Windermere, Florida · Real Estate & Relocation Guide

Windermere, FL: a small town on thirteen lakes.

The Butler Chain at the end of the street. A Friday farmers market in Town Square. Golf, gated estates and the parks about 15 to 20 minutes away. Here is how to find the Windermere neighborhood that fits the way you want to live.

1925Town of Windermere incorporated
13Connected lakes on the Butler Chain
5,000+Acres of water on the chain
34786Main zip code for Windermere homes
Why people move here

A lake town that decided to stay small.

Windermere was platted in 1887 on a strip of land between the lakes and named for Lake Windermere in England's Lake District. It became a town in 1925, and it has worked hard ever since to keep its small-town feel. The Town itself is home to about 3,000 people.

Here is the part most out-of-state buyers miss. A Windermere mailing address and the Town of Windermere are not the same thing. The 34786 zip code covers a much bigger area, including gated golf communities, Butler Chain estates and newer neighborhoods outside Town limits. Rules, taxes, services and even lake access can change from one side of a street to the other.

That is where a local guide earns their keep. I check every address for Town or county, HOA and water access before you fall in love with it.

Windermere is where my clients land when the lake, the golf course and the parks all have to be close.

Windermere at a glance

🛥 The Butler Chain of Lakes, Florida's first lake system named an Outstanding Florida Water (1985)

🏰 Roughly 15 to 20 minutes to Walt Disney World

⛳ Golf and club communities like Isleworth and Keene's Pointe

🥕 Friday farmers market in downtown Town Square

🏫 Served by Orange County Public Schools, an A-rated district

🏠 Lakefront estates, guard-gated communities, single-family neighborhoods and townhomes

Proximity to the magic

Drive times from Windermere

Windermere sits just north of Walt Disney World, with the 429 to the west and Dr. Phillips to the east. You get quiet lake streets at home and the parks, Restaurant Row and the airport within reach.

  • Walt Disney World ~15 to 20 min
  • Dr. Phillips and Restaurant Row ~10 to 15 min
  • Downtown Winter Garden ~15 min
  • Ocoee ~15 min
  • Downtown Orlando ~25 to 30 min
  • Orlando International Airport (MCO) ~30 to 35 min

Approximate off-peak drive times from downtown Windermere. Times vary a lot across the 34786 zip code, and two-lane roads around the lakes slow down at rush hour. Send me your work address and I will map your real commute from any street before you choose.

Where to live

Find your part of Windermere

Windermere has 85 communities, and they live very differently. Start with the lifestyle, then pick the community. Each link opens that community's guide with live listings.

Golf + club

Golf & Country Club

Windermere's best-known golf communities, with club amenities, lakes and some of the most private streets in Central Florida.

Best for: upsizers and executives relocating who want a club lifestyle close to home.

Low maintenance

Townhomes

Townhome communities that keep the Windermere schools and location without the yard work.

Best for: downsizers and first-time Windermere buyers.

Next door

Winter Garden, Ocoee & Oakland

Windermere borders Winter Garden, and Ocoee and Oakland are a short drive north. If you are comparing West Orange towns, start with these guides.

Best for: buyers deciding between West Orange towns.

Schools

Orange County Public Schools

Windermere is served by Orange County Public Schools, which earned an A as a district in 2024-25. Because 34786 covers such a big area, zoned schools vary a lot by neighborhood.

Elementary schools serving Windermere addresses include Windermere, Sunset Park, Thornebrooke and Castleview. Middle schools include Bridgewater, Gotha and Horizon West. High schools include Windermere High, which opened in 2017, along with Olympia and West Orange. Windermere Preparatory School is a private option nearby. Always confirm zoning for a specific home before you write an offer.

Quick notes

School grades change every year. Check the Florida Department of Education's latest release for each school.

OCPS adjusts boundaries as West Orange grows, so a neighbor's school is not always your school.

I check the zoned schools on every home I show you.

Life in Windermere

What a weekend looks like

🛥 The Butler Chain

Thirteen connected lakes and more than 5,000 acres of water for boating, skiing, fishing and paddleboarding, with public ramps at nearby county parks.

🥕 Friday Farmers Market

Local growers, food and makers set up every Friday in Town Square in downtown Windermere.

🍔 Food Truck Night

A monthly evening in Town Square where neighbors bring chairs and dogs.

🏃 Run Among the Lakes

The Town's 5K and 10K race through the lake streets, one of Windermere's long-running traditions.

🌳 Parks & Preserves

Central Park, Lake Down Park and Town Square in town, plus the trails at Tibet-Butler Preserve a few minutes south.

🍽 Dr. Phillips Dining

Restaurant Row on Sand Lake Road is about 10 to 15 minutes east for date night and client dinners.

The numbers

Windermere market snapshot

A townhome near the 535 and a guard-gated estate on Lake Butler are two different markets, so one overall median mostly tracks which homes happened to close. Here is each type of home on its own, from Stellar MLS, for the 12 months ending September 30, 2026.

