New Listings in Winter Park, FL This Week
The homes that just listed are the ones you have a shot at before everyone else: the best-priced ones go under contract in days. This page lists every Winter Park listing from the last week, newest first, with price, size and community, refreshed every night from the live MLS record.
45 homes came on the market in Winter Park, FL in the last 7 days — about 6 a day — at a median asking price of $660,000 ($135,000 to $3,395,000 for the middle 80%). That is 20% of the 220 homes currently for sale. The most new listings are in Winter Park Villas (3) and ZIP 32789 (31).
New listings in Winter Park this week
| Listing | Community | Asking | $ / sq ft | Listed |
|---|---|---|---|---|
| 540 N Pennsylvania Avenue 4 bd · 2 ba · 1,652 sf · Single Family Residence | Winter Park Villas | $3,950,000 | $2,391 | 0d |
| 160 W Rockwood Way 5 bd · 5.5 ba · 4,015 sf · Single Family Residence | Forest Hills | $3,395,000 | $846 | 0d |
| 1421 Michigan Avenue 5 bd · 3 ba · 2,031 sf · Half Duplex | Attilio G Panacciones | $586,567 | $289 | 0d |
| 1071 Aragon Avenue 2 bd · 2.5 ba · 1,851 sf · Townhouse | Seville Park | $575,000 | $311 | 0d |
| 157 E New England Avenue #302 940 sf · Office | New England | $425,000 | $452 | 0d |
| 1415 Harmon Avenue 3 bd · 2.5 ba · 1,700 sf · Townhouse | Henkels | $3,060 | $2 | 0d |
| 620 Virginia Drive 6 bd · 5 ba · 4,677 sf · Single Family Residence | Timberlane Shores | $3,890,000 | $832 | 1d |
| 1773 Walnut Avenue 5 bd · 4.5 ba · 3,784 sf · Single Family Residence | Conwill Estates | $2,725,000 | $720 | 1d |
| 311 E Morse Boulevard #1-5 3 bd · 3 ba · 2,316 sf · Condominium | Phillips Circle | $2,475,000 | $1,069 | 1d |
| 2260 Mulbry Drive 5 bd · 4 ba · 3,246 sf · Single Family Residence | Lake Forest Park | $1,925,000 | $593 | 1d |
| 2308 Mulbry Drive 4 bd · 3.5 ba · 2,530 sf · Single Family Residence | Lake Forest Park | $1,699,000 | $672 | 1d |
| 250 Killarney 4 bd · 3.5 ba · 2,568 sf · Single Family Residence | Killarney Estates | $1,600,000 | $623 | 1d |
| 462 W Lyman Avenue 3 bd · 2.5 ba · 1,944 sf · Single Family Residence | Winter Park Villas | $1,595,000 | $820 | 1d |
| 952 Moss Lane 4 bd · 3.5 ba · 3,474 sf · Single Family Residence | Maitland Shores | $1,319,950 | $380 | 1d |
| 1922 Hammerlin Avenue 3 bd · 2.5 ba · 1,873 sf · Single Family Residence | Edgewood | $1,300,000 | $694 | 1d |
| 1278 S Pennsylvania Avenue #13 3 bd · 2.5 ba · 1,957 sf · Condominium | Casa Jardin Condo | $799,000 | $408 | 1d |
| 250 Carolina Avenue #205 2 bd · 2 ba · 1,311 sf · Condominium | Park West Condo | $739,000 | $564 | 1d |
| 508 Brechin Drive 3 bd · 2 ba · 1,783 sf · Single Family Residence | Kenilworth Shores | $639,000 | $358 | 1d |
| 811 Overspin Drive 2 bd · 1 ba · 749 sf · Single Family Residence | Dubsdread Heights | $349,000 | $466 | 1d |
| 151 N Orlando Avenue #242 2 bd · 1 ba · 710 sf · Condominium | Lake Killarney Condo | $269,000 | $379 | 1d |
| 222 Lewfield Circle 2 bd · 2 ba · 953 sf · Condominium | Stratford A | $189,900 | $199 | 1d |
| 1695 Lee Road #A101 3 bd · 2 ba · 1,149 sf · Condominium | Waterfall Cove | $154,900 | $135 | 1d |
