What it really costs to own in Florida.
Cypresswood Enclave HOA fees
Winter Haven, Polk County · 33884
Homes in Cypresswood Enclave (Winter Haven) pay a median $5,196 a year in HOA dues, about $433 a month, based on 6 listings. Half fall between $5,196 and $5,220. None of the listings we reviewed report a CDD.
What the dues cover
- Private Road100% of listings
- Pool83% of listings
- Guard - 24 Hour83% of listings
- Maintenance Grounds67% of listings
- Common Area Taxes50% of listings
- Escrow Reserves Fund33% of listings
Live inventory
For sale in Cypresswood Enclave right now
4 active listings
Cypresswood Enclave cost questions
How much are HOA fees in Cypresswood Enclave?
Homes in Cypresswood Enclave (Winter Haven) pay a median $5,196 a year in HOA dues, about $433 a month, based on 6 listings. Half fall between $5,196 and $5,220.
Does Cypresswood Enclave 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 Cypresswood Enclave, before the mortgage?
HOA and property tax come to about $642 a month at the medians (property tax median $2,507 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 Cypresswood Enclave 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 6 addressesin subdivisions matching “CYPRESSWOOD ENCLAVE”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.
Compare nearby communities
- Cypresswood Patio HomesWinter Haven · HOA $1,560/yr
- CypresswoodWinter Haven · HOA $1,825/yr
- Garden Grove OaksWinter Haven · HOA $780/yr
- Seasons at Shores of Lake DellDundee · HOA $1,212/yr
- Florida Highland CoWinter Haven · HOA $1,224/yr
- Seasons at Bella VistaDundee · HOA $1,348/yr
- Inman GrovesWinter Haven · HOA $593/yr
- Orchid Springs VillWinter Haven · HOA $5,382/yr
- Cypress LandingWinter Haven · HOA $1,000/yr
- Planters WalkWinter Haven · HOA $95/yr
- Sol VistaDundee · HOA $1,776/yr
- Vienna SquareWinter Haven · HOA $4,320/yr
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