Naples, FL · Waterfront & Boating Communities
Winding Cypress
Winding Cypress is a residential community in Naples, Collier County, Southwest Florida.
Market Snapshot
Winding Cypress market data
Live from the MLS · updated continuously. See all 7 listings →
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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Homes for sale in Winding Cypress
No active listings in Winding Cypress right now
New homes list here weekly, search nearby or ask Rick to watch this community for you.
At a Glance
Winding Cypress at a glance
Amenities & Lifestyle
What you get living in Winding Cypress
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.
Estimates only. Florida Homestead Exemption (when you qualify) can knock $750-1,500 off the annual tax bill.
Schools
Schools serving Winding Cypress
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.
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Similar communities to consider
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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.
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?
- Flood zone varies by parcel, Rick verifies the exact zone for any address before you offer.
- 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, $6,250-$13,750/yr insurance, 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.