Winding Cypress Naples: Homes, Nature Amenities & Living Guide
Nature instead of golf — a boardwalk, bird-watching overlooks, and 800+ acres of preserve wrap about 770 DiVosta homes and villas off U.S. 41 East in South Naples, with a resort pool, the Shady Palm Café, tennis, pickleball, and bocce.
Homes for sale in Winding Cypress
Browse every active Winding Cypress home on the live MLS — updated continuously, with full details, photos, and private showings on request.
See all Winding Cypress homes for sale →Winding Cypress leads with nature instead of golf: it’s a gated, preserve-wrapped community in South Naples, built by DiVosta Homes (a PulteGroup brand). It sits off U.S. 41 East (Tamiami Trail) just southeast of the Collier Boulevard (CR-951) intersection in the 34114 ZIP — about nine miles southeast of downtown Naples and immediately south of Verona Walk. DiVosta assembled roughly 850 acres here in 2015 and built the community out over about 2015–2022 — around 770 single-family homes and attached villas (sources cite 766–774) wrapped in more than 800 acres of preserve and about 80 acres of lakes, backing up to the Picayune Strand State Forest.
The community is built around nature and low-maintenance resort living rather than golf — there is no golf course here. The amenity core centers on a clubhouse and the Shady Palm Café, a poolside bar and restaurant, alongside a resort-style pool and spa, a fitness center and movement studio, clay tennis and pickleball courts, bocce, a fire pit, two dog parks, and — most distinctively — a nature boardwalk with bird-watching overlooks and miles of walking and biking trails through the preserve.
DiVosta homes here are known for solid concrete-block construction, natural gas, and association-maintained lawns, and the community carries both an HOA and a CDD (Community Development District). Exact dues and the CDD assessment vary by home and change over time, so confirm the current figures for any specific address before you rely on them.
What makes Winding Cypress different
- A rare Naples community built around <strong>nature</strong> rather than golf — 800+ acres of preserve, a boardwalk, and bird-watching overlooks backing to Picayune Strand State Forest.
- DiVosta/Pulte construction with <strong>natural gas</strong> and association-maintained lawns.
- Resort amenities without golf dues — the Shady Palm Café, resort pool and spa, tennis, pickleball, and bocce.
- Single-family homes and attached villas behind one gate, so a genuine range of price points.
Home types to know
Attached villas
Lower-maintenance, single-story twin villas around 1,500–1,600 sq ft (commonly 2 bed + den) — the entry point.
Single-family
One-story DiVosta plans from roughly 1,540 to 2,600+ sq ft (some larger to ~3,000+), 2–4 bedrooms — plans include Abbeyville, Martin Ray, Pinnacle, Tangerly Oak, Summerwood, and Stonewater (verify specs by listing).
What it’s like to live in Winding Cypress
Winding Cypress is one of the few Naples communities that leads with nature instead of golf. Roughly 770 DiVosta homes sit inside more than 800 acres of preserve and about 80 acres of lakes, with a nature boardwalk, bird-watching overlooks, a picnic pavilion, and miles of walking and biking trails threading the wetlands — and the 76,000-acre Picayune Strand State Forest right at the back door. It’s an all-ages community (not 55+), and there is no golf course or golf membership.
The social core is the clubhouse and the Shady Palm Café — a poolside bar and restaurant with a barefoot bar and happy hours — opening to a resort-style pool and spa. Rounding it out are a fitness center and a movement room for yoga and classes, clay tennis and pickleball courts, lighted bocce, a fire pit, and two dog parks (small and large), with a full-time activity director keeping a year-round events calendar going.
It suits full-time and seasonal living alike — a newer, low-maintenance home in a quiet, nature-forward setting without country-club formality or golf dues. The trade-offs are the South Naples location — about 25–30 minutes to downtown Naples and the Gulf beaches — and that, like much of the market, homes here have been slow to sell, so buyers have room to be selective.
