I Ranked Windermere's Priciest Neighborhoods, and Price Per Square Foot Does Not Follow Price

By Brenden Rendo, Realtor · Updated October 12, 2026

Every list of Windermere's most expensive neighborhoods you can find online stops at Isleworth and calls it a day. That is not useful if you are actually shopping here, because the interesting part of this zip code is not which gate has the biggest number behind it. It is that the price per square foot does not follow the price. On October 8, 2026 I pulled every active residential listing in 34786 out of Stellar MLS, folded the subdivision labels the same way our city pages do, and ranked the neighborhoods that carry enough listings to produce a median worth printing. Old-town Windermere asks more per foot than Keene's Pointe while sitting $1.19 million lower on median price. Every active listing in one of the top seven neighborhoods is new construction at builder pricing. And inside this luxury market, 54.26% of single-family sellers are already asking less than they opened at.

What this ranking is, and what it is not

Three things before a single number, because this is the part most neighborhood rankings skip and it is the part that decides whether the numbers mean anything.

These are asking prices, not sale prices and not home values. Every figure below comes from active listings in Stellar MLS on October 8, 2026. An asking price is what a seller hopes to get. It is not what the house is worth and it is not what the last one closed for. If you want an estimate on a specific address, start with the home value estimator and then have me check it against actual closings, because an automated number on a Windermere lakefront lot is close to a coin flip.

A median built on two listings is not a neighborhood price. Windermere has 71 named single-family subdivisions carrying at least one active listing right now. Only 15 of them carry 4 or more. That means 78.87% of the named subdivisions in this zip code are too thin to rank, and I have left all 56 of them out rather than publishing a "median" that is really one seller's opinion. The 15 that made the cut hold 108 of the 188 active single-family listings, or 57.45% of the market. Every row in the table below states its listing count so you can see exactly how much weight it carries.

Single family is kept separate from attached housing. The ranking covers single-family homes only. Windermere's 33 active townhomes and 8 active condominiums are a different product at a different price, and mixing them into a neighborhood median drags it somewhere useless. They get their own section near the bottom.

One more note on the clock. Days on market here is computed as the larger of the MLS cumulative figure and the days since the home actually went on market, which catches relisted homes that would otherwise reset to day one. It runs higher than the raw feed field that most sites publish. That is a change in counting, not a change in the market, so do not read it against a number you saw somewhere else in the spring.

The ranking: 15 Windermere neighborhoods by median asking price

Single-family active listings in zip 34786, pulled from Stellar MLS on October 8, 2026. Sorted by median asking price. "Active" is the number of listings the median is built on.

Source: first-party Stellar MLS pull, active single-family residential listings in PostalCode 34786, October 8, 2026. Subdivision labels are folded so phase and unit numbers collapse into one neighborhood, which is why Keene's Pointe shows 18 listings rather than being split across four rows. Lakes of Windermere appears in Stellar as the label "Lakes/Windermere" and Peachtree Park records carry the label "Lakes/Windermere-Peachtree," so Peachtree Park is a village inside Lakes of Windermere rather than a separate community.

What the money actually buys at each tier

The table is a ladder with four clear rungs, and the thing that changes between them is not quality. It is square footage and water.

Above $2 million: Isleworth, Casabella, Keene's Pointe, Casa Del Lago. Median homes here run 3,848 to 5,732 square feet. This is the gated, guard-staffed, golf-and-lakefront tier, and it is where Windermere's reputation comes from. Isleworth alone holds 24 active listings with a median of 5,732 square feet, and its asking prices run from the high $2 millions to a $19,500,000 estate. Keene's Pointe is the volume leader in this tier at 18 active listings and a median of 5,089 square feet for $2,579,500, which works out to the lowest price per square foot of the four. If your requirement is a large house behind a gate and you are flexible on which gate, that gap is the trade to study.

$1 million to $1.4 million: Gotha Town, Windermere Town, Palms at Windermere. Medians of 3,008 to 3,530 square feet. This tier is the most mixed of the four and the easiest to misread, because one of the three is a builder community and one is a catch-all label. More on both below.

