Luxury Homes for Sale in Windermere, FL
The luxury market in Windermere starts at $1,450,000 — 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.
95 luxury homes are for sale in Windermere, FL at $1,450,000 and up — median asking $3,290,000, the top listing at $27,000,000, $668 per square foot. 100 homes closed above $1,450,000 in the last 12 months at a median of $2,500,000. 41% of the luxury inventory is waterfront; 8% is new construction. Median days on market: 49.
Newest luxury listings in Windermere
The most expensive homes for sale in Windermere
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 5603 Marleon Drive | $27,000,000 | 22,108 | $1,221 | — |
| 5192 Vardon Drive | $19,500,000 | 13,494 | $1,445 | — |
| 5036 Latrobe Drive | $18,750,000 | 15,337 | $1,223 | Isleworth |
| 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 |
| 9323 Gladys Garden Court | $11,900,000 | 9,770 | $1,218 | Isleworth |
| 9832 Laurel Valley Drive | $11,750,000 | 11,100 | $1,059 | Isleworth |
| 4226 Downeast Lane | $9,750,000 | 5,316 | $1,834 | — |
| 5092 Isleworth Country Club Drive | $8,500,000 | 7,100 | $1,197 | Isleworth |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Isleworth | 23 | $4,999,500 |
| Keenes Pointe | 13 | $2,685,000 |
| Casabella | 5 | $3,580,000 |
| lake butler estates | 3 | $1,775,000 |
| Windermere Town | 3 | $2,175,000 |
| Gotha Town | 3 | $3,750,000 |
| Casa Del Lago | 3 | $3,100,000 |
| Bellaria | 2 | $2,897,500 |
| Sunset Bay | 1 | $4,995,000 |
| Lake Down Pointe | 1 | $13,995,000 |
| Lake Crescent Reserve | 1 | $1,830,000 |
| Marina Bay Estates | 1 | $1,500,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,450,000–$1,500,000 | 2 | 2% |
| $1,500,000–$2,000,000 | 17 | 18% |
| $2,000,000–$3,000,000 | 21 | 22% |
| $3,000,000–$5,000,000 | 28 | 29% |
| $5,000,000+ | 27 | 28% |
How to read this
Luxury is defined here as asking prices at or above $1,450,000. Counts, medians and closings come from active and closed MLS listings as of October 5, 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 244 homes for sale in Windermere and what $1M buys across Orange County.