Winding Cypress in Naples Florida is a gated community in Naples. Featuring single family homes from 1,542-2,589+ Sq. Ft., 2-3 Bedrooms to 2.0-3.0 Baths. Featuring 80 acres of lakes and 800+ acres of natural preserves. Amenities include a resort style pool, clubhouse, exercise room, and more.
The community is located just off County Road 951 Collier Blvd. in Naples. Winding Cypress is bordered on the East by Naples Reserve, on the West by Lely Resort, on the North by Verona Walk.
We are not affiliated with the HOA or management of the WINDING CYPRESS community. We do not handle rentals within the WINDING CYPRESS community.
Our role is as a real estate brokerage, dedicated to assisting buyers and sellers with their real estate needs within the WINDING CYPRESS community.
Call 239-229-9926
WINDING CYPRESS not the home community you are looking for?
If you enjoy reading the latest news and reviews and historical archived blog posts discussing pricing, lot selection and other topics, then check out our WINDING CYPRESS BLOG POSTS.
Photos are are a great way to envision a home community, and we offer 10 WINDING CYPRESS PHOTO(S) TO VIEW.
WINDING CYPRESS is located in Naples, Collier County, Florida.
The community offers AMENITIES Community amenities are quite common in Naples and you can certainly expect higher fees as the number of amenities increase.
WINDING CYPRESS offers 9 FLOOR PLAN(S) to choose from.
Take a look at the COMMUNITY SITE MAP to get the layout of the community and review the numbered lot positions.
To find out what the current weather is in WINDING CYPRESS, check out the live WEATHER CONDITIONS.
The community is located in a Community Development District(CDD). Find out more about a CDD here.
The builder of this community offered certain features as standards, and here you will find a detailed list of those standards .
If you are interested in selling your WINDING CYPRESS property, please reach out to us for a no obligation FREE market analysis.
Historic Palm Cottage, 5th Ave South, 3rd Street, Naples Train Museum, Barefoot Beach Preserve, Tin City, Naples Winter Wine Festival, Naples Botanical Garden, Corkscrew Swamp Sanctuary, Naples Pier and Beaches, Lowdermilk Beach, Revs Institute, Big Cypress, Greenway, The Bird Rookery Swamp, Rookery Bay Environmental Learning Center, and Air Boat Rides.
Community News-Stay Informed
WINDING CYPRESS Latest News and Information
Saturday 14th of February 2026
WINDING CYPRESS Weather Forecast
WINDING CYPRESS CDD
WINDING CYPRESS is located within a Community Development District(CDD). A CDD is essentially a tax-free municipal bond that the homeowners pay off over time. The bond is structured to pay for the infrastructure and/or maintenance of the community. The CDD annual debt service is listed as a non-ad valorem tax on the homeowners annual tax bill which makes the total tax bill higher. Many master planned communities in SW Florida do have a CDD. One of the main reasons for a CDD would be to make the new home prices lower since the infrastructure costs are not bundled in the new home price.
WINDING CYPRESS Amenities & Info
Gated Community pool Tennis HOA fees $200-$300 per month CDD community 24 hour guard gated Dog Park Bocce ball 20 min from beach Clubhouse Pickle ball Natural Gas Irrigation water included in fees Lawn care included in fees No age restrictions Boardwalk Community garden Spa Furnished models to tour Inventory homes available Build time 4-6 months 40 min from airport
WINDING CYPRESS Site Map
Saturday 14th of February 2026
Naples Median Price Trend
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GOOD NEWS FOR BUYERS, RESALE HOME INVENTORY AND NEW HOME INVENTORY CONTINUES TO RISE IN SOUTHWEST FLORIDA. THE BUILDERS ARE REDUCING PRICES AND GIVING BUYER INCENTIVES. SELLERS ON MLS ARE CUTTING PR...
Categories: Winding Cypress - Naples, FL By Ken O'Brian
Blog Post: SAVE UP TO $55,000, WHEN YOU ACT BY MARCH 24TH, TOWARD BUILDING YOUR NEW DREAM HOME AT WINDING CYPRESS, LOCATED IN NAPLES. OFFER AVAILABLE ON CLASSIC AND ESTATE SERIES HOMES.* PERSONALIZE THE PERFECT ...
