We analyze thousands of real estate agents in Clearwater’s Winding Wood Village 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 April 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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Information and statistics on the latest trends in the Winding Wood Village real estate market, updated for April 2026. *
Winding Wood Village currently leans toward sellers, with the market gauge at 17 indicating a Seller's Market. Fewer homes are available compared with the wider Clearwater area, with just 5 properties on the market locally versus 871 across the city.
Home values show a mixed picture, with the typical home value at $222,250, down 10.71% from last year but up 6.85% over the past month. At the same time, the median list price holds steady at $215,000 with no month-over-month change, and about 16.67% of recent sales closed above asking as the average sale-to-list ratio sits near 0.99.
Conditions are moving more quickly than before, as the median time on market has dropped to 35 days, falling 40.68% month over month and 56.25% year over year, while inventory has jumped 150% from last month even as it is still down 64.29% from a year ago. Looking ahead to March 2026, the typical home value is projected to edge up to $229,375 with inventory expected to rise slightly to 6 homes, and Agent Pronto can connect both buyers and sellers with a skilled local agent to navigate these trends.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Winding Wood Village offers residents a warm, neighborly community with tree-lined streets, convenient amenities, and a strong sense of safety and belonging.
Winding Wood Village in Clearwater offers low maintenance living with townhome style residences, mature trees, and easy access to everyday necessities. Located just east of US 19, the neighborhood puts major corridors, grocery options, and local employers within a short drive while maintaining a quieter residential setting.
Residents enjoy practical amenities such as a community pool, covered parking, and walkable interior streets. Outdoor time is easy to find with nearby Philippe Park and Moccasin Lake Nature Park offering trails, picnic areas, and water views. Everyday errands are straightforward in surrounding Clearwater, with shopping, services, and healthcare all within a convenient radius.
Families often look to local schools such as McMullen-Booth Elementary School, Safety Harbor Middle School, and Countryside High School, along with nearby branches of the Clearwater Public Library System. Weekends can include trips to Clearwater Beach, cultural stops in Pinellas County, or dining around Safety Harbor and Dunedin.
Because Winding Wood Village has its own association rules, maintenance standards, and resale patterns, working with an agent who knows this specific community and greater Tampa Bay can prevent surprises. Agent Pronto connects you with a local real estate professional who understands Winding Wood Village, helping both buyers and sellers move forward with less stress and more confidence.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Paula was absolutely amazing to work with through the home buying process. Her attention to detail was incredible. She was always available to help answer any questions that we had and was continually looking to help us get the best possible deal. I would recommend her time and time again.”
“Lawrence Lanni was extremely well versed in the market. He made the selling & buying process very simple & stress free for us. He went above & beyond with communication. Highly recommend him to anyone looking to buy or sell.”
“This is the 2nd time I've utilized Debra's services. She is very good at her job. She is knowledgeable, efficient, always available and cares about the customer. I highly recommend her to anyone looking to buy or sell. Thanks, Debra!!”
“I would like to thank Century 21 and Mrs. Valentina Moreno For her services she was very instrumental in helping my wife and me with our first Home. She was very informative with the process Very eager and motivated So we are very happy with our new home in the Connerton community of Land O Lakes Florida. Sincerely, Mr. & Mrs Diaz”
“Cory did an excellent job from start to finish. He was professional, responsive, and made the entire process smooth and stress-free. I really appreciated his attention to detail and clear communication. Highly recommend working with him.”
“Luis was absolutely AMAZING! He went above and beyond to make sure we found the perfect home for our family within our budget. Luis was very attentive to every detail in the home buying process. I can not express how grateful we are for Luis.”
“Jack dressed and presented himself as very professional. He was an attentive listener and receptive. Jack understood my needs with my search and focused on properties that would "check all my boxes". Jack was patient, flexible, and made himself available around my work schedule. Jack even went above and beyond by answering a question or two at the time of closing and after. He made being a first time homebuyer less stressful and helped me understand the process better.”
“Becky was incredible to work with and helped us not only with the purchase of our home in Florida, but was a huge help through our whole process of moving from Minnesota and even assisted with finding a rental until we could find a place to build. Truly went above and beyond and took the time to really understand what we want. Highly recommend!”
“Realtor for us was Jen Tobey. She came to initial meeting prepared and educated. She is professional & and market knowledgeable. We signed up with her. She showed the home several times and gave us good feedback. When the house was sold the process went smoothly, even though it was a probate sale. All of my phone calls, emails and text messages were immediately answered. What a pleasure working with her after dealing with courts, judges, banks, lawyers, financial advisors, retailers, inspectors and roofers to name a few. We also had a wonderful title company handle the closing.”
“Michelle was great to work with. She helped us through each process of purchasing our new home. She made herself available for all questions and concerns.”
“Jamie had been informative and friendly the whole process! 5 stars for her ⭐️⭐️⭐️⭐️⭐️ !! Thanks Jamie for your presence and for the present at the closing.”
“Frances Vella is professional, responsive and knowledgeable about the local market. She took the time to understand exactly what I was looking for and guided me through every step of the process. I found the perfect home and with Frances' negotiating skills I paid $20,000. less than asking price. I highly recommend Frances Vella to anyone looking to buy or sell.”
“Stephanie took care of everything and made the process of selling my first home a breeze. She was very professional and made herself available when I needed something. She went out of her way to keep my house in the front of the market and walked me through every step. I would highly recommend Stephanie to anyone who wants to seek their home.”
“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.”
“Sam sheen realty was FANTASTIC !! I COULDN'T HAVE ASKED FOR BETTER AGENTS”
“Trustworthy, professional, supportive in an emotional time. Managed expectations, good communication.”
“Tyler is very knowledgeable and keeps your best interest in mind. Through his work he shows that he cares a lot about his clients and is dedicated to finding a home that fits the needs of the buyer while making the process both easy and efficient. He's proved a great resource to talk about the various considerations when it comes to buying a property. I would recommend Tyler to anyone trying to purchase thier home.”
“I would highly recommend Ben if you are considering buying or selling a property! As a first time home buyer in this difficult market I was naturally a bit nervous. He listened carefully to what I was looking for and searched diligently to find properties that met my needs. He was thorough in his showings providing wisdom and insight. Once I found the right home, he promptly submitted my offer and helped me to negotiate a great deal. He was kind, friendly, prompt, and extremely enjoyable to work with. It felt like having a trusted friend guiding me through the process. Cannot recommend enough!”
“A pleasure to be represented by Maggie Neal always professional,courteous and looks out for my best interests.”
“Yandy Estrada was an excellent choice for us to help us buy our house, he helped and guided us every step of the way. Their trust and professionalism made every step of this adventure very easy. Definitely in our next investment I would choose Yandy Estrada and Rosa Leon again.”
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 Winding Wood Village. 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.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Winding Wood Village Realtor® or real estate agent today.
