Costs of owning

What it really costs to own in Florida.

Windward Square HOA fees

Winter Park, Seminole County · 32792

Homes in Windward Square (Winter Park) pay a median $1,186 a year in HOA dues, about $99 a month, based on 9 listings. Half fall between $1,176 and $1,186. None of the listings we reviewed report a CDD.

HOA, median
$1,186/yr
About $99 a month
CDD, median
None reported
Property tax, median
$4,131/yr
Seller's bill; resets after a sale
Monthly, before mortgage
$443
HOA + tax at the medians

What the dues cover

  • Pool78% of listings
  • Maintenance Grounds67% of listings
  • Private Road33% of listings
  • Recreational Facilities33% of listings
  • Common Area Taxes22% of listings
  • Management22% of listings

Amenities listed: Pool, Clubhouse, Gated, Playground, Recreation Facilities, Tennis Court(s).

Live inventory

For sale in Windward Square right now

3 active listings

2302 Barbados Dr
ActivePrice reduced
Townhouse for sale
$275,000
$20k
2 bed2 bath1,544 sqft0.09 acre lot
2302 Barbados Dr
Winter Park, FL, 32792
Brokered by KELLER WILLIAMS REALTY AT THE PARKS
2275 Island Run
Active
Townhouse for sale
$299,990
3 bed2 bath1,467 sqft0.10 acre lot
2275 Island Run
Winter Park, FL, 32792
Brokered by U KEY REALTY
2487 Harbour Way
ActivePrice reduced
Townhouse for sale
$270,000
$30k
3 bed3 bath1,803 sqft0.09 acre lot
2487 Harbour Way
Winter Park, FL, 32792
Brokered by LOKATION
See all 3 Windward Square homes

Windward Square cost questions

How much are HOA fees in Windward Square?

Homes in Windward Square (Winter Park) pay a median $1,186 a year in HOA dues, about $99 a month, based on 9 listings. Half fall between $1,176 and $1,186.

Does Windward Square have a CDD?

None of the listings we reviewed report a CDD. Check the tax bill on any home you're serious about: a CDD shows up there as a separate assessment.

What does it cost each month to own in Windward Square, before the mortgage?

HOA and property tax come to about $443 a month at the medians (property tax median $4,131 a year). Insurance and the mortgage come on top. Property tax resets after a sale under Florida's homestead rules, so a buyer's bill can be higher than the seller's.

Where do these numbers come from?

Stellar MLS via Repliers listings in Windward Square from January 2026 to October 2026: homes for sale now plus closed sales in that period, one data point per address (rentals excluded). Fees are converted to annual figures. Individual homes vary by association and home type, so confirm the exact fee on any home before you make an offer.

Source: Stellar MLS via Repliers, January 2026 to October 2026. Medians from 9 addressesin subdivisions matching “WINDWARD SQUARE”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.

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