Windermere, Florida.
Eleven lakes, guard gates, A-rated schools, and fifteen minutes to Disney. Windermere is where we live, and the market we know at the street level.
Median $714K · Pending in ~29 days · Updated August 2026
Windermere sits on the Butler Chain of Lakes, eleven connected lakes designated an Outstanding Florida Waterway. The town itself keeps dirt roads and oak canopy on purpose. Around it, the gated golf communities hold some of the most valuable homes in Central Florida.
Who it fits: families anchored to Windermere High and Windermere Prep, executives who want lake life within a short drive of the parks and the airport, and buyers who treat a home as a long term asset. Who it does not fit: anyone who resents HOA structure or needs walkable urban energy. That is Winter Garden's job.
The communities that matter.
Six names come up in nearly every Windermere search. Here is the honest one line version of each.
| Community | Range | Known For |
|---|---|---|
| Isleworth | $2.8M to $14M+ | Arnold Palmer golf, 24/7 guard gate, celebrity pedigree |
| Keene's Pointe | $1.3M to $7.5M | Nicklaus golf, Butler Chain access, 14 villages |
| Lake Butler Sound | $2.5M to $12M+ | Guard gated custom lakefront, private docks |
| Lakes of Windermere | ~$762K median | Waterfront options without the gate |
| Summerport | ~$517K median | Tennis, pickleball, walkable Publix |
| Windermere Trails | ~$540K median | Pool, splash pad, closest to Disney |
Why families stay.
Windermere High is A-rated with a graduation rate near 99 percent, and Windermere Preparatory School anchors the private side. Weekends run on the water: skiing on Lake Butler, sunset docks, and the little downtown's Friday food trucks.
Disney is 10 to 15 minutes. The airport is 30. That combination, lakes plus schools plus proximity, is what holds value here through every cycle.
What buyers ask us.
Is Windermere a good place to live?
It combines the Butler Chain of Lakes, A-rated schools including Windermere High, and a 10 to 15 minute drive to Disney. The tradeoffs are price, with a median around $714,000 as of mid 2026, and HOA or club costs in the gated communities. For buyers who can carry it, it is one of the strongest long term markets in Central Florida.
How much does a home here cost in 2026?
The typical Windermere value is about $714,000. Non gated neighborhoods run roughly $500,000 to $760,000, Keene's Pointe has a median near $2.1 million, and Isleworth runs from about $2.8 million to well past $10 million.
What is the Butler Chain of Lakes?
Eleven connected lakes designated an Outstanding Florida Waterway. Homes with direct access, private docks and skiable water carry some of the highest premiums in the metro, and pricing depends heavily on which lake and which shoreline. That nuance is exactly what we advise on.
Do Isleworth and Keene's Pointe require club membership?
Both are built around private golf clubs. Membership structures and fees change, so we confirm current requirements with the club before our clients write an offer.
Buying or selling on the lakes?
We live here. Ask us anything, from dock permits to which gate guards wave you through fastest.