$901,920Average Value$411Average Price per Sq Ft8Homes For Sale
Gated living next to a Naples nature preserve
Just off the Tamiami Trail, Winding Cypress combines the scenery of a nature preserve with the convenience and security of a gated community. Part of the Picayune Strand Forest surrounds the east side with thick trees and fills the neighborhood with egrets, turtles and other wildlife. A home in Winding Cypress also comes with access to on-site amenities and activities, from hobby club meetings to dinner at the exclusive clubhouse restaurant. “If you love the lifestyle of Florida, it’s like that island living, but it’s not crazy expensive like downtown Naples,” says Chelsi Murphy, the activities director for Winding Cypress, who has lived in Naples for 30 years. “It’s almost affordable luxury living; you get good bang for your buck.”
Winding Cypress has four brand new pickleball courts.
Winding Cypress is adjacent to the beautiful scenery of Picayune Strand Forest.
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A walk through the Picayune Strand Forest
All homeowners can access the clubhouse, pool, dog park, community garden and tennis, bocce and pickleball courts. These amenities are meeting places for Winding Cypress’s clubs for tennis, water aerobics, crafting and gardening. The community borders the Picayune Strand Forest, with a boardwalk and picnic area over part of the nature reserve. Winding Cypress is within 4 miles of public and private golf courses, including Eagle Creek Golf and Country Club and The Classics Country Club. Boat owners can dock along Rookery Bay at the Tarpon Club Marina or Naples Cruise Club, less than 10 miles away.
The clubhouse at Winding Cypress has many fantastic amenities.
Winding Cypress has a dog park with two separate areas for dogs of different sizes.
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Private dinner and drinks at Shady Palm Café
Shady Palm Café is the main feature of the clubhouse. Overlooking the pool, the restaurant is exclusive to residents and their guests. It is open five days a week, and the bar also serves drinks during neighborhood parties. “Every community has its own DNA, its own amenities. Our big focus is our restaurant and the fact it’s really supported by our residents,” says Glenn Dobrydney, the general manager for Winding Cypress, who has been in Naples for 15 years. Winding Cypress is 2 miles from Tamiami Crossing and Shops at Eagle Creek on Collier Boulevard, with clothing shops and grocery stores like Walmart, Aldi and Publix.
Shady Palm Café at the clubhouse in Winding Cypress is a great place for a quick lunch.
Home Goods & other large Box stores are just down the road from Winding Cypress on US-41.
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Custom waterfront homes and Winding Cypress villas
There are only around 800 homes and villas in Winding Cypress. Most single-family homes are in Coastal Contemporary and Mediterranean Revival styles, and owners can customize the developer's standard floor plans. Every property is professionally landscaped with a trimmed lawn and flower-filled garden. A villa may cost $500,000 to $700,000. Lakefront homes are priced from $700,000 to $900,000, while custom properties are $900,000 to $1.5 million. A staffed gate encloses the entire neighborhood, and the community's CAP Index crime score is 1 out of 10, below the national average score of 4.
Hurricanes and high winds in southwest Florida
Naples is prone to hurricanes, high winds and floods. Hurricane Irma in 2017, Hurricane Ian in 2022 and Hurricane Milton in 2024 all impacted the city. Winding Cypress’s inland location protects it from flooding and some storm damage, but strong winds occur throughout the year.
Collier Blvd is the Hurricane Evacuation route off US-41.
Efforts are underway to restore Naples Pier, which took heavy damage during a 2022 hurricane.
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Halfway between Naples and Marco Island
Highway 41, also known as the Tamiami Trail, connects Tampa to the north and Miami to the east. The highway leads to Naples proper, 10 miles away. Houses of worship like St. Demetrius Orthodox Church and St. Finbarr Chapel are also on this highway. Marco Island is 11 miles to the south, and Collier Area Transit (CAT) has daily routes between Naples and Marco Island. Both cities have executive airports for private flights, and Southwest Florida International Airport is 42 miles away in Fort Myers. Physicians Regional on Collier Boulevard is the closest healthcare facility, 3 miles away.
Student-athletes can attend Lely High School
Children may attend Lely Elementary School, Manatee Middle School and Lely High School through the Collier County School District, all of which have B grades on Niche. Lely High has over a dozen sports teams, and the school’s alums include professional athletes like NFL wide receiver Keith Eloi and Olympic swimmer Asmahan Farhat. Florida SouthWestern State College - Collier Campus is 4 miles from Winding Cypress.
