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Winter Park, FL real estate

Compare top Winter Park real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 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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Winter Park real estate Market Report.

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

Latest Rolling 3-Month Snapshot

Jul 1, 2026 - Sep 30, 2026

Median sale price
$840K
+5% from Q2 '26
Median list price
$895K
-10% from Q2 '26
Active listings
376
+6.2% from Q2 '26
Homes sold
143
-2.1% from Q2 '26
New pendings
149
-12% from Q2 '26
New listings
202
+4.1% from Q2 '26

Quarterly Pricing Trends for Winter Park

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

Quarterly Pricing Trends for Winter Park Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $555K Median sale price in Jan 2022 - Mar 2022: $505K Median sale price in Apr 2022 - Jun 2022: $683K Median sale price in Jul 2022 - Sep 2022: $527K Median sale price in Oct 2022 - Dec 2022: $565K Median sale price in Jan 2023 - Mar 2023: $726K Median sale price in Apr 2023 - Jun 2023: $715K Median sale price in Jul 2023 - Sep 2023: $780K Median sale price in Oct 2023 - Dec 2023: $877K Median sale price in Jan 2024 - Mar 2024: $873K Median sale price in Apr 2024 - Jun 2024: $850K Median sale price in Jul 2024 - Sep 2024: $695K Median sale price in Oct 2024 - Dec 2024: $805K Median sale price in Jan 2025 - Mar 2025: $870K Median sale price in Apr 2025 - Jun 2025: $725K Median sale price in Jul 2025 - Sep 2025: $794K Median sale price in Oct 2025 - Dec 2025: $770K Median sale price in Jan 2026 - Mar 2026: $717K Median sale price in Apr 2026 - Jun 2026: $800K Median sale price in Jul 2026 - Sep 2026: $840K Median list price in Oct 2021 - Dec 2021: $500K Median list price in Jan 2022 - Mar 2022: $622K Median list price in Apr 2022 - Jun 2022: $680K Median list price in Jul 2022 - Sep 2022: $627K Median list price in Oct 2022 - Dec 2022: $655K Median list price in Jan 2023 - Mar 2023: $730K Median list price in Apr 2023 - Jun 2023: $778K Median list price in Jul 2023 - Sep 2023: $782K Median list price in Oct 2023 - Dec 2023: $850K Median list price in Jan 2024 - Mar 2024: $837K Median list price in Apr 2024 - Jun 2024: $863K Median list price in Jul 2024 - Sep 2024: $799K Median list price in Oct 2024 - Dec 2024: $725K Median list price in Jan 2025 - Mar 2025: $735K Median list price in Apr 2025 - Jun 2025: $825K Median list price in Jul 2025 - Sep 2025: $872K Median list price in Oct 2025 - Dec 2025: $800K Median list price in Jan 2026 - Mar 2026: $985K Median list price in Apr 2026 - Jun 2026: $995K Median list price in Jul 2026 - Sep 2026: $895K Oct 2021 - Dec 2021 Median sale price $555K Median list price $500K Jan 2022 - Mar 2022 Median sale price $505K Median list price $622K Apr 2022 - Jun 2022 Median sale price $683K Median list price $680K Jul 2022 - Sep 2022 Median sale price $527K Median list price $627K Oct 2022 - Dec 2022 Median sale price $565K Median list price $655K Jan 2023 - Mar 2023 Median sale price $726K Median list price $730K Apr 2023 - Jun 2023 Median sale price $715K Median list price $778K Jul 2023 - Sep 2023 Median sale price $780K Median list price $782K Oct 2023 - Dec 2023 Median sale price $877K Median list price $850K Jan 2024 - Mar 2024 Median sale price $873K Median list price $837K Apr 2024 - Jun 2024 Median sale price $850K Median list price $863K Jul 2024 - Sep 2024 Median sale price $695K Median list price $799K Oct 2024 - Dec 2024 Median sale price $805K Median list price $725K Jan 2025 - Mar 2025 Median sale price $870K Median list price $735K Apr 2025 - Jun 2025 Median sale price $725K Median list price $825K Jul 2025 - Sep 2025 Median sale price $794K Median list price $872K Oct 2025 - Dec 2025 Median sale price $770K Median list price $800K Jan 2026 - Mar 2026 Median sale price $717K Median list price $985K Apr 2026 - Jun 2026 Median sale price $800K Median list price $995K Jul 2026 - Sep 2026 Median sale price $840K Median list price $895K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
25
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 (Jul 2026 - Sep 2026).

