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.
71 homes came on the market in Winter Park, FL in the last 7 days — about 10 a day — at a median asking price of $589,900 ($150,000 to $3,600,000 for the middle 80%). That is 24% of the 291 homes currently for sale. The most new listings are in Kenilworth Shores (2) and ZIP 32789 (38).
New listings in Winter Park this week
| Listing | Community | Asking | $ / sq ft | Listed |
|---|---|---|---|---|
| 901 Golfview Terrace 5 bd · 5.5 ba · 5,479 sf · Single Family Residence | — | $6,995,000 | $1,277 | 0d |
| 702 Via Bella 4 bd · 5.5 ba · 3,720 sf · Single Family Residence | Palmer Ave Lakeside Prop | $4,400,000 | $1,183 | 0d |
| 160 W Rockwood Way 5 bd · 5.5 ba · 4,015 sf · Single Family Residence | Forest Hills | $3,395,000 | $846 | 0d |
| 1409 Aster Court 4 bd · 2 ba · 2,050 sf · Single Family Residence | — | $589,900 | $288 | 0d |
| 1071 Aragon Avenue 2 bd · 2.5 ba · 1,851 sf · Townhouse | Seville Park | $575,000 | $311 | 0d |
| 3209 Heartwood Avenue 4 bd · 2 ba · 1,627 sf · Single Family Residence | Bel Aire Pines | $449,900 | $277 | 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 |
| 825 Palmer Avenue 5 bd · 6 ba · 5,122 sf · Single Family Residence | J Kronenberger | $5,195,900 | $1,014 | 1d |
| 540 N Pennsylvania Avenue 4 bd · 2 ba · 1,652 sf · Single Family Residence | Winter Park Villas | $3,950,000 | $2,391 | 1d |
| 1742 Temple Drive 4 bd · 5 ba · 3,658 sf · Single Family Residence | Lake Knowles Terrace | $3,695,999 | $1,010 | 1d |
| 200 S Interlachen Avenue #350 3 bd · 3.5 ba · 3,110 sf · Condominium | — | $2,350,000 | $756 | 1d |
| 918 Enclave Place 5 bd · 4.5 ba · 3,713 sf · Single Family Residence | the Enclave | $2,125,000 | $572 | 1d |
| 2007 Edwin Boulevard 4 bd · 3.5 ba · 3,314 sf · Single Family Residence | Eastgate | $1,995,000 | $602 | 1d |
| 513 Dunraven Drive 5 bd · 4.5 ba · 3,560 sf · Single Family Residence | Kenilworth Shores | $1,950,000 | $548 | 1d |
| 2614 Parkland Drive 4 bd · 3.5 ba · 3,307 sf · Single Family Residence | Parklando | $1,890,000 | $572 | 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 |
| 504 W Swoope Avenue 3 bd · 2.5 ba · 2,563 sf · Townhouse | Vilasa Townhomes | $1,300,000 | $507 | 1d |
| 913 Moss Lane 3 bd · 2 ba · 1,887 sf · Single Family Residence | Maitland Shores | $950,000 | $503 | 1d |
| 2052 Wood Thrush Lane 4 bd · 3 ba · 2,807 sf · Single Family Residence | Waters Edge At Hawks Crest | $900,000 | $321 | 1d |
| 1278 S Pennsylvania Avenue #13 3 bd · 2.5 ba · 1,957 sf · Condominium | Casa Jardin Condo | $799,000 | $408 | 1d |
| 739 Roughbeard Road 5 bd · 3 ba · 2,194 sf · Single Family Residence | winter park pines | $780,000 | $356 | 1d |
| 250 Carolina Avenue #205 2 bd · 2 ba · 1,311 sf · Condominium | Park West Condo | $739,000 | $564 | 1d |
| 5316 Halyard Court 3 bd · 2 ba · 1,380 sf · Single Family Residence | — | $495,000 | $359 | 1d |
| 712 Baffie Avenue 3 bd · 1 ba · 1,304 sf · Single Family Residence | Dubsdread Heights | $448,000 | $344 | 1d |
| 2818 Ambergate Road 3 bd · 2 ba · 1,398 sf · Single Family Residence | Winter Park Estates | $429,900 | $308 | 1d |
| 5405 Justine Way 3 bd · 2 ba · 1,247 sf · Single Family Residence | Wrenwood | $399,900 | $321 | 1d |
| 7506 Cranes Creek Court #30 3 bd · 2.5 ba · 1,861 sf · Townhouse | — | $365,000 | $196 | 1d |
| 2526 Passamonte Drive #10F 3 bd · 2.5 ba · 1,790 sf · Condominium | — | $335,000 | $187 | 1d |
| 7530 Cranes Creek Court 3 bd · 2.5 ba · 1,545 sf · Townhouse | — | $309,900 | $201 | 1d |
| 170 Balfour Drive #1 2 bd · 2 ba · 1,032 sf · Condominium | — | $299,000 | $290 | 1d |
| 188 Sandlewood #1 2 bd · 2.5 ba · 1,133 sf · Condominium | — | $290,000 | $256 | 1d |
| 7454 Wynnewood Square #188 3 bd · 2.5 ba · 1,151 sf · Condominium | — | $229,000 | $199 | 1d |
| 222 Lewfield Circle 2 bd · 2 ba · 953 sf · Condominium | Stratford A | $189,900 | $199 | 1d |
| 1695 Lee Road #D107 1 bd · 1 ba · 638 sf · Condominium | — | $180,000 | $282 | 1d |
| 200 Saint Andrews Boulevard #3408 1 bd · 1 ba · 793 sf · Condominium | Four Seasons Condo | $170,000 | $214 | 1d |
| 7476 Woodburn Court #38 2 bd · 2.5 ba · 1,031 sf · Condominium | — | $170,000 | $165 | 1d |