| 3021 Aaron Burr Avenue #3 2 bd · 2.5 ba · 1,090 sf · Condominium | Colonies | $140,000 | $128 | 1d |
| 3020 Antique Oaks Circle #129 2 bd · 2 ba · 1,018 sf · Condominium | Parkview Village | $135,000 | $133 | 1d |
| 2500 Lee Road #143 1 bd · 1 ba · 645 sf · Condominium | Lakeside Manor Apartments Condo | $130,000 | $202 | 1d |
| 330 W Morse Blvd #104 1,790 sf · Medical Office | winter park comm winter park | $93,080 | $52 | 1d |
| 2661 Via Tuscany 4 bd · 4.5 ba · 3,880 sf · Single Family Residence | Maitland Shores | $5,999,990 | $1,546 | 2d |
| 857 Brock Street 5 bd · 5.5 ba · 4,827 sf · Single Family Residence | Park Grove | $4,650,000 | $963 | 2d |
| 1257 Wading Waters Circle 6 bd · 5 ba · 5,239 sf · Single Family Residence | Waters Edge At Hawks Crest | $1,600,000 | $305 | 2d |
| 720 Pansy Avenue 3 bd · 4 ba · 2,191 sf · Single Family Residence | Villa View Park | $1,350,000 | $616 | 2d |
| 471 Holt Avenue 4 bd · 3 ba · 2,528 sf · Single Family Residence | Winter Park Villas | $995,999 | $394 | 2d |
| 1250 S Denning Drive #127 2 bd · 2 ba · 908 sf · Condominium | Mead Garden | $245,000 | $270 | 2d |
| 3651 N Goldenrod Road #C109 2 bd · 2 ba · 840 sf · Condominium | Lancelot | $165,000 | $196 | 2d |
| 2825 Mulford Avenue 2 bd · 2 ba · 1,249 sf · Single Family Residence | Orangewood Park | $629,000 | $504 | 3d |
| 2626 Ambergate Road 3 bd · 1 ba · 1,143 sf · Single Family Residence | Winter Park Estates | $380,000 | $332 | 3d |
| 5108 Lazy Oaks Drive #5108 2 bd · 2 ba · 1,008 sf · Condominium | Lazy Oaks Condo | $269,000 | $267 | 3d |
| 2260 Coldstream Drive 4 bd · 2 ba · 1,509 sf · Single Family Residence | Brookshire Heights | $699,000 | $463 | 4d |
| 274 N Ranger Boulevard 3 bd · 2 ba · 1,420 sf · Single Family Residence | winter park pines | $669,900 | $472 | 4d |
| 7307 Sandscove Court #5 23,760 sf · Warehouse | North Goldenrod Commerce Park | $42,000 | $2 | 4d |
| 285 Lewfield Circle #285 1 bd · 1 ba · 678 sf · Condominium | Stratford A | $147,000 | $217 | 5d |
| 1546 Miller Avenue 4 bd · 3.5 ba · 2,984 sf · Single Family Residence | Lawndale | $1,419,900 | $476 | 6d |
| 4039 Cool Water Court 4 bd · 2 ba · 2,124 sf · Single Family Residence | Lake Waunatta Woods | $739,777 | $348 | 7d |
| 1016 Aragon Avenue 4 bd · 3 ba · 1,840 sf · Half Duplex | Seville Park | $660,000 | $359 | 7d |
| 3302 Royal Street 3 bd · 2 ba · 1,197 sf · Half Duplex | Coronation | $279,900 | $234 | 7d |
| 2500 Lee Road #220 2 bd · 1 ba · 851 sf · Condominium | Lakeside Manor Apartments Condo | $199,900 | $235 | 7d |
Where the new listings are
| Community | City | New this week | Median asking |
|---|---|---|---|
| Winter Park Villas | Winter Park | 3 | $1,595,000 |
| Seville Park | Winter Park | 2 | $617,500 |
| Lake Forest Park | Winter Park | 2 | $1,812,000 |
| Maitland Shores | Winter Park | 2 | $3,659,970 |
| Lakeside Manor Apartments Condo | Winter Park | 2 | $164,950 |
| Stratford A | Winter Park | 2 | $168,450 |
How to read this
A listing counts as new when its MLS days-on-market is seven or fewer at the nightly refresh; relists under a new MLS number count as new. Prices are asking prices. Source: live MLS feeds compiled by Momentum Research, updated September 15, 2026..