Lely High School is a B+ ranking school in East Naples with 1,600 students
Manatee Middle School in East Naples ranked as a B rated school.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
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Crime and Safety
1 - Low Crime, 10 - High Crime
Winding Cypress
US
Homicide
1
4
Sexual Assault
2
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
4
4
Motor Vehicle Theft
4
4
Larceny
2
4
Crime Score
3
4
Source: WhatIsMyCrimeRisk.com
Winding Cypress Demographics and Home Trends
On average, homes in Winding Cypress, Naples sell after 139 days on the market compared to the national average of 58 days. The median sale price for homes in Winding Cypress, Naples over the last 12 months is $835,000, down 2% from the median home sale price over the previous 12 months.
Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located
Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown NaplesThis summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house
Set on a private corner homesite with breathtaking long lake views, this like-new contemporary residence built in 2022 offers an exceptional blend of style, comfort and modern functionality within the sought-after community of Winding Cypress. Designed with a great room and split-bedroom floor plan, this three-bedroom plus den, two-bath home with a two-car garage showcases light-filled interiors,
Michelle ThomasPremier Sotheby's International Realty
This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious corner lot making it ideal for privacy while maintaining a stunning lake view. The turnkey designer furnishings have hardly been used and it's a pet free home. Outside the private oasis features a spa with waterfall, plenty of
Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring
BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf
Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out.Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in ready experience. Every
Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded
Beautiful two bedrooms plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armoire for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool and peaceful lake
Property Id: 957106Escape from stress in this clean, like-new ELEGANT POOL VILLA, completely updated & FURNISHED. Incomparably upgraded for our discriminating guests. #Lease Options||Available June 2026||6-Month Lease June - Nov 2026$3,500/month + utilities||6-10-Month Lease Spanning High Season$4,347/month + utilities||11-12-Month
Available after July 10th, 2026: Attached villa in the highly sought after community of Winding Cypress. This home boasts 2 bedrooms plus a den which can be used as a 3rd bedroom, 2 full bathrooms and a 2 car garage. Well maintained and fully furnished including household items (kitchen, linens, etc.) The community is situated off of Collier Blvd close to US41 (Tamiami Trl) which is a 15 minute
From the moment you arrive at the stunning entry, Winding Cypress invites you into this wonderful community. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own
Beautifully furnished 3+Den single family home in the highly sought-after, gated community of Winding Cypress in Naples. This thoughtfully appointed home offers a comfortable and stylish escape, perfect for enjoying the Southwest Florida lifestyle during season. The residence features an open-concept layout filled with natural light, a well-equipped kitchen ideal for entertaining, and inviting
Beautiful turnkey furnished single-family home in the sought-after gated community of Winding Cypress, available now in the off-season or during season. Built in 2015, this spacious residence features 4 bedrooms, 3 bathrooms, and a versatile upstairs loft, offering plenty of room for comfortable living and entertaining. Enjoy an open and inviting floor plan with stylish furnishings and
Seasonal Rental available for 2027. Turnkey Furnished, and ready for you to enjoy. This 2 story Summerwood model home with Breathtaking Pool and Spa offers a spectacular open floor plan. This home has a very large, beautiful Gourmet kitchen with Dining area, generous Great room with baby Grand Piano, 3 Bedrooms, 3 bathrooms on the main floor, 1 bedroom, 1 bathroom, plus a very large loft on the
LUXURY WINDING CYPRESS VACATION RENTAL IN NAPLES FLORIDA / BACKYARD OASIS WITH A PRACTICE PUTTING GREEN, INFINITY SPA, FIRE TABLE AND OVERSIZED HEATED POOL. NOW BOOKING SEASON 2027 7052 Live Oak Drive is Your Private Southwest Florida Escape. The ideal home for vacation getaways or extended stays all year round. This 2 Bed, 2 Bath Home with a Den / Office offers 2 King Beds and all the comforts
Beautiful turnkey furnished single-family home available now for an annual lease in the sought-after gated community of Winding Cypress. Built in 2015, this spacious residence features 4 bedrooms, 3 bathrooms, and a versatile upstairs loft, offering plenty of room for comfortable living and entertaining. Enjoy an open and inviting floor plan with stylish furnishings and move-in-ready convenience.
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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