$850,000 to $1 million: Windermere Isle, Westside Village. Medians of 2,443 and 2,680 square feet, both with a median year built of 2018. Newer construction, smaller lots, no gate guard, and the amenity package is a community pool rather than a golf course. Windermere Isle's median listing has been sitting 209 days.

Under $800,000: Windermere Trails, Summerport, Lake Sawyer South, Lakes of Windermere, Silver Woods, Peachtree Park. Medians of 1,934 to 2,989 square feet. Six of the 15 neighborhoods on the list, and the reason it is worth telling people that a Windermere address does not require seven figures. Windermere Trails carries 9 active listings at a $780,000 median with the shortest median time on market in the bottom tier at 66 days, which is what a correctly priced house in this band looks like.

Price per square foot tells a different story than price

Re-sort the same 15 neighborhoods by price per square foot and the order breaks. Isleworth still leads at $951. But second place goes to Casabella at $598, third to Casa Del Lago at $594, and fourth to Windermere Town at $548, which pushes Keene's Pointe and its $506 down to fifth even though Keene's Pointe asks $1.19 million more at the median.

Windermere Town is the old town itself, the small grid of streets between the lakes with the brick roads and the 1990s and earlier houses. Its median home is 3,008 square feet, roughly 2,100 square feet smaller than the Keene's Pointe median, and it asks 8.30% more per foot. You are buying the location and the lot, and the house is almost incidental to the price.

The same logic runs in reverse at the other end of the list. Silver Woods has the oldest housing stock in the ranking with a median year built of 1986 and the smallest median home at 1,934 square feet, yet it asks $300 per square foot, which is more per foot than Windermere Trails, Summerport, Lake Sawyer South, Lakes of Windermere and Peachtree Park, all of which are newer. Small older homes on established lots price high per foot. That is not an anomaly, it is how per-foot pricing works, and it is why I will not let a buyer shop on price per square foot alone either.

The one number that genuinely looks out of place is Palms at Windermere at $330 per square foot while asking $1,040,490. That is the lowest price per foot of anything on this list above $1 million, and the reason is the next section.

The new construction trap, and the one neighborhood it lands on

A builder community whose every active listing is a brand new house at base pricing will climb a ranking like this on newness alone. That misleads anyone comparing it to an established neighborhood, and pre-construction listings are worse, because the price can be attached to a house that does not exist yet. So I measured it rather than assuming.

Across all 229 active residential listings in 34786, 14 qualify as new construction, or 6.11%. Among single-family only it is 12 of 188, or 6.38%. For scale, I ran the same count on the neighboring 34787 zip the same morning and got 113 of 459 active single-family listings, or 24.62%, so Windermere is roughly a quarter as builder-driven as Horizon West next door. Six of the 229 listings, 2.62%, are marked Under Construction or Pre-Construction, meaning the house is not finished.

How "new" was defined, because the MLS flag alone is not trustworthy. I counted a listing as new construction if Stellar's NewConstructionYN flag is true or the year built is 2024 or later, then cross-checked both. The flag by itself found 11 listings. Year built 2024 or later found 14. Palms at Windermere is the exact case that proves the point: all 4 of its active listings were built in 2025 or 2026, but one of them, a $1,270,000 home built in 2025, carries the new-construction flag as false. Trust the flag alone and you would call that neighborhood 3 of 4 new instead of 4 of 4.

So Palms at Windermere's seventh-place finish at a $1,040,490 median is builder pricing on houses with a median year built of 2026. It is a real price and a real neighborhood, but it is not comparable to Windermere Town one row above it, where the median house was built in 1992. Three of the four are listed in the high $900,000s to $1,090,990 and 3 of the 4 are already asking below what they opened at.

Isleworth is the other place the split matters, in the opposite direction. Its 24 active listings include 3 new builds: an $11,900,000 home finished in 2026, a $6,500,000 home finished in 2026, and an $18,750,000 Pre-Construction listing with a 2027 year built. Those three pull the headline median up. Strip them out and Isleworth's resale median is $4,395,000 at $927 per square foot, against $5,149,750 at $951 with them in. The resale figure is the one to use if you are comparing Isleworth to a neighborhood that has no builder inventory.

