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.
65 luxury homes are for sale in Winter Garden, FL at $1,000,000 and up — median asking $1,389,000, the top listing at $18,900,000, $380 per square foot. 92 homes closed above $1,000,000 in the last 12 months at a median of $1,285,000. 26% of the luxury inventory is waterfront; 8% is new construction. Median days on market: 62.
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 |
| 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 |
| 17144 Phil C Peters Road | $2,550,000 | 4,633 | $550 | Lake Avalon Groves |
| 15505 Shorebird Lane | $2,500,000 | 5,287 | $473 | Lakeshore Preserve |
| 15675 Panther Lake Drive | $2,399,000 | 4,213 | $569 | Lakeshore Preserve |
| 16870 Sanctuary Drive | $2,250,000 | 4,132 | $545 | Sanctuary Twin Waters |
| 15475 Shorebird Lane | $2,190,000 | 4,253 | $515 | Lakeshore Preserve |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Lakeshore Preserve | 9 | $1,950,000 |
| Watermark | 4 | $1,125,000 |
| Avalon Cove | 3 | $1,999,000 |
| Lake Avalon Groves | 3 | $2,550,000 |
| Oakland Park | 3 | $1,195,000 |
| Twinwaters | 3 | $1,080,000 |
| hickory hammock | 2 | $1,579,500 |
| 30 North Park | 2 | $1,122,000 |
| Lakeview Village Estates | 2 | $1,147,170 |
| Waterside At Johns Lake | 2 | $1,324,495 |
| Avalon Ridge | 2 | $1,574,500 |
| lake star at ovation | 2 | $1,594,950 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 36 | 55% |
| $1,500,000–$2,000,000 | 15 | 23% |
| $2,000,000–$3,000,000 | 12 | 18% |
| $3,000,000–$5,000,000 | 1 | 2% |
| $5,000,000+ | 1 | 2% |
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 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 720 homes for sale in Winter Garden and what $1M buys across Orange County.