Winding Cypress

Winding Cypress is a general-population, gated community in south Naples developed by DiVosta Homes, a division of PulteGroup, which purchased an additional 850 acres to expand the site in May 2015 for $15.36 million; the community’s HOA was registered with the state in January 2014, and active home sales and construction were underway by early 2016. Unlike some neighboring, similarly styled DiVosta communities, Winding Cypress has no golf course and is explicitly marketed and categorized as a "non-golf" gated community, with its defining character instead built around its setting: nearly two-thirds of the property is preserved as natural habitat, with more than 800 acres of on-site preserve and 80 acres of lakes threaded by walking and biking trails, a boardwalk, and a bird-wading overlook, sited directly adjacent to Picayune Strand State Forest (the site of the ongoing Everglades-related Picayune Strand Restoration Project, formerly known as Southern Golden Gate Estates). Housing spans attached villas around 1,500-1,600 square feet and single-family homes ranging from roughly 1,542 square feet up to more than 4,000 square feet in later phases, though the community’s total planned-home count is reported inconsistently across sources (766, 774, "about 800," or as few as 700 depending on the source and its vintage), likely reflecting a genuine, multi-phase build-out spanning roughly a decade rather than a single clean figure. The community markets itself as gated, but a resident-only south entrance directly off US-41/Tamiami Trail is explicitly described as unguarded, meaning guests must enter through the main, guarded Collier Boulevard gate — a meaningful nuance worth disclosing rather than presenting the community as fully controlled-access at every entrance. A search-snippet-derived source describes "mixed reviews from residents, with some praising the peaceful and well-kept atmosphere, while others express disappointment with the community’s management and high HOA fees," though the underlying resident comments themselves could not be independently retrieved and this should be characterized cautiously rather than quoted in detail. A First Street Foundation flood-risk model reportedly rates 86.3 percent of Winding Cypress properties as currently carrying some flood risk, rising to 98.5 percent over 30 years, with 814 properties identified as at risk over that period and the area noted as protected by four flood-risk-reduction projects; this is a model-based statistical projection, not a claim that most homes have already flooded, and that distinction should be preserved in any discussion of it. This research found no source specifically documenting Hurricane Ian’s impact on Winding Cypress itself in September 2022, despite well-documented general Naples-area flooding and damage in that storm; given the community’s inland, preserve-adjacent, lake-managed setting a few miles from the coast, this should be treated as a genuine information gap rather than an assumption that the community was either spared or significantly damaged. Buyers should also weigh the community’s roughly 8-to-9-mile distance from downtown Naples as a real trade-off against more centrally located in-town options, and should confirm current HOA dues, CDD assessment, and any resale transfer fee directly with the community’s management company rather than rely on the approximate figures found in this research, since even secondary real-estate sources give inconsistent totals for the community’s basic size and fee figures. Given the community’s ongoing, decade-long build-out, buyers considering a new-construction purchase here should also ask directly how many phases remain and whether nearby construction traffic or infrastructure work is likely to continue for several more years before assuming the community is fully finished. Because the community’s own basic figures, from total homes to acreage to fees, are reported inconsistently across nearly every secondary source found in this research, buyers should treat the numbers above as a reasonable starting range rather than a precise, confirmed accounting, and should request the current HOA and CDD budget documents directly before making a purchase decision.

Age Restriction

Winding Cypress is confirmed as a general-population community with no legal age restriction; multiple independent sources describe it explicitly as a mix of retirees and families. One directory site (Seniorly.com) lists it under an "active adult" informational category, but no source cites an actual 55-plus deed restriction or HOA covenant, so this should be treated as a minor point of directory ambiguity rather than a genuine conflict.

Housing Types

• Attached villas
• Single-family homes

Pricing

DiVosta Homes purchased 850 additional acres for Winding Cypress in May 2015 for $15.36 million, expanding an earlier land assemblage; the community’s HOA corporate entity was registered with Florida in January 2014, and active new-home sales and construction were underway by early 2016. Total planned homes are reported inconsistently across sources: 766 is the most frequently repeated figure, with others citing 774, "about 800 home lots" as originally designed capacity, or a lower 700-home figure as of a March 2019 news article describing an earlier build-out phase; one outlier claim of "over 2,000 homes at full build-out" is uncorroborated and likely reflects confusion with a different project. Total acreage is similarly reported as either roughly 1,100 acres or "more than 1,500 acres," which may reflect the community’s land assemblage growing over time through the 2015 purchase. Consistently reported regardless of total acreage: more than 800 acres of natural preserve and 80 acres of lakes within the community. Villa floor plans run roughly 1,500-1,600 square feet; single-family models range from roughly 1,542 square feet up to more than 4,000 square feet in later phases. Original 2016 launch pricing ran roughly $270,000 to $440,000; current listings (across several differently dated 2025-2026 snapshots) span roughly $509,900 to $1,750,000, with reported medians ranging from about $800,000 to $949,900 depending on the specific month and source, so these should be treated as approximate, not exact, figures.

Fees & Assessments

HOA Dues: HOA dues are reported at roughly $300 to $400 per month, varying by section or product type, though no source provided a precise current fee schedule by home type. A separate Community Development District assessment, reported at roughly $700 to $1,100 per year and billed via the annual property tax bill, funds water-management and wetland-preserve system maintenance, restoration and mitigation, limited utilities, landscaping, and major roadways. One source (not independently corroborated by a second) cites a one-time transfer fee of $1,000 plus a $250 application fee at resale; this figure could not be confirmed against a primary HOA document.

Amenities

• The Club at Winding Cypress, a clubhouse with lounge areas, a catering kitchen, an activity/community room, and locker rooms
• Resort-style heated pool and spa with an outdoor "barefoot bar"
• Shady Palm Café, an on-site resident restaurant
• Fitness center, a separate movement studio, and an outdoor yoga studio
• Tennis courts, pickleball courts, and bocce ball courts
• Two dog parks and a community garden
• Walking and biking trails, a boardwalk with a pavilion, and a "bird wading overlook"
• No golf course; the community is explicitly categorized as a "non-golf" gated community

Getting Around

Healthcare: Physicians Regional Medical Center–Collier Boulevard sits directly on Collier Boulevard, the same road as Winding Cypress’s main guarded entrance, strongly suggesting a short drive, though this research could not obtain an exact mileage or drive time between the two via a mapping tool.

Airport: Downtown Naples is reported at roughly 8 to 9 miles, or about a 15-minute drive. Naples Municipal Airport is reported at roughly 10.4 miles (about a 20-minute drive), and Southwest Florida International Airport at roughly 37 miles (about a 40-minute drive), though neither figure was independently mapped.