Find the perfect real estate agent in Winewood, Tallahassee, FL

We analyze top real estate agents in Tallahassee’s Winewood neighborhood and across the country to find you the most proven local agents, for free.

Real estate in Tallahassee’s Winewood neighborhood.

Compare the top real estate agents in Winewood

Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for July 2025. *

* 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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Home buyers and sellers love Agent Pronto.

We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent. Here’s what some of them have had to say about our service.

“My agent went far and beyond what I expected. She helped find cleaners for the house, as well as people to dispose of things I did not wish to keep. She kept in touch over several idle months. Excellent!”
5 stars
BN
Barbara N.
Tallahassee, FL
“Lynn went beyond her duties. 5 star for service and communication and customer care with kindness. will do more business with Her.”
5 stars
JC
Jasmin C.
Panama City Beach, FL
“Going through Agent Pronto was a great experience. Service was excellent and being connected with Steven Ritter from Concierge Realty was a blessing to my wife and I. We had not purchased a new home since 2001. Steven was very patient and understanding and provided his experience and opinion throughout the process which helped us finally decide on our forever home. Not only did we purchase a new home but made a new friend. We would highly recommend Steven Ritter to anyone looking to purchase a home in the Jacksonville, FL area. Thank you!”
5 stars
RC
Robert C.
Lake City, FL
“The agent, Patricia, was professional, energetic, and empathetic to my needs. She went the extra mile to make sure I had the place that was right and then made sure all details were taken care of, so I could move in without worry.”
5 stars
HK
Harry K.
Tampa, FL
“I had a great experience with Team Bonson and would highly recommend them for any realtor needs!”
5 stars
SW
Sharon Jane W.
Cape Coral, FL
“The sale of my sister's property in Orlando went smoothly thanks to Buffy the listing agent referred by Agent Pronto. She did a good job.”
5 stars
JP
Jane P.
Orlando, FL
“Lara was great to work with. She is very knowledgeable, professional and personable. I would recommend her for any real estate transactions.”
5 stars
GT
Greg T.
Jacksonville, FL
“Gave us excellent service. Extremely satisfied!!”
5 stars
JW
Jim W.
St. Petersburg, FL
“Gerry was very helpful from the beginning. He assisted me with all phases of the sale including getting a loan officer and insurance agent. Gerry was always available and replied promptly to text messages or phone calls. I was able to see the properties I requested and he always gives his feedback or input on each. He was a pleasure to work with and I greatly recommend him.”
5 stars
MH
Michele H.
Lake Worth, FL
“Efficient and effective. A very good experience.”
5 stars
JK
Jerry K.
Cape Coral, FL

Winewood real estate Market Report.

Information and statistics on the latest trends in the Winewood real estate market, updated for July 2025. *

The typical home value in Winewood is projected to be $172,630 for the month of June. May’s finalized data reported the typical value of a home in the neighborhood to be $173,500—down 11.03% over the previous 12 months. For comparison, city-level data pegged home values at $275,500 in Tallahassee for the most recent reporting period. That number is expected to float around $278,280 in June.

Winewood had 6 new listings and 7 listings that went under contract in May, increasing the area’s total available inventory to 9—up 28.57% from the previous month. Inventory is projected to have further increased in June.

The median listing price for homes in Winewood fell 0.87% from April to May, bringing the current median listing price to $170,000. Based on projected data for June, listing prices may continue to fall.

The number of days that homes have been on the market prior to going under contract fell year-over-year. In May 2025, the median time for a listed property to go pending was 135 days, compared to 198 days in May 2024. However, in recent months the median number of days from listed to pending appears to be rising. That trend is predicted to have carried through to this June.

Real estate in Tallahassee’s Winewood neighborhood.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Winewood has to offer.

Winewood offers residents a vibrant community full of charming amenities and ample opportunities for social connection.

Winewood stands as one of the most welcoming neighborhoods in Tallahassee, offering a delightful blend of residential comfort and urban convenience perfect for families, professionals, and retirees alike. Residents enjoy easy access to local attractions, such as the peaceful nature trails and recreational spaces at Tom Brown Park, which is an ideal spot for outdoor enthusiasts and those looking to bask in the area's natural beauty.

Winewood is renowned for its proximity to quality education, with schools like Fairview Middle School and WT Moore Elementary, both recognized within the Leon County school system. The educational atmosphere is further enriched by the close location of Florida State University, giving the community a vibrant academic presence and an opportunity for lifelong learning.

Neighboring districts such as Betton Hills and Eastgate offer additional dining, shopping, and entertainment options, ensuring residents never run short of exciting excursions. When it comes to everyday conveniences, Winewood benefits from nearby grocery stores, family-owned cafes, and quick commutes to downtown Tallahassee.

For those considering selling or purchasing a home in Winewood, working with a knowledgeable real estate agent recommended through Agent Pronto grants insider access and ensures a seamless transition, whether joining or leaving this welcoming neighborhood.

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Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!

Sarah W.

Take the guesswork out of finding an agent.

With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.

We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Winewood to qualify the best agents for your specific needs.

We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.

Data analysis with a human touch.

Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Tallahassee. But we don’t stop there.

Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.

Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!


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. 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.