Luxury Homes for Sale in Winter Park, FL
The luxury market in Winter Park starts at $1,050,000 — about 1.5× the city’s median asking price. 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.
104 luxury homes are for sale in Winter Park, FL at $1,050,000 and up — median asking $1,949,750, the top listing at $6,995,000, $658 per square foot. 191 homes closed above $1,050,000 in the last 12 months at a median of $1,840,000. 13% of the luxury inventory is waterfront; 38% is new construction. Median days on market: 51.
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 |
| 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 |
| 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 |
| 231 Chelton Circle | $4,700,000 | 5,550 | $847 | Forest Hills |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| the Enclave | 8 | $2,200,000 |
| Kenilworth Shores | 5 | $2,700,000 |
| Killarney Estates | 5 | $1,250,000 |
| Charmont | 5 | $2,089,000 |
| Winter Park Village | 4 | $1,588,500 |
| Lake Knowles Terrace | 3 | $2,549,000 |
| J Kronenberger | 3 | $5,195,900 |
| Sylvan Heights | 3 | $1,750,000 |
| Forest Hills | 3 | $3,395,000 |
| South Lakemont Shores | 3 | $1,498,000 |
| Winter Park Villas | 3 | $2,495,000 |
| Vilasa Townhomes | 2 | $1,349,500 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,050,000–$1,500,000 | 25 | 24% |
| $1,500,000–$2,000,000 | 30 | 29% |
| $2,000,000–$3,000,000 | 22 | 21% |
| $3,000,000–$5,000,000 | 18 | 17% |
| $5,000,000+ | 9 | 9% |
How to read this
Luxury is defined here as asking prices at or above $1,050,000. 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 356 homes for sale in Winter Park and what $1M buys across Orange County.