What it really costs to own in Florida.
Waterside HOA fees
Winter Garden, Orange County · 34787, 34761
Homes in Waterside (Winter Garden) pay a median $2,580 a year in HOA dues, about $215 a month, based on 5 listings. Half fall between $292 and $2,580. None of the listings we reviewed report a CDD.
What the dues cover
- Common Area Taxes20% of listings
- Pool20% of listings
- Maintenance Grounds20% of listings
- Recreational Facilities20% of listings
Amenities listed: Clubhouse, Fitness Center, Playground, Pool, Recreation Facilities.
20% 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 Waterside right now
6 active listings
Waterside cost questions
How much are HOA fees in Waterside?
Homes in Waterside (Winter Garden) pay a median $2,580 a year in HOA dues, about $215 a month, based on 5 listings. Half fall between $292 and $2,580.
Does Waterside 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 Waterside, before the mortgage?
HOA and property tax come to about $915 a month at the medians (property tax median $8,394 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 Waterside 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 5 addressesin subdivisions matching “WATERSIDE”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Waterside / Johns LakeWinter Garden · HOA $2,580/yr
- TwinwatersWinter Garden · HOA $2,208/yr
- Carriage Pointe A-I and LWinter Garden · HOA $1,084/yr
- Hickory HammockWinter Garden · HOA $2,823/yr
- Alexander RidgeWinter Garden · HOA $2,532/yr
- Stone CreekWinter Garden · HOA $548/yr
- Belle MeadeWinter Garden · HOA $2,000/yr
- Stoneybrook WestWinter Garden · HOA $2,920/yr · CDD $775/yr
- Johns CoveOakland · HOA $2,077/yr
- Johns LandingOakland · HOA $1,150/yr
- Oakland TrailsOakland · HOA $1,260/yr
- Oakland TrlsOakland · HOA $1,270/yr
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