Living in Windermere, FL: Who It Fits, and Who Should Look Elsewhere

Photo: Town of Windermere, Florida, Public domain, via Wikimedia Commons

Windermere is two things that share a name. The Town of Windermere is a small lakefront place of a few thousand people with dirt roads, a 1980 median build year and about twenty sales a year. The Windermere address is 34786, a zip code that runs from Isleworth and Keene's Pointe across the Horizon West line to $390,000 townhomes, and it sells several hundred homes a year. Almost everything written about living here describes the first and prices the second, which is why this page separates them.

The Town of Windermere is a small incorporated town on the Butler Chain of Lakes, and the population and income figures here describe that town. The listing and sales figures describe every home with a Windermere address, which is zip code 34786 and reaches well into Horizon West, so most of what sells as Windermere is outside the town limits.

Who Windermere Fits, and Who It Doesn't

Strong fit: buyers from about $1 million up who want lakefront, acreage or a gated estate community, because that is what the name actually stands for: single-family houses here closed at a median of about $966,000 last year, the 85 lakefront sales ran at a median of $2,100,000, and Keene's Pointe alone closed more than 50; families who want the Windermere address and its school zones at a Horizon West price, since Summerport, Lakes of Windermere and Windermere Trails put a house under $700,000 and Wickham Park a townhome under $500,000, provided they understand that is not the town; buyers who want choice at the top end, because more homes on an acre or more sold here in the last year than in Winter Garden or Dr. Phillips.

Weaker fit: anyone who expects the town for under $800,000, because the old core closed twenty-one homes at $890,000 and most of them are 1970s and 1980s houses that need work; buyers who want new construction, since only a few dozen new homes closed here in a year, most of them in the Palms at Windermere; daily commuters to downtown Orlando or the east side, because the mean commute is the longest of the three towns on this page and the Butler chain sits between here and everything; and anyone who assumes a 34786 address puts them in the Town of Windermere, because it usually does not, and the taxes, roads and services differ across that line.

Still deciding between towns? We pulled the closed sales around a $1,000,000 budget and put Windermere side by side with its neighbors: what $1,000,000 actually buys in each. Square footage, bedrooms, year built, and how many came with a pool.

Where Is Windermere, and What Makes It Different?

Windermere sits in southwest Orange County on the Butler Chain of Lakes, west of Dr. Phillips and south of Winter Garden, with the Horizon West villages spreading out to its west and south. The town is a small incorporated place with its own rules about roads and lots; the address is the 34786 zip code that surrounds it. The mean commute is 30.9 minutes, longer than either Winter Garden or Dr. Phillips, because there is no highway through here and the lakes force every trip around them. The Census population has fallen since 2019, but that count covers only the small town, while most homes sold with a Windermere address sit outside it.

Windermere Housing Market Snapshot (2026)

Over the last twelve months 652 homes sold in Windermere at a median of $789,250, down 6.0% against the twelve months before. Per square foot, which strips out any change in the size of what sold, it was about flat. In September 2026, 45 homes closed at a median of $632,000 and the typical one went under contract in 32 days. One month is too small a sample to read a direction from, which is why the twelve-month figure leads here. There are 221 active residential listings as of October 23, 2026, with a median asking price of $1,220,000, or $350 per square foot.

Wondering whether it is a buyer's or seller's market around Windermere? We publish that answer for Orange County as a whole, from current MLS data: Is Orange County a buyer's or seller's market?

New Construction and Resale Are Not the Same Market

Every price figure quoted for Windermere mixes brand new homes with existing ones. Split apart, the last twelve months looked like this.

The new construction row rests on fewer than 50 sales in at least one of the two years, so read that change as noise rather than a trend.

Best Neighborhoods in Windermere, FL: Communities to Know

Windermere is one address and four markets, and which one a house sits in sets its price: a square foot in Isleworth sold for more than three times what one did on the Horizon West side.

• The Town of Windermere, the original lakefront village on the Butler Chain, unpaved streets and 1970s and 1980s homes on large lots: 21 closings over the last twelve months at a median of $890,000 and a 1980 median build year, and the lakefront lots here and around the chain are where the town's real money sits
• The gated estate communities, Isleworth, Keene's Pointe, Lake Butler Sound, Waterstone and Glenmuir: Keene's Pointe closed 47 at $1,625,000 plus eleven more under two other Keene's Pointe plat labels, seven of them at $3,840,000, Isleworth 12 at $4,093,750 and Waterstone 7 at $1,500,000, and across the whole address the 76 sales on an acre or more ran at $1,963,000
• The Horizon West side with a Windermere address, Summerport, Lakes of Windermere, Windermere Trails, Westside Village and Windermere Terrace, all outside the town limits: typical sales ran from about $560,000 in Summerport to about $675,000 in Westside Village, most built between 2005 and 2018, and the pace varies by community, from about two weeks to contract in Summerport to more than ten weeks in Windermere Trails and Westside Village
• Townhomes and condos, Wickham Park, Preston Square and the Lakeside condos: 103 townhomes closed at a median of $390,000 and 29 condos at $315,000, which is about a fifth of everything that sold as Windermere and the reason the headline median sits so far below what a house here costs

Ask which side of the town line a listing sits on before you ask anything else. The address has one median, a single-family house has a higher one, and the median in the town itself is somewhere the portals cannot compute because about twenty sales is not a sample.

