What it really costs to own in Florida.
Windsor Hills HOA fees
Kissimmee, Osceola County · 34747
Homes in Windsor Hills (Kissimmee) pay a median $2,060 a year in HOA dues, about $172 a month, based on 45 listings. Half fall between $2,050 and $4,908. None of the listings we reviewed report a CDD.
HOA by home type
| Single-family homes | $2,050/yr | 27 listings |
| Townhomes and villas | $2,096/yr | 14 listings |
| Condos | $4,247/yr | 4 listings |
Condos and townhomes usually pay more because their dues cover the building, roof or exterior insurance.
What the dues cover
- Guard - 24 Hour80% of listings
- Pool69% of listings
- Cable TV67% of listings
- Maintenance Grounds56% of listings
- Internet49% of listings
- Trash49% of listings
Amenities listed: Fitness Center, Gated, Playground, Pool, Tennis Court(s), Clubhouse.
82% of listings report a second association (often a master HOA). The figures above don't include that second fee, so the total can be higher.
Live inventory
For sale in Windsor Hills right now
44 active listings
Windsor Hills cost questions
How much are HOA fees in Windsor Hills?
Homes in Windsor Hills (Kissimmee) pay a median $2,060 a year in HOA dues, about $172 a month, based on 45 listings. Half fall between $2,050 and $4,908.
Does Windsor Hills 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 Windsor Hills, before the mortgage?
HOA and property tax come to about $717 a month at the medians (property tax median $6,546 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 Windsor Hills 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 45 addressesin subdivisions matching “WINDSOR HILLS”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Ventura at Windsor Hills CondoKissimmee · HOA $4,248/yr
- Crestwynd BayKissimmee · HOA $4,000/yr
- Rolling Hills EstatesKissimmee · HOA $635/yr
- Formosa ValleyKissimmee · HOA $4,308/yr
- Summerville ResortKissimmee · HOA $6,300/yr
- Formosa GardensKissimmee · HOA $1,500/yr
- OakwaterKissimmee · HOA $5,940/yr
- Oakwater CondoKissimmee · HOA $5,940/yr
- Lake Wilson ReserveKissimmee · HOA $2,520/yr
- Four Seasons at OrlandoKissimmee · HOA $4,884/yr · CDD $3,612/yr
- Wyndham PalmsKissimmee · HOA $3,258/yr
- Wyndham Palms CondoKissimmee · HOA $4,044/yr
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