Gotha Town, or why a median can lie to you

Gotha Town lands fifth at a $1,392,500 median, and I would not use that number for anything.

Gotha is the small historic hamlet inside 34786 that carries a Windermere mailing address, and Stellar's "Gotha Town" label functions as a catch-all for the surrounding acreage rather than a single subdivision. Its 6 active listings run from $450,000 on a 1989 house to $4,750,000 on a 2008 house, with a $3,750,000 Under Construction home built in 2027 sitting in the middle of the range. That is better than a 10x spread inside one label. The median sits at $1,392,500 because that happens to be where the middle of six very different properties falls, and it describes none of them.

Strip the new build out and the Gotha Town resale median drops to $1,090,000 at $384 per square foot. That is more honest, and it is still a number built on five properties with almost nothing in common. If you are looking at Gotha specifically, the only sensible approach is property by property, and the median is noise.

The same caution applies in a milder form to every row with 4 or 5 listings. A four-listing median is directional, not definitive. The 24-listing Isleworth median and the 18-listing Keene's Pointe median are the two figures on this page I would actually lean on.

The buyer side of a luxury market

None of this reads like a market where sellers hold all the cards, and that is the part a glossy neighborhood ranking never mentions.

Of the 188 active single-family listings in 34786, 124 of them, or 65.96%, have been on the market 60 days or more. The median single-family listing has been sitting 100 days. And 102 of the 188, or 54.26%, are now asking less than their original list price, at a 5.51% median reduction. In other words, more than half the sellers in Windermere's single-family market have already told you in public that their first number was wrong.

That pattern shows up unevenly across the ranking. Silver Woods has all 4 of its active listings below their original asking price. Summerport is at 5 of 6 and Lake Sawyer South at 4 of 5. In the top tier it is thinner: Isleworth is 10 of 24 and Casabella is 2 of 5, which is what you expect in a segment where a seller can afford to wait out a slow year. Keene's Pointe is the exception at 10 of 18, with a 131-day median time on market.

Two listings are worth calling out for patience alone. Peachtree Park's median time on market is 254 days and Windermere Isle's is 209. A neighborhood median above 200 days is not a pricing quirk, it is a standing invitation to make an offer with terms.

This is consistent with what the wider metro is doing. The Orlando Regional REALTOR Association's August 2026 report put the area at 4.9 months of supply, up from 4.4 in July, with a $400,676 median sale price and homes averaging 64 days on market. Six months of supply is the conventional line for a balanced market, so the metro is closer to balance than it has been in years. Worth knowing when you read that figure: ORRA's reporting footprint includes Osceola County, which we do not serve, so it is a wider geography than the four counties I work in. Our coverage is Orange, Seminole, Lake and Volusia.

Financing is the other half of why Windermere sellers are waiting. Freddie Mac's Primary Mortgage Market Survey put the 30-year fixed average at 7.28% in the week of October 1, 2026, up from 6.76% the week of September 10. On a $2.5 million purchase that move is not a rounding error, and it is a large part of why the 60-plus-day share here is where it is.

Townhomes and condominiums in 34786

Attached housing is a separate market and I keep it that way, because folding 33 townhomes into a single-family median does nothing but distort both.

Windermere's 33 active townhomes carry a $415,000 median asking price at $255 per square foot, with a median of 1,644 square feet and a median year built of 2014. The 8 active condominiums run a $323,500 median at $244 per square foot. One attached community in the zip has enough listings to stand on its own: Lakeside at Lakes of Windermere, with 6 active condominiums at a $309,998 median and $254 per square foot.

If attached is what you are shopping, the Windermere townhomes search is the right starting point, and understand that the carrying cost math is different: association dues and, for condominiums, reserve funding are a real part of the monthly number here.

How to use this if you are buying or selling here

If you are buying. Pick your tier on square footage and location first, then shop across neighborhoods inside it instead of fixating on one gate. The Keene's Pointe and Casa Del Lago comparison is the clearest example on this page: $231,000 less at Casa Del Lago buys you 1,241 fewer median square feet. Go in knowing that 65.96% of the single-family inventory is 60 days or older, because an offer on a 130-day listing is a different negotiation than an offer on a 20-day listing. Browse what is currently reduced on the Orange County price reduced homes page, and use the 34786 zip code page for the live inventory behind these numbers.

