$899,848Average Value$417Average Price per Sq Ft20Homes 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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to let others know what life in this neighborhood is like.
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 128 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 $850,000, down 1% 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
Single Family home in Winding Cypress -Ready for the season!! This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile
The View !!!!!!!! built in 2022 Move in Ready ! Like new Contemporary style mystique model 3 bdrm den 2bath in Winding Cypress. Location Location with this breathtaking long lake view , last home on street on long landscaped corner affords plenty of privacy.Some of the Upgraded features consist of a widened paved recently sealed driveway comfortably fitting 2 cars side by side, zero clearance
Over 2200 Sq ft complete with your own POOL this is a great opportunity! Don't waitCheck out this impeccably maintained residence offers an exceptional living experience. The open floor plan features THREE spacious bedrooms, a versatile den or flex room, and two full bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated LVP
Winding Cypress – PRICE REDUCED TO SELL- Rare opportunity to purchase in this community at this price point. Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 4 bedrooms or use the 4TH bedroom as a den. Two full
OPPORTUNITY AWAITS – LOWEST PRICE AVAILABLE! Welcome to the largest villa model in Winding Cypress, featuring a rare private front entrance and expanded foyer that sets the tone for this thoughtfully designed home. This spacious 2-bedrooms and massive den offers an open yet defined living concept with abundant natural light and seamless indoor-outdoor flow. Enjoy a long list of builder upgrades
Welcome to this beautifully designed residence located within one of Naples' most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it
Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The
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
Discover your dream home in the prestigious Winding Cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal for
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
Available for Season 2026 and 2027! 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
Available for 2026 season! Welcome to this beautifully appointed seasonal rental located in the highly sought after Winding Cypress community. This spacious home offers three bedrooms plus a den, three full bathrooms, and a two and a half car garage. Fully turnkey furnished and thoughtfully designed, the home features an open concept floor plan that flows seamlessly from the interior living
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
Discover Your Dream Home in Naples! Presenting the rare Winding Cypress model, the stunning Cressida villa. This beautiful home features a spacious private yard and lanai, perfect for entertaining or relaxing in paradise. Inside, a dedicated front entrance and a large foyer welcome you into an open yet well-defined living area. The master bedroom has a king-size bed, the guest bedroom includes a
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
Light, bright and beautifully updated two bedroom 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 size bed and den has a queen size Murphy bed. Spacious attached 2-car garage. Water filter system purifies all water throughout the villa. Sit back and relax with your coffee in the morning or
This newly completed and spacious PET FRIENDLY home offers 3 bedrooms (King, King & 2 Twins) plus a den that is equipped with a queen-size murphy bed. This home is full of entertaining options that allow you to bring the extended family along. With its open floor plan as well as zero-corner sliders that blend the interior seating with the outside kitchen and bar. As soon as you drive through the
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