Blog Post: SAVE UP TO $35,000 - RECEIVE A POOL AT NO ADDITIONAL COST AT WINDING CYPRESS*---ENJOY AN ENDLESS SUMMER WITH A POOL AT NO ADDITIONAL COST AT WINDING CYPRESS IN NAPLES, SELECT HOMESITES ONLY. NOW EXTEN...
Blog Post: INVENTORY HOMES TODAY::MARTIN RAY
7554 GERANIUM WAY, NAPLES, FLORIDA 34114
$459,690
3
BEDROOMS
2
BATHROOMS
2,107
SQ. FT.
2
CAR GARAGE
10901
LOT #
STAINLESS GAS APPLIANCES & 42...
We have just purchased a home in Bonita Springs Florida, we started looking a year ago and finally found and closed on a home just a little over a year later. The Realtor we used was Ken O'Brian from Southwest Coast Realty out of Naples. First let me say I am a builder, land developer, and appraiser in Illinois for over 30 years and in that time I have worked with hundreds of Realtors and I can truly say there are only four of them I would ever recommend and Ken is certainly on the top of that very short list.
Ken was always their when we needed him, he is extremely knowledgeable about the entire southwest gulf coast area and is very professional. He constantly stayed not only in touch with us but insurance people, lawyers, home inspectors, ETC. He is also a wealth of information if you are coming from out of town he can recommend any and all other professional people needed to buy or sell a home.
Don, Chicago
Client review
My travels to all parts of FL have been plentiful over the last several years. A year ago while vacationing I found a home I was very interested in and had to see it right then. It was a Sunday evening and I had gotten Ken O'Brian's name and number from a friend. I called and without hesitation Ken said he would meet at the property. Ken had to drive 30 minutes to the location. He was there with in 35 minutes including travel time. Although that property didn't work out for me.
Ken and I stayed in contact over the year. Ken sent me homes that were suited for all my needs. A few more fell through the cracks until recently. Ken found me the home of my dreams. He went way above and beyond the duties of a realtor. Ken is more then professional. He stays in contact always through email and always follows up with a text to notify you of the email. He is patient and very understanding but most importantly listened to my wants and needs. As I am a buyer out of state, he hooked me up with all the right people. Ken is your guy!
Laurie, Chicago
Client review
Ken, I just wanted to say thank you for helping us find a vacation home in Naples. Our trust in you was very well placed. We were a little nervous about the process of buying a home in Florida, but you guided us through the whole process. You took the time to explain the area to us, and helped us match our requirements to what the various communities had to offer. Your patience while we kept asking for listings was appreciated.
When we had our choices narrowed and we came down to Naples, your insights on setting our offer price let us get the place we wanted at a good price. Even on the closing day, you found a small issue, highlighted it to our lawyer and got the problem immediately resolved. End to end it was a great experience, and I would heartily recommend South West Coast Realty to not only other Canadians looking for a vacation home, but to anyone looking for a home in South West Florida. Thanks again.
Linda, Canada
Client review
Services
Selling your home
Yes, we can! Our team of experienced real estate agents are experts in the local market and have the knowledge and resources to get your home sold quickly and for the best price. We will work with you to create a customized marketing plan that will get your home maximum exposure and attract the right buyers. We will also provide you with expert advice and guidance throughout the entire process to ensure that you get the best possible outcome.
Our real estate buyers agent service is designed to help buyers find the perfect property for their needs. We provide a comprehensive service that includes researching the local market, identifying potential properties, negotiating the best price, and helping to secure financing. We also provide advice on matters, such as contracts and inspections, and can help with the closing process. Our goal is to make the home buying process as stress-free and successful as possible.
Real estate technology is a broad term that encompasses a variety of tools and services used to facilitate the buying, selling, and renting of real estate. This technology includes online listing services, virtual tours, 3D home tours, digital contracts, and more. Real estate technology can help streamline the process of buying and selling a home, making it easier and more efficient for both buyers and sellers.
The latest Southwest Florida real estate market report is always a favorite here as there are over 3,000 clients that currently receive the report via email. You can also receive it by signing up here on this website. The report provides an overview of the current market conditions in Southwest Florida, including median sales prices, inventory levels, and days on market. It also provides a look at the current trends in the area, such as the number of homes sold, the average sale price, and the average days on market.