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Real estate in Tallahassee’s Winewood neighborhood.

Compare top Winewood real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 2026.*


* 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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Winewood real estate Market Report.

Information and statistics on the latest trends in the Winewood real estate market. *

Latest Rolling 3-Month Snapshot

Jun 1, 2026 - Aug 31, 2026

Median sale price
$149K
-64% from Q2 '26
Median list price
$165K
-48% from Q2 '26
Active listings
11
-8.3% from Q2 '26
Homes sold
4
-20% from Q2 '26
New pendings
5
No change from Q2 '26
New listings
6
No change from Q2 '26

Quarterly Pricing Trends for Winewood

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Winewood Q3 '21 Q3 '22 Q3 '23 Q3 '24 Q3 '25 Q2 '26 Median sale price in Jul 2021 - Sep 2021: $122K Median sale price in Oct 2021 - Dec 2021: $119K Median sale price in Jan 2022 - Mar 2022: $135K Median sale price in Apr 2022 - Jun 2022: $120K Median sale price in Jul 2022 - Sep 2022: $136K Median sale price in Oct 2022 - Dec 2022: $140K Median sale price in Jan 2023 - Mar 2023: $195K Median sale price in Apr 2023 - Jun 2023: $140K Median sale price in Jul 2023 - Sep 2023: $138K Median sale price in Oct 2023 - Dec 2023: $194K Median sale price in Jan 2024 - Mar 2024: $179K Median sale price in Apr 2024 - Jun 2024: $195K Median sale price in Jul 2024 - Sep 2024: $215K Median sale price in Oct 2024 - Dec 2024: $143K Median sale price in Jan 2025 - Mar 2025: $177K Median sale price in Apr 2025 - Jun 2025: $165K Median sale price in Jul 2025 - Sep 2025: $176K Median sale price in Oct 2025 - Dec 2025: $173K Median sale price in Jan 2026 - Mar 2026: $187K Median sale price in Apr 2026 - Jun 2026: $415K Median list price in Jul 2021 - Sep 2021: $120K Median list price in Oct 2021 - Dec 2021: $106K Median list price in Jan 2022 - Mar 2022: $120K Median list price in Apr 2022 - Jun 2022: $125K Median list price in Jul 2022 - Sep 2022: $150K Median list price in Oct 2022 - Dec 2022: $140K Median list price in Jan 2023 - Mar 2023: $119K Median list price in Apr 2023 - Jun 2023: $138K Median list price in Jul 2023 - Sep 2023: $156K Median list price in Oct 2023 - Dec 2023: $231K Median list price in Jan 2024 - Mar 2024: $182K Median list price in Apr 2024 - Jun 2024: $181K Median list price in Jul 2024 - Sep 2024: $179K Median list price in Oct 2024 - Dec 2024: $186K Median list price in Jan 2025 - Mar 2025: $150K Median list price in Apr 2025 - Jun 2025: $189K Median list price in Jul 2025 - Sep 2025: $186K Median list price in Oct 2025 - Dec 2025: $165K Median list price in Jan 2026 - Mar 2026: $200K Median list price in Apr 2026 - Jun 2026: $315K Jul 2021 - Sep 2021 Median sale price $122K Median list price $120K Oct 2021 - Dec 2021 Median sale price $119K Median list price $106K Jan 2022 - Mar 2022 Median sale price $135K Median list price $120K Apr 2022 - Jun 2022 Median sale price $120K Median list price $125K Jul 2022 - Sep 2022 Median sale price $136K Median list price $150K Oct 2022 - Dec 2022 Median sale price $140K Median list price $140K Jan 2023 - Mar 2023 Median sale price $195K Median list price $119K Apr 2023 - Jun 2023 Median sale price $140K Median list price $138K Jul 2023 - Sep 2023 Median sale price $138K Median list price $156K Oct 2023 - Dec 2023 Median sale price $194K Median list price $231K Jan 2024 - Mar 2024 Median sale price $179K Median list price $182K Apr 2024 - Jun 2024 Median sale price $195K Median list price $181K Jul 2024 - Sep 2024 Median sale price $215K Median list price $179K Oct 2024 - Dec 2024 Median sale price $143K Median list price $186K Jan 2025 - Mar 2025 Median sale price $177K Median list price $150K Apr 2025 - Jun 2025 Median sale price $165K Median list price $189K Jul 2025 - Sep 2025 Median sale price $176K Median list price $186K Oct 2025 - Dec 2025 Median sale price $173K Median list price $165K Jan 2026 - Mar 2026 Median sale price $187K Median list price $200K Apr 2026 - Jun 2026 Median sale price $415K Median list price $315K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
22
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jun 2026 - Aug 2026).

Year-over-year, Winewood’s rolling three-month prices have moved lower even as the broader Tallahassee market has inched higher. The typical home value in Winewood is down around the mid-teens percent from a year ago, while Tallahassee as a whole has seen prices rise just over 7 percent in the same period.

Inventory and activity have both cooled in Winewood compared with last year. Active listings are down by more than two-fifths, and homes sold over the rolling three-month window have also declined by a high-teens percentage, even as months of supply has trended down sharply from last year’s higher levels toward a more balanced range.

