Luxury Homes for Sale in Winter Garden, FL
The luxury market in Winter Garden starts at $1,000,000. 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.
77 luxury homes are for sale in Winter Garden, FL at $1,000,000 and up — median asking $1,350,000, the top listing at $18,900,000, $397 per square foot. 97 homes closed above $1,000,000 in the last 12 months at a median of $1,275,000. 29% of the luxury inventory is waterfront; 5% is new construction. Median days on market: 52.
Newest luxury listings in Winter Garden
The most expensive homes for sale in Winter Garden
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 5758 Hamlin Groves Trail | $18,900,000 | — | — | Hamlin Southwest |
| 13377 Lake Butler Boulevard | $5,995,000 | 6,000 | $999 | — |
| 15614 Espalier Way | $4,300,000 | 6,601 | $651 | signature lakes |
| 13542 Sunset Lakes Circle | $3,799,000 | 5,450 | $697 | Sunset Lakes |
| 4004 Rex Drive | $2,790,000 | 1,804 | $1,547 | Lake Avalon Groves |
| 15522 Shorebird Lane | $2,700,000 | 6,400 | $422 | Lakeshore Preserve |
| 7693 Green Mountain Way | $2,600,000 | 5,115 | $508 | Summerlake Pd |
| 7301 Wild Blackberry Trail | $2,600,000 | 5,403 | $481 | — |
| 15505 Shorebird Lane | $2,500,000 | 5,287 | $473 | Lakeshore Preserve |
| 13377 Lake Butler Boulevard | $2,500,000 | 4,961 | $504 | — |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Lakeshore Preserve | 10 | $1,574,500 |
| Watermark | 5 | $1,100,000 |
| Avalon Cove | 3 | $1,999,000 |
| Oakland Park | 3 | $1,195,000 |
| Twinwaters | 3 | $1,080,000 |
| hickory hammock | 2 | $1,559,500 |
| Lake Roberts Landing E | 2 | $1,300,000 |
| Summerlake Pd | 2 | $2,500,000 |
| Lakeview Village Estates | 2 | $1,147,170 |
| Lake Avalon Groves | 2 | $2,282,500 |
| Avalon Ridge | 2 | $1,574,500 |
| West Lake Hancock Estates | 2 | $1,650,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 42 | 55% |
| $1,500,000–$2,000,000 | 16 | 21% |
| $2,000,000–$3,000,000 | 15 | 19% |
| $3,000,000–$5,000,000 | 2 | 3% |
| $5,000,000+ | 2 | 3% |
How to read this
Luxury is defined here as asking prices at or above $1,000,000. 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 693 homes for sale in Winter Garden and what $1M buys across Orange County.