Inventory in Winter Park has been building in this rolling three-month view, with active listings up about 9 percent year over year and new listings jumping more than 27 percent. Months of supply has risen sharply to just over five months, more than doubling from a year ago, while homes sold and pending sales are both down slightly compared with last year, signaling slower contract flow.

Pricing has stayed relatively firm despite the looser conditions, with the typical home value up nearly 6 percent year over year. List prices are only modestly higher than a year ago, and the average sale-to-list ratio has edged down while the share of homes selling above asking is now under 9 percent, indicating buyers have more room to negotiate.

Time on market has stretched, with the median days on market increasing to 56 days, about 15 percent longer than a year ago and roughly double just a few months earlier. With more options for buyers and more patience required for sellers, Agent Pronto can connect both buyers and sellers with an experienced local agent who understands these shifting dynamics and can guide them through each step of the process.



Learn more about what Winter Park has to offer.

Winter Park offers residents a charming, pedestrian-friendly community with excellent schools, vibrant arts and culture, lush parks, and a welcoming mix of local shops and restaurants.

Winter Park offers tree lined streets, lakeside recreation, and quick access to downtown Orlando, making it appealing for both long time residents and newcomers. Daily life centers around walkable destinations like Central Park and Park Avenue, where you can move easily between cafés, boutiques, and cultural venues without relying on the car for every errand.

Commuters value the Winter Park Station with SunRail connections toward Orlando and beyond, while I‑4 and major arterials keep regional trips practical. Families look closely at local schools such as Winter Park High School, plus nearby parks like Mead Botanical Garden for everyday outdoor time. Lakes Osceola, Virginia, and Maitland support boating and paddleboarding, and you are minutes from shopping and dining in neighboring Orlando and Maitland.

Cultural amenities add depth, from the Charles Hosmer Morse Museum of American Art to events hosted by Rollins College. Neighborhoods vary from established streets near College Quarter to quieter residential pockets by Winter Park Pines and Orwin Manor, each with its own character, price points, and traffic patterns.

Choosing the right Winter Park agent means having someone who understands school zones, lakefront regulations, condo associations, and shifting demand, which can greatly reduce stress whether you are buying or selling. Agent Pronto connects you with a local professional who can guide each step with clear, informed advice for both buyers and sellers.

Find your Winter Park 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.

“Zack from the first time we met in 2024 worked in my best interest and help our family get what we needed and as our family grew we called him again to help us find a house that better fit our needs he and Arnold worked to find exactly what we were looking for they listen and found it . In the first week grateful for them and will let anyone I know to give him a call , If you are looking for a home or rental him and his team are who you need to go with they did a outstanding job”

Joseph Cuba · Port Saint Lucie, FL

Photo of The Greenberg Group
Coastal Real Estate Professionals LLC
“Duc is not only my Realtor but also a great friend. He helped us find an amazing investment property in downtown Orlando at an unbeatable price. He answered all our questions upfront and guided us confidently throughout the entire process. We had such a great experience that we’re already working with him to purchase another property!”

Isabele · Orlando, FL

Photo of Duc Thang Nguyen
Alliance Real Estate Group
“Rich Noto is fantastic! He’s hardworking, dedicated, and extremely knowledgeable. We’re based in New York, and he has helped us tremendously with getting our new home ready in Orlando, Florida. Having someone we trust looking out for us while we’re out of state has made such a difference. He truly cares about his clients and their best interests. We’re grateful for all his help and highly recommend him!”

