“Michelle Olds is a high octane, efficient and caring agent! I would strongly recommend her for your real estate dealings.”
LPT Realty
- 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 June 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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Winding Cypress real estate Market Report.
Information and statistics on the latest trends in the Winding Cypress real estate market. *
Latest Rolling 3-Month Snapshot
Mar 1, 2026 - May 31, 2026
Median sale price
$630K
-13%
from
Q1 '26
Median list price
$1M
+24%
from
Q1 '26
Active listings
27
-13%
from
Q1 '26
Homes sold
18
+29%
from
Q1 '26
New pendings
19
+36%
from
Q1 '26
New listings
8
-50%
from
Q1 '26
Quarterly Pricing Trends for Winding Cypress
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winding Cypress
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Winding Cypress
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Winding Cypress
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winding Cypress
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Winding Cypress
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
14
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Homes in Winding Cypress are taking longer to sell in this rolling three-month view, with the median time on market at 112 days compared with much quicker turnarounds seen in prior years. Even with that slower pace, only 1.6 months of supply is available, which still points to a seller’s market. A smaller share of homes, about 16 percent, is going under contract within two weeks. This mix of slower overall timelines and tight inventory creates a nuanced backdrop for both sides of the table.
Prices have adjusted over the past year, with the typical home value down notably from a year ago while the median list price is up year over year. Fewer owners are putting homes up for sale, as new listings have dropped sharply compared with last year. At the same time, the number of homes sold and pending sales has risen significantly.
Buyers are seeing fewer bidding wars, with only a small share of homes selling above list price and an average sale-to-list ratio just under 100 percent. Active listings have fallen compared with a year ago, so options are more limited even though properties sit longer. With these shifting dynamics in Winding Cypress, buyers and sellers can both benefit from an Agent Pronto–recommended real estate professional who understands how to navigate this evolving market.
Learn more about what Winding Cypress has to offer.
Winding Cypress offers residents a welcoming, family-friendly community with abundant green spaces, well-maintained amenities, and convenient access to parks, schools, and neighborly gatherings.
Winding Cypress attracts buyers who want resort-style amenities with a quieter, nature-focused feel, and sellers who know the value of a well-kept, gated community. Set just off U.S. 41, it appeals to full-time residents, snowbirds, and investors seeking newer construction, energy-efficient homes, and strong community programming.
Most properties are single-family homes and villas with open-concept layouts, covered lanais, and lake or preserve views that take advantage of the nearby Picayune Strand State Forest. Residents value the extensive on-site amenities, including resort and lap pools, pickleball, tennis, and a lively clubhouse. Access to Gulf beaches and downtown Naples dining is straightforward, while everyday shopping and services are close along the Tamiami Trail corridor.
Active adults appreciate walking paths and social clubs, while those focused on wellness enjoy proximity to North Collier Regional Park and area golf courses. Seasonal owners look for low-maintenance living and rental potential that fits within community rules. Families and visitors often explore the Naples Botanical Garden or waterfront restaurants at Bayfront.
Because values in Winding Cypress can shift block by block depending on water views, lot orientation, and proximity to community features, it is essential to work with an agent who understands these neighborhood-level nuances. Agent Pronto can connect both buyers and sellers with a real estate professional who knows Winding Cypress in detail and can align strategy with your specific goals.
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“Matt and his wife were very helpful throughout the sales process. They went above and beyond to facilitate the sale and showings of our home. Communication was excellent throughout.”
Century 21 Selling Paradise
“We would like to thank Barrett for his time and effort in finding our perfect home. Barrett went out of his way helping us make decisions. He polite and pleasant never making us feel rushed. His southern style is charming. We will think of him as a friend. Thank you Barrett great job. Best of luck with you future closings.”
Century 21 Ocean
“I can't express how happy we were with the experience we had working with Shaina. She was so helpful and accommodating with every request and every question we had. She went above and beyond every step of the way. She made us feel comfortable and confident in our search for our new home all the way through our closing. Anything that came up she was right there to handle it for us. It was so nice to have a Realtor that acted both professional and as a friend. I would highly recommend her to anyone I know. Thanks Shaina!!”
The Jason Mitchell Group Jason Mitchell Group
“Mr. Kevin Daly was a 'master chef' negotiator and the secret sauce to a smooth closing. He listened to all of our needs, tailored the search, and found the perfect home -- a true recipe for success. Mr. Daly had a genuine personable approach that made us feel comfortable. Dealing with him was a breath of fresh air. I would highly recommend Mr. Daly to my family, friends, and others.”
Century 21 Sunbelt Realty
“Jari was excellent at showing us homes in our range and interest. He did a wonderful job at closing the deal. We felt valued and appreciated.”
eXp Realty The Team
“Adelynn has been everything you would want in a Realtor to be! She was always available to talk and answer questions, and if she wasn't sure of something, she found out asap. Adeylnn treated us with absolute kindness and respect, and would highly recommend her to friends and family without hesitation. We have invited her to our first BBQ in our new home!”
eXp Realty Gulf Pointe
“Miguel was very professional and always gave us great advice! The property was sold very fast! 👏👏👏”
MS
Century 21
“Thank you century 21 and Katie Wetherell with working with us to purchase our first home in Florida. Katie did an outstanding job for us in everyway possible and went above any expectatios!! Katie is a very bubbly spirit person and does an amazing job and will recomend to many friends and family!!! Thank you Katie for a great job making a dream come truefor our family! Thanks also for your continuing frienship with me and my family hopefully for many years to come. Terry and Carrie Van Dyke and entire family”
Century 21 Sunbelt Realty
“I would recommend Kimberly to anyone trying to sell a high-priced home. She is knowledgeable about the market and was able to sell our house in 2 weeks, even though it had previously sat on the market for 9 months pre-COVID. Her customer service is excellent, and she is helpful with questions and contacts throughout the selling process.”
Orlando Regional Realty, Inc.
“John Rice was exceptional to work with. His professionalism, clear communication, and responsiveness made the entire process smooth and stress-free. He was always available to answer questions and made sure every detail was handled with care. I would confidently recommend him to anyone looking for a trusted realtor.”
Century 21 Selling Paradise
“James was the absolute best agent to work with! I would recommend him to everyone as his knowledge and professionalism is unmatched. James treated us with kindness and dignity and went above and beyond to make sure we were happy. The communication with James was beyond impressive and he always made sure we were his number 1 priority. Thank you James for all you did to make buying our new home so much fun!”
Century 21 Sunbelt Realty
“Jerry ROCKS! We love Jerry and his great team. He has consistently showed up with excellence.”
Home Legacy Realty
“Sherry Bourque got my house up and sold so quick. We had a high volume of people coming through. The closing process was smooth.I would so recommend Sherry and her team anytime.”
Diamond Key Real Estate
“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 REMAX Realty Team
“Larry is by far the most AMAZING Realtor. He was always very responsive to my calls, texts, request, etc. We built up such a great relationship through this crazy process, that even after we closed on our new home, he reached out to check on us. He is always looking to get the best deal for his clients. He is like family now to us and will always have his own seat next to the firepit in our backyard. I would DEFINETLY recommend Larry to anyone and everyone looking to buy or sell. AMAZING.. Can't say enough Great things about Larry.”
Charles Rutenberg Realty Charles Rutenberg
“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.”
Anchor Group Real Estate
“Krysta Sylvester helped us look for that perfect house for over 7 months. I could not be happier with the dedication and knowledge Krysta shared with us, as we were from another state. She does not disappoint, I will not go with any other agent in the future. Thank you Krysta.”
Compass Florida LLC - The Fuerst Team
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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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 Cypress Realtor® or real estate agent today.
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