Windermere, FL Homes for Sale: Neighborhoods and What They Sell For
664 sales in a year, 223 homes on the market, 4.0 months of supply
What is actually for sale in Windermere right now?
As of October 18, 2026 there were 223 homes on the market in Windermere ZIP 34786 — 187 single-family homes, 27 townhomes and 9 condominiums. Over the preceding twelve months, 664 homes changed hands. That is 4.0 months of supply: under about four months generally favors sellers and over about six favors buyers, so Windermere as a whole sits close to balanced.
The headline number hides the more useful one. Of those 223 listings, 119 are priced at $1,000,000 or more — and at that level the market is noticeably softer than the ZIP overall. More on that below.
| Metric | Windermere (ZIP 34786) |
|---|---|
| Closed sales, trailing 12 months | 664 |
| Median closed price | $780,000 |
| Middle half of the market | $520,000 – $1,300,000 |
| Full range | $280,000 – $13,200,000 |
| Median price per square foot | $284 |
| Median days on market | 35 |
| Sales at or above $1,000,000 | 253 |
| Homes for sale today | 223 |
| Months of supply | 4.0 |
Source: StellarMLS via MLS Grid, residential closed sales October 18, 2025 to October 18, 2026 by close date; active inventory as of October 18, 2026. Confidence: Verified/StellarMLS.
What do homes in Windermere actually sell for?
The median closed price over the last twelve months was $780,000, at a median of $284 per square foot. The middle half of the market ran from $520,000 to $1,300,000. 253 sales closed at or above $1,000,000, 94 at or above $2,000,000, 48 at or above $3,000,000, and the highest reached $13,200,000.
A range that wide is the first thing to understand about Windermere. ZIP 34786 is not one market: it holds lakefront estates on the Butler Chain, golf-course residences in guard-gated communities, and production-built neighborhoods to the west, all under the same five digits. The 664 sales break down as 531 single-family homes, 106 townhomes, 26 condominiums and 1 other attached home. A single Windermere median describes almost nothing specific — the neighborhood, and on the Chain the water, set the price.
Windermere neighborhoods by the numbers
A selection of Windermere neighborhoods — established and high-volume communities — each with at least five closed sales in the last twelve months, ranked by median sold price. It is not a complete list of the ZIP. Names are as recorded in StellarMLS, with every phase and unit of a community combined.
| Neighborhood (as recorded in StellarMLS) | Sold, 12 mo | Median sold | Range | For sale now |
|---|---|---|---|---|
| Isleworth | 14 | $4,093,750 | $2,750,000 – $11,500,000 | 23 |
| Casabella | 6 | $3,037,500 | $2,100,000 – $3,150,000 | 5 |
| Reserve at Lake Butler Sound | 8 | $1,887,500 | $1,335,000 – $2,460,000 | 3 |
| Keene’s Pointe | 61 | $1,650,000 | $945,000 – $13,200,000 | 19 |
| Waterstone | 6 | $1,525,000 | $1,350,000 – $4,029,999 | 1 |
| Butler Bay | 5 | $1,450,000 | $1,050,000 – $1,999,000 | 3 |
| Palms at Windermere | 27 | $1,082,946 | $970,000 – $1,290,376 | 5 |
| Windermere Isle | 9 | $995,000 | $690,000 – $1,150,000 | 5 |
| Windermere Downs | 8 | $925,000 | $670,000 – $2,404,000 | 1 |
| Glenmuir | 11 | $849,000 | $515,000 – $1,030,000 | 0 |
| Lake Sawyer South | 25 | $637,000 | $365,000 – $1,014,500 | 6 |
| Windermere Trails | 29 | $625,000 | $385,000 – $1,045,000 | 11 |
| Lake Cawood Cove | 7 | $592,146 | $552,238 – $1,184,072 | 2 |
| Lakes of Windermere | 42 | $532,500 | $302,500 – $1,951,000 | 16 |
Source: StellarMLS via MLS Grid, residential closed sales October 18, 2025 to October 18, 2026 by close date; active inventory as of October 18, 2026. Confidence: Verified/StellarMLS.
Two cautions on reading it. A median from five or ten sales moves sharply with a single lakefront or golf-front property, so treat the smaller rows as a range rather than a price. And a neighborhood absent from the table is not a neighborhood without value — it is either outside this selection or did not record five sales in the window.
The $1 million-plus market: the softer tier
Above $1,000,000, Windermere recorded 253 sales at a median of $1,610,000 ($410 per square foot), with a median of 37 days on market. Against that, 119 homes are listed at $1,000,000 or more today — 5.6 months of supply, compared with 4.0 for the ZIP as a whole.
| Metric | $1,000,000 and above |
|---|---|
| Closed sales, trailing 12 months | 253 |
| Median closed price | $1,610,000 |
| Median price per square foot | $410 |
| Median days on market | 37 |
| Listed today at $1,000,000 or more | 119 |
| Months of supply | 5.6 |
Source: StellarMLS via MLS Grid, residential closed sales October 18, 2025 to October 18, 2026 by close date; active inventory as of October 18, 2026. Confidence: Verified/StellarMLS.
