We analyze thousands of real estate agents in Tallahassee’s Winewood neighborhood 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 August 2026.*
77 recent sales
$26K-$1.05M price range
$329K median price
* 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.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
Information and statistics on the latest trends in the Winewood real estate market. *
Apr 1, 2026 - Jun 30, 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 (Apr 2026 - Jun 2026).
Year-over-year, Winewood’s rolling three-month numbers show a sharp jump in prices alongside cooling activity. The typical home value over the latest three-month period is up by more than 150 percent from a year ago, while median list prices have climbed over 60 percent even as active listings have fallen by roughly a quarter.
Looking at the most recent rolling three months ending in June 2026, inventory is limited, with only 11 active listings and just 6 new listings entering the market. Homes are taking longer to sell, with the median days on market rising to 83, yet months of supply sits at 3.8, matching the broader Tallahassee market and signaling moderate balance between buyers and sellers.
Sales activity in Winewood has held fairly steady, with homes sold and pending sales both only slightly higher than a year ago despite the large increase in prices. Sellers are seeing fewer bidding wars, as the share of homes selling above list has dropped to zero and the average sale-to-list ratio has edged down to just over 95 percent. Buyers weighing Winewood against Tallahassee overall, and sellers trying to price correctly in this shifting environment, can both benefit from Agent Pronto helping them find a local real estate agent who knows these trends well.
Winewood offers residents a welcoming, family-friendly enclave with well-kept parks, convenient amenities, and easy access to outdoor recreation and everyday services.
Winewood in Tallahassee offers a practical mix of residential comfort and everyday convenience, appealing to both long‑time locals and future residents. Located near the heart of the city, it provides quick access to major routes, government offices, and downtown employers, which keeps commutes manageable and routines predictable.
The neighborhood sits close to plenty of shopping and services, with nearby destinations like Logan Square Shopping Center and Apalachee Parkway retail options making errands straightforward. Outdoor time is easy to enjoy at spaces such as Cascades Park and Tom Brown Park, where trails, playgrounds, and open fields offer room to unwind. Families appreciate proximity to local schools and the broader educational resources of Florida State University and Florida A&M University.
Cultural and civic amenities are within reach as well. Residents can take advantage of events at Tallahassee-Leon County Civic Center and library services through LeRoy Collins Leon County Public Library, while the broader Tallahassee area offers additional neighborhoods such as Betton Hills and Killearn Estates for comparison. Nearby Leon County resources support everything from parks to community programming.
Navigating different pockets of Winewood, evaluating school zones, and understanding micro‑market trends can feel complex. A real estate professional who works Winewood every day can explain pricing, timing, and contract details clearly, helping buyers compete confidently and helping sellers position their homes strategically. Agent Pronto connects both buyers and sellers with the right local agent so that each step feels more organized and less stressful.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Meeting Diane randomly at an open house was the best thing to happen in my search for a home. She is the most friendly, detail oriented, and knowledgable realtor I've worked with in all of Florida. Her drive to ensure you're heard, cared for, and that you understand everything along the home buying process is second to none. Thank you Diane!”
“Dania is an excellent person and top tier realator. I wouls( will) highly recommend her to anyone.”
“From the moment that we met David, he made it clear that he was here to help us find our new home. His knowledge of the area, attention to detail, and responsiveness were second to none. He was able to give clear honest information that we used in the decision making without pressure or agenda. A fantastic agent!”
“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!””
“Mình tìm được anh Thắng trên Facebook. Anh làm việc tận tâm nhanh gọn và giải thích rất cặn kẽ quá trình mua nhà của mình diễn ra rất suôn sẻ. ai đang tìm người Việt làm môi giới bất động sản ở Orlando cứ gọi anh Thắng là an tâm”
“I have been with Karen for close to 10 years. She has sold my second condo that I owned in Pompano-Colonial Gardens and I purchased the new one in Pompano-PalmAire back in 2017. Just recently she sold my Palm Aire condo and I purchased my 3rd and hopefully last in Wynmoor-coconut Creek. She is really very knowledgeable of what she shows to people. Not only does she listen to what we request she hears and brings it to the table.... What a great real estate agent. We really connected and consider her a friend. I have referred her to several of my family and several friends that are looking.”
“Crystal was an absolute pleasure to work with. She was knowledgeable, attentive, and trustworthy. She was always available to answer questions and was an excellent negotiator. Anyone would be lucky to have her represent them.”
“Our home sold in record timing for area, TWO DAYS. Thank you for the fantastic professional photos. Great communication between Susan , Lori & ourselves. Thank you ladies very much.”
“Cathleen Cornish was so very helpful as she was always available to answer our questions and very knowledgeable during the entire process of our home buying from Ohio to Florida. Thank you Cathleen for your assistance !!”
“This is my second transaction with Charles, buying an investment property Charles and Lynn are amazing. I recommend them to everyone.”
“We found Tanya to be very professional and knowledgeable. She was always there for us and was very patient with our numerous questions. We would definitely use her services again if the opportunity arises!”
“We were very impressed with the service provided.”
“Regla is an amazingly wonderful agent and extremely professional and knowledgeable. I will recommend her to anyone who is looking to buy or sell their property!”
“Millie is the perfect agent to work. She helped us buy a new home. Her knowledge of the area and the different neighborhoods was invaluable. She is great at communication always keeping us in the loop, excellent at negotiation and very professional at all times. You can't go wrong choosing Millie to represent you for your real estate needs.”
“Great to work with”
“Matt and Candie were excellent to work with. Matt's knowledge of construction issues and contacts with all kinds of service providers was extremely helpful. Matt always answered the phone and gladly took on any requests or questions we had with immediate response. We have actually made our first good friends in Cape Coral by working with Matt and Candie. We could not recommend them enough.”
“Stephanie was very professional. She understood what I needed and she delivered 110%. Communicated very well with me during all aspects of the sale, from gently helping me keep the motivation I needed to get the property ready to sell, to real time negotiations at the point of sale. I highly recommend Stephanie for your next real estate adventures!”
“We highly recommend Travis Crow of Century 21. We closed on our property last week, and throughout the entire process he kept us informed every step of the way. He promptly responded to our calls and text messages whenever we had questions, and his communication was excellent. Travis was professional, knowledgeable, and always represented our interests well. He proved to be trustworthy, respectful, and a pleasure to work with from start to finish. We truly appreciated his dedication and would not hesitate to recommend him to anyone looking for an outstanding realtor.”
“She was amazing!!! Especially when it came to navigating our lender and some issues of staying within our time frame of the contract, she really provided excellent service and care! Love her and will definitely use her again when the time comes.”
“Michelle is very wonderful person and felt completely safe in all decision process through with buying and selling property, definitely will refer her and have her as my realtor in future. Thank you!”
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 Winewood. 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 Winewood Realtor® or real estate agent today.
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