We analyze thousands of real estate agents in Winter Park and nationwide to find you proven local professionals, for free.
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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Information and statistics on the latest trends in the Winter Park real estate market. *
Mar 1, 2026 - May 31, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Winter Park’s rolling three-month snapshot through May 2026 shows a steady flow of homes moving through the pipeline, with 216 new listings and 162 pending sales alongside 136 closings. Active inventory is roughly flat year over year, while months of supply has eased to 4.1, signaling more balance than in the tighter conditions seen a couple of years ago.
Pricing is responding firmly to this activity, with the typical home value around $800,000 and up about 7% from a year earlier on a rolling three-month basis. Sellers are also aiming higher, as the median list price has surged nearly 48% year over year, pushing the average sale-to-list ratio just under 96% even as the share of homes selling above list has ticked up.
Momentum in days on market is especially notable, with the median time to sell dropping to 27 days and running far faster than a year ago. Shorter marketing times combined with moderate months of supply suggest buyers must still act decisively, while sellers face more informed pricing dynamics than in the tightest seller’s markets of recent years. Buyers and sellers who want to navigate these conditions smoothly can turn to Agent Pronto to connect with a local Winter Park real estate agent who fits their needs.
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.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“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!!”
“Danny is great real estate agent you can trust and rely on”
“Shelby was professional and available for questions. Enjoyed working with her.”
“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”
“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.”
“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!”
“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.”
“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!”
“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”
“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!”
“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!!”
“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.”
“Thank you for selling my house! It was a pleasure having you as my realtor!”
“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.”
“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!”
“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!”
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.
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 Winter Park Realtor® or real estate agent today.
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