HOA Communities in Windermere, Florida (2026)

Windermere, Florida has 2 HOA communities listed on HOA's HUB, with monthly dues ranging from $275 to $300 and a median of $288. That places Windermere slightly below the state average for Florida. The local mix skews toward a mix of single-family homes and condominiums. Most communities here (100%) are pet-friendly with rental-friendly bylaws in the majority of associations.

Windermere is home to 2 tracked HOA communities in Windermere County. Across the city, monthly HOA fees span $275 to $300 (median $288). The most common shared amenities across Windermere HOAs are Walking Trails, Parks, Pool. That is roughly 12% below the Florida statewide median of $326. Among the higher-profile associations tracked here is Isleworth Community Association with monthly dues near $300.

Windermere HOA Market Snapshot

Communities
2
tracked
Median Fee
$288/mo
avg $288/mo
Fee Range
$275–$300
monthly
Pet Friendly
100%
2 of 2
Rentals OK
100%
2 of 2
Airbnb OK
50%
1 of 2

Most Common Amenities

Walking Trails (1)Parks (1)Pool (1)Playground (1)

Where Windermere Is on the Map

Windermere, Florida is located at approximately 28.501, -81.535. The map below shows the surrounding area, including neighborhoods where the HOA communities listed on this page are located.

Frequently Asked: HOAs in Windermere, Florida

How big is the HOA market in Windermere, Florida?

HOA's HUB tracks 2 HOA communities in Windermere, Florida across 1 county.

How much do HOA dues cost in Windermere?

The median monthly HOA fee in Windermere is approximately $288 (range $275–$300). Fees vary by amenity package, building age, and whether the community is single-family, condo, or townhome.

Is Windermere in Windermere County?

Windermere is located primarily in Windermere County, Florida.

What amenities do Windermere HOA communities typically offer?

Across the 2 Windermere communities we track, the most frequently offered amenities are Walking Trails, Parks, Pool, Playground. Higher-fee associations often include more of these; simpler communities tend to offer fewer.