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.
103 luxury homes are for sale in Winter Park, FL at $1,000,000 and up — median asking $2,070,000, the top listing at $6,995,000, $694 per square foot. 199 homes closed above $1,000,000 in the last 12 months at a median of $1,810,000. 13% of the luxury inventory is waterfront; 35% is new construction. Median days on market: 71.
Newest luxury listings in Winter Park
The most expensive homes for sale in Winter Park
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 901 Golfview Terrace | $6,995,000 | 5,479 | $1,277 | — |
| 1260 Alabama Drive | $6,900,000 | 6,396 | $1,079 | J Kronenberger |
| 698 N New York Avenue | $6,195,000 | 5,096 | $1,216 | — |
| 1571 Woodland Avenue | $6,000,000 | 7,397 | $811 | Comstock Park |
| 1011 Mckean Circle | $6,000,000 | 4,806 | $1,248 | Palmer Park |
| 2228 Azalea Place | $5,600,000 | 5,152 | $1,087 | Maitland Shores |
| 313 Sylvan Drive | $5,500,000 | 4,775 | $1,152 | Sylvan Park |
| 2661 Via Tuscany | $5,500,000 | 3,880 | $1,418 | Maitland Shores |
| 1166 Palmer Avenue | $5,500,000 | 5,181 | $1,062 | Palmer Ave Lakeside Prop |
| 825 Palmer Avenue | $5,195,900 | 5,122 | $1,014 | J Kronenberger |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Kenilworth Shores | 6 | $2,845,000 |
| the Enclave | 6 | $2,097,500 |
| Killarney Estates | 4 | $1,212,500 |
| Charmont | 4 | $1,894,450 |
| Comstock Park | 3 | $2,629,000 |
| J Kronenberger | 3 | $5,195,900 |
| Sylvan Heights | 3 | $1,750,000 |
| Forest Hills | 3 | $3,390,000 |
| Lawndale | 3 | $1,399,900 |
| Winter Park Villas | 3 | $3,950,000 |
| Lake Knowles Terrace | 2 | $3,047,498 |
| Vilasa Townhomes | 2 | $1,349,500 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 26 | 25% |
| $1,500,000–$2,000,000 | 25 | 24% |
| $2,000,000–$3,000,000 | 22 | 21% |
| $3,000,000–$5,000,000 | 20 | 19% |
| $5,000,000+ | 10 | 10% |
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 24, 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 398 homes for sale in Winter Park and what $1M buys across Orange County.