process, Chandra was always professional and accessible when needed, which is essential. Her level of attentiveness to details, her expertise and years of experience are key components when buying or selling your home. Chandra is a forerunner in the field of real estate!!!!”
“James Clark and the team are the best I would say and strongly recommend him. His market insights and negotiation skills are excellent. Cosidering the market conditions and how long we are in the market, we got a decent offer if not good, however on top of that buyers were requesting for more fixes based on inspection. James negotiated well and kept them very minimal. We wanted to do RON closing as we are remote sellers. Seems this is new for their title company. He made sure they are able to do the RON closing which is a hassle free closing. Thanks again James for your help”
“Once again Paula came through for us. She was always available for us whenever we needed her. Second home purchase for us with Paula, and once again she was on top of everything.”
“David is a great Broker/Agent. Always a pleasure to work with.”
“Five-Star Realtor Experience! 🌟 Working with eXp Realty, The Fuentes Team [Elsa & Tony], was an absolute dream from start to finish. Their professionalism, deep market knowledge, and genuine care for our needs made the entire home-buying process smooth and stress-free. They were always available to answer questions, offered honest advice, and went above and beyond to ensure we found the perfect home. What truly sets [Realtor's Name] apart is their attention to detail and commitment to client satisfaction. From the first showing to closing day, they were with us every step of the way, advocating for our best interests and making us feel confident in every decision. If you're looking for a realtor who is not only skilled but also kind, trustworthy, and passionate about helping people—look no further. We couldn’t be happier with our experience and highly recommend Central Florida Homes | Serving Kissimmee & Surrounding Areas to anyone in need of a top-tier real estate professional!”
“Kimberly has been wonderful throughout this entire process of selling my home. I can't say enough about how awesome she was in answering questions or anything I needed during this time. I highly recommend Kimberly”
“6:57 1 (24, .. . ★ Local Guide 3 days ago Whether you're selling a house or buying a house, it can be very stressful so having the right person on your side is very important and we are forever grateful for having Cassandra on our side and her closing team. They went above and beyond and always had our best interest first. Cassandra worked even while she was admitted at the hospital. She was amazing and was always attentive to how I was feeling even when she was not feeling well made sure we were always treated fairly And that things got done on time .we were well informed on all details at all times and felt confident that Cassandra was there to help us in any doubts or questions or concerns we had and helped resolve them we highly recommend her”
“Highly processional. Great to work with.”
“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!”
“Thank you so much for all your help with this move. I really appreciate it. You were so attentive and listen to all my needs.”
“It was a very great experience with Debra Meyers representing my property. She was always available to discuss property & offers presented on the property, would gladly look forward to working with her on a future purchase.”
“Evelyn was so wonderful to work with. She truly cares about her clients and is detail oriented throughout every step of the way. She is very knowledgeable and so helpful. Working with her made the difference through a thorough and complicated process. She will advocate for you and be beside you through it all. Would recommend to anyone!”
“Excellent experience”
“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!”
“Patty is a pleasure to work with. Florida was not a market that I had experience with, but Patty's knowledge and expertise put me at ease from our first Zoom meeting. She is very personable, and has a great attention to detail which I really appreciate. Patty would go the extra mile to perform any research necessary to address my questions or concerns. It is no surprise she is a leader in her market. I would definitely look forward to work with Patty again.”
“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”
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”
“Deanna, thank you for staying the course. You had to re-center me a few times since I had family "stuff" happening simultaneously. I needed someone I could trust and I'm thankful that my friend recommended you.”
“Zac Hernandez was brilliant in the entier process and I cannot thank him enough. You are lucky to have him on the Keller Williams team. He guided me through every step of the way and was not only professional, but very kind and patient with me. Thank you, Zac!”
“Christine was awesome to work with. She kept me totally up to date with the process. She was kind and pleasant adding a personal touch. I would totally recommend Christine to any one buying a home.”
Information and statistics on the latest trends in the Windermere real estate market, updated for October 2025. *
The typical home value in Windermere is projected to be $3,411,250 for the month of October. September’s finalized data reported the typical value of a home in the city to be $2,750,000—up 192.86% over the previous 12 months. For comparison, county-level data pegged home values at $435,000 in Orange County for the most recent reporting period. That number is expected to float around $441,380 in October.
Windermere had 8 new listings and 8 listings that went under contract in September, decreasing the area’s total available inventory to 29—down 9.38% from the previous month. Inventory is projected to have further decreased in October.
Of those 29 active listings, 34.48% reduced their price in the month of September. The median listing price for homes in Windermere grew 36.45% from August to September, bringing the current median listing price to $1,712,500. Based on projected data for October, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In September 2025, the median time for a listed property to go pending was 108 days, compared to 126 days in September 2024. In recent months the median number of days from listed to pending appears to be decreasing. That trend is predicted to have carried through to this October.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Windermere offers residents a serene, lakeside lifestyle, abundant outdoor recreation, top-notch schools, and a welcoming, close-knit community that blends small-town charm with easy access to regional amenities.
Windermere seamlessly blends upscale lakefront living with the warmth of a close-knit community, creating an inviting haven for residents and newcomers alike. Surrounded by the sparkling Butler Chain of Lakes, this tranquil town offers breathtaking water views, winding streets shaded by ancient oaks, and a strong sense of hometown pride. Its picturesque downtown district features locally owned cafes and boutiques, while neighborhood parks such as Central Park provide serene spaces for community gatherings and family fun.
Education is a point of pride, with highly-rated schools like Windermere Elementary School and Windermere High School consistently excelling in academics and extracurriculars. Families appreciate the focus on enriched learning environments and abundant after-school opportunities, fostering growth both in and out of the classroom.
With Orlando just minutes away, Windermere enjoys access to world-class arts, dining, and entertainment. At the same time, the town retains its peaceful charm, making it a favorite among those seeking respite from city bustle. Outdoor enthusiasts delight in ample boating and fishing opportunities, while golf lovers can tee off at the championship Isleworth Golf & Country Club.
Windermere delivers the best of both worlds: secluded, scenic living with coveted amenities and connectivity. Whether searching for your dream home or preparing to list, Agent Pronto can help you connect with trusted local agents to navigate your next step in Windermere’s exceptional community.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Windermere to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Windermere. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Tips and market insights to make your Windermere real estate journey a success.
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.
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