Winding Cypress Homes for Sale

Roughly half of Winding Cypress is set aside as preserve and lake, and that shows up in Naples buyers' shortlists more than any floor plan does. The Fahey Team works with buyers across this DiVosta and Pulte community off Collier Boulevard, where attached villas and single-family homes generally run from the mid $500,000s into the $900,000s. Homes here were built from 2014 onward, so the roofs, systems, and impact glass are still young. That combination, low-maintenance construction paired with wetland views and a bundled amenity campus, is why so many second-home and seasonal buyers end up here rather than in older South Naples neighborhoods.

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Winding Cypress at a Glance

County

Collier County, Florida

Setting

Gated community on Collier Boulevard in South Naples, minutes from Marco Island and Naples beaches

Housing

Attached villas and single-family homes built by DiVosta and Pulte beginning in 2014, roughly 1,500 to 3,300 square feet

Known for

Preserve and lake views, the Shady Palm Cafe, resort pool, tennis, pickleball, and bocce

Typical prices

Mid $500,000s to about $900,000 depending on floor plan and view

Home Styles and Price Context

Two categories cover most listings. Attached villas, including the Ellenwood plan, are the entry point and usually trade at the lower end of the range, with two bedrooms plus a den and a two-car garage. Single-family plans such as Summerwood, Abbeyville, Martin Ray, and Stonewater climb from there, topping out with extended lanais and lake frontage. Coastal-contemporary elevations, tile roofs, and paver drives are standard. Because construction is recent, insurance and maintenance costs tend to be lower here than in Naples homes built before the 2000s.

Daily Life

Mornings often start on the boardwalk trail through the wetland preserve, where wading birds are routine rather than rare. The Shady Palm Cafe handles casual lunches without leaving the gates. Publix and everyday shopping are a short drive north on Collier Boulevard, and I-75 access at Exit 101 puts downtown Naples and Fifth Avenue South about 25 minutes away. Marco Island beaches are closer still. Lely Elementary, Manatee Middle, and Lely High School serve the area through Collier County Public Schools.

Winding Cypress Expertise from the Fahey Team

Buyers deciding between an Ellenwood villa in the mid $500,000s and a lake-view Stonewater near the top of the range are really weighing maintenance against square footage, and the Fahey Team has closed on both sides of that decision.