$315,000Condos, median sale price29 closed sales, 38 days on market, 97% of list price. Down 0.5% from $316,500 the year before.
$390,000Townhomes, median sale price104 closed sales, 38 days on market, 98% of list price. Down 5.8% from $414,000 the year before.
$970,000Single-family homes, median sale price529 closed sales, 35 days on market, 97% of list price. Down 0.5% from $975,000 the year before.

September 2026: single-family homes sold at an $800,000 median across 35 sales, down 23.8% from $1,050,000 across 53 sales in September 2025. Most of that is the mix: 7 single-family homes over $1.5 million closed that month, against 17 a year earlier. The same month had 2 condos and 11 townhomes close, too few for a monthly median. Property type is how the listing agent entered it in Stellar MLS. 663 closed sales in all in the 34786 zip code over the 12 months. Each community guide has its own market card. Stellar MLS figures as of the dates shown, deemed reliable but not guaranteed. For live comps on a specific Windermere home, request a custom report.

Live MLS listings

Windermere homes for sale right now

Straight from the MLS. Save the search and get new Windermere listings the day they hit.

Start of list of properties

Nearby Communities

Windermere not quite the fit? These are right next door.

Is Windermere your fit?

Three kinds of buyers land here

Moving from out of state

You want the lake, the schools and the parks close, and you are doing all of it from a laptop. Windermere has 85 communities and two very different kinds of address. I have driven these streets, and I can narrow it to the three that fit before you book the flight.

Need more room

You have outgrown the first house and want a bigger yard, a gate, a community pool and the school zone you want, without giving up the drive to work. Windermere's gated communities are built for that next step.

Ready for less house

Less lawn, more life. A townhome or a smaller lake home near Town Square, with the farmers market on Friday and Restaurant Row a short drive away.

Free guides

Buying or selling in Windermere?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Windermere works, from Town versus county addresses to what to verify on HOA, lake access and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Windermere, FL FAQ

How far is Windermere from Walt Disney World?

Most Windermere neighborhoods are about 15 to 20 minutes from Walt Disney World off-peak. Communities on the south and west side of the 34786 zip code are usually the quickest.

What is the median home price in Windermere, FL?

It depends on the type of home, so I report each one separately. Per Stellar MLS, for the 12 months ending September 30, 2026, in the 34786 zip code condos sold at a $315,000 median across 29 sales, townhomes at $390,000 across 104 sales, and single-family homes at $970,000 across 529 sales. Compared with the year before: condos down 0.5%, townhomes down 5.8% and single-family homes down 0.5%. A single overall median would mostly track how many lakefront and golf estates happened to close.

What do homes sell for in different Windermere neighborhoods?

Over the 12 months ending September 30, 2026, among Windermere communities with 5 or more closed sales of a type, Stellar MLS medians in the condo and townhome communities ranged from $305,000 at Lakeside at Lakes of Windermere to $437,500 at Vineyards, and in the single-family neighborhoods from $500,000 at Wickham Park to $4,350,000 at Isleworth. Keene's Pointe was the busiest, with 62 closings at a $1,762,500 median. Every community guide below has its own Stellar MLS market card.

Is a Windermere address the same as the Town of Windermere?

No. The Town of Windermere is a small incorporated town of about 3,000 residents. The 34786 zip code is much larger and includes many neighborhoods in unincorporated Orange County. Taxes, rules, services and lake access can differ, so confirm the jurisdiction for every address.

What is the Butler Chain of Lakes?

The Butler Chain is 13 connected lakes, including Lake Butler and Lake Down, with more than 5,000 acres of water. In 1985 it became the first lake system in Florida designated an Outstanding Florida Water.

What zip code is Windermere, FL?

Most Windermere homes use the 34786 zip code. Some nearby lake and Dr. Phillips area homes use 32836, so confirm the city and county on each address.

What schools serve Windermere?

Orange County Public Schools serves Windermere and earned an A as a district in 2024-25. Zoned schools include Windermere, Sunset Park and Thornebrooke elementary, Bridgewater and Gotha middle, and Windermere, Olympia and West Orange high schools, depending on the address. Verify with the OCPS School Locator.

Does Windermere have golf communities?

Yes. Isleworth, Keene's Pointe and Windermere Club are among the best-known golf and club communities in the area. Membership and amenities vary by community.

When does the Windermere farmers market happen?

The Windermere Farmers Market is held on Fridays in Town Square in downtown Windermere. The Town also hosts a monthly food truck night.

Your next step

Get your Windermere Move Plan

Give me 30 minutes, tell me your timeline and how you want to live. I will send back:

  • The 3 Windermere communities that fit you best
  • What homes there are actually closing for, straight from Stellar MLS
  • Town or county, lake access and zoned schools for each one
  • Your real commute, mapped from those streets

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Information deemed reliable but not guaranteed. Drive times are approximate. Market data from Stellar MLS as of the dates shown. Buyers should verify Town or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. Community listing links show live MLS results and may include nearby homes. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.