If you are selling. Your competition is not the whole zip code, it is the 4 to 24 listings in your subdivision, and in most of Windermere that number is small enough to name. A 5.51% median reduction across the market means the sellers who priced at last year's comps are the ones paying for it in time. Price against the current actives in your own subdivision, not against the Isleworth headline, and take the per-square-foot figure for your specific neighborhood seriously rather than the city-wide $402.

If you are investing. The spread between resale and new construction is where the work is. Windermere's new-build single-family median is $4,625,000 at $774 per square foot against a resale median of $1,395,000 at $397. That gap is mostly a mix effect rather than a premium, since the new builds here are concentrated at the very top of the market, which is exactly why the citywide new-versus-resale comparison should never be used as a renovation-value argument. Do that math inside one subdivision or not at all.

For the wider picture behind this zip code, the Central Florida housing market hub carries the four-county data, and the Orange County zip code hub lets you compare 34786 against everything around it. For single-family inventory specifically, the Windermere single-family homes search is the matching live feed.

Questions I get about Windermere pricing

What is the most expensive neighborhood in Windermere, FL?

Isleworth, by a wide margin. Its 24 active single-family listings carry a median asking price of $5,149,750 and $951 per square foot as of October 8, 2026, with individual listings running up to $19,500,000. The second-place neighborhood, Casabella, has a median asking price of $3,580,000.

Can you buy a single-family home in Windermere for under $700,000?

Yes. Six of the 15 ranked neighborhoods have median asking prices under $800,000, and four of those are under $700,000: Lake Sawyer South at $649,000, Lakes of Windermere at $612,000, Silver Woods at $609,950 and Peachtree Park at $594,500. Those are asking prices on active listings, not sale prices.

Why is Windermere Town more expensive per square foot than Keene's Pointe?

Because per-square-foot pricing follows location and lot, not house size. Windermere Town's median home is 3,008 square feet asking $548 per square foot, while Keene's Pointe's median home is 5,089 square feet asking $506. Windermere Town is the historic town grid between the lakes, so a buyer there is paying for the location and the lot more than for the structure.

How much of Windermere's for-sale inventory is new construction?

14 of the 229 active residential listings in 34786, or 6.11%. Among single-family listings alone it is 12 of 188, or 6.38%. Six listings, 2.62% of the total, are marked Under Construction or Pre-Construction, meaning the home is not finished. One neighborhood, Palms at Windermere, is entirely new construction across all 4 of its active listings.

Are Windermere home prices falling?

These are asking prices on active listings, so they cannot answer that question in either direction. What they do show is pressure on the asking side: 54.26% of the 188 active single-family listings are now priced below their original asking price at a 5.51% median reduction, and 65.96% have been on the market 60 days or more. That is a market where sellers are adjusting, which is different from a market where values have dropped.

How many listings is each neighborhood median based on?

Between 4 and 24, and the count is printed in the table for every row. Only 15 of Windermere's 71 named single-family subdivisions carry 4 or more active listings, so the remaining 56 are excluded as too thin to produce a meaningful median. The two figures built on the most listings are Isleworth at 24 and Keene's Pointe at 18.

If you are looking at a specific Windermere street or subdivision, I will pull the actual closed sales and the current actives for that exact neighborhood rather than handing you a city-wide number. Call or text me, Brenden Rendo, at 407-616-9019, or start with the 34786 inventory and send me the three addresses you want run.

Data note: all Windermere figures in this post come from a first-party Stellar MLS pull of active residential listings in zip 34786 on October 8, 2026 (229 listings). Days on market is the larger of the MLS cumulative figure and days since the listing went on market, which runs higher than the raw feed field published elsewhere. Asking prices are not sale prices, not appraised values and not a prediction. I am a Realtor, not an appraiser or a lender, and nothing here is a valuation or a guarantee of what any home will sell for.