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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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Windermere real estate Market Report.

Information and statistics on the latest trends in the Windermere real estate market. *

Latest Rolling 3-Month Snapshot

Mar 1, 2026 - May 31, 2026

Median sale price
$1M
-9.5% from Q1 '26
Median list price
$1.5M
-34% from Q1 '26
Active listings
51
No change from Q1 '26
Homes sold
15
+15% from Q1 '26
New pendings
23
+44% from Q1 '26
New listings
26
-3.7% from Q1 '26

Quarterly Pricing Trends for Windermere

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Windermere Q2 '21 Q2 '22 Q2 '23 Q2 '24 Q2 '25 Q1 '26 Median sale price in Apr 2021 - Jun 2021: $873K Median sale price in Jul 2021 - Sep 2021: $930K Median sale price in Oct 2021 - Dec 2021: $969K Median sale price in Jan 2022 - Mar 2022: $847K Median sale price in Apr 2022 - Jun 2022: $1M Median sale price in Jul 2022 - Sep 2022: $875K Median sale price in Oct 2022 - Dec 2022: $1.2M Median sale price in Jan 2023 - Mar 2023: $1.4M Median sale price in Apr 2023 - Jun 2023: $1.2M Median sale price in Jul 2023 - Sep 2023: $1M Median sale price in Oct 2023 - Dec 2023: $1.6M Median sale price in Jan 2024 - Mar 2024: $765K Median sale price in Apr 2024 - Jun 2024: $1.9M Median sale price in Jul 2024 - Sep 2024: $1M Median sale price in Oct 2024 - Dec 2024: $975K Median sale price in Jan 2025 - Mar 2025: $1.3M Median sale price in Apr 2025 - Jun 2025: $1.1M Median sale price in Jul 2025 - Sep 2025: $1.6M Median sale price in Oct 2025 - Dec 2025: $975K Median sale price in Jan 2026 - Mar 2026: $1.2M Median list price in Apr 2021 - Jun 2021: $724K Median list price in Jul 2021 - Sep 2021: $1.5M Median list price in Oct 2021 - Dec 2021: $870K Median list price in Jan 2022 - Mar 2022: $1.1M Median list price in Apr 2022 - Jun 2022: $929K Median list price in Jul 2022 - Sep 2022: $1.2M Median list price in Oct 2022 - Dec 2022: $1.5M Median list price in Jan 2023 - Mar 2023: $1.1M Median list price in Apr 2023 - Jun 2023: $1.3M Median list price in Jul 2023 - Sep 2023: $933K Median list price in Oct 2023 - Dec 2023: $1.2M Median list price in Jan 2024 - Mar 2024: $1.5M Median list price in Apr 2024 - Jun 2024: $1.4M Median list price in Jul 2024 - Sep 2024: $1.4M Median list price in Oct 2024 - Dec 2024: $1.6M Median list price in Jan 2025 - Mar 2025: $1.4M Median list price in Apr 2025 - Jun 2025: $1.4M Median list price in Jul 2025 - Sep 2025: $1.4M Median list price in Oct 2025 - Dec 2025: $1.4M Median list price in Jan 2026 - Mar 2026: $2.3M Apr 2021 - Jun 2021 Median sale price $873K Median list price $724K Jul 2021 - Sep 2021 Median sale price $930K Median list price $1.5M Oct 2021 - Dec 2021 Median sale price $969K Median list price $870K Jan 2022 - Mar 2022 Median sale price $847K Median list price $1.1M Apr 2022 - Jun 2022 Median sale price $1M Median list price $929K Jul 2022 - Sep 2022 Median sale price $875K Median list price $1.2M Oct 2022 - Dec 2022 Median sale price $1.2M Median list price $1.5M Jan 2023 - Mar 2023 Median sale price $1.4M Median list price $1.1M Apr 2023 - Jun 2023 Median sale price $1.2M Median list price $1.3M Jul 2023 - Sep 2023 Median sale price $1M Median list price $933K Oct 2023 - Dec 2023 Median sale price $1.6M Median list price $1.2M Jan 2024 - Mar 2024 Median sale price $765K Median list price $1.5M Apr 2024 - Jun 2024 Median sale price $1.9M Median list price $1.4M Jul 2024 - Sep 2024 Median sale price $1M Median list price $1.4M Oct 2024 - Dec 2024 Median sale price $975K Median list price $1.6M Jan 2025 - Mar 2025 Median sale price $1.3M Median list price $1.4M Apr 2025 - Jun 2025 Median sale price $1.1M Median list price $1.4M Jul 2025 - Sep 2025 Median sale price $1.6M Median list price $1.4M Oct 2025 - Dec 2025 Median sale price $975K Median list price $1.4M Jan 2026 - Mar 2026 Median sale price $1.2M Median list price $2.3M
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
22
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).

