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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 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 worked with Evelyn to find our forever home. She was incredible, I can't imagine having anyone else as our realtor. what we wanted in a home changed so many times while we were looking. Each time we changed our mind on what we wanted, Evelyn was very understanding, attentive and encouraging. She assured us that we would find our perfect home. Evelyn was an incredible negotiator, has impeccable attention to detail, and worked extremely hard the entire time we were her clients. We felt that we were truly in good hands, with a person who had our best interest in mind. I highly recommend Evelyn to everyone!!”

Kevin Schmitz · Altamonte Springs, FL

Photo of Evelyn Hartnett
Southern Realty Enterprises Inc.
“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
“Working with David Dorman has been an exceptional experience from start to finish. David is extremely responsive—we primarily communicated via text, and he always replied promptly and thoughtfully. Throughout the entire process, he kept me well informed and ensured that I understood every step along the way. What I appreciated most was our open and honest dialogue. I truly felt that David was on my side, always advocating for me and working hard to achieve the best outcome for the sale of my home. His knowledge and expertise were evident in every interaction, and his professionalism truly stands out in the industry. I was so pleased with the experience that I am now using David’s services to purchase my next home—and we were under contract in no time! I would not hesitate to recommend David to anyone seeking a dedicated, knowledgeable, and trustworthy real estate professional.”

Chris Rockwell · Orlando, FL

Photo of David Dorman
Century 21 Carioti
“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.
“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
“It was a very great experience with Debra Meyers representing my property. She was always available to discuss property & offers presented on the property, would gladly look forward to working with her on a future purchase.”

Francis Kass · Jacksonville, FL

Photo of Debra & Jacob Myers
CanZell 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
“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
“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!”

Deborah Richelieu · Pompano Beach, FL

Photo of David Mohabir
RE/MAX Interaction Realty LLC
“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
“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.”

Susan A. · Haines City, FL

Photo of Christine Smith
eXp Realty
“Viewings and closure of offer was a very smooth experience with Karuna. Given the right inputs she set up all viewings without a hitch and we hit our planned viewings as per schedule agreed. She helped close my offer quickly. My experience with post closure paperwork was also smooth and on time as agreed.”

Jas Mamak · Berkeley Heights, NJ

Photo of Karuna Singhvi
PRIMROSE REALTY
“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.”

Zahima · Spring Hill, FL

Photo of Yandy Estrada
Century 21 Century21 Rosa Leon
“Fabio was very professional, open, transparent, and reliable throughout the entire process. He really cared about us, understood our entire needs... Best realtor I've ever met.”

Isabel C G. · Poinciana, FL

Photo of Fabio Gomez Jr
AXEN Realty
“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.”

Anaís Balbás · Deland, FL

Photo of Acts Home Team
Keller Williams Advantage Realty

Winter Park real estate Market Report.

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

The typical home value in Winter Park is projected to be $702,500 for the month of November. October’s finalized data reported the typical value of a home in the city to be $722,500—down 14.5% over the previous 12 months. For comparison, county-level data pegged home values at $443,000 in Orange County for the most recent reporting period. That number is expected to float around $447,000 in November.

Winter Park had 52 new listings and 59 listings that went under contract in October, decreasing the area’s total available inventory to 170—down 10.99% from the previous month. Inventory is projected to have further decreased in November.

Of those 170 active listings, 38.82% reduced their price in the month of October. The median listing price for homes in Winter Park fell 19.64% from September to October, bringing the current median listing price to $722,400. Based on projected data for November, listing prices may continue to fall.

The number of days that homes have been on the market prior to going under contract rose year-over-year. In October 2025, the median time for a listed property to go pending was 62 days, compared to 52 days in October 2024. 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 November.

Winter Park, FL real estate
29
Seller’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 Winter Park has to offer.

Winter Park offers residents a vibrant, walkable town with tree-lined streets, lush parks, strong schools, diverse cultural amenities, and a welcoming, close-knit community.

Winter Park is where oak-canopied streets, lake views, and a lively cultural calendar turn everyday errands into a stroll worth savoring. Along Park Avenue, cafés and boutiques frame Central Park, and the acclaimed Charles Hosmer Morse Museum of American Art showcases the world’s largest collection of Tiffany glass. Across Lake Virginia, the lakeside campus of Rollins College adds lectures, theater, and music to the community rhythm, while the Scenic Boat Tour glides past boathouses and birdlife on the city’s chain of lakes.

Families value strong academics through Orange County Public Schools and sought-after programs at Winter Park High, plus a rich mix of youth sports and after‑school arts. Green time is easy at Mead Botanical Garden and Dinky Dock Park, and Saturdays begin at the beloved Winter Park Farmers’ Market. Commuters appreciate quick connections via the SunRail Winter Park Station to Orlando.

Housing spans brick-street bungalows, classic Mediterranean Revival homes, and modern lakefront architecture, with many addresses walkable to schools, parks, and Park Avenue. Annual marquee events—from the Sidewalk Art Festival to holiday boat parades—keep the calendar full without sacrificing the town’s easy pace.

Thinking about a move within town or across the country? Whether you’re buying your first home or selling a lakefront retreat, Agent Pronto can introduce you to a top local agent who knows Winter Park inside and out.

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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