What it really costs to own in Florida.
Winding Bay HOA fees
Winter Garden, Orange County · 34787
Homes in Winding Bay (Winter Garden) pay a median $1,217 a year in HOA dues, about $101 a month, based on 6 listings. Half fall between $1,212 and $1,224. None of the listings we reviewed report a CDD.
What the dues cover
Amenities listed: Pool, Playground.
Live inventory
For sale in Winding Bay right now
7 active listings
Winding Bay cost questions
How much are HOA fees in Winding Bay?
Homes in Winding Bay (Winter Garden) pay a median $1,217 a year in HOA dues, about $101 a month, based on 6 listings. Half fall between $1,212 and $1,224.
Does Winding Bay 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 Winding Bay, before the mortgage?
HOA and property tax come to about $751 a month at the medians (property tax median $7,790 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 Winding Bay 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 6 addressesin subdivisions matching “WINDING BAY”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Lake Star at OvationWinter Garden · HOA $2,280/yr
- Northlake at OvationWinter Garden · HOA $1,008/yr
- Storey GroveWinter Garden · HOA $2,652/yr
- Harvest at OvationWinter Garden · HOA $2,550/yr
- Osprey RanchWinter Garden · HOA $1,152/yr
- Harvest / OvationWinter Garden · HOA $2,490/yr
- Encore / OvationWinter Garden · HOA $2,700/yr
- Encore at OvationWinter Garden · HOA $2,700/yr
- Westhaven at OvationWinter Garden · HOA $1,788/yr
- WaterleighWinter Garden · HOA $3,060/yr · CDD $2,000/yr
- Del Webb OasisWinter Garden · HOA $7,710/yr
- Serenade at OvationWinter Garden · HOA $1,920/yr
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