Luxury Homes for Sale in Windermere, FL
The luxury market in Windermere starts at $1,400,000 — about 1.5× the city’s median asking price. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see luxury communities in Orange County.
64 luxury homes are for sale in Windermere, FL at $1,400,000 and up — median asking $2,849,500, the top listing at $15,900,000, $595 per square foot. 94 homes closed above $1,400,000 in the last 12 months at a median of $2,175,000. 44% of the luxury inventory is waterfront; 9% is new construction. Median days on market: 40.
Newest luxury listings in Windermere
The most expensive homes for sale in Windermere
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 6119 Grosvenor Shore Drive | $15,900,000 | 14,068 | $1,130 | Keenes Point |
| 12488 Park Avenue | $15,500,000 | 13,425 | $1,155 | Chaine Du Lac |
| 3057 Porto Lago Court | $13,995,000 | 12,067 | $1,160 | Lake Down Pointe |
| 728 Forest Street | $10,200,000 | 6,457 | $1,580 | Windermere Town |
| 9317 Gladys Garden Court | $7,999,000 | 8,038 | $995 | Gardens/Isleworth |
| 9349 Tibet Pointe Circle | $6,995,000 | 7,529 | $929 | Keenes Pointe |
| 9061 Ron Den Lane | $6,900,000 | 6,300 | $1,095 | Down Acres Estates |
| 6055 Louise Cove Drive | $6,900,000 | 7,158 | $964 | Isleworth West |
| 8342 Boyla Court | $6,700,000 | 8,133 | $824 | Keenes Pointe |
| 800 W 2Nd Avenue | $5,999,000 | 5,511 | $1,089 | Aladar On Lake Butler |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Keenes Pointe | 11 | $2,474,000 |
| Casabella | 5 | $3,599,000 |
| Windermere Town | 5 | $2,175,000 |
| lake butler estates | 3 | $1,775,000 |
| reserve at lake butler sound | 3 | $1,549,000 |
| Gotha Town | 3 | $3,750,000 |
| Casa Del Lago | 3 | $3,100,000 |
| Bellaria | 3 | $2,800,000 |
| Weatherstone On Lake Olivia | 2 | $2,522,500 |
| Sunset Bay | 1 | $4,995,000 |
| Lake Down Pointe | 1 | $13,995,000 |
| Lake Crescent Reserve | 1 | $1,830,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,400,000–$1,500,000 | 2 | 3% |
| $1,500,000–$2,000,000 | 18 | 28% |
| $2,000,000–$3,000,000 | 15 | 23% |
| $3,000,000–$5,000,000 | 17 | 27% |
| $5,000,000+ | 12 | 19% |
How to read this
Luxury is defined here as asking prices at or above $1,400,000. Counts, medians and closings come from active and closed MLS listings as of September 15, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 255 homes for sale in Windermere and what $1M buys across Orange County.