Costs of owning

What it really costs to own in Florida.

Crestwynd Bay HOA fees

Kissimmee, Osceola County · 34747

Homes in Crestwynd Bay (Kissimmee) pay a median $4,000 a year in HOA dues, about $333 a month, based on 12 listings. Half fall between $4,000 and $4,000. None of the listings we reviewed report a CDD.

HOA, median
$4,000/yr
About $333 a month
CDD, median
None reported
Property tax, median
$3,302/yr
Seller's bill; resets after a sale
Monthly, before mortgage
$609
HOA + tax at the medians

What the dues cover

  • Pool100% of listings
  • Internet83% of listings
  • Maintenance Grounds83% of listings
  • Cable TV75% of listings
  • Trash75% of listings
  • Maintenance Structure67% of listings

Amenities listed: Pool.

Live inventory

For sale in Crestwynd Bay right now

8 active listings

2693 Andros Ln
Active
Townhouse for sale
$300,000
3 bed3 bath1,187 sqft0.03 acre lot
2693 Andros Ln
Kissimmee, FL, 34747
Brokered by AURA HOMES, LLC.
2685 Andros Ln
ActivePrice reduced
Townhouse for sale
$234,000
$31k
3 bed3 bath1,187 sqft0.03 acre lot
2685 Andros Ln
Kissimmee, FL, 34747
Brokered by REAL BROKER, LLC
2691 Andros Ln
ActivePrice reduced
Townhouse for sale
$259,000
$21k
3 bed3 bath1,595 sqft0.04 acre lot
2691 Andros Ln
Kissimmee, FL, 34747
Brokered by KELLER WILLIAMS REALTY AT THE PARKS
7631 Long Island Dr
ActivePrice reduced
Townhouse for sale
$229,000
$26k
3 bed3 bath1,187 sqft0.02 acre lot
7631 Long Island Dr
Kissimmee, FL, 34747
Brokered by ORCHARD BROKERAGE, LLC
7601 Acklins Rd
ActivePrice reduced
Townhouse for sale
$269,000
$46k
3 bed3 bath1,595 sqft0.04 acre lot
7601 Acklins Rd
Kissimmee, FL, 34747
Brokered by LPT REALTY, LLC
2680 Mayaguana St
ActivePrice reduced
Townhouse for sale
$252,000
$21k
3 bed3 bath1,362 sqft0.02 acre lot
2680 Mayaguana St
Kissimmee, FL, 34747
Brokered by LPT REALTY, LLC
2682 Mayaguana St
ActivePrice reduced
Townhouse for sale
$290,000
$3k
3 bed3 bath1,595 sqft0.04 acre lot
2682 Mayaguana St
Kissimmee, FL, 34747
Brokered by FLORIDA HOMES REALTY & MORTGAGE
2626 Andros Ln
ActivePrice reduced
Townhouse for sale
$245,900
$43k
3 bed3 bath1,362 sqft0.02 acre lot
2626 Andros Ln
Kissimmee, FL, 34747
Brokered by TURNKEY HOMES REAL ESTATE CORP
See all 8 Crestwynd Bay homes

Crestwynd Bay cost questions

How much are HOA fees in Crestwynd Bay?

Homes in Crestwynd Bay (Kissimmee) pay a median $4,000 a year in HOA dues, about $333 a month, based on 12 listings. Half fall between $4,000 and $4,000.

Does Crestwynd Bay 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 Crestwynd Bay, before the mortgage?

HOA and property tax come to about $609 a month at the medians (property tax median $3,302 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 Crestwynd Bay 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 12 addressesin subdivisions matching “CRESTWYND BAY”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.

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