“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!”
- Agent Pronto
- Florida
- Winter Park
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for March 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, updated for March 2026. *
The typical home value in Winter Park is projected to be $566,880 for the month of February. January’s finalized data reported the typical value of a home in the city to be $618,750—down 31.25% over the previous 12 months. For comparison, county-level data pegged home values at $428,040 in Orange County for the most recent reporting period. That number is expected to float around $422,590 in February.
Winter Park had 57 new listings and 43 listings that went under contract in January, increasing the area’s total available inventory to 161—up 5.23% from the previous month. Inventory is projected to have further increased in February.
Of those 161 active listings, 25.47% reduced their price in the month of January. The median listing price for homes in Winter Park fell 0.06% from December to January, bringing the current median listing price to $739,000. Based on projected data for February, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In January 2026, the median time for a listed property to go pending was 57 days, compared to 60 days in January 2025. However, in recent months the median number of days from listed to pending appears to be falling. That trend is predicted to have carried through to this February.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
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.
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“Mình rất hài lòng khi làm việc với Thắng. Em rất nhiệt tình, trung thực và luôn phản hồi nhanh mỗi khi tôi cần hỗ trợ. Highly recommended!!!”
“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!!”
“David is truly a professional and dedicated to his trade. Extremely strong communication and answered all concerns in a timely fashion. It is clear David has a great deal of experience in real estate and it shows! Would highly recommend David and 100% will utilize him again in the future if it is needed.”
“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.”
“Thank you for selling my house! It was a pleasure having you as my realtor!”
“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 ...”
“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 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.”
“I highly recommend Rich Noto for new home construction. He was a fantastic advocate throughout my build, especially since I was relocating from Pennsylvania to Florida. Living states away, he sent detailed videos of construction progress and found defects during various inspections. His communication and availability far exceeded my expectations. Rich has a keen eye for potential issues and a deep understanding of building codes that many other agents, and even some inspectors, might miss. He truly knows the critical phases of construction, from the foundation on, and when to schedule inspections. He understands the tricks builders use to hide problems and is a fierce advocate for his clients. I have no doubt he saved me from future headaches. He is an invaluable resource who ensured I ended up with a high-quality home.”
“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!”
“The agent, Patricia, was professional, energetic, and empathetic to my needs. She went the extra mile to make sure I had the place that was right and then made sure all details were taken care of, so I could move in without worry.”
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”
“David Mohabir provided an excellent experience for us as were searched for our first condo. David was very patient and thorough. I sent him properties, he sent us properties and when we were discouraged he motivated us to not give up on our search for the condo! One Saturday morning David called us and that was the best day! We found the condo that was best for us. David has also heped us on the journey to post our home up as a rental property. Thank you! Thank you David! He is the best of the best!”
“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!”
“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.”
Frequently Asked Questions
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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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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.
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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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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 Winter Park Realtor® or real estate agent today.
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