What’s inside the gates
Winding Cypress: the amenity campus from the air
The Winding Cypress numbers that decide it
Median list price across 20 homes on the market ($535K–$1.70M). Asking prices, not values.
Naples-area MLS snapshot. Full trends below.
HOA Not published by the association — listings report about $1,440–$1,646/quarter (unverified); confirm via estoppel. Each home also carries a $440/yr food & beverage minimum for the community café (2025 figure; it can change up to 10% a year) · CDD Yes — Winding Cypress CDD, on the property-tax bill. FY2027: $1,643.98/yr (villas), $1,748.98 (50-foot lots) and $1,854.98 (65-foot lots) in Phases 1 & 2; $2,223.98 (50-foot) and $2,338.98 (65-foot) in Phase 3. Each is $794.98 operations plus bond debt
Illustrative — fees vary by association. Verify per home.
The January after closing, the assessed value resets to roughly your purchase price — the seller’s current bill is not a preview of yours.
FEMA zones vary by parcel, and FEMA letters (LOMA/LOMR‑F) that change a home’s zone never appear on the map layer.
Winding Cypress home prices & trends
Winding Cypress is a newer, DiVosta-built market where the mix of attached villas and single-family homes swings the headline number. Heading into 2026 it had cooled modestly with the broader South Naples market: the trailing-12-month median sale price ran about $835,000 (down roughly 2% year over year), with recent monthly medians nearer $899,000 and an average sale price around $823,000. These are dated, mix-driven figures — treat them as a starting point, not an appraisal. As of 2026 · verify against current listings.
Homes here have taken time to sell — averaging roughly 115–126 days on market. Recent active inventory spanned about $535K to $1.7M across villas and single-family homes, with a same-day IDX snapshot showing a median list near $935,000 and about $413 per square foot. Villas and smaller single-family homes anchor the entry point in the mid-$500Ks to $600Ks, while larger homes and premium preserve or lake lots run toward and past $1M. A handful of closings can move these numbers, so verify against current listings and recent comps for the specific home type, lot, and view before pricing an offer. As of 2026 · verify against current listings.
What it costs to own in Winding Cypress
- Monthly HOA
- Not published by the association — listings report about $1,440–$1,646/quarter (unverified); confirm via estoppel. Each home also carries a $440/yr food & beverage minimum for the community café (2025 figure; it can change up to 10% a year)
- CDD (on the tax bill)
- Yes — Winding Cypress CDD, on the property-tax bill. FY2027: $1,643.98/yr (villas), $1,748.98 (50-foot lots) and $1,854.98 (65-foot lots) in Phases 1 & 2; $2,223.98 (50-foot) and $2,338.98 (65-foot) in Phase 3. Each is $794.98 operations plus bond debt
- Golf
- None
- One-time capital
- $1,050 Resale Capital Assessment, paid by the buyer at closing (2025 figure; the Board sets it each year and may raise it no more than 10% a year), plus a sale application fee — listings report about $250 (unverified)
- Est. recurring monthly
- Three layers: HOA dues — not published; listings report about $1,440–$1,646/quarter (unverified) — plus CDD $1,748.98–$2,223.98/yr on a 50-foot lot (FY2027) and the $440/yr food & beverage minimum (2025)
Dues typically cover: Master association common expenses; the HOA also bills a landscaping assessment that varies by lot size, and villas carry an added villa assessment (amounts not published)
Approximate, as of October 2026; varies by home type and sub-association — a comparison aid, not a quote. Excludes property tax, insurance, and utilities. Always verify exact numbers per home.
Property taxes after you buy in Winding Cypress
On Winding Cypress’s current median list price of $899,000, the county + school reference rate alone (~8 mills) pencils to about $7,210/yr before exemptions — and the full bill runs higher once independent districts and non‑ad‑valorem assessments (including the CDD) are added.
Estimate, not a tax bill or tax advice. Exemptions, caps, and portability: the Collier property-tax guide. Exact figures for any address: the Collier County Property Appraiser’s estimator.
