The best way to find top real estate agents in Winewood, Tallahassee, FL

We analyze thousands of real estate agents in Tallahassee’s Winewood neighborhood and nationwide to find you proven local professionals, for free.

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 August 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

May 1, 2026 - Jul 31, 2026

Median sale price
$150K
-64% from Q2 '26
Median list price
$183K
-42% from Q2 '26
Active listings
10
-9.1% from Q2 '26
Homes sold
5
No change 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: $185K Median list price in Apr 2026 - Jun 2026: $318K 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 $185K Apr 2026 - Jun 2026 Median sale price $415K Median list price $318K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
20
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 (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.



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.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“I came into town for just over 24 hours. Lili had plenty of homes ready for me to look at. Included was the perfect home for us. I wrote the offer on my way to the airport and lily made it all easy from there.”

Karas · Summerfield, FL

Photo of Whittington Team
Soundings
“Professional, responsive, and knwoledgeable. Paula was always responsive, always pointing out great ideas and assisted us with navigating the new Florida laws as they differ by State. She brought her A game to the table and was super.”

Robert Doyle · Ruskin, FL

Photo of Paula McConahay
Century 21 Affiliated
“Ella es muy muy profesional y positiva me encanto como nos trato como clientes y personas me encantaría que toda mi familia la pudiera conocer y trabajar con ella Grasias muchísimas gracias Dennise”

Saúl Acevedo · Plant City, FL

Photo of Dennisse Nieves
CENTURY 21 Affiliated
“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.”

Jeff and Marge Swartwout · Cape Coral, FL

Photo of Bonson Team
Century 21 Selling Paradise
“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.”

Alison · Sarasota, FL

Photo of Catherine Calix
Engel & Völkers Engel & Volkers
“The best real estate selling decision we ever made was hiring Dania to represent us.  She is an extraordinary real estate agent with a truly rare combination of skills.  She is a fantastic marketer and negotiator, who is highly analytical, very data-driven, and extremely well-organized.  Dania is also a joy to meet with and talk to and she communicates better than any realtor I've known.  Once we went under contract, Dania was proactive and all over the details, assuring every deliverable date was met so that our closing was worry free.  While these characteristics set her apart, one of the most striking things about her is that she is always accessible.  Whenever I called her—day or night, weekdays or weekends—she always answered cheerfully and thoroughly addressed my questions.  Dania is an incredible agent and an even better person.”

Greg · St. Petersburg, FL

Photo of Dania Perry
Century 21 Jim White and Associates
“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.”

Jeremy and Yvonne Mullins · Sarasota, FL

Photo of Laurine Gauthier
Century 21 Beggins Enterprises
“Chris did a great job.”

Lance Oij · Apollo Beach, FL

Photo of Chris Reade
Century 21 Beggins Enterprises
“Abbey was an amazing asset to us in the purchase of our new home and the sale of previous home. She was attentive, thoughtful, and task-oriented. She made sure we took the proper steps to accomplish the difficulties of selling and buying a home at the same time. There was no way we could have done this without her. I HIGHLY recommend Abbey; she was fantastic.”

Mike Petrarca · Lake Worth, FL

Photo of Abbey Adair
Century 21 Realty Professionals
“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.”

Jaime Villalba · Greenacres, FL

Photo of Gabriel Galvez
eXp Realty
“Patti is a true professional. I had my doubts how fast my father's house would sell due to market conditions. Patti suggested a strategic listing price to attract buyers quickly. I was also on a short timeline for the proceeds of the sale, since my elderly father was now living with me and his cost of care was ballooning and coming fast. Patti eased my worried mind and said, let me worry about the sale of his house. Long story short, Patti contracted at a sale price higher than the list price and closed the deal in a matter of weeks, not months. Patti and her people handled everything flawlessly, especially the HOA and management issues. Me and my family are happy sellers and I would recommend Patti to everyone who asks for a true realtor. Thanks again Patti !”

Gus · Tamarac, FL

Photo of Patti Davila
Century 21 Hansen Realty
“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”

D · West Melbourne, FL

Photo of Duc Thang Nguyen
Alliance Real Estate Group
“David Dorman was outstanding to work with. From the very beginning, he was personable, easy to talk to, and genuinely listened to what we wanted in a home. With his 27 years of real estate experience, he quickly narrowed down our options, combining his expertise with the homes my wife had already found. Thanks to his guidance, we found the right house and had an offer submitted within just two days of looking. Our closing turned out to be far more difficult than expected, but David remained calm, patient, and reassuring throughout the entire process. Whenever challenges came up, he helped us work through them without adding stress. His steady guidance and professionalism made a huge difference and ultimately helped us close successfully on our new home. If you’re looking for an experienced, knowledgeable Realtor who truly cares about his clients and keeps a level head when things get complicated, I highly recommend David Dorman.”

Kerry Purdy · Clermont, FL

Photo of David Dorman
Century 21 Carioti
“Karen has performed past and present sales and purchases with me. I think her train for thought relates to all of her clients. She is very knowledgeable and interested in the clients him/her overall investment and satisfaction. As mentioned before I would and did recommend her to family and friends. She has a great personality and would fit any clients personality and needs. She's the best!”

Georgann Danzuso · Pompano Beach, FL

Photo of Karen Kelley
Century 21 Hansen Realty
“Smooth process Quick responses”

Bill Snyder · Monticello, FL

Photo of The Jacobs Chavez Team
Coldwell Banker Hartung
“She was great to work with fun and always upfront. She definitely knew her Real Estate. I would definitely recommend her to anybody.”

Theresa Fisher · Fernandina Beach, FL

Photo of Tammy Tingle
Century 21 Miller Elite
“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!”

V Politte · Merritt Island, FL

Photo of Diane Teran
Lpt Realty
“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!””

Joseph Sandusky · Sanford, FL

Photo of Gary Berkson
RE/MAX Central Realty
“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.”

Alezandria Turner · Kissimmee, FL

Photo of Crystal Washington Booth
Century 21 BE 3
“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.”

Laura Wabrick · Port Orange, FL

Photo of Susan Summers
Century 21 Sundance Realty

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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