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 September 2026.*
63 recent sales
$75K-$1.05M price range
$310K 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. *
May 1, 2026 - Jul 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 (May 2026 - Jul 2026).
Year-over-year, Winewood’s rolling three-month data shows softer prices and leaner inventory alongside an uptick in closings. Typical home values are down compared to last year while homes sold are up nearly 29 percent, indicating buyers are finding opportunities even as values ease.
Looking at the latest rolling three-month period ending in July 2026, the typical home value is about $150,000 with a median list price near $183,000. Homes are spending a median of 46 days on the market and the average sale-to-list price ratio is about 96.6 percent, suggesting sellers often accept modest discounts from asking.
Supply conditions point to a moderate seller’s advantage, with months of supply at 3.8 and the broader Tallahassee market at a similar 3.9 months. Active listings in Winewood are down more than 40 percent from a year ago and no recent sales have closed above list price, highlighting the importance of sharp pricing and strategy. Agent Pronto can connect buyers navigating these shifting conditions and sellers aiming to stand out with an experienced local agent in Winewood.
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.
“I cannot say enough wonderful things about Deb. She seamlessly handled both the sale of my home and the purchase of my new one. Her dedication is unmatched—she answered every late-night text and early-morning call without hesitation. She truly goes above and beyond for her clients and feels like family by the end of the process. Thank you, Deb!”
“Patti's professionalism was the key to success in selling my property. I worked with Patti prior when I was president of my co-op. Any closings always went smoothly when she was involved, that's why I chose her. Communication was of the upmost importance due to the fact that I was not available during the sale. Patti listened to my request, devised a game plan and went into action. In a buyers market, the property sold quickly in the price range we were targeting. Patti did all the work! I strongly recommend Patti Davila and Century 21 handsen group for any of your real estate needs.”
“My husband and I are out of state buyers for our second home. Tammy's local knowledge was invaluable as we decided on the best place for us to buy. Her attention to detail is exemplary and she supported us through the whole process. I would recommend Tammy to anyone as a realtor.”
“Stephanie was recommended to us. Stephanie was Absolutely amazing through the entire process of purchasing our home and even aftet we closed. There were several hiccups which were not due to anything Stephanie did, but she did find resolutions. She was so responsive when we had a question or concern. She called, texted and emailed in a very timely manner. Stephanie went above and beyond. She was AMAZING to work with. We cannot say how grateful we are that Stephanie was recommended to us. I would recommend her to anyone in the market to buy or sell a home. She is very knowledgeable about the market and the area. Stephanie works well with the other agents, mortgage companies and title companies. Stephanie should be Agent of the year!! Please contact Stephanie for any Real Estate needs you may have!! We love Stephanie.”
“Valentina provided realistic expectations during the sales process given current market conditions. She is very knowledgeable of the area and trends occurring in our Tampa community. I especially appreciated her quick responses to any questions and concerns we had.”
“Dania’s expertise in the local market was obvious from day one. She provided exceptional remote-sale support. She was extremely professional, trustworthy, communicative, accessible and went above and beyond from beginning to end.”
“Dennisse was such a pleasure working with! She had my back from the beginning and was there with me every step of the way. She did her research and negotiated with passion to make sure I had the best deal possible. She treated me like family and I would highly recommend her to anyone looking to buy a home. Thank you so much Dennisse for everything!”
“I cannot recommend Evelyn highly enough! She helped me navigate a very challenging transaction in which the seller and selling agent were often unprepared. She remained proactive, organized, and focused on finding solutions at every step. Even when unexpected issues arose, she stayed ahead of them, kept me informed, and made sure nothing jeopardized our closing date. She consistently prioritized my needs, advocated for my best interests, and went far beyond what was expected to ensure we closed on time. She was always responsive, patient with my questions, and willing to do whatever was necessary to move the process forward. Her professionalism, dedication, attention to detail, and genuine commitment to her clients are truly exceptional. I am incredibly grateful for everything she did to help me purchase my home and would confidently recommend her to anyone looking for a realtor who will truly go above and beyond!”
