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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“Miguel exceeded all expectations. More importantly, he executed the sale of this home above list price and quickly. Market trends were not in our favor, so a comprehensive plan was needed, and Miguel delivered. Thank you!!”
“As I mentioned I used Kevin as my agent when I bought my house in N. Naples He was AWESOME.. So it stands to reason that IF & or when I sold it I would have to reach out to Kevin again!!! He Also was my agent BEFORE my house sold on my new house that I had built! I already recommended Kevin to a childhood friend who will be calling him in a few weeks he told me!! Kevin went WAY beyond his duties as my agent to make sure everything was great and it was!!! Having Kevin as your agent is a no brainer!!! Worked togather 3 times now!!! Nough said !!! Thank you Kevin”
“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.”
“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 !”
“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 $1,017,500 for the month of August. July’s finalized data reported the typical value of a home in the city to be $855,000—down 14.5% over the previous 12 months. For comparison, county-level data pegged home values at $600,000 in Collier County for the most recent reporting period. That number is expected to float around $590,750 in August.
Winding Cypress had 3 new listings and 4 listings that went under contract in July, decreasing the area’s total available inventory to 21—down 8.7% from the previous month. Inventory is projected to have further decreased in August.
Of those 21 active listings, 42.86% reduced their price in the month of July. The median listing price for homes in Winding Cypress grew 39.1% from June to July, bringing the current median listing price to $925,000. Based on projected data for August, 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 July 2025, the median time for a listed property to go pending was 161 days, compared to 270 days in July 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 August.
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 residents a welcoming, well-planned community with abundant green spaces, diverse amenities, and easy access to outdoor recreation and neighborhood services.
Winding Cypress is a nature-forward, resort-style community on the quiet, south side of Naples in Collier County, where boardwalks weave through protected preserves and daily life often starts with a sunrise walk or a lap in the lagoon pool. Residents enjoy a contemporary clubhouse, fitness center, pickleball and tennis courts, a dog park, and even a community garden—plus an on-site restaurant for easy, social evenings close to home.
Weekend adventures come naturally here. Kayakers can launch into the mangrove estuaries of the Rookery Bay National Estuarine Research Reserve, and plant lovers find year-round color at the Naples Botanical Garden. Golf, Gulf beaches, and the dining and galleries of downtown are minutes away, while the sugar-soft shores of Marco Island invite quick day trips. Everyday conveniences are plentiful, with shopping, services, and healthcare options throughout south Naples and nearby Golden Gate.
Families are served by Collier County Public Schools, with nearby campuses and magnet offerings, and adults will appreciate easy access to US‑41 and I‑75 for commuting or coastal road trips. Whether you’re seeking a lock‑and‑leave home base or a full-time sanctuary immersed in Southwest Florida’s ecology, Winding Cypress offers a polished blend of amenities, privacy, and proximity to the places you’ll frequent most.
If you’re planning a move, or considering selling in Winding Cypress, Agent Pronto can connect you with a skilled local real estate agent to guide every step.
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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