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 July 2026. *
79 recent sales
$26K-$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. *
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).
Year-over-year, Winewood’s rolling three-month data shows rising values alongside tighter inventory. Typical home value is up about 8 percent over the past year, while months of supply has dropped sharply to 2.3, reinforcing its current seller’s market status.
In the latest rolling period ending May 2026, homes sold have climbed roughly 44 percent compared with a year ago, yet new listings are down more than 30 percent. That combination of stronger sales and fewer fresh listings keeps options limited for buyers, even as the number of active listings is slightly lower than a year ago.
Compared with the broader Tallahassee market, Winewood’s typical home value sits well below the citywide median sale price, but inventory here is notably tighter than the 4 months of supply reported across the city. With nearly half of recent listings going off the market in two weeks and about 28 percent of homes selling above list price, conditions can move quickly, so Agent Pronto can connect both buyers and sellers with an agent who understands how to navigate this pace.
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.
“Susan was attentive and extremely helpful during the process of selling our home. Her experience and expertise was very obvious and appreciated. Being out fo state, we needed someone we could rely on and Susan was 100% that person!”
“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.”
“David did an excellent job marketing the home, was prompt in replying to questions and explained the process clearly.”
“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.”
“Dania Perry is by far the best realtor we have come across in our 30 years of buying and selling property. Her expertise in the St Petersburg market is unsurpassed, and she truly has her clients best interest at heart. Organized, efficient, professional, and a master negotiator, we would never use anyone else!”
“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!”
“I would recommend Patti unreservedly. A professional through and through, extremely knowledgeable of the current market and properties available. Intelligent and friendly, resourceful, and available at nearly all times to answer the many questions that arise during the search and purchase processes. Well done from start to finish, thank you Patti.”
“Where to begin?? I met Abbey in the fall of 2022. I had either just stepped outside our front door or I had just pulled in when I saw her walking in front of our house and she was smiling and carrying corn 🌽 husks. The kind you see in the market during fall season. So I said hello and she smiled and introduced herself as Abbey our neighborhood realtor and that she's, "all ears!" Hence, the corn 🌽 husks. She briefly told me what she does and if I need a realtor or know of anyone who is looking for one to reach out to her. She gave me her business card 3x5 beautiful card with the corn 🌽 and her photo on it. So I invited her in to show her my house and get her thoughts on what my house would fetch in the market. She gave me an honest opinion and at the time - there was inventory shortage of single homes and war bidding's going on. So, I said, "Great, if I sell, I will call you!" 2026 I called Abbey and said, "let's sell my house." And she did it in seven days!! God blessed our prayers!”
“Larry always goes above and beyond for his clients. This is the 3rd time we have used him and we will never use someone else. His vendor recommendations are always great, he held my 1 month old so we could sign papers, & drove 3 hours away to show us a home. You'll never find someone who works harder for you than Larry! Highly recommend.”
“Working with Tony was an absolute pleasure. As a first time seller, I was completely overwhelmed, stressed and anxious. Tony's extensive knowledge of my neighborhood really put my mind at ease. He was always calm and patient with my ridiculous questions. His Dedication, Professionalism and quick response to my phone calls, texts and emails were amazing. Getting from listing day to closing day in exactly 45 days proves his market expertise and pricing it perfect to the market. It was an incredible, smooth and efficient transaction with no major hiccups. I will highly recommend Tony if you want an agent who delivers fast results. Muchos Gracias Tony !!!”
“Tammy did an outstanding job selling our home and provided exellent guidance throughout the process. Any and all of our questions were answered promptly. I would recommend Tammy to anyone selling or buying a home on or off Amelia Island!”
“Danny is great real estate agent you can trust and rely on”
“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”
“She listened and understood what was needed/wanted. She was aggressive with offers and getting compensations. Would use her again.”
“Mary and Alex are a wonderful team. They were very professional. Their communication was on top of everything. Mary has a calming voice so when things got stressful she was very calming to talk to. They both got my house an offer, in contract and sold in 4 months! I highly recommend them.”
“Laurine was a delight to work with again! This is the second house she has helped me purchase. Laurine knows what questions to ask sellers and gets all the information needed to make a quality house purchase. I would highly recommend her for any purchase in Florida!”
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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