Costs of owning

What it really costs to own in Florida.

Isleworth HOA fees

Windermere, Orange County · 34786

Homes in Isleworth (Windermere) pay a median $14,688 a year in HOA dues, about $1,224 a month, based on 26 listings. Half fall between $14,688 and $14,688. None of the listings we reviewed report a CDD.

HOA, median
$14,688/yr
About $1,224 a month
CDD, median
None reported
Property tax, median
$33,607/yr
Seller's bill; resets after a sale
Monthly, before mortgage
$4,025
HOA + tax at the medians

What the dues cover

  • Guard - 24 Hour92% of listings
  • Security81% of listings
  • Cable TV77% of listings
  • Internet69% of listings
  • Escrow Reserves Fund62% of listings
  • Maintenance Grounds62% of listings

Amenities listed: Playground, Gated, Cable TV, Security, Optional Additional Fees.

Live inventory

For sale in Isleworth right now

24 active listings

5092 Isleworth Country Club Dr
Active
House for sale
$8,500,000
4 bed5 bath7,100 sqft0.93 acre lot
5092 Isleworth Country Club Dr
Windermere, FL, 34786
Brokered by ISLEWORTH REALTY LLC
4906 Aviva Garden CT
Active
House for sale
$3,850,000
4 bed6 bath6,605 sqft0.26 acre lot
4906 Aviva Garden CT
Windermere, FL, 34786
Brokered by THE SIMON SIMAAN GROUP
9310 Isleworth Gardens Dr
Active
House for sale
$3,595,000
3 bed5 bath4,333 sqft0.26 acre lot
9310 Isleworth Gardens Dr
Windermere, FL, 34786
Brokered by ISLEWORTH REALTY LLC
6126 Payne Stewart Dr
Active
House for sale
$3,250,000
3 bed4 bath2,848 sqft0.29 acre lot
6126 Payne Stewart Dr
Windermere, FL, 34786
Brokered by IRWIN REALTY GROUP LLC
5192 Vardon Dr
Active
House for sale
$19,500,000
6 bed10 bath13,494 sqft2.27 acre lot
5192 Vardon Dr
Windermere, FL, 34786
Brokered by IRWIN REALTY GROUP LLC
5186 Vardon Dr
Active
House for sale
$4,395,000
6 bed6 bath4,739 sqft1.01 acre lot
5186 Vardon Dr
Windermere, FL, 34786
Brokered by ISLEWORTH REALTY LLC
5036 Latrobe Dr
ActiveNew construction
House for sale
$18,750,000
6 bed9 bath15,337 sqft0.69 acre lot
5036 Latrobe Dr
Windermere, FL, 34786
Brokered by ISLEWORTH REALTY LLC
5373 Isleworth Country Club Dr
Active
House for sale
$7,200,000
5 bed6 bath5,993 sqft0.52 acre lot
5373 Isleworth Country Club Dr
Windermere, FL, 34786
Brokered by STOCKWORTH REALTY GROUP
See all 24 Isleworth homes

Isleworth cost questions

How much are HOA fees in Isleworth?

Homes in Isleworth (Windermere) pay a median $14,688 a year in HOA dues, about $1,224 a month, based on 26 listings. Half fall between $14,688 and $14,688.

Does Isleworth 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 Isleworth, before the mortgage?

HOA and property tax come to about $4,025 a month at the medians (property tax median $33,607 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 Isleworth 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 26 addressesin subdivisions matching “ISLEWORTH”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.

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