$901,490Average Value$429Average Price per Sq Ft18Homes 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 135 days on the market compared to the national average of 53 days. The median sale price for homes in Winding Cypress, Naples over the last 12 months is $830,000, down 2% from the median home sale price over the previous 12 months.
Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and
Move in Ready 3 year old 3 bdrm den 2bath Mystic model at Winding Cypress. Here are some of the reasons we are we different from the rest . widened paved driveway comfortablly fitting 2 cars side by side, corner lot for privacy, beautiful long lake view on WC largest lakes, 4ft extended garage for larger vehicles plus overhead storage with Mini a/c split in garage. whole house generator, impact
Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples' most dynamic lifestyle communities. The screened
Michelle ThomasPremier Sotheby's International Realty
This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in kitchen and bathrooms, den
Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with
Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand
Property Id: 9571066 to 24-month $4,447/m+4-Month $7K/m+Escape from stress in this clean, like-new ELEGANT POOL VILLA, maintained, updated & FURNISHED. Incomparably upgraded for discriminating guests. CENTRALLY LOCATED, gated resort living, MINUTES to Marco Island, Naples Pier, shopping, beaches, golf, downtown & I75. THREE BEDS, including thick mattress QUEEN PULL-OUT in DEN.
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
Welcome to your dream vacation home in Naples, Florida! This charming property in Winding Cypress offers a wonderful opportunity for comfortable living in a vibrant community. With a 5 minute drive to grocery & convenience stores, you’ll have everything you need right at your fingertips. Located just a short drive from Marco Island and Downtown Naples with a large variety of shops and
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