Windermere, FL
Lakefront estates + golf-country club living, 15 miles west of downtown Orlando.
Data as of 2026-04-01. Refreshed quarterly.
Windermere is a 1.8-square-mile incorporated town surrounded by Orange County subdivisions, sitting on the Butler Chain of Lakes — eleven interconnected lakes that are the recreational center of west Orlando. The town proper is small (under 4,000 residents) but the broader Windermere ZIP code (34786) extends into Isleworth, the Reserve at Lake Butler Sound, and other large-lot subdivisions that share the school zoning.
The buyer pool here is largely high-net-worth — Orlando-area entrepreneurs, athletes (Tiger Woods's former Isleworth residence is the canonical example), and second-home executives from the Northeast. Average lot sizes are 1-3 acres, which by Florida standards is sprawling.
Within Windermere itself, the town has resisted commercial development — there's no Publix or chain restaurant inside the town limits. Day-to-day services are reached by driving 5-10 minutes to Winter Garden or the SR-535 corridor.
What makes it distinctive
Things that move the needle.
Butler Chain of Lakes access
The single biggest value driver. Direct chain-lake access (with a boathouse and a dock that can launch into navigable water) carries an 80-100% premium over off-chain comparables.
Country-club concentration
Isleworth, Bay Hill, Keene's Pointe — three major golf clubs within ten minutes. Initiation + dues are non-trivial; verify HOA mandates before buying inside a club community.
Top-rated schools across the board
Windermere High School + Bridgewater Middle + Sunset Park Elementary all hit GreatSchools 9-10. School-zone borders matter — verify before assuming.
Privacy + estate parcels
Many Windermere properties carry deed restrictions on visibility from the road, photography, and short-term rentals. Worth a deed-review during due-diligence.
Want to buy in Windermere?
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Frequently asked
Common questions about Windermere.
How does Windermere compare to Dr. Phillips?
Dr. Phillips is denser, more service-rich (Restaurant Row is in DrP), and has tighter inventory. Windermere skews larger-lot, more rural-feeling, slightly less walkable, and roughly 20-30% more expensive on a per-square-foot basis.
Is Windermere worth it without Butler Chain access?
Yes — Windermere school zoning + the broader prestige of the town extends value beyond chain-lake parcels. Median home prices in non-chain Windermere subdivisions still run $750K-$1.2M.
What's the property tax burden on a $2M Windermere estate?
Roughly $20-26K/year combining county + town + special assessments, with homestead. Higher if the property's inside a CDD-assessed sub-community.
Data is hand-curated by REHL editors from a mix of public records, MLS feed inputs, and listing aggregator analytics. Refreshed at least quarterly; the "as of" date above is current. Numbers shift constantly in active markets — for the most current view of any specific property, ask the REHL agent we match you with. We aim for honest, not flattering.
School ratings draw from a blend of state assessments and public school-rating databases; verify zoning for your specific address before relying on these scores. Property tax estimates assume primary-residence homestead and standard millage rates as of the publish date.