What should I know about HOAs in Clermont, Winter Garden, and Windermere?

Want the 411 on HOAs? Get the facts about Home Owners Associations' fees, rules, and resale impact across the Clermont, Winter Garden, and Windermere communities.

BUYING A HOMEGENERAL REAL ESTATE

Eric Stalnaker

9/23/20251 min read

HOAs—some buyers love them, others break out in hives. Central Florida has them everywhere, but not all are created equal.

Here’s what you’re paying for:

Basic HOAs (Minneola, Groveland): Often around $75-$125/month, covering community maintenance for signage and common areas.
Mid-range HOAs (Clermont, Winter Garden): $150–$250/month for pools, playgrounds, or gated security.
Luxury HOAs (Windermere, Montverde): $350–$600+ for resort-style amenities, landscaping, and sometimes lake access.

Pros:

Maintained neighborhoods protect property values.
Amenities add lifestyle value (and resale appeal).
Uniform standards keep curb appeal consistent.

Cons:

Rules can be strict—painting your door blue might require an act of Congress.
Assessments can pop up if communities need major repairs.
Investor restrictions might limit renting flexibility.
Some "Watch-Dog" neighbors

2026 trends:
Buyers are more HOA-aware than ever. Communities with strong management and transparent budgets are selling faster. Those with fee creep or poor communication? Not so much.

Bottom line:
HOAs aren’t bad—they’re just a trade-off. Know the fees, read the rules, and make sure the community fits your lifestyle before you sign.

Want a list of Central Florida neighborhoods with reasonable HOA fees and top resale potential? I’ll send you my curated local breakdown.