What it really costs to own in Florida.
Highland Ridge HOA fees
Winter Garden, Orange County · 34787
Homes in Highland Ridge (Winter Garden) pay a median $1,278 a year in HOA dues, about $107 a month, based on 12 listings. Half fall between $1,260 and $1,320. None of the listings we reviewed report a CDD.
What the dues cover
- Pool50% of listings
- Maintenance Grounds25% of listings
Amenities listed: Pool, Playground.
Live inventory
For sale in Highland Ridge right now
5 active listings
Highland Ridge cost questions
How much are HOA fees in Highland Ridge?
Homes in Highland Ridge (Winter Garden) pay a median $1,278 a year in HOA dues, about $107 a month, based on 12 listings. Half fall between $1,260 and $1,320.
Does Highland Ridge 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 Highland Ridge, before the mortgage?
HOA and property tax come to about $786 a month at the medians (property tax median $8,152 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 Highland Ridge 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 12 addressesin subdivisions matching “HIGHLAND RDG”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Del Webb OasisWinter Garden · HOA $7,710/yr
- Harvest / OvationWinter Garden · HOA $2,490/yr
- Harvest at OvationWinter Garden · HOA $2,550/yr
- Westhaven at OvationWinter Garden · HOA $1,788/yr
- Osprey RanchWinter Garden · HOA $1,152/yr
- Grove Residence and Spa Hotel CondoWinter Garden · HOA $11,698/yr · CDD $2,128/yr
- Grove ResortWinter Garden · HOA $10,849/yr · CDD $2,050/yr
- Grove Resort and SpaWinter Garden · CDD $2,127/yr
- Grove Resort and Spa Hotel CondoWinter Garden · HOA $11,788/yr · CDD $2,128/yr
- Winding BayWinter Garden · HOA $1,217/yr
- Serenade at OvationWinter Garden · HOA $1,920/yr
- Lake Star at OvationWinter Garden · HOA $2,280/yr
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