Naples, FL · Waterfront & Boating Communities

Winding Cypress

Winding Cypress is a residential community in Naples, Collier County, Southwest Florida.

Waterfront & Boating Communitiessingle-familyLuxury · $900K+FEMA Zone AE

Market Snapshot

Winding Cypress market data

Live from the MLS · updated continuously. See all 7 listings →

Active Listings
7
for sale now
Median List Price
$1,250,000
active inventory
Median $/Sq Ft
$424
list price ÷ sqft
Avg Days on Market
76
days listed
Price Range
$575,000-$1,349,500
low to high
Sold (90 days)
$815,000
5 closed · median
Homes Built
2015-2021
Typical Home
3 bed · 2,515 sq ft
Waterfront
57% of homes
Private Pool
71% of homes
Median sold price · Winding Cypress
$815,000last 3 months13.6% vs $717,500 prior 3 months

Figures reflect current active listings (and recent closed sales where available) tagged to Winding Cypress. Medians are indicative, not an appraisal, ask Rick for a comparative market analysis on a specific home.

On the Map

Where Winding Cypress sits

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Available Now

Homes for sale in Winding Cypress(7)

Newest listings first.

See all 7 homes →View on map →

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Recently Sold

Recent sales in Winding Cypress

HomeBd / BaSq FtSoldSold Price
6787 Pennyroyal Drive, Naples3 / 22,076Sep 2026$900,000
7460 Blackberry Drive, Naples3 / 22,188Aug 2026$815,000
7022 Live Oak Drive, Naples3 / 22,078Aug 2026$700,000
7473 Winding Cypress Drive, Naples4 / 22,018Jul 2026$900,000

Closed sales from the last 12 months. Ask Rick for a full comparable-sales report on any home you're considering.

At a Glance

Winding Cypress at a glance

Price Range
Luxury
Typically $900K+
Flood Zone
Zone AE
High risk · 1% annual chance · BFE established
high-confidence estimate, verify by address
Community Type
single-family
Region
Naples

Amenities & Lifestyle

What you get living in Winding Cypress

Waterfront

Drive Times

Location & access

  • 🏖️ Nearest Beach25 min
  • ✈️ RSW Airport46 min
  • 🏙️ Downtown Fort Myers24 min
  • 🏥 Nearest Hospital22 min
  • 🛣️ I-75 Access26 min

Cost of Ownership

Estimated yearly costs for a luxury-tier home

Florida estimates based on a $1,250,000 home in Winding Cypress. Actual numbers vary, book a Strategy Session for a live, parcel-specific quote.

Property Tax
$16,250
~$1,354/mo · Collier County millage ~1.3%
Insurance (incl. flood)
$15,000, $27,500
Flood + wind in high-risk zone
HOA Estimate
$0, $150/mo
Typically low/none

Estimates only. Florida Homestead Exemption (when you qualify) can knock $750-1,500 off the annual tax bill.

⚠️ Flood Zone Accuracy Note

Winding Cypress is mapped primarily in Zone AE

All sample points within Winding Cypress returned Zone AE. Individual parcels may differ, flood zones are assigned per parcel by FEMA, not per community.

Before making an offer, always verify the exact flood zone for the specific property address:

🔍 Verify on FEMA Map Service Center →Ask Rick for the Exact Zone →

Source: FEMA National Flood Hazard Layer · sampled at 5 points per community · confidence: high

Schools

Schools serving Winding Cypress

Elementary
Lely Elementary School
A
FL DOE score 65/100 · 2024-25 grade
Middle
Manatee Middle School
A
FL DOE score 66/100 · 2024-25 grade
High
Lely High School
A
FL DOE score 64/100 · 2024-25 grade

Assigned schools based on current MLS listings in Winding Cypress, with Florida Department of Education 2024-25 grades. Collier County uses zoning and school-choice options that can change by address and year, so confirm the exact assignment with the district before you offer.

Compare

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Ready to Look Closer?

Get live numbers for Winding Cypress

HOA dues, current listings, recent sales, builder incentives, all change weekly. Book a free Strategy Session and I'll pull a live snapshot for Winding Cypress tailored to your timeline and budget.

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Good Questions

Winding Cypress, frequently asked questions

What are home prices like in Winding Cypress?
Winding Cypress is in the luxury price tier, typically Typically $900K+. List prices vary by size, age, condition, and current inventory; search current listings or ask Rick for live comps.
What FEMA flood zone is Winding Cypress in?
Winding Cypress is mapped primarily in FEMA Zone AE, High risk · 1% annual chance · BFE established. Individual parcels can differ; Rick verifies the exact zone for any address.
What schools are near Winding Cypress?
Per current MLS listings, Winding Cypress is served by Lely Elementary School (grade A), Manatee Middle School (grade A), Lely High School (grade A). Collier County uses zoning and school-choice options that can vary by address, so confirm the exact assignment before you offer.
What does it cost to own a home in Winding Cypress?
For a $1,250,000 home, estimate roughly $16,250/yr property tax, $15,000-$27,500/yr insurance (incl. flood), and $0-$150/mo HOA. Full breakdown in the SWFL cost cheatsheet.
What amenities does Winding Cypress offer?
Winding Cypress features Waterfront. Compare similar communities on the interactive map.