“Ryan was great to work with. He was prompt and gave good updates throughout our home purchasing process.”
The Jason Mitchell Group Jason Mitchell Real Estate Group LLC
- Agent Pronto
- Florida
- Winding Cypress
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 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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“Working with Zulay has been an absolute pleasure. She truly goes the extra mile — always proactive, patient, and professional. Although I’ve been in real estate for quite some time, my experience with the Section 8 program was limited, and she not only helped move the transaction forward successfully but also took the time to explain every step of the process. I sincerely appreciate her dedication and support. It was a real pleasure working with you, Zulay!”
Florida Realty of Miami
“Kimberly has been wonderful throughout this entire process of selling my home. I can't say enough about how awesome she was in answering questions or anything I needed during this time. I highly recommend Kimberly”
Orlando Regional Realty, Inc.
“Jerry ROCKS! We love Jerry and his great team. He has consistently showed up with excellence.”
Home Legacy Realty
“James Boyer was always on top of it. I was informed throughout the entire process, from photos/videos to marketing the property. He wasn't only able to sell this one but was able to bring several buyers for our other model homes. I have worked with other agents and James sets the standard very high, I have always had to chase our agents for updates but not with James. I am very happy we chose James out of the many agents we interviewed to list our new construction homes. This one was under contract in days from listing and like many others we are pending before completion. I would recommend James to anyone looking to sell their house in South West Florida.”
Century 21 Sunbelt Realty
“Thank you so much for all your help with this move. I really appreciate it. You were so attentive and listen to all my needs.”
Coastal Real Estate Professionals LLC
“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!!”
MS
Century 21
“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”
Century 21 Sunbelt Realty
“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.”
Century 21 Ocean
“Matt was amazing ! Extremely knowledgeable with the market and went over and above the call of duty when helping us locate our new home !”
Century 21 Selling Paradise
“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.”
Century 21 Sunbelt Realty
“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!”
Baird & Warner Century 21 Selling Paradise
“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!”
EXP Realty
“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.”
Compass
“Everything was perfect, they did a great job.”
Top Selling Realty
“Agent Pronto introduced me to a very professional agent, Christina Diaz. Thank you, Christina - you made this transaction very quick & easy.”
eXp Realty LLC
“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.”
RE/MAX Realty Team
“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.”
eXp Realty, LLC
“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.”
Charles Rutenberg Realty Charles Rutenberg
“George Cabezas is hard worker always accessible, did a great job.”
Exp Realty
Winding Cypress real estate Market Report.
Information and statistics on the latest trends in the Winding Cypress real estate market, updated for October 2025. *
The typical home value in Winding Cypress is projected to be $853,750 for the month of October. September’s finalized data reported the typical value of a home in the city to be $862,500—down 24.01% over the previous 12 months. For comparison, county-level data pegged home values at $588,750 in Collier County for the most recent reporting period. That number is expected to float around $574,400 in October.
Winding Cypress had 3 new listings and 3 listings that went under contract in September, decreasing the area’s total available inventory to 18—down 14.29% from the previous month. Inventory is projected to have further decreased in October.
Of those 18 active listings, 22.22% reduced their price in the month of September. The median listing price for homes in Winding Cypress fell 2.76% from August to September, bringing the current median listing price to $899,000. Based on projected data for October, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In September 2025, the median time for a listed property to go pending was 89 days, compared to 34 days in September 2024. However, in recent months the median number of days from listed to pending appears to be falling. That trend is predicted to have carried through to this October.
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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.
Learn more about what Winding Cypress has to offer.
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.
Frequently Asked Questions
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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 Cypress. 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.
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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.
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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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