Windermere, FL Homes and Real Estate
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.
$710K
Typical home value (Zillow, September 2026)
48
About how many days homes take to go pending (Zillow, September 2026)
11
Connected lakes on the Butler Chain
10–15
Minutes to Disney · 30 to the airport
Living in Windermere
We live in Windermere, and we sell it street by street. The town sits on the Butler Chain of Lakes, eleven connected lakes designated an Outstanding Florida Waterway, and keeps its dirt roads and oak canopy on purpose.
Around the town, gated golf communities like Isleworth and Keene’s Pointe hold some of the most valuable homes in Central Florida. What the area offers: Windermere High, A-rated, and Windermere Preparatory School; lake life on skiable water; and a short drive to the parks and the airport.
The town itself is small on purpose: oak canopy over dirt roads, a little downtown with Friday food trucks, and docks where weekends start with a ski run on Lake Butler. That character is deliberate, and it is a large part of what buyers pay for.
What it does not offer: walkable urban energy, or a way around HOA and club costs in the gated communities. For a real downtown, read our Winter Garden guide.
Windermere home prices and market
Windermere values are holding in 2026, but homes are taking longer to sell and closed prices in the 34786 zip have come off last year’s highs.
Zillow’s typical Windermere value was $709,948 at the end of September 2026, up 0.8 percent over the year, with homes going pending in about 48 days. In the 34786 zip, Redfin’s median sale price over the three months ending September 2026 was $764,775, down 15.5 percent from the same months a year earlier. Homes took 57 median days to sell, up from 45, and 172 homes sold in September.
Windermere market figures
| Measure | Figure | Source |
|---|---|---|
| Typical home value | $709,948 | Zillow, September 2026, up 0.8% in a year |
| Days to pending | About 48 | Zillow, September 2026 |
| Median sale price, 34786 | $764,775 | Redfin, three months to September 2026, down 15.5% in a year |
| Sales, 34786 | 172 | Redfin, September 2026 |
| Median days on market, 34786 | 57 | Redfin, three months to September 2026 |
| Homes with a price drop, 34786 | 38.1% | Redfin, three months to September 2026 |
Our read in the October report: the gated and lakefront segments are still moving, because those buyers are less rate sensitive. The $600,000 to $900,000 band is where a 7.4 percent mortgage rate (Orlando Regional REALTOR Association, September 2026) bites, and where a listing that misses its first two weeks starts chasing the market down.
For context, the Orlando metro median sale price was $399,610 in September 2026, with 5.3 months of supply and an average of 66 days on market (Orlando Regional REALTOR Association). A Zillow typical value and a closed-sale median measure different things, so compare Windermere with its own history rather than with the metro line.
What that means here: if you are selling, price for the market you are in, not the one from spring, because the first fourteen days carry the most weight, and a rate buydown or closing cost credit often nets more than a price cut of the same size. If you are buying, more supply means more choice, so ask for the credit before you ask for the price.
Sources: Zillow Home Value Index, as of September 30, 2026; Redfin housing market data for 34786, three months ending September 2026; Orlando Regional REALTOR Association, September 2026. From our October 2026 market report. Updated October 2026.
Neighborhoods and prices
Six names come up in nearly every Windermere search. Here is the honest one line version of each.
Three of the six are guard gated: Isleworth, Keene’s Pointe and Lake Butler Sound, where custom lakefront and private docks set the top of the market. The other three are where most Windermere searches start: Lakes of Windermere for waterfront without the gate, Summerport for tennis, pickleball and a walkable Publix, and Windermere Trails for the shortest drive to Disney.
| Community | Recent price | Known for |
|---|---|---|
| Isleworth | $4.09M median, 16 sales | Arnold Palmer golf, 24/7 guard gate, celebrity pedigree |
| Keene’s Pointe | $1.65M median, 61 sales | Nicklaus golf, Butler Chain access, 14 villages |
| Lake Butler Sound | $1.68M median, 7 sales (The Reserve at Lake Butler Sound) | Guard gated custom lakefront, private docks |
| Lakes of Windermere | $540K median, 41 sales | Waterfront options without the gate |
| Summerport | $559K median, 36 sales | Tennis, pickleball, walkable Publix |
| Windermere Trails | $622K median, 28 sales | Pool, splash pad, closest to Disney |
Windermere homes for sale
8291 Procida Isle Ln is our Windermere listing: $775,000, four bedrooms, a saltwater pool and solar.
Windermere schools
Windermere High has earned an A from the Florida Department of Education in every graded year since its first two, with a 99.5 percent graduation rate in 2024–25 (Orange Observer, September 2026), and Windermere Preparatory School anchors the private side. Zones follow the address rather than the town name, so confirm any specific home with the Orange County Public Schools locator before you write an offer, or ask us about a school zone and we will check it with you.
Weekends run on the water: skiing on Lake Butler, sunset docks, and the little downtown’s Friday food trucks.
Commute times from Windermere
Disney is 10 to 15 minutes away and the airport about 30, close enough for a daily drive to the parks or a regular flight without giving up the lakes. That combination, lakes plus schools plus proximity, is what holds value here through every cycle.
| Destination | Drive |
|---|---|
| Disney | 10 to 15 minutes |
| Orlando International Airport | About 30 minutes |
What a Windermere seller says
“Such an amazing team. Everything was so seamless and well prepared. They felt more like family than an agent.”
Windermere market reports
Every monthly report that covers Windermere, newest first. All market reports
- West Orlando Market, October 2026 · October 2026
- West Orlando Market, September 2026 · September 2026
Windermere real estate questions
What buyers ask us most. Something else on your mind? Call (813) 992-3073.
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 typical value (Zillow) around $710,000 as of September 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 in Windermere cost in 2026?
The typical value (Zillow) for Windermere is about $710,000 as of September 2026. In the 34786 zip, the median closed sale was $764,775 over the three months ending September 2026 (Redfin). Inside the gates, over the twelve months to October 2026, Keene’s Pointe sold at a median of $1.65 million on 61 sales and Isleworth at a median of about $4.1 million on 16 sales (Stellar MLS).
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, and membership structures and fees change, so we confirm current requirements with the club before our clients write an offer. The details are in our Isleworth and Keene’s Pointe guides.
Buying or selling on the lakes?
We live here. Ask us anything, from dock permits to which gate guards wave you through fastest. Read how we approach selling a home in Windermere and buying a home in Windermere.