“Lili was recommended by a friend who lives in The Villages. From the first phone call or text, Lili was very prompt at responding to my call or text question. She even supported me while she was on vacation. Lili negotiated a lot of the furniture to come with the house. That was something I certainly didn't expect since the owner was just moving down the street. Even though the owner had just lowered the price by $30,000, Lili still got the home for me for a lower price than that, with furniture. Thank you for always picking up when I called or responding promptly to my text messages. Lili. This was the quickest home purchase I've ever made. My husband had recently passed of cancer. I knew this was his/our plan. It was hard on me, but Lili, along with my friends, helped me through it. THANK YOU, Lili!”
“I was looking at houses online - kind of a hobby of mine - until I found a house I loved & hoped to afford. I hadn't owned a home in nearly 13 years. Tom Noelke popped up & introduced himself - has his own brokerage AND was able to show me that house the very next morning. He was SO knowledgeable & professional, and educated me on down payments, DeSantis' $10,000 First Time Homebuyer program, even discussed the whys & when I'd like to buy. He wrote a contract that night at my request! That seller wanted a cash deal so declined my contract immediately. I found another dream home & Tom Noelke "held my hand" from showing me the home, same day contract & negotiation, all the way to closing - quicker than I thought possible! I am exceedingly pleased with Tom Noelke and recommend him specifically to anyone looking to buy.”
“Abbey was an absolute dream to work with! I recently hired her to manage the rental listing for my condo, and she made the entire process seamless from start to finish. She is exceptionally knowledgeable about local market pricing, ensuring we listed at a competitive rate based on size, location, and amenities. Beyond her market insight, Abbey provides a true end-to-end service: she gave excellent recommendations on high-impact updates to attract renters faster, coordinated stunning professional photography, drafted the lease, handled all communications with potential applicants, and made time to show the unit repeatedly. Abbey is responsive, transparent, and an incredible communicator. Whether you are buying, selling, or renting out a property, Abbey delivers top-tier results with zero stress. I cannot recommend her highly enough!”
“Thanks for all of your help Karen it was a pleasure working with you.”
“Larry was great. Went above and beyond. Would highly recommend.”
“Crystal is not only my soror and friend, but she is also an exceptional real estate professional. While our relationship is personal, the sale of my home was strictly business—and highly professional. From start to finish, Crystal set and managed expectations, communicated consistently, and demonstrated an incredible depth of knowledge throughout the entire process. She treated the sale of my home as if she were selling her own home, and that level of care and attention was evident every step of the way. I was extremely pleased with the entire experience. Crystal made the process seamless and gave me complete confidence that my home would sell for the listed price. She not only works hard—she works SMART! I will absolutely refer Crystal to my friends and family. And when the time comes for me to purchase my next home, Crystal is the ONLY agent I will call! Thank you, Crystal, for making what could have been a stressful experience such a smooth and successful one!”
“Matt and Candie are simply the best, professional,responsive and knowledgeable throughout the entire process. They listened carefully to our needs, communicate clearly, and made everything feel smooth and stress free. I truly appreciated their guidance and attention to detail, and I would highly recommend them to anyone buying or selling a home.”
“I first met Catherine Calix at an Open House event, in a unit of the Condominium I was interested in. She was friendly and helpful at the Open House.When I subsequently made an offer on the property a few days later, she ame to see me at my convenience and a most satisfactory relationship built up from that stage. I canot fault, indeed must highly praise, the service she provided from start to finish. Catherine went above and beyond throughout the buying process, culminating in a Closing Contract on the day of my choice. I would thoroughly recommend Catherine to any future Buyer - one could not have a better realtor.”
“Laurine has a real estate knowledge second to none and was instrumental in getting our condo sold after she was successful in helping us purchase our new home. We had a limited time and she was able to get it all done. We highly recommend her services.”
“Chris did a great job.”
“Mr. Galvez has a BIG heart, and he is very knowledgeable of what he does; for Mr. Galvez, his clients come first. I am very grateful of Mr. Galvez, and I will get his services if I need to buy or sell a property.”
“Thắng làm việc rất chuyên nghiệp, phản hồi nhanh và đặc biệt là tư vấn rất có tâm, sẽ liên lạc lại Thắng nếu cần”
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.
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