Luxury Homes for Sale in Winter Park, FL
The luxury market in Winter Park 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.
110 luxury homes are for sale in Winter Park, FL at $1,000,000 and up — median asking $2,100,000, the top listing at $6,900,000, $711 per square foot. 209 homes closed above $1,000,000 in the last 12 months at a median of $1,810,000. 11% of the luxury inventory is waterfront; 36% is new construction. Median days on market: 59.
Newest luxury listings in Winter Park
The most expensive homes for sale in Winter Park
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 1260 Alabama Drive | $6,900,000 | 6,396 | $1,079 | Orange County |
| 901 Golfview Terrace | $6,795,000 | 5,479 | $1,240 | Orange County |
| 1571 Woodland Avenue | $6,000,000 | 7,397 | $811 | Orange County |
| 1011 Mckean Circle | $6,000,000 | 4,806 | $1,248 | Orange County |
| 1200 Via Salerno | $5,995,000 | 5,476 | $1,095 | Cloister Grove |
| 698 N New York Avenue | $5,995,000 | 5,096 | $1,176 | Orange County |
| 1441 Grove Terrace | $5,950,000 | 5,796 | $1,027 | Orange County |
| 2228 Azalea Place | $5,600,000 | 5,152 | $1,087 | Orange County |
| 2661 Via Tuscany | $5,500,000 | 3,880 | $1,418 | Orange County |
| 1166 Palmer Avenue | $5,500,000 | 5,181 | $1,062 | Orange County |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Orange County | 24 | $4,597,500 |
| Kenilworth Shores | 6 | $2,325,000 |
| the Enclave | 6 | $2,097,500 |
| Lake Knowles Terrace | 4 | $2,274,500 |
| Killarney Estates | 4 | $1,212,500 |
| Lawndale | 4 | $1,389,900 |
| Sylvan Heights | 3 | $1,750,000 |
| Charmont | 3 | $1,699,900 |
| Vilasa Townhomes | 2 | $1,337,500 |
| Winter Park Residential | 2 | $1,600,000 |
| Sylvan Lake Shores | 2 | $1,562,000 |
| Comstock Park | 2 | $2,057,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 29 | 26% |
| $1,500,000–$2,000,000 | 23 | 21% |
| $2,000,000–$3,000,000 | 25 | 23% |
| $3,000,000–$5,000,000 | 21 | 19% |
| $5,000,000+ | 12 | 11% |
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 November 14, 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 394 homes for sale in Winter Park and what $1M buys across Orange County.