David Zhou · Winter Garden, FL

Photo of Rich Noto
Dalton Wade Real Estate Group
“Evelyn was the best. She was attentive to our needs and got to know us better before speaking with potential buyers. She was thorough in everything that we asked her to do, including working with vendors on repair projects after the inspection was done. We liked her recommendations on the appearance of our condo before it went on the market. We would definitely recommend her to others that are selling a condo in our neighborhood.”

Lynda Jobman · Altamonte Springs, FL

Photo of Evelyn Hartnett
Southern Realty Enterprises Inc.
“Deanna is very knowledgeable, patient, understanding, and trusthworthy. I believe that she is the best realtor out there, and when it comes to my realestate purchase/sell, she is the realtor.”

Faustin Norzelus · Ocoee, FL

Photo of DeAnna Balcerak
Century 21 Professional Group Inc
“​I cannot say enough wonderful things about Deb. She seamlessly handled both the sale of my home and the purchase of my new one. Her dedication is unmatched—she answered every late-night text and early-morning call without hesitation. She truly goes above and beyond for her clients and feels like family by the end of the process. Thank you, Deb!”

Nancy Harris · Spring Hill, FL

Photo of Debra & Jacob Myers
CanZell Realty
“I was looking at houses online - kind of a hobby of mine - until I found a house I loved & hoped to afford. I hadn't owned a home in nearly 13 years. Tom Noelke popped up & introduced himself - has his own brokerage AND was able to show me that house the very next morning. He was SO knowledgeable & professional, and educated me on down payments, DeSantis' $10,000 First Time Homebuyer program, even discussed the whys & when I'd like to buy. He wrote a contract that night at my request! That seller wanted a cash deal so declined my contract immediately. I found another dream home & Tom Noelke "held my hand" from showing me the home, same day contract & negotiation, all the way to closing - quicker than I thought possible! I am exceedingly pleased with Tom Noelke and recommend him specifically to anyone looking to buy.”

Valerie Catiller · Deland, FL

Photo of Tom Noelke
eXp Realty
“Professional, responsive, and knwoledgeable. Paula was always responsive, always pointing out great ideas and assisted us with navigating the new Florida laws as they differ by State. She brought her A game to the table and was super.”

Robert Doyle · Ruskin, FL

Photo of Paula McConahay
Century 21 Affiliated
“David Dorman was outstanding to work with. From the very beginning, he was personable, easy to talk to, and genuinely listened to what we wanted in a home. With his 27 years of real estate experience, he quickly narrowed down our options, combining his expertise with the homes my wife had already found. Thanks to his guidance, we found the right house and had an offer submitted within just two days of looking. Our closing turned out to be far more difficult than expected, but David remained calm, patient, and reassuring throughout the entire process. Whenever challenges came up, he helped us work through them without adding stress. His steady guidance and professionalism made a huge difference and ultimately helped us close successfully on our new home. If you’re looking for an experienced, knowledgeable Realtor who truly cares about his clients and keeps a level head when things get complicated, I highly recommend David Dorman.”

Kerry Purdy · Clermont, FL

Photo of David Dorman
Century 21 Carioti
“Shelby went above and beyond for my family and I throughout the entire process. I was a first time home buyer and she answered all my questions without hesitation. I would highly recommend her to anyone I know looking for a new home.”

Megan Pletcher · Longwood, FL

Photo of Shelby Martin
RE/MAX Town & Country
“Since we worked with Gary previously, he knew us personally. Through some time spent in looking in different areas Gary found us the ideal home close where we needed it to be. Without a doubt Gary is extremely patient and diligently works to provide exactly what we wanted and needed. We cannot think of another broker that we would want to work with as Gary is a true “Professional”. All we can say is “Gary, Thank You for providing exactly what we wanted and we will recommend you to everyone we know!””

Joseph Sandusky · Sanford, FL

Photo of Gary Berkson
RE/MAX Central 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
“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
“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 · Orlando, FL

Photo of Madeleine Haughwout
Coldwell Banker Realty
“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

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 Winter Park. 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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