What are home prices like in Windward Cay?

Windward Cay is in the mid price tier, typically Typically $450K – $900K. List prices vary by size, age, condition, and inventory. Search current listings at /search.

What FEMA flood zone is Windward Cay in?

Windward Cay is mapped primarily in FEMA Zone AE, High risk · 1% annual chance · BFE established. Parcels can differ; Rick verifies the exact zone for any address.

What schools are near Windward Cay?

Closest schools to Windward Cay: Cape Coral High School (6.4 mi), Heritage Charter Academy of Cape Coral (6.6 mi). Browse all at /schools.

What does it cost to own a home in Windward Cay?

For a $650,000 home in Windward Cay: ~$8,450/yr property tax, $7,800-$14,300/yr insurance incl. flood, and $300-900/mo HOA. See the cost cheatsheet at /swfl-relocation-cost-cheatsheet.

What amenities does Windward Cay offer?

Windward Cay features Golf. Compare similar communities at /communities.

Naples, FL · Golf & Country Club Communities

Windward Cay

Windward Cay is a residential community in Naples, Collier County, Southwest Florida.

Golf & Country Club CommunitiescondoMid · $450K – $900KFEMA Zone AE

Market Snapshot

Windward Cay market data

Live from the MLS · updated continuously. See all 6 listings →

Active Listings

for sale now

Median List Price

$712,000

active inventory

Median $/Sq Ft

$404

list price ÷ sqft

Avg Days on Market

days listed

Price Range

$425,000-$2,795,000

low to high

Homes Built

1997-2003

Typical Home

3 bed · 1,826 sq ft

Waterfront

33% of homes

Median sold price · Windward Cay

$725,000last 6 monthsnot enough sold data to compare

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

On the Map

Where Windward Cay sits

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Available Now

Homes for sale in Windward Cay(6)

Newest listings first.

See all 6 homes →View on map →

Swipe to see more →

Recently Sold

Recent sales in Windward Cay

Home	Bd / Ba	Sq Ft	Sold	Sold Price
4650 Yacht Harbor Drive 133, Naples	2 / 2	1,589	Apr 2026	$725,000
4650 Yacht Harbor Drive 121, Naples	3 / 2.5	2,019	Mar 2026	$665,000
4700 Yacht Harbor Drive 613, Naples	2 / 2	1,830	Mar 2026	$350,000
4460 YACHT HARBOR Drive, Naples	2 / 2	2,166	Feb 2026	$1,075,000

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

At a Glance

Windward Cay at a glance

Price Range

Mid

Typically $450K – $900K

Flood Zone

Zone AE

High risk · 1% annual chance · BFE established

high-confidence estimate, verify by address

Community Type

condo

Region

Naples

Amenities & Lifestyle

What you get living in Windward Cay

Golf

Drive Times

Location & access

🏖️ Nearest Beach15 min
✈️ RSW Airport46 min
🏙️ Downtown Fort Myers10 min
🏥 Nearest Hospital12 min
🛣️ I-75 Access26 min

Cost of Ownership

Estimated yearly costs for a mid-tier home

Florida estimates based on a $650,000 home in Windward Cay. Actual numbers vary, book a Strategy Session for a live, parcel-specific quote.

Property Tax

$8,450

~$704/mo · Collier County millage ~1.3%

Insurance (incl. flood)

$7,800, $14,300

Flood + wind in high-risk zone

HOA Estimate

$300, $900/mo

Condo association range

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

⚠️ Flood Zone Accuracy Note

Windward Cay is mapped primarily in Zone AE

All sample points within Windward Cay 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 Nearby

Top schools within 8 miles of Windward Cay

Cape Coral High School

6.4 mi

Highpublic· DOE Grade B· Score 65/100

Heritage Charter Academy of Cape Coral

6.6 mi

K-8charter· Score 40/100

Compare

Ready to Look Closer?

Get live numbers for Windward Cay

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

Ask About Windward Cay →Find Communities Like This (90-sec quiz)

Good Questions

Windward Cay, frequently asked questions

What are home prices like in Windward Cay?: Windward Cay is in the mid price tier, typically Typically $450K – $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 Windward Cay in?: Windward Cay 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 Windward Cay?: Closest schools include Cape Coral High School (6.4 mi), Heritage Charter Academy of Cape Coral (6.6 mi). Browse all on the schools directory.
What does it cost to own a home in Windward Cay?: For a $650,000 home, estimate roughly $8,450/yr property tax, $7,800-$14,300/yr insurance (incl. flood), and $300-$900/mo HOA. Full breakdown in the SWFL cost cheatsheet.
What amenities does Windward Cay offer?: Windward Cay features Golf. Compare similar communities on the interactive map.