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 June 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

Mar 1, 2026 - May 31, 2026

Median sale price
$187K
+0.5% from Q1 '26
Median list price
$363K
+96% from Q1 '26
Active listings
13
No change from Q1 '26
Homes sold
7
+75% from Q1 '26
New pendings
8
+33% from Q1 '26
New listings
4
-43% from Q1 '26

Quarterly Pricing Trends for Winewood

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

Quarterly Pricing Trends for Winewood Q2 '21 Q2 '22 Q2 '23 Q2 '24 Q2 '25 Q1 '26 Median sale price in Apr 2021 - Jun 2021: $107K 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 list price in Apr 2021 - Jun 2021: $115K 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 Apr 2021 - Jun 2021 Median sale price $107K Median list price $115K 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
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
16
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 (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.



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.

“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 !!!”

Grace Cruz · Kissimmee, FL

Photo of The Fuentes Team
eXp Realty
“Travis Crow was very valuable in selling our parent's home. He listed and provided marketing for just the right couple to buy and enjoy our family home. He was pleasant and very knowledgable about all our concerns. Inspections and closing went well due to his diligence and understading of real estate. We highly recommend Travis for the sale of your home and property!”

Barbara Thompson · Milton, FL

Photo of Travis Crow
Century 21 AmeriSouth Realty
“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!”

Peter Smadu · Fernandina Beach, FL

Photo of Tammy Tingle
Century 21 Miller Elite
“Michelle Olds is a high octane, efficient and caring agent! I would strongly recommend her for your real estate dealings.”

Mladen Vladic · Pinellas Park, FL

Photo of Michelle Olds
LPT Realty
“Danny is great real estate agent you can trust and rely on”

Shiv Chudasama · Eustis, FL

Photo of Danny Dhannu
Elite Investors Reatly Luxury Real Estate
“She listened and understood what was needed/wanted. She was aggressive with offers and getting compensations. Would use her again.”

Aishah Bartolome · Kissimmee, FL

Photo of Cassandra Kelly
Century 21 Wolfs Crossing Realty
“Stephanie was absolutely amazing throughout the entire home-selling process. She worked incredibly quick, and within just a few days of listing my home, I had multiple offers. We listed on Thursday evening, and I accepted an offer that Sunday. As a first-time home seller, I had a lot of questions, and she was always quick to respond with honest, knowledgeable answers. She kept me informed every step of the way and made sure I understood the process from start to finish. One thing I appreciated was that I lived more than an hour away from the property and Stephanie made everything seamless by handling details on-site, coordinating with contractors and buyers when needed, and keeping things moving without requiring me to make constant trips. Whenever an issue came up, she addressed it immediately and kept me updated. Her professionalism, communication, and dedication made what could have been a stressful experience feel easy. I highly recommend her to anyone buying or selling a house.”

Laura · Cantonment, FL

Photo of Stephanie Bartek
Century 21 AmeriSouth Realty
“Abbey has been a blessing to work with from the onset of our search for a new home right up through the closing process. Her professionalism, support and transparency have been nothing short of excellent. She has been 100% committed to helping us through what has been an emotional transition and has gone above and beyond anything we might have expected. We now have family members who have decided to relocate to Florida. We have recommended wholeheartedly that they work with Abbey and have shared her contact information with them.”

Cathi and Willie Castillo · Greenacres, FL

Photo of Abbey Adair
Century 21 Realty Professionals
“Matt and his wife were very helpful throughout the sales process. They went above and beyond to facilitate the sale and showings of our home. Communication was excellent throughout.”

Shawn Burke · Cape Coral, FL

Photo of Bonson Team
Century 21 Selling Paradise
“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.”

Patricia Harris · Port St Lucie, FL

Photo of Mary  Castro
eXp Realty ~ The Five Star Group
“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!”

Tim · Boca Raton, FL

Photo of Laurine Gauthier
Century 21 Beggins Enterprises
“David Dorman has sold my husband all of his previous homes and sold them as he moved and upgraded as well. Even so I wanted David to map out his strategy for selling my rental property home. He valued it correctly, promoted it quickly, got significant views and offers and held on until he negotiated the right deal. He knew how to not spend time off market with buyers who wouldn't complete the deal and steered me in the right directions. The home sold much faster than expected for what I was hoping to get. David gives each client the same world class service whether you Home range is $200K or Millions. Thank you David and Century 21 for making this process stress free.”

Moe Merkel · Orlando, FL

Photo of David Dorman
Century 21 Carioti
“Working with Lila was the absolute best part of this experience. From our very first conversation, she was completely focused on my goals, incredibly responsive, and made me feel like her top priority. I am so grateful for her guidance and support.”

Chomphunut Kittijaruphakdee · Middleburg, FL

Photo of Lila Keim
Century 21 Miller Elite
“Diane Teran is a very knowledgeable and experienced agent with excellent professional skills. She pays attention to the client needs and details. Diane is always willing to help and answering client's questions even beyond her working schedule. She has pleasant manners in communication with her clients and makes clients feel comfortable. Diane has personal approach with every client which helps to accommodate people's needs. I enjoyed working with Diane and would recommend her to anyone.”

Olga Sharonova · Poinciana, FL

Photo of Diane Teran
Lpt Realty
“Phililp Pisano,III answered all of my questions and provided any type of information or services I needed. He was very helpful and honest.”

Nancy Meskimen · Sarasota, FL

Photo of Sarasota Gulf Coast Living
Michael Saunders & Company
“Susan Summers was an excellent realtor to work with by myself. Can be very difficult to get along with but Susan made everything work. I would recommend her again to anyone and I will be using her on my next purchase of a home. She's the best. She understands what the client needs. She's just not a realtor. She's a friend.”

John Craveiro · Port Orange, FL

Photo of Susan Summers
Century 21 Sundance Realty
“Huge thank you to Eddie Petasne for helping us find and buy our new apartment! Eddie not only helped us choose the perfect place, but also guided us through all the paperwork, legal details, and every step of the process. Professional, knowledgeable, and always ready to help — we truly appreciate all your hard work and support. Highly recommended!”

Yakov Zherebetskiy · Hollywood, FL

Photo of Eddie Petasne
Century 21 King Realty
“Chasity Hill understood that my house was built in 1945, my parents home since 1973, therefore sentimental and a challenge to find the right buyer. Chasity kept frequent communication with me since I live out of state. Her compassion and understanding was amazing. She did an excellent job and I highly recommend her.”

Susie Brantley · Carrabelle, FL

Photo of Chasity Hill
Century 21 Collins Realty
“Brian is the most wonderful realtor. He was very helpful and made buying a house a much easier experience than we thought it would be.We would recommend him to everyone. He is also very knowledgeable and extremely professional”

Glenn and Tracy Viola · Weeki Wachee, FL

Photo of Brian Baker
Five Star Realty
“Carolina was great! We were in a hard situation with the sellers but she fought for us every step of the way. She cared about us and took our calls and texts everyday, we truly could not have asked for a better agent. We will forever be grateful for her helping us buy our first home and will reccomend anyone to her moving from out of state to Florida like us!”

Matthew King Sarah King · Riverview, FL

Photo of Carolina Aguiar
Century 21 Circle

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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