What it really costs to own in Florida.
Oakland Park HOA fees
Winter Garden, Orange County · 34787
Homes in Oakland Park (Winter Garden) pay a median $2,500 a year in HOA dues, about $208 a month, based on 16 listings. Half fall between $2,500 and $4,276. None of the listings we reviewed report a CDD.
What the dues cover
- Pool63% of listings
- Maintenance Grounds25% of listings
Amenities listed: Pool, Clubhouse, Playground, Park, Trail(s).
Live inventory
For sale in Oakland Park right now
12 active listings
Oakland Park cost questions
How much are HOA fees in Oakland Park?
Homes in Oakland Park (Winter Garden) pay a median $2,500 a year in HOA dues, about $208 a month, based on 16 listings. Half fall between $2,500 and $4,276.
Does Oakland Park 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 Oakland Park, before the mortgage?
HOA and property tax come to about $905 a month at the medians (property tax median $8,363 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 Oakland Park 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 16 addressesin subdivisions matching “OAKLAND PARK”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Grove / OaklandOakland · HOA $1,800/yr
- Lakeview ReserveWinter Garden · HOA $800/yr
- Westside TownhomesWinter Garden · HOA $728/yr
- Briley FarmOakland · HOA $1,800/yr
- Longleaf / OaklandOakland · HOA $5,106/yr
- Johns LandingOakland · HOA $1,150/yr
- Townhomes Winter GardenWinter Garden · HOA $5,088/yr
- Southern Pines CondoWinter Garden · HOA $5,424/yr
- Cypress ReserveWinter Garden · HOA $900/yr
- Hull Island / OaklandOakland · HOA $1,980/yr
- Johns CoveOakland · HOA $2,077/yr
- Black Lake ParkWinter Garden · HOA $1,480/yr
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