We analyze top real estate agents in Clearwater’s Winding Wood Village neighborhood and across the country to find you the best veteran and military-friendly local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for August 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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“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.”
“Valentina set my expectations of the sale from the very beginning. She brought me along every step of the way and was knowledgeable about the process. Even through the delay, which was on the sellers side, she was persistent in her communication and advocating for our inconvenience. Thank you!”
“Jamie was strongly recommended to me and she did not disappoint. She's very knowledgeable about marketing and the area. Communication was fantastic and I could always reach her with every question or worry; she had a solution for literally everything. She always brings with her a lot of patience and a big smile. 10/10 recommend!”
“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.”
“Trustworthy, professional, supportive in an emotional time. Managed expectations, good communication.”
“Larry was by far the best realtor I've worked with. I've met with a few in the past and he takes the cake. He made looking for a house feel like a fun experience instead of a cut and dry transaction. And the number of resources he had at his fingertips. I had a question/inpection request, he knew a person. I was really impressed. I am always bragging about the team I had in getting me into my house, with Larry being the ring leader.”
“Paula Mcconahay was very patient with us. She made sure that she was able to make time for us, even when we would keep adding houses to our list of possibles. Paula was very attentive to what we were looking for, and her input on the houses we looked at was extremely helpful. I could not be happier of Paula being reccommended to us.”
“Luis exceeded all of my expectations. I've never purchased a home before, so I was quite nervous about the process. However, Luis made all of my anxieties disappear like a magician. He took the time to answer all of our questions and always had a thorough answe. It also felt like he always prioritized getting back to us when we reached out for anything. He was more than prepared for our trips out to see houses, doing research before hand. Throughout the entire process, he was prompt and helped move the process along. We didn't feel rushed either. He was clear in his communication, especially when he needed something from us. I could write a novel about how wonderful it was to work with Luis. I plan to make sure his name is well known in my network for any real estate needs. Thank you for making our dreams come true, Luis! ⭐️⭐️⭐️⭐️⭐️”
“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.”
“We had a great experience with Leeroy. He is knowledgeable, attentive, and accommodating. He is also efficient, communicative, and understands our needs. Five stars for our agent, Leeroy. He made the whole process smooth and stress-free. I couldn't be happier. It was our blessing to work with him. Thank you.”
“Our Agent Karen was wonderful.”
“The realtor was excellent. Brian Hollenbeck went above and beyond. I was really impressed with all aspects of the process, thanks to Brian.”
“Teri was thorough, knew the area, walked the property and was professional and personable! ”
“Kevin was very kind, listened, responded to all my questions, and got my house listed with beautiful pictures to show the beauty of my house. All went as smooth as possible!”
“Very impressed by his professionalism and desire to help. Always available and attentive to answer any question l had in a clear and simple way.”
“We were SO fortunate to receive a call from Lottie Creech who responded to my inquiry on your site. Mrs. Creech is sweet, kind, knowledgeable and diligent. She guided us through a home search, connecting us with a very qualified home inspector resulting in our successfully purchasing a fabulous home with extensive grounds in the Lake Bernadette community. Anyone engaging Lottie Creech to assist them will be thankful they did.”
“Please see the previous comments. Tiffany is the best and truly world class! Tiffany was so wonderful to work with. She knew everything we needed and led us through a very unusual market with results beyond our expectations! We would not have trusted anyone else and she was gracious and kind even when we may not have been. We have referred our friends to work with her, she is the best. Grateful to her and the team.”
“Larry was more than a Real Estate Agent. He was more like a Family Friend. I am truly blessed and grateful to have worked with him. My home is everything I imagined it would be.”
Information and statistics on the latest trends in the Winding Wood Village real estate market, updated for August 2025. *
The typical home value in Winding Wood Village is projected to be $216,500 for the month of July. June’s finalized data reported the typical value of a home in the neighborhood to be $221,000—down 15.81% over the previous 12 months. For comparison, city-level data pegged home values at $381,500 in Clearwater for the most recent reporting period. That number is expected to float around $364,750 in July.
Winding Wood Village had 3 new listings and 7 listings that went under contract in June, decreasing the area’s total available inventory to 7—down 36.36% from the previous month. Inventory is projected to have further decreased in July.
The median listing price for homes in Winding Wood Village grew 2.93% from May to June, bringing the current median listing price to $265,000. Based on projected data for July, listing prices may continue to grow.
The number of days that homes have been on the market prior to going under contract fell year-over-year. In June 2025, the median time for a listed property to go pending was 104 days, compared to 124 days in June 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this July.
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 charming and welcoming community atmosphere with convenient access to local amenities and outdoor recreation.
Winding Wood Village pairs relaxed, low‑maintenance living with everyday convenience in the Countryside area of Clearwater. Tree‑canopied streets, single‑story villas, and a community pool create an easygoing backdrop, while exterior care handled by the association helps free up weekends. Shopping, dining, and entertainment are just minutes away at Countryside Mall, and quick access to US‑19 and SR‑580 puts Dunedin, Safety Harbor, and the wider Pinellas County corridor within a short drive. For local programs, beaches, and recreation centers, the City of Clearwater website keeps residents in the know.
Families appreciate strong public school options: Leila G. Davis Elementary, Safety Harbor Middle, and Countryside High serve the area, offering robust academics, arts, and athletics. Weekends can swing from bayside picnics under ancient oaks at Philippe Park to shell‑hunting and sunset walks at Honeymoon Island State Park. The result is a neighborhood that makes daily life smooth—near employers, errands, and green spaces—while still feeling like a retreat at home.
Whether you’re upsizing, downsizing, or securing a lock‑and‑leave home close to the coast, Winding Wood Village delivers an appealing blend of comfort, location, and value. If you’re exploring a move, Agent Pronto can connect you with a top local real estate pro for buying or selling.
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!
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 Winding Wood Village 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.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Clearwater. But we don’t stop there.
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Tips and market insights to make your Clearwater real estate journey a success.
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.
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.
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