Current conditions show a neighborhood where buyers have a bit more time and sellers face more negotiation. Homes are taking a median of about 52 days to go under contract, the average sale-to-list price ratio has slipped to just under 93 percent, and none of the recent sales closed above list price, a clear shift from the multiple-offer environment seen in earlier years. Whether you are a buyer looking to interpret these changing dynamics or a seller trying to price and position your home effectively, Agent Pronto can connect you with an agent who understands the Winewood market in detail.



Learn more about what Winewood has to offer.

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.

Find your Winewood real estate agent today →


Trusted by over 500,000 buyers and sellers.

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“Extremely helpful. Made the process quick and easy”

Jeffrey Swanson · Tallahassee, FL

Photo of The Jacobs Chavez Team
Coldwell Banker Hartung
“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”

Jim Dadio · Hallandale Beach, FL

Photo of Rowand Group
Canvas Real Estate
“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.”

Ricardo Cristobal · Parrish, FL

Photo of Dennisse Nieves
CENTURY 21 Affiliated
“I had a wonderful experience working with Abbey on my condo rental in Boynton Beach. She was professional from start to finish and kept me informed every step of the way, so I never had to wonder where things stood. She was genuinely helpful and someone I felt I could trust completely. I'd highly recommend Abbey to anyone looking for a real estate agent in the area!”

Christine · Boynton Beach, FL

Photo of Abbey Adair
Century 21 Realty Professionals
“I do not have sufficient words to express my gratitude to you as my realtor. Allow me to say now “ THANK YOU SO MUCH “ for everything Your patience Your kindness Your thorough service and guidance we appreciate you and will always recommend you to our family for buying or selling. You got a friends and client in us. Beyond grateful we have met you. You are the sweetest and kindest 🙌🏿.”

Sherlande · Lake Worth, FL

Photo of Diane Teran
Lpt Realty
“Dania and her team were exceptionally professional. They did a tremendous amount of research on comps prior to listing. They have a great number of contacts with buyers in our price range, which was high. They were very careful in staging the home and were always present at showings. Her team created great presentation materials for advertising the home. She is a great communicator and an even better negotiator/strategist. If you want to sell a home, particularly in the higher price range, she is the absolute best.”

Jonathan Wolf · Redington Shores, FL

Photo of Dania Perry
Century 21 Jim White and Associates
“We've engaged with Susan on three property transactions in the last five years (buying and selling) and she is exactly what you would expect from a Real Estate agent. A consummate professional dedicated to her craft. Knowledgable, friendly, efficient, timely and always makes us feel comfortable along every step of the process. She always strives for the best outcome whether we're buying or selling. Highly recommend!”

Louis and Rebecca · New Smyrna Beach, FL

Photo of Susan Summers
Century 21 Sundance Realty
“Tammy and the team at Century 21 were amazing to work. Tammy made our home purchase easy from the showings to the closing. Her knowledge of the market and relationships with other agents and service providers proved beneficial. We would highly recommend Tammy!”

Mark · Fernandina Beach, FL

Photo of Tammy Tingle
Century 21 Miller Elite
“Stephanie was with us for the sale of our home and the purchase of our new home. She was with us all the way responding promptly to our concerns, as well as, the buyers realtor. We had a few hiccups with the sale of our home but Stephanie's knowledge and understanding helped us overcome all of the issues we faced. Our home sold quickly and we couldn't have asked for a better outcome. Her communication and negotiation skills regarding the purchase of our new home was excellent. We were able to view homes quickly and find our new home in the area. I would recommend Stephanie, as her goal is to produce results and provide honest feedback every step of the way.”

Allison J Bryan Meyers · Pensacola, FL

Photo of Stephanie Bartek
Century 21 AmeriSouth Realty
“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.”

Jason Villarreal · Sarasota, FL

Photo of Michelle Olds
LPT Realty
“Mandie did an awesome job, it made buying my first home a lot easier”

Joseph Cook · Youngstown, FL

Photo of Mandie Kadel
Century 21 Commander Realty
“Patricia's supper professional and knowledgeable and easy to talk”

Anthony Costagliola · Pompano Beach, FL

Photo of Patti Davila
Century 21 Hansen Realty
“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.”

Matthew MacPherson · Palmetto, FL

Photo of Larry Lanni
eXp Realty
“I enjoyed working with Allison on every level. She did a great job marketing the property and I trusted her judgement.”

Martin Cole · Parkland, FL

Photo of Allison Kaufman
Century 21 Stein Posner
“Best quality from Narallia was her resopnsiveness & communication with me. She slway responded quiclky And kept me informed I really appreciated that”

Larry Fuchs · Dania Beach, FL

Photo of Natallia Ivanova
Compass Florida LLC
“​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!”

Nancy Harris · Spring Hill, FL

Photo of Debra & Jacob Myers
CanZell Realty
“Brian did a great job on helping us to find the right condo. We started our search without not really knowing what we were looking for. Brian helped us figure it out. I looked at a lot of properties, until we narrowed it down to 4 And we found what we were looking for. Thanks Brian!”

Rey P. · South Pasadena, FL

Photo of Brian Hollenbeck
Coldwell Banker Realty
“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.”

Overby · Tampa, FL

Photo of Valentina Moreno
Century 21 Circle
“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!”

Chad Dunlap · Altamonte Springs, FL

Photo of Evelyn Hartnett
Southern Realty Enterprises Inc.
“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!”

KJ Hotchkiss · The Villages, FL

Photo of Whittington Team
Soundings

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 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.


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