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 October 2026.*
80 recent sales
$75K-$1.05M price range
$320K 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. *
Jul 1, 2026 - Sep 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 (Jul 2026 - Sep 2026).
Year-over-year, Winewood’s rolling three-month data points to softer prices and slower movement. The typical home value is down around the mid-teens in percentage terms from last year, while median days on market have risen about 22 percent to 90 days, signaling that homes are taking longer to sell.
Inventory and listing activity have also pulled back compared with a year ago. Active listings are down roughly a third and new listings are off nearly half, yet pending sales have surged by about 100 percent, suggesting buyers who are in the market are committing even as supply tightens.
In the most recent rolling period ending in September 2026, Winewood’s typical home value sits at about $148,500 with a median list price near $185,500. With 4.8 months of supply, an average sale-to-list ratio just under 93 percent, and no recent sales closing above list price despite the broader Tallahassee area having higher prices overall, both buyers and sellers can benefit from an Agent Pronto–recommended agent to navigate this nuanced market and get the guidance they need.
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.
“Abbey was excellent to work with. This was a very hard sale as the new buyers were brutal. She did everything possible to make the deal happen. She is very professional and went above and beyond what other agents would have done. We have nothing but high praise for her. We would recommend Abbey to anyone who needs a realtor that really works for her client. We love her and could not be happier with the outcome.”
“Stephanie Bartek was everything we could have asked for in a realtor and more. She stepped in after our agent, Travis, tragically passed away and never missed a beat. During such a difficult time, she handled the transition with compassion and professionalism and kept everything moving smoothly. She was excellent with negotiations, offered thoughtful ideas, and helped us navigate the entire sale from out of state. She truly provides full service. When we had belongings left behind after our move, Stephanie and her husband loaded them into moving pods at no cost to us. That kindness and willingness to go above and beyond meant so much to our family. Stephanie took care of both the sale and the people behind it. We are so grateful for everything she did and wholeheartedly recommend her!”
“Susan has been been absolutely fantastic throughout all of our real estate transactions over the past few years. She's on top of every step, every party, for every transaction. She's responsive, timely, and demonstrates that she cares about what's important to us. She's earned the trust of our immediate and extended family, and we highly recommend for your buying and selling needs!”
“Duc is not only my Realtor but also a great friend. He helped us find an amazing investment property in downtown Orlando at an unbeatable price. He answered all our questions upfront and guided us confidently throughout the entire process. We had such a great experience that we’re already working with him to purchase another property!”
“Muy profesional, a cualquier hora que se llamara siempre fui atendido con cualquier duda, en cada paso que debía dar siempre estuvo ella guiando y velando que todo saliera correctamente”
“I would not even consider working with anyone else other than Dania Perry.”
“Evelyn was the best. She was attentive to our needs and got to know us better before speaking with potential buyers. She was thorough in everything that we asked her to do, including working with vendors on repair projects after the inspection was done. We liked her recommendations on the appearance of our condo before it went on the market. We would definitely recommend her to others that are selling a condo in our neighborhood.”
“We appreciated Tammy's knowledge of the property. It was instumental in our decision.”
“Diane was the realtor I needed as a first-time home buyer. She took the time to understand what I could actually afford and found a place that fit my price range, without pushing me toward something outside it. Every step of the way she was patient with my questions, kind when I was unsure, and genuinely supportive. She never made the process feel rushed or overwhelming, and she stayed steady when I needed guidance. I cannot say enough good things about her. If you are buying for the first time or even if you're buying for the 10th time and want someone who will look out for you from start to finish, Diane is the one to call.”
“Lila was absolutely wonderful to work with throughout my entire home-buying experience. From the beginning, she was professional, patient, knowledgeable, and always willing to answer any questions I had. She kept me informed throughout the process and made sure I understood what was happening at each step. Buying a home can be stressful and overwhelming, but Lila made the experience much easier and gave me confidence throughout the process. She was always responsive and went above and beyond to make sure everything went smoothly. I truly appreciate all of her hard work and dedication. I would definitely recommend Lila to my family, friends, and anyone looking for a reliable and trustworthy real estate agent.Best realtor in the world.”
“It's great to have Tony on your side, he is Knowledgeable, always thinking ahead. He will guide you in detail. You will have a stress-free experience. Tony, Keep up the great service, Thank You.”
“We worked with Matt and Candie on real estate transactions in Cape Coral, FL, Ft. Myers, FL and Madison, WI. With all 4 transactions, their knowledge of the market and neighborhoods was excellent. They have great negotiation skills when it came to purchasing and selling our homes. They were also very helpful in all the aspects of selling and buying a new home. Whether you needed help finding a service provider to get something repaired, coordinating with getting utilities switched over, or getting your modem out of the home before closing, Matt & Candie were always there. They are really great partners to have when selling or buying your home!”
“Extremely helpful. Made the process quick and easy”
“Chip did a great job maneuvering through a difficult sale. He always kept in informed and responded immediately when ever I emailed or text him. He was a pleasure to work with”
“Would absolutely recommend Dennisse. She is the best. Principle-centered, highly competent, empathetic, tenacious, candid...all the qualities of a technically competent and caring professional. Most profound thanks for the great service. One can tell this is far more than a job to Dennisse, it is her ministry.”
“First time home buyer here. From day one Michelle ensured I was taken care of. She took the time to walk me through all the processes and gave valuable input that helped me find my beautiful new home! Grateful for the time and energy she and her team put in to make the process easy and smooth. 10/10! I will be recommended all my my friends and family looking to purchase property out this way to work with Michelle.”
“Mandie did an awesome job, it made buying my first home a lot easier”
“Patricia's supper professional and knowledgeable and easy to talk”
“Larry was an absolute gem during our home buying process. He actively sought out properties that met our needs/desires and brought them to the table ASAP. We placed multiple offers on properties and Larry guided us with his expertise of the market and leveraged practical comparisons to make the correct offers. In the end, we found our new home in under 3 weeks of working with Larry, and we couldn't be happier. We would gladly use Larry again on a future buy, and highly recommend him to others.”
“I enjoyed working with Allison on every level. She did a great job marketing the property and I trusted her judgement.”
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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