What it really costs to own in Florida.
Woodland Crossings HOA and CDD fees
Wildwood, Sumter County · 34785
Homes in Woodland Crossings (Wildwood) pay a median $150 a year in HOA dues, about $13 a month, based on 29 listings. Half fall between $150 and $150. 100% of listings with a known CDD status (29) report one, with a median $2,430 a year collected on the property tax bill.
What the dues cover
- Maintenance Grounds21% of listings
Amenities listed: Pool, Playground, Pickleball Court(s).
Live inventory
For sale in Woodland Crossings right now
12 active listings








Woodland Crossings cost questions
How much are HOA fees in Woodland Crossings?
Homes in Woodland Crossings (Wildwood) pay a median $150 a year in HOA dues, about $13 a month, based on 29 listings. Half fall between $150 and $150.
Does Woodland Crossings have a CDD?
Yes, most homes. 100% of the 29 listings with a known CDD status report one, and 29 gave an amount: a median $2,430 a year (range $2,430 to $2,856). Listings are a sample, not the district's records, so check the tax bill for the exact home. The CDD is billed on the property tax bill, not by the HOA. Part of it usually pays down bonds that end on a set date, while the operations part continues.
What does it cost each month to own in Woodland Crossings, before the mortgage?
HOA and CDD come to about $215 a month at the medians. Not enough listings reported property tax to include it. 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 Woodland Crossings 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 29 addressesin subdivisions matching “WOODLAND CROSSINGS”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Tillman OaksWildwood · HOA $972/yr
- Highfield at Twisted OaksWildwood · HOA $168/yr · CDD $2,132/yr
- Twisted OaksWildwood · HOA $1,488/yr · CDD $1,960/yr
- Sumter CrossingOxford · HOA $1,200/yr
- Oxford OaksOxford · HOA $743/yr
- Triumph SouthWildwood · HOA $756/yr
- Grand Oaks ManorOxford · HOA $1,800/yr
- BeaumontWildwood · HOA $1,824/yr · CDD $3,105/yr
- Lakeside LandingsOxford · HOA $2,280/yr
- Villages of ParkwoodOxford · HOA $960/yr
- Densan ParkOxford · HOA $1,020/yr
- The VillagesThe Villages · HOA $2,423/yr · CDD $763/yr
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