The gap is widest at the very top. Isleworth recorded 14 sales in twelve months at a median of $4,093,750, and 23 homes there are on the market today. Keene’s Pointe is the volume community of the luxury tier, with 61 sales at a median of $1,650,000 and 19 currently for sale.
For a buyer, that means more choice and more time, and room to negotiate on terms as well as price. For an owner at this level it is the opposite message — a listing has real competition, and the price has to be right on the first day.
What should a buyer expect in Windermere?
The median sold home spent 35 days on the market. Inventory is deep enough to be selective, but not so deep that the right house waits indefinitely.
- Choose the neighborhood before the house. The spread between neighborhood medians in the table above is wider than the spread within most of them. Location inside the ZIP decides more of the price than square footage does.
- On the Butler Chain, verify the water. Frontage, depth at the dock, and whether a lake is open to the rest of the Chain by boat are separate questions, and a listing’s “waterfront” field does not answer any of them. Confirm each before you are under contract.
- Price against the right comparables. Compare a home to recent sales in its own neighborhood and on its own type of lot, not to the ZIP median.
- Get the insurance quote early. Roof age and construction drive Florida premiums, and on an older estate the quote can change the economics. Ask for it on the specific address during the inspection period, not after closing.
What should an owner know before selling in Windermere?
Under $1,000,000, sellers hold the stronger hand: supply there is 3.0 months. Above it, 119 competing listings and 5.6 months of supply mean buyers compare carefully and take their time — the median sold home in that tier spent 37 days on the market.
The most common and most expensive mistake at this level is to price from the neighborhood’s best sale rather than from the comparables that genuinely match the home: the same water, the same lot, the same era of construction. Automated estimates make this worse in Windermere, because a model that blends Chain frontage, golf frontage and interior lots will be wrong in both directions.
If you would like to know what your home would realistically sell for today, request a private valuation — it is prepared from StellarMLS comparables, not an algorithm.
How does Windermere compare to Winter Park, Doctor Phillips and Lake Nona?
Of the five markets below, Windermere has the second-highest median sold price. The table compares them on identical terms — same source, same twelve months — so the differences are real rather than an artifact of different date ranges.
| Market | Sold, 12 mo | Median sold | Median days on market | Months of supply |
|---|---|---|---|---|
| Windermere (ZIP 34786) | 664 | $780,000 | 35 | 4.0 |
| Lake Nona (ZIPs 32827 + 32832) | 1,029 | $620,000 | 40 | 5.0 |
| Winter Park (ZIP 32789) | 464 | $875,000 | 30 | 4.1 |
| Doctor Phillips / Bay Hill (ZIP 32819) | 424 | $539,500 | 44 | 5.8 |
| Winter Garden / Horizon West (ZIP 34787) | 2,003 | $599,999 | 30 | 4.3 |
Source: StellarMLS via MLS Grid, residential closed sales October 18, 2025 to October 18, 2026 by close date; active inventory as of October 18, 2026. Confidence: Verified/StellarMLS.
Related reading: the Windermere luxury market guide, Isleworth, Keene’s Pointe and Butler Chain waterfront.
Frequently asked questions
What ZIP code is Windermere, Florida?
Windermere’s ZIP code is 34786. The ZIP covers considerably more ground than the Town of Windermere itself, taking in the Butler Chain communities and newer neighborhoods to the west and south. Every figure on this page is for ZIP 34786.
How much do homes in Windermere sell for?
Over the twelve months to October 18, 2026, the median closed price in ZIP 34786 was $780,000, or $284 per square foot. The middle half of sales ran from $520,000 to $1,300,000. 253 sales closed at or above $1,000,000 and the highest reached $13,200,000.
How many homes are for sale in Windermere right now?
As of October 18, 2026 there were 223 residential listings in ZIP 34786: 187 single-family homes, 27 townhomes and 9 condominiums. 119 were priced at $1,000,000 or more.
Is Windermere a buyer’s or a seller’s market?
Across the whole ZIP it is balanced, at 4.0 months of supply. The $1,000,000-plus tier carries more inventory, at 5.6 months, which gives buyers at that level more choice and more room to negotiate than the overall figure suggests.
Which Windermere neighborhoods are gated?
Isleworth and Keene’s Pointe are both guard-gated. Gate status varies by neighborhood and can change, so confirm it for any specific street before relying on it.
What sells for the most in Windermere?
Of the neighborhoods with at least five sales, Isleworth carries the highest median, at $4,093,750 across 14 sales. The single highest sale in the ZIP over the period was $13,200,000.
Working with a Windermere broker
Chase Checho is the broker and owner of Chase Aaron Real Estate, licensed in Florida (BK3447990), and represents luxury residential and commercial clients across Orlando. Every figure on this page comes from StellarMLS and is refreshed from the source rather than estimated.
Whether you are buying into Windermere or want to know what your home there is genuinely worth, reach him directly at (352) 638-6645 or [email protected].