| 2500 Lee Road #123 1 bd · 1 ba · 645 sf · Condominium | Lakeside Manor Apartments Condo | $169,900 | $263 | 1d |
| 1695 Lee Road #C206 2 bd · 1 ba · 881 sf · Condominium | Waterfall Cove | $140,000 | $159 | 1d |
| 302 Lewfield Circle #302 1 bd · 1 ba · 678 sf · Condominium | Stratford A | $140,000 | $206 | 1d |
| 3021 Aaron Burr Avenue #3 2 bd · 2.5 ba · 1,090 sf · Condominium | Colonies | $140,000 | $128 | 1d |
| 173 Scottsdale Square #173 1 bd · 1 ba · 785 sf · Condominium | Winter Park Woods Condo | $100,000 | $127 | 1d |
| 330 W Morse Blvd #104 1,790 sf · Medical Office | Winter Park Comm | $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 |
| 100 S Interlachen Avenue #401 3 bd · 2 ba · 1,639 sf · Condominium | Cloisters Condo | $850,000 | $519 | 2d |
| 870 N Phelps Avenue 4 bd · 3 ba · 2,301 sf · Single Family Residence | — | $850,000 | $369 | 2d |
| 3150 Shady Pine Avenue 4 bd · 2 ba · 1,624 sf · Single Family Residence | — | $439,900 | $271 | 2d |
| 3651 N Goldenrod Road #C109 2 bd · 2 ba · 840 sf · Condominium | Lancelot | $165,000 | $196 | 2d |
| 200 Saint Andrews Boulevard #704 1 bd · 1 ba · 793 sf · Condominium | Four Seasons Condo | $159,000 | $201 | 2d |
| 7453 Daniel Webster Drive #A5 2 bd · 2 ba · 1,063 sf · Condominium | Colonies | $150,000 | $141 | 2d |
| 276 Detmar Drive 4 bd · 5 ba · 4,202 sf · Single Family Residence | — | $3,600,000 | $857 | 3d |
| 662 Granville Drive 5 bd · 5.5 ba · 4,478 sf · Single Family Residence | Park Grove | $3,495,000 | $780 | 3d |
| 1803 Barker Drive 4 bd · 3 ba · 3,463 sf · Single Family Residence | South Lakemont Shores | $2,190,000 | $632 | 3d |
| 555 E Lake Sue Avenue 4 bd · 4 ba · 3,776 sf · Single Family Residence | — | $2,095,000 | $555 | 3d |
| 100 S Virginia Avenue #201 3 bd · 3 ba · 2,756 sf · Condominium | Winter Park Residential | $1,450,000 | $526 | 3d |
| 5108 Lazy Oaks Drive #5108 2 bd · 2 ba · 1,008 sf · Condominium | Lazy Oaks Condo | $269,000 | $267 | 3d |
| 698 N New York Avenue 5 bd · 5.5 ba · 5,096 sf · Single Family Residence | — | $6,195,000 | $1,216 | 4d |
| 2260 Mulbry Drive 5 bd · 4 ba · 3,246 sf · Single Family Residence | Lake Forest Park | $1,925,000 | $593 | 4d |
| 1256 S Pennsylvania Avenue #9 3 bd · 2.5 ba · 1,957 sf · Townhouse | Casa Jardin Condo | $950,000 | $485 | 4d |
| 2572 Fifeshire Drive 4 bd · 2.5 ba · 2,578 sf · Single Family Residence | — | $925,000 | $359 | 4d |
| 7307 Sandscove Court #5 23,760 sf · Warehouse | North Goldenrod Commerce Park | $42,000 | $2 | 4d |
| 2417 Chantilly Avenue 4 bd · 3.5 ba · 2,718 sf · Single Family Residence | Winter Park Village | $1,579,000 | $581 | 5d |
| 266 N Ranger Boulevard 4 bd · 3 ba · 1,692 sf · Single Family Residence | winter park pines | $724,900 | $428 | 5d |
| 192 Balfour Drive #2 2 bd · 2 ba · 1,287 sf · Condominium | — | $319,000 | $248 | 5d |
| 532 Langholm Drive 5 bd · 4.5 ba · 4,050 sf · Single Family Residence | Kenilworth Shores | $2,990,000 | $738 | 6d |
| 250 Carolina Avenue #202 3 bd · 2 ba · 1,450 sf · Condominium | Park West Condo | $699,000 | $482 | 6d |
| 2626 Ambergate Road 3 bd · 1 ba · 1,143 sf · Single Family Residence | Winter Park Estates | $380,000 | $332 | 6d |
| 3334 Young Street 3 bd · 2 ba · 1,706 sf · Single Family Residence | Winter Park Forest | $474,900 | $278 | 7d |
| 2136 Linden Road 3 bd · 1.5 ba · 1,185 sf · Single Family Residence | — | $365,000 | $308 | 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 |
|---|---|---|---|
| Kenilworth Shores | Winter Park | 2 | $2,470,000 |
| Four Seasons Condo | Winter Park | 2 | $164,500 |
| Park West Condo | Winter Park | 2 | $719,000 |
| Lake Forest Park | Winter Park | 2 | $1,812,000 |
| Maitland Shores | Winter Park | 2 | $3,474,995 |
| Lakeside Manor Apartments Condo | Winter Park | 2 | $184,900 |
| Stratford A | Winter Park | 2 | $164,950 |
| Colonies | Winter Park | 2 | $145,000 |
| Casa Jardin Condo | Winter Park | 2 | $874,500 |
| Winter Park Estates | Winter Park | 2 | $404,950 |
| winter park pines | Winter Park | 2 | $752,450 |
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 October 5, 2026. and this week’s Winter Park price reductions.