Windermere’s rolling three-month numbers through May 2026 point to a cooler market than a year ago. Typical home values are down about 9% year over year, and the median list price has slipped nearly 8% over the same period. Sales volume has also eased, with homes sold down roughly 30% compared with last year.

Looking at the latest rolling quarter, pricing and activity show a mixed picture. The typical home value now sits around $1.05 million while the median list price is roughly $1.51 million, and homes are spending a median of 63 days on the market. Supply has shifted notably, with months of supply rising to 5.5, more than doubling from a year ago and signaling more options for buyers.

Conditions have softened from the intense pace of recent years, as no recent sales closed above list price and the average sale-to-list ratio has edged down to about 94%. At the same time, buyers are not rushing quite as quickly as before, even though more than half of listings still go off market within two weeks. This mix of moderating prices, longer marketing times, and increased inventory creates a different set of trade-offs for both sides of the table. Whether you are a buyer trying to capitalize on these shifts or a seller working to position your home correctly, Agent Pronto can connect you with a Windermere agent who understands the latest trends.



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.

Find your Windermere real estate agent today →


Trusted by over 500,000 buyers and sellers.

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

“Working with Tony was an absolute pleasure. As a first time seller, I was completely overwhelmed, stressed and anxious. Tony's extensive knowledge of my neighborhood really put my mind at ease. He was always calm and patient with my ridiculous questions. His Dedication, Professionalism and quick response to my phone calls, texts and emails were amazing. Getting from listing day to closing day in exactly 45 days proves his market expertise and pricing it perfect to the market. It was an incredible, smooth and efficient transaction with no major hiccups. I will highly recommend Tony if you want an agent who delivers fast results. Muchos Gracias Tony !!!”

Grace Cruz · Kissimmee, FL

Photo of The Fuentes Team
eXp Realty
“There were issues going into buying our first home but Chandra made the process smooth, fast and was with us every step of the way. She got us the best possible deal & made sure on closing day we were taken care of. Absolutely love her!!”

Morgan Davis · Deland, FL

Photo of Chandra  Mosley
Oliver Mosley Realty
“Danny is great real estate agent you can trust and rely on”

Shiv Chudasama · Eustis, FL

Photo of Danny Dhannu
Elite Investors Reatly Luxury Real Estate
“Shelby was professional and available for questions. Enjoyed working with her.”

F Hofland · Apopka, FL

Photo of Shelby Martin
RE/MAX Town & Country
“Mình được người quen giới thiệu Thắng và rất vui khi được làm việc cùng Thắng. Thắng rất tận tâm, vui vẻ, luôn lắng nghe nhu cầu của khách hàng và hỗ trợ rất nhiệt tình trong suốt quá trình tìm nhà. Không tạo áp lực, luôn tư vấn rõ ràng để mình có thể đưa ra quyết định phù hợp. Nếu bạn đang tìm realtor nói tiếng Việt được tại Orlando, mình rất recommend Thắng”

Kim · Altamonte Springs, FL

Photo of Duc Thang Nguyen
Alliance Real Estate Group
“She listened and understood what was needed/wanted. She was aggressive with offers and getting compensations. Would use her again.”

Aishah Bartolome · Kissimmee, FL

Photo of Cassandra Kelly
Century 21 Wolfs Crossing Realty
“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
“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
“Al Spry can assist you whether you're planning to purchase or sell a property. He has a deep knowledge of the area and offers great ideas and recommendations. He's a great listener which proved valuable while narrowing down the many options and decisions faced. I highly recommend Al Spry for all your real estate transactions.”

Roy Harmon · Orlando, FL

Photo of Al Spry
Beacon Real Estate & Associates
“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
“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.
“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 have worked with Adry Narvaez before as in my prior review, I could not imagine a more committed, resposible, knowledgeable and personable person to work with. She is the best in her field. She has brought me to my dream hopm and for that reason I regret I might not need to work with her again, however I sm lucky to have gained and empathic and true friend.”

Jose Luis Arguello · Poinciana, FL

Photo of Adry Narvaez
eXp Realty Top Listing Group
“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.

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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