“My wife and myself are so happy how this process went. We have been saving for years and wanted to have a home for our girls. Zack and his team helped us achieve this very fast.”

We analyze top real estate agents in Winter Park and across the country to find you the best veteran and military-friendly local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 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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“My wife and myself are so happy how this process went. We have been saving for years and wanted to have a home for our girls. Zack and his team helped us achieve this very fast.”
“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!”
“David was the perfect partner in selling our home in Clermont. From the moment I met him, I felt at ease and entrusted this important transation to him. He worked with me through various challenges as we prepared the home for sale and marketed the house perfectly. We accepted a full price offer just a day after it went on the market! As we navigated several buyer inspections, David communicated results and advised on next steps. As I had to travel out of the country for business as the sale concluded, he was crucial in helping me make buyer-requested repairs that resulted in less expense than the credit we were considering offering. David is funny and charming and made the entire experience pleasant. I highly recommend working with him!”
“Needed to sell my home while living aboard. James was knowledgeable and offered a plan I could trust. Compared to the other agents he gave me the reality of the market and set real expectations. Communication was key and he delivered.”
“I have worked with 2 other realtors in the past, but I have to day Kimberley was the best. We developed a trusted partnership and I had complete confidence in her experiences and recommendations. She kept me informed proactively and also responded timely to any questions. I wholeheartedly recommend Kimberley as your next realtor”
“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!”
“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.”
“Great job done by Daniel...”
“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!”
“Evelyn is great! She is very helpful and was willing to show us any house we wanted to look at. She is great at communicating and understand what is most important for you and your family.”
“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.”
“Paula Mcconahay was very patient with us. She made sure that she was able to make time for us, even when we would keep adding houses to our list of possibles. Paula was very attentive to what we were looking for, and her input on the houses we looked at was extremely helpful. I could not be happier of Paula being reccommended to us.”
“Chandra Mosley is AMAZING! She was so patient with me from the idea of me purchasing a home 2 years ago to helping make it a reality now. I appreciate her understanding, attentiveness, and knowledge. She made sure I understood every step of the process, understood my style, jumped in to provide me with additional resources during and after closing, and continue to support now that I am in my home in any way she can. I said YES to the best realtor/broker and the best buying experience tailored to fit my needs!! I will definitely work with her again when purchasing my next property!!”
“Yandy Estrada was an excellent choice for us to help us buy our house, he helped and guided us every step of the way. Their trust and professionalism made every step of this adventure very easy. Definitely in our next investment I would choose Yandy Estrada and Rosa Leon again.”
“I was looking for an agent to buy a new property, the first name that came to mind was Karuna. I had worked with her 5 years ago, buying and selling my first house and was very satisfied with her services. I love her professionalism, patience, flexibility and ability to always be on top of everything. If you looking for a great home purchase experience, Karuna is your go to agent.”
“Chaz and Chi Chi Tyler were very helpful and understood very well what we needed for our new home. They were able to find a great house for us in a matter of days. I would highly recommend them.”
“Danny is by the far the best, he is very patient, knowledgeable, honest, and he truly takes care of the client no matter what. Thank you Danny so Much for what you do, and I will always conduct business in the future with you.”
“Please see the previous comments. Tiffany is the best and truly world class! Tiffany was so wonderful to work with. She knew everything we needed and led us through a very unusual market with results beyond our expectations! We would not have trusted anyone else and she was gracious and kind even when we may not have been. We have referred our friends to work with her, she is the best. Grateful to her and the team.”
“I can’t speak highly enough of my real estate agent, Julia Meffen is the best! She was thorough and professional and great to work with. She made what could have been a stressful and difficult process as seamless as could be. She is very knowledgeable, accessible, and communicates clearly, making the process easy. She really went above and beyond and worked through several challenging buyers. She was great at giving me the right advice; my house sold with multiple offers and above the asking price. I highly recommend Julia Meffen without any reservations.”
“We had a great experience with Mark Johnson. From the start he sat down to work with us and figure out exactly want our wants and needs we’re coming into the home buying process. He provided us with recommended associates to make the process smooth while encouraging us to do what we thought was best for our situation. Mark always responded quickly to any questions or concerns that we had and was on top of every situation. He was extremely flexible when scheduling viewings and being available to meet our needs. Mark made the home buying process less stressful by explaining all the details of offers and contracts. I’m the end we got a beautiful home all thanks to Mark. We would definitely use his services again and recommend him to all our family and friends.”
Information and statistics on the latest trends in the Winter Park real estate market, updated for August 2025. *
The typical home value in Winter Park is projected to be $831,250 for the month of July. June’s finalized data reported the typical value of a home in the city to be $755,000—up 17.05% over the previous 12 months. For comparison, county-level data pegged home values at $435,000 in Orange County for the most recent reporting period. That number is expected to float around $430,000 in July.
Winter Park had 74 new listings and 67 listings that went under contract in June, decreasing the area’s total available inventory to 198—down 3.88% from the previous month. Inventory is projected to have further decreased in July.
Of those 198 active listings, 35.35% reduced their price in the month of June. The median listing price for homes in Winter Park grew 3.57% from May to June, bringing the current median listing price to $827,500. Based on projected data for July, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In June 2025, the median time for a listed property to go pending was 19 days, compared to 0 days in June 2024. In recent months the median number of days from listed to pending appears to be increasing. That trend is predicted to have carried through to this July.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winter Park offers residents a vibrant blend of cultural arts, beautiful parks, and charming historic neighborhoods that foster a lively and welcoming community atmosphere.
Winter Park radiates a rare blend of sophistication and warmth, drawing both families and professionals seeking more than just a picturesque setting. Renowned for its historic Park Avenue, the city offers a walkable landscape brimming with boutiques, acclaimed restaurants, and vibrant galleries. Meandering along lush, oak-canopied streets, residents frequent the iconic Central Park for art festivals and seasonal concerts, while the sparkling lakes scattered throughout, like Lake Virginia, provide an idyllic backdrop for paddleboarding or sunset strolls.
Education remains at the heart of Winter Park’s appeal. Families benefit from highly rated schools such as Winter Park High School and Glenridge Middle School, renowned for their academic excellence and extracurricular diversity. The prestigious Rollins College, perched on the shores of Lake Virginia, infuses the city with a lively collegiate atmosphere and cultural vibrancy.
In addition to its rich local culture, Winter Park enjoys close proximity to Orlando, making it easy to explore world-class attractions while savoring a peaceful retreat from urban bustle. The charm extends into the neighborhoods, with nearby Maitland and Baldwin Park offering additional dining, shopping, and recreational opportunities.
For prospective residents or current homeowners considering their next step, Agent Pronto connects buyers and sellers with trusted real estate agents who know Winter Park inside and out, ensuring a smooth and successful transition in this coveted community.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Winter Park to qualify the best agents for your specific needs.
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Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Winter Park. But we don’t stop there.
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Tips and market insights to make your Winter Park real estate journey a success.
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. 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.
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