Buyer watch-list for Winding Cypress
| Check this | Why it matters |
|---|---|
| CDD assessment | Winding Cypress sits within the Winding Cypress CDD (funding water management, preserves, and roads). A non-ad-valorem line appears on the tax bill — confirm the exact amount and remaining bond term for the specific home. |
| HOA dues & what’s included | Dues reportedly cover lawn care, irrigation water, and natural gas plus the amenities — but aggregator amounts ($300–$400/mo, ~$4,200/yr) are unverified. Confirm the current figure, reserves, and any special assessment via estoppel. |
| Villa vs. single-family | Attached villas are lower-maintenance and lower-priced; single-family homes offer more size. Pricing, association, and fees differ by product — match it to your budget and maintenance preference. |
| No golf on site | Despite the resort amenities, there’s no course or golf membership. Buyers who want bundled golf should look elsewhere; here the draw is the preserve, boardwalk, and racquet/lawn sports. |
| Preserve/lake lot & view | Exposure drives price — preserve- and lake-view lots command a premium. Verify the lot premium and any preserve or wetland setback and maintenance responsibilities. |
| Insurance, roof age & flood zone | Homes are newer (roughly 2015–2022), but verify the flood zone, wind-mitigation features, roof age, and a current insurance quote per address. |
| Distance to town & beaches | South Naples location means about 25–30 minutes to downtown Naples and the Gulf beaches — weigh that against the nature setting and newer construction. |
Winding Cypress location
In the printable map: community boundary · 62 named streets · 1,659 building outlines · lakes & water
About this outline. Winding Cypress sits inside the WINDING CYPRESS land entitlement, which also covers Verona Walk. The county records one boundary for the whole entitlement, so the outline above is larger than Winding Cypress alone — it is the parent boundary, not this community's own.
62 named streets in Winding Cypress (county records)
- Adriana CT
- Alessandria CT
- Arrowhead WAY
- Bellini WAY
- Benelli CT
- Blackberry DR
- Borboni CT
- Bromeliad DR
- Carducci CT
- Chenille CT
- Chianti LN
- Clamshell LN
- Cocoplum ST
- Deimille CT
- Donatello CT
- Emilia LN
- Erice CT
- Ferrara CT
- Firenze LN
- Garibaldi CT
- Genova CT
- Geranium WAY
- Greenbriar CT
- Hernando CT
- Ionio CT
- Jacaranda LN
- Josefa WAY
- Julia LN
- Karina CT
- Leopardi CT
- Lily WAY
- Live Oak DR
- Marconi CT
- Minori LN
- Mockingbird CT
- Novara CT
- Orvieto CT
- Palermo CT
- Pennyroyal DR
- Portofino CT
- Querce CT
- Ravello CT
- Rimini WAY
- Rozzini LN
- Sabal Palm RD
- Salerno CT
- Sicilia CT
- Sorrento LN
- Tommasi CT
- Toscana CT
- Umberto CT
- Valentina CT
- Verducci CT
- Veronawalk BLVD
- Veronawalk CIR
- Wilfredo CT
- Winding Cypress BLVD
- Winding Cypress DR
- Wiregrass CT
- Xenia LN
- Yasmina WAY
- Zurigo LN
From the Collier County road centreline layer, which covers public roads. Gated communities keep interior streets private, so this list can be shorter than what you'll drive.
Boundary from Collier County and the City of Naples · street centrelines from Collier County · buildings and water © OpenStreetMap contributors. Drawn from public records and unofficial — boundaries are approximate, verify any specific address with the county. Look up a specific address → · Printable map
Winding Cypress and 14 of the closest beaches, courses & everyday places — tap a pin for details. Open the full Naples map →
Winding Cypress fronts U.S. 41 East (Tamiami Trail) just southeast of the Collier Boulevard (CR-951) intersection, immediately south of Verona Walk, and is typically reached by taking Collier Blvd south from I-75 (Exit 101). Everyday shopping and dining at Tamiami Crossing and Freedom Square are minutes away; Marco Island is a short drive south, and downtown Naples and the Gulf beaches are about 25–30 minutes northwest.
