We analyze top real estate agents in Winding Cypress and across the country to find you the most proven 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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“My wife and myself are so happy how this process went. We have been saving for years and wanted to have a home for our girls. Zack and his team helped us achieve this very fast.”
“Barrett was a pleasure to work with during the house search process. He was professional and knowledgeable in the real estate field. Barrett was very patient and empathetic to our needs. He was responsive and friendly throughout.”
“You can't go wrong chosing James Boyer as your realtor. He bent over backwards to accomodate our needs, as we were from out-of-state. Tremendous work ethic! His communication was excellent and did research on several things we had questions about. James Boyer is a very knowledgeable and personable young man.”
“Jerry is honest, trustworthy and knows real estate and our market very well.”
“I have worked with Kevin in the past that is why I KNOW I had to use him again.. Kevin was more the knowledgable and helpful and he goes beyond your expectation.. Beyond satisfied with Kevin Daly.. TY Kevin”
“Very professional service. Quickly to respond. The best.”
“Matt was amazing ! Extremely knowledgeable with the market and went over and above the call of duty when helping us locate our new home !”
“I am writing to enthusiastically recommend Miguel Salvat for your consideration as a real estate professional. I've had the pleasure of working with Miguel for years. I've always been impressed by the knowledge of the local market and his ability to guide me through the process with patience and expertise. Miguel is incredibly responsive to my questions and concerns, always available to answer my phone calls or emails promptly. Miguel is not only knowledgeable but also a true professional. He's always acted with integrity and professionalism, ensuring that all aspects of the transaction were handled smoothly and ethically. I'm impressed by his customer service skills, as he is always willing to go the extra mile to make sure I was satisfied from begingn to closing. A true profesinal in this industry for many years !”
“Katy, Is professional and has a friendly demeanor. She is patient and knowledgeable with the local market. She went above and beyond to successfully sell my property. I highly recommend working with her.”
“I have worked with 2 other realtors in the past, but I have to day Kimberley was the best. We developed a trusted partnership and I had complete confidence in her experiences and recommendations. She kept me informed proactively and also responded timely to any questions. I wholeheartedly recommend Kimberley as your next realtor”
“My husband and I highly recommend Realtor, John Rice due to his professionalism, knowledge of the market, his attention and dedication towards us as clients in showing us homes that met our criteria, and his personality, which is always caring and supportive. From the start of the process to the closing, John Rice has been "by our side" every step of the way and made this an even more enjoyable experience!”
“From the first time we met, he made me feel comfortable and assured. No matter what time I called, he would always call back or text, always let me know what I was facing, would never tell me what to do...if I had to do all over again he is the person I want to deal with!”
“Evan made buying and selling my homes a pleasant experience.. His knowledge and expertise was comforting as he guided me through the entire process. I would use Evan as my realtor again in the future.”
“Everything was perfect, they did a great job.”
“Agent Pronto introduced me to a very professional agent, Christina Diaz. Thank you, Christina - you made this transaction very quick & easy.”
“Tom and Diane Winford were simply outstanding. The hardest working and most competent realtors I ever met. They went the extra mile, and then more miles beyond that. We could not have been more pleased.”
“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.”
“George Cabezas is hard worker always accessible, did a great job.”
“Everything went smoothly and I was kept informed during the entire process. The real estate agent, Tammy Garcia, was extremely professional and knowledgeable about the market conditions, ethical responsibility, and the entire selling process.”
Information and statistics on the latest trends in the Winding Cypress real estate market, updated for August 2025. *
The typical home value in Winding Cypress is projected to be $415,000 for the month of July. June’s finalized data reported the typical value of a home in the city to be $530,000—down 37.65% over the previous 12 months. For comparison, county-level data pegged home values at $620,000 in Collier County for the most recent reporting period. That number is expected to float around $622,500 in July.
Winding Cypress had 2 new listings and 6 listings that went under contract in June, decreasing the area’s total available inventory to 12—down 25.0% from the previous month. Inventory is projected to have further decreased in July.
Of those 12 active listings, 50.0% reduced their price in the month of June. The median listing price for homes in Winding Cypress fell 39.53% from May to June, bringing the current median listing price to $782,500. Based on projected data for July, 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 June 2025, the median time for a listed property to go pending was 100 days, compared to 150 days in June 2024. In recent months the median number of days from listed to pending appears to be decreasing. 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 Cypress offers its residents a vibrant community with innovative amenities and a welcoming atmosphere that enhances their quality of life.
Winding Cypress is a thoughtfully planned community where natural beauty meets modern convenience, offering a lifestyle perfect for both relaxation and adventure. This private, gated neighborhood is renowned for its miles of scenic walking trails winding through protected preserves, allowing residents to encounter Southwest Florida's unique flora and fauna right outside their doorstep. The centerpiece of the community is a 10,000-square-foot clubhouse complete with resort-style swimming pool, state-of-the-art fitness center, and on-site dining at Shady Palm Café—ensuring leisure and recreation are always within easy reach.
Outdoor enthusiasts will appreciate easy access to the Picayune Strand State Forest and the pristine shores of Naples Beach, just a short drive away. The neighborhood’s location also means an array of shopping, fine dining, and entertainment opportunities in Naples and Collier County are close at hand. Families benefit from proximity to top-rated schools within the Collier County Public Schools system, including Manatee Elementary School, Manatee Middle School, and Lely High School, all celebrated for academic excellence and robust extracurriculars.
Residents of Winding Cypress enjoy a calendar packed with social gatherings, pickleball matches, and countless other activities that help neighbors quickly become friends. Whether you’re looking to put down roots or seek a tranquil retreat, Winding Cypress stands out as a place where every day can be tailored to your lifestyle. If you’re considering buying or selling a home here, Agent Pronto connects you with knowledgeable, experienced real estate professionals to ensure a seamless experience from start to finish.
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 Cypress 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 Winding Cypress. 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!
Tips and market insights to make your Winding Cypress 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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