What it really costs to own in Florida.
Winding Hollow HOA fees
Winter Springs, Seminole County · 32708
Homes in Winding Hollow (Winter Springs) pay a median $575 a year in HOA dues, about $48 a month, based on 7 listings. Half fall between $575 and $600. None of the listings we reviewed report a CDD.
What the dues cover
Amenities listed: Playground.
Live inventory
For sale in Winding Hollow right now
1 active listing
Winding Hollow cost questions
How much are HOA fees in Winding Hollow?
Homes in Winding Hollow (Winter Springs) pay a median $575 a year in HOA dues, about $48 a month, based on 7 listings. Half fall between $575 and $600.
Does Winding Hollow 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 Hollow, before the mortgage?
HOA and property tax come to about $459 a month at the medians (property tax median $4,927 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 Hollow 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 7 addressesin subdivisions matching “WINDING HOLLOW”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- ParkstoneWinter Springs · HOA $1,800/yr
- Jesups Reserve TownhomesWinter Springs · HOA $3,600/yr
- Hickory GroveWinter Springs · HOA $4,272/yr
- Jesups LandingWinter Springs · HOA $2,792/yr
- Mount GreenwoodWinter Springs · HOA $2,280/yr
- SeasonsWinter Springs · HOA $1,656/yr
- Casa Park VillasWinter Springs · HOA $2,484/yr
- DeersongWinter Springs · HOA $1,529/yr
- Tuscany PlaceWinter Springs · HOA $4,740/yr
- Legacy Park ResidentialCasselberry · HOA $2,778/yr
- Wedgewood Tennis VillasWinter Springs · HOA $1,080/yr
- Country ClubWinter Springs · HOA $1,400/yr
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