Approximate drive times from Winding Cypress
- I-75 (Collier Blvd / Exit 101)~12 min
- Marco Island~18 min
- Downtown Naples / 5th Ave S~28 min
- Gulf beaches (Naples)~28 min
- RSW International Airport~45 min
Approximate, off-peak driving times — they vary with traffic and season.
Schools & zoning
Collier County Public Schools — this South Naples corridor has historically fed Lely Elementary, a Lely-feeder middle school (commonly Manatee or East Naples Middle), and Lely High School, but attendance zones change. Verify current assignments with Collier County Public Schools.
Winding Cypress: pros & cons
Pros
- Genuinely nature-first — 800+ acres of preserve, a boardwalk, and bird-watching, backing to Picayune Strand
- No bundled golf dues; resort amenities and low-maintenance living
- Newer DiVosta/Pulte homes with natural gas and association-maintained lawns
- Both single-family and villa options behind one gate
Worth weighing
- A CDD adds a non-ad-valorem assessment to the tax bill — verify the per-home amount
- Off US-41 East; downtown Naples and the Gulf beaches are about 25–30 minutes away
- HOA dues and inclusions vary and aren’t officially confirmed here — verify for the specific home
- Homes have been slow to sell (100+ days on market) — price and negotiate accordingly
Winding Cypress questions, answered
Who built Winding Cypress and when?
DiVosta Homes, a PulteGroup brand, developed Winding Cypress. DiVosta acquired roughly 850 acres in 2015 and built the community out over about 2015–2022. It’s now essentially built out with around 770 homes (sources cite 766–774).
Does Winding Cypress have golf?
No. Winding Cypress is a nature- and amenity-focused community with no golf course and no golf dues. The focus is the preserve, nature boardwalk, resort pool, and racquet and lawn sports.
Is there a CDD at Winding Cypress?
Yes — the Winding Cypress Community Development District funds water management, preserves, and roadways, and a non-ad-valorem assessment appears on the tax bill — for FY2027, about $1,644 to $2,339 a year by phase and lot ($794.98 of operations plus $849–$1,544 of bond debt). Confirm the per-home amount and remaining term before buying.
What kinds of homes are in Winding Cypress?
Single-family homes and attached villas built by DiVosta — there are no condos or townhomes. Villas start around 1,500 square feet, and single-family homes run from roughly 1,540 up to 3,000+ square feet across nine DiVosta designs.
What do homes in Winding Cypress sell for?
Over the past year the median sale price has run around $835,000 (down about 2% year over year), with recent monthly medians nearer $899,000 and an average around $823,000 — roughly $413 per square foot. Villas and smaller single-family homes anchor the entry point in the mid-$500Ks to $600Ks, while larger homes and premium preserve or lake lots run toward and past $1M. These are neighborhood averages and small monthly sale counts move them, so verify against current listings and recent closings for any specific home. (As of 2026 · verify against current listings.)
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Morning on the nature boardwalk, binoculars out at the bird-watching overlooks while the wetlands wake up. Back along the roughly two-mile loop, then a swim in the resort pool and lunch at the Shady Palm Café without leaving the gates. Lighted bocce after dinner — with the 76,000-acre Picayune Strand State Forest right at the community’s back door. Could you see yourself here?
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Sources & notes: DiVosta — Winding Cypress official community page · Winding Cypress HOA — community amenities · Winding Cypress, Florida — Wikipedia (CDP, location, coordinates) · Business Observer — DiVosta buys 850 acres of Winding Cypress (2015) · Winding Cypress market snapshot (Homes.com) · Winding Cypress floor plans & current listings (Homes & Docks). Figures change — verify any specific number before relying on it.