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.
89 luxury homes are for sale in Winter Park, FL at $1,000,000 and up — median asking $1,749,000, the top listing at $6,900,000, $616 per square foot. 195 homes closed above $1,000,000 in the last 12 months at a median of $1,800,000. 13% of the luxury inventory is waterfront; 42% is new construction. Median days on market: 68.
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 | J Kronenberger |
| 1571 Woodland Avenue | $6,000,000 | 7,397 | $811 | Comstock Park |
| 2661 Via Tuscany | $5,999,990 | 3,880 | $1,546 | Maitland Shores |
| 2228 Azalea Place | $5,600,000 | 5,152 | $1,087 | Maitland Shores |
| 313 Sylvan Drive | $5,500,000 | 4,775 | $1,152 | Sylvan Park |
| 231 Chelton Circle | $4,950,000 | 5,550 | $892 | Forest Hills |
| 857 Brock Street | $4,650,000 | 4,827 | $963 | Park Grove |
| 1525 Granville Drive | $4,595,000 | 5,211 | $882 | Park Grove |
| 229 Alexander Place | $4,250,000 | 4,431 | $959 | Alexander Place |
| 1441 Cardinal Court | $3,995,000 | 4,066 | $983 | Winflor Court |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| the Enclave | 7 | $2,275,000 |
| Kenilworth Shores | 5 | $1,999,990 |
| Charmont | 5 | $2,299,000 |
| Killarney Estates | 4 | $1,262,500 |
| Lawndale | 4 | $1,409,950 |
| Lake Forest Park | 3 | $1,699,000 |
| Maitland Shores | 3 | $5,600,000 |
| Winter Park Village | 3 | $1,598,000 |
| Sylvan Heights | 3 | $1,750,000 |
| Forest Hills | 3 | $3,395,000 |
| Winter Park Villas | 3 | $2,495,000 |
| Lake Knowles Terrace | 2 | $1,987,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 26 | 29% |
| $1,500,000–$2,000,000 | 30 | 34% |
| $2,000,000–$3,000,000 | 14 | 16% |
| $3,000,000–$5,000,000 | 14 | 16% |
| $5,000,000+ | 5 | 6% |
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 337 homes for sale in Winter Park and what $1M buys across Orange County.