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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 December 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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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.

“My wife and I are so happy to have chosen Cassandra as our realtor! This was our first home buying experience and we did not know where to begin. Right from the beginning, she explained how the process works and walked us through many homes based of our preferences. It did not matter to her how many homes we went through, she did not push us to make a decision and wanted us to continue until we found a home (in our case a model home in a new community) that we felt comfortable and right. When we finally selected our home, she was there every step of the way throughout the process (from the first contract being signed to design studio to pre dry wall and pre closing inspections to closing and everything else in between). She is just amazing! We felt as if we were her extended family with how much she cared for us and her communication was spot on, always got back to us when we had a question (in a reasonable time). She is truly an amazing woman and will fight for your dream home!”

Anthony Freire · Kissimmee, FL

Photo of Cassandra Kelly
Century 21 Wolfs Crossing Realty
“Evelyn is a highly skilled and knowledgeable realtor in Orlando. She handled getting the property cleaned up, painted, and pressure washed and got us our asking price in a down market with comps below what we sold for. Wouldn't consider anyone else in Orlando after working with her.”

Dan G · Altamonte Springs, FL

Photo of Evelyn Hartnett
Southern Realty Enterprises Inc.
“David and Vicki were amazing to work with. They answered all our questions and requests promptly. They were honest and never pushy. David was amazingly quick to return calls and texts. Top notch customer service. We thoroughly enjoyed working with them and when we decide to upgrade we would love to work with them again.”

Courtney Tyska · Orlando, FL

Photo of David Dorman
Century 21 Carioti
“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
“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”

Joel · Ocala, FL

Photo of Debra & Jacob Myers
CanZell Realty
“Tony is the best !..answered my questions & was very patient when i was confused about the process”

C. McKinney · Haines City, FL

Photo of Tony & Elsa Fuentes
eXp Realty
“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
“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”

Raj · Oviedo, FL

Photo of C21 Alton Clark
CENTURY 21 Alton Clark
“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.”

Robert Dietrich · Sun City Center, FL

Photo of Paula McConahay
Century 21 Affiliated
“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”

Karen Weingartner · Davenport, FL

Photo of Kimberley Beaudry
Orlando Regional Realty, Inc.
“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 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
“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.”

Martha DeBustamante · Wanaque, NJ

Photo of Patricia Hernandez
Keller Williams Realty At The Lakes
“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
“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!”

Michael Welsh · Birmingham, MI

Photo of Daniel Yasells
LPT Realty
“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.”

C. Salter-Luster · Chesapeake, VA

Photo of DeAnna Balcerak
Century 21 Professional Group Inc
“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!”

Jonathan Panciotti · Orlando, FL

Photo of Zac Hernandez
Keller Williams Advantage 2 Realty

Windermere real estate Market Report.

Information and statistics on the latest trends in the Windermere real estate market, updated for December 2025. *

The typical home value in Windermere is projected to be $652,500 for the month of December. November’s finalized data reported the typical value of a home in the city to be $865,000—down 8.71% over the previous 12 months. For comparison, county-level data pegged home values at $440,000 in Orange County for the most recent reporting period. That number is expected to float around $439,510 in December.

Windermere had 7 new listings and 2 listings that went under contract in November, increasing the area’s total available inventory to 35—up 12.9% from the previous month. Inventory is projected to have further increased in December.

Of those 35 active listings, 37.14% reduced their price in the month of November. The median listing price for homes in Windermere fell 66.4% from October to November, bringing the current median listing price to $945,000. Based on projected data for December, listing prices may continue to fall.

The number of days that homes have been on the market prior to going under contract fell year-over-year. In November 2025, the median time for a listed property to go pending was 86 days, compared to 153 days in November 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 December.

Windermere, FL real estate
100
Buyer’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

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 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.

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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