The 15 communities in Windermere where the most homes have sold over the last twelve months, each with its own page:

• Keene's Pointe
• Summerport
• Palms at Windermere
• Lake Sawyer South
• Windermere Town
• Isleworth
• Lake Burden South
• Silver Woods
• Westside Village
• Preston Square
• Ashlin Park
• Windermere Terrace
• Providence
• Tildens Grove
• Waterstone

Another 97 Windermere communities have their own page too. You can also browse every Windermere listing in one place.

Windermere vs. Winter Garden vs. Dr. Phillips: The Honest Comparison

Winter Garden is the neighbor that shares the Horizon West growth without the estate tier, at a much lower asking median and per square foot. Dr. Phillips is the closer comparison for the top of this market: established, on the same chain of lakes, a shorter commute, and an asking median that sits under Windermere's because it has no Isleworth. Windermere is the most expensive of the three on asking price and asking price per square foot, and the name itself is part of what buyers pay for.

Schools, Commute, and Day-to-Day Life

Orange County Public Schools serves the city, and assignment varies by address rather than by city name, so confirm the zoning for the specific property before you buy on a school reputation.

Mean travel time to work is 30.9 minutes, against 28.5 from Winter Garden.

Is Windermere, FL Safe?

Windermere has no municipal police agency reporting usable figures to the FBI, so there is no city-level crime rate to publish here, and inventing one would be worse than saying so. The nearest available figure belongs to the Orange County Sheriff's Office, whose reported violent crime rate is 522.2 per 100,000 residents against 323.5 for Florida as a whole. That is a county-wide figure covering unincorporated areas rather than Windermere itself, so read it as context for the wider area and not as a measurement of this town.

Figures are reported offenses from the FBI Crime Data Explorer for the Orange County Sheriff's Office (ORI FL0480000), 2022, the most recent year that agency reported in a usable form. Reporting years differ between agencies, so this is compared to the Florida rate for the same year and is not comparable to another town's page.

Cost of Living in Windermere, FL

Housing is the line that moves a Central Florida budget. Windermere's median asking price is $1,220,000 against a median household income of $156,042, which puts a home at about 7.82 times household income here. That ratio, rather than the sticker price, is the number worth carrying between towns, and it is why a cheaper town is not automatically a more affordable one.

Florida charges no state income tax, so the property tax line matters more here than it would elsewhere, and a homestead exemption reduces the taxable value of a primary residence. Millage varies by taxing district, so treat any single quoted rate as an estimate until the specific parcel is checked.

Frequently Asked Questions

Is Windermere, FL a good place to live?

It depends on whether your income comes with you. Against the 60 places this site tracks across Orange, Seminole, Lake and Volusia counties, with that group's middle last measured on October 9, 2026, the median asking price of $1,220,000 is higher than most and the mean commute of 30.9 minutes is longer than most. The median household income here is $156,042, which puts housing at 7.82 times income, a heavier load than in most of those places. For remote workers and retirees who bring their income with them, that matters less. For someone earning a local wage, it is one of the harder places in the group to buy. Who it fits, and who it does not, is laid out at the top of this page.

What is the median home price in Windermere, FL?

The median sale price was $632,000 in September 2026 across 45 closed sales. Over the last twelve months 652 homes sold at a median of $789,250, down 6.0% against the twelve months before. The median asking price across 221 active listings is $1,220,000, or $350 per square foot.

Is Windermere cheaper than Winter Garden?

On the asking median, no: $1,220,000 against $592,495. Measured against household income, Windermere is at 7.82 times income and Winter Garden at 5.57, so on that basis Winter Garden is the more affordable of the two. See what $1,000,000 buys in each town.

Is Windermere, FL safe?

There is no city-level crime rate for Windermere, because no municipal police agency here reports usable figures to the FBI. The nearest measure is the Orange County Sheriff's Office, which is county-wide rather than specific to this town.

What is the cost of living in Windermere, FL?

Housing is the deciding line. A median asking price of $1,220,000 against a median household income of $156,042 puts a home at roughly 7.82 times income, and Florida charges no state income tax, which shifts weight onto the property tax line.

What school district serves Windermere, FL?

Orange County Public Schools. Assignment varies by address within the city, so confirm the zoning for the specific property.

Thinking About a Move to Windermere?

I work these four counties every week and I will tell you when a town is wrong for you. If you want the numbers for your budget before you tour anything, start with what $1,000,000 buys across Windermere and its neighbors, or call me at 407-616-9019.

You can also browse homes for sale in Windermere, which updates with current inventory.