$951,709Average Value$440Average Price per Sq Ft22Homes 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
On average, homes in Winding Cypress, Naples sell after 136 days on the market compared to the national average of 52 days. The median sale price for homes in Winding Cypress, Naples over the last 12 months is $850,000, down 3% from the median home sale price over the previous 12 months.
Introducing a luxury estate site with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled
Sophisticated living with serene views in this rarely available Abbeyville model built in 2021. This home provides a shining example of comfort, style, and thoughtful design. Ideally positioned to offer peaceful water and sunset views, has been meticulously maintained and invites you to enjoy the absolute best in a Florida lifestyle.Step inside through a welcoming entryway and discover an
Enjoy resort-style living in this Winding Cypress community near 5th Avenue and Marco Island. This home features a private pool, sunroom and the community’s largest covered lanai. Designed for year-round comfort, it offers a new air-conditioning system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized
Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a glass-tiled
Welcome to this charming 2-bedroom plus den, 2-bath single-family home in the highly desirable community of Winding Cypress. Built in 2017, this residence offers 1,544 square feet of thoughtfully designed living space. The interior is light and bright, featuring easy-care tile floors in the main living areas, a breakfast bar for casual dining, and carpet in the bedrooms for added comfort. The den
A stunning new pool and outdoor lanai, complement this exquisitely designed home, which offers tranquil views of the lake. This property features three bedrooms plus a den and three bathrooms, making it ideal for vacationing. The interior boasts a bright and airy coastal contemporary style with an open floor plan.This is a perfect vacation rental!
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
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