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.
27 homes came on the market in Winter Park, FL in the last 7 days — about 4 a day — at a median asking price of $499,000 ($260,000 to $2,500,000 for the middle 80%). That is 8% of the 329 homes currently for sale. The most new listings are in Eastgate (2) and ZIP 32789 (15).
New listings in Winter Park this week
| Listing | Community | Asking | $ / sq ft | Listed |
|---|---|---|---|---|
| 470 W Comstock Avenue 6 bd · 6.5 ba · 6,134 sf · Single Family Residence | Orange County | $5,480,000 | $893 | 0d |
| 1008 N Pennsylvania Avenue 4 bd · 4.5 ba · 3,530 sf · Single Family Residence | — | $2,500,000 | $708 | 0d |
| 2718 Eastern Parkway 4 bd · 4.5 ba · 3,308 sf · Single Family Residence | Parklando | $2,450,000 | $741 | 0d |
| 1250 S Denning Drive #203 2 bd · 2 ba · 908 sf · Condominium | — | $260,000 | $286 | 0d |
| 2507 Lafayette Avenue 4 bd · 5 ba · 2,675 sf · Single Family Residence | Winter Park Village | $1,850,000 | $692 | 1d |
| 3148 Nicholson Drive 3 bd · 2 ba · 1,577 sf · Single Family Residence | Wrenwood | $449,000 | $285 | 1d |
| 2821 Chantilly Avenue 3 bd · 2 ba · 1,440 sf · Single Family Residence | Winter Park Manor | $415,000 | $288 | 1d |
| Address withheld 4 bd · 4.5 ba · 2,830 sf · Single Family Residence | Lake Killarney Shores | $2,100,000 | $742 | 2d |
| 531 Worthington Drive 3 bd · 3 ba · 2,626 sf · Single Family Residence | Kenilworth Shores | $1,100,000 | $419 | 2d |
| 1400 Pelican Bay Trail 5 bd · 3.5 ba · 3,600 sf · Single Family Residence | — | $968,000 | $269 | 2d |
| 640 N Park Avenue #26 2 bd · 2 ba · 858 sf · Condominium | Park Aire Condo | $629,500 | $734 | 2d |
| 1934 Taylor Avenue 4 bd · 1.5 ba · 1,470 sf · Single Family Residence | Eastgate | $499,000 | $339 | 2d |
| 535 N Interlachen Avenue #302 2 bd · 2 ba · 970 sf · Condominium | Andalucia Apartments | $485,000 | $500 | 2d |
| 2885 Roxbury Road 3 bd · 2 ba · 1,511 sf · Single Family Residence | — | $450,000 | $298 | 2d |
| 662 Trinidad Court #662 1 bd · 1 ba · 759 sf · Condominium | Winter Park Villas | $177,000 | $233 | 2d |
| 1140 Washington Avenue #16C 3 bd · 2.5 ba · 2,069 sf · Townhouse | — | $739,000 | $357 | 3d |
| 1386 Clematis Lane 4 bd · 3 ba · 1,714 sf · Single Family Residence | — | $417,000 | $243 | 3d |
| 1507 Golfside Drive 3 bd · 2 ba · 2,003 sf · Single Family Residence | Greenview At Winter Pines | $849,000 | $424 | 5d |
| 3157 Shady Pine Avenue 3 bd · 2 ba · 1,495 sf · Single Family Residence | Bel Aire Pines | $425,000 | $284 | 5d |
| 2176 Crandon Avenue 2 bd · 1 ba · 959 sf · Single Family Residence | Olympia Heights Annex | $399,000 | $416 | 5d |
| 1663 N Park Avenue 4 bd · 5 ba · 3,640 sf · Single Family Residence | dixie terrace winter park | $2,750,000 | $755 | 6d |
| 1824 Jessica Court 4 bd · 2.5 ba · 2,582 sf · Single Family Residence | Waterbridge | $1,149,000 | $445 | 6d |
| 1735 Meadowgold Lane 3 bd · 2 ba · 1,768 sf · Single Family Residence | — | $480,000 | $271 | 6d |
| 506 Lander Road 3 bd · 2 ba · 1,346 sf · Single Family Residence | Eastgate | $450,000 | $334 | 6d |
| 2315 Kestrel Perch Place 4 bd · 3.5 ba · 2,553 sf · Single Family Residence | — | $739,000 | $289 | 7d |
| 700 Melrose Avenue #B23 2 bd · 2 ba · 1,074 sf · Condominium | Winter Park Gardens Condo | $295,000 | $275 | 7d |
| 3019 Antique Oaks Circle #127 1 bd · 1 ba · 749 sf · Condominium | Parkview Village | $139,998 | $187 | 7d |
Where the new listings are
| Community | City | New this week | Median asking |
|---|---|---|---|
| Eastgate | Winter Park | 2 | $474,500 |
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 November 14, 2026. and this week’s Winter Park price reductions.