Skip the search. We analyze thousands of real estate agents in Windermere and nationwide to find you proven local pros, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for January 2026. *
202 recent sales
$135K-$2.13M price range
$500K 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.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“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.”
“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.”
“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.”
“David was an absolute standout realtor and made buying our recent home an incredibly positive experience. He responded lightning-fast to every question or request—often within minutes—which gave us so much confidence throughout the process. His deep knowledge of the market and local area was clear from day one; he provided insightful, practical information that truly helped us make the smartest decisions for our family. What stood out most was how present and supportive he was every single step of the way—from the initial search and showings, through negotiations and inspections, all the way to closing. He explained everything clearly and patiently (no jargon overload!), anticipated potential issues before they became problems, and always put our best interests first. Thanks to David, what could have been a stressful process felt smooth, exciting, and even enjoyable. I can't recommend David highly enough!”
“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!”
“Thank you for selling my house! It was a pleasure having you as my realtor!”
“Evelyn Hartnett uses her years of experience and knnowllege as a realtor in working with the client in establishing a sellinng price for the property. She was always professional. She gives a realistic picture in the selling of the property by looking at comprable pfoperty and unique feature of the property. She provided good insight into the timing of a potential sale and she was quite accurate. My huusband and I felt quite confident that our condo would sell. Her ethics are beyond reproach. She handled all the paperwork and did the sale negotiations keeping us aware of the issues. We trusted her implicitly. She kept us informed throughout the process. We have utmost respect for her both as a person and realtor. I would highly recommend her to potential sellers.”
“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.”
“Debra is a true Superstar! Not only did she help us find our forever home for retirement, she drove over an hour each way to get to the area we were looking at, and she did that several times over the course of two weeks for inspections and closing. Debra knows this business and is a true professional in every sense. Thank you so much for your hard work, and thank you for being our friend. (You too Dave 😁) Joel & Marlene”
“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 ...”
“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!”
“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.”
“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”
“Daniel is an amazing person to work with. The level of communication and knowledge that he brings to the table everyday is top notch. I would recommend him to anyone looking to purchase a new home or sell their existing home. People say they care about their clients, Daniel shows this in his actions and commitment. It was a pleasure having the opportunity to work with him!”
“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!”
Information and statistics on the latest trends in the Windermere real estate market, updated for January 2026. *
The typical home value in Windermere is projected to be $383,500 for the month of January. December’s finalized data reported the typical value of a home in the city to be $544,000—down 6.21% 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 $432,500 in January.
Windermere had 5 new listings and 8 listings that went under contract in December, decreasing the area’s total available inventory to 30—down 14.29% from the previous month. Inventory is projected to have further decreased in January.
Of those 30 active listings, 20.0% reduced their price in the month of December. The median listing price for homes in Windermere grew 26.98% from November to December, bringing the current median listing price to $1,200,000. Based on projected data for January, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In December 2025, the median time for a listed property to go pending was 6 days, compared to -6 days in December 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this January.
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.
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.
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.
