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.
24 homes came on the market in Winter Park, FL in the last 7 days — about 3 a day — at a median asking price of $565,000 ($93,080 to $3,495,000 for the middle 80%). That is 7% of the 326 homes currently for sale. The most new listings are in Kenilworth Shores (2) and ZIP 32789 (13).
New listings in Winter Park this week
| Listing | Community | Asking | $ / sq ft | Listed |
|---|---|---|---|---|
| 506 Lander Road 3 bd · 2 ba · 1,346 sf · Single Family Residence | Eastgate | $450,000 | $334 | 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 |
| 2330 Westminster Ct. 5 bd · 3 ba · 3,296 sf · Single Family Residence | Glencoe | $985,000 | $299 | 1d |
| 624 Dunraven Drive 3 bd · 2 ba · 1,762 sf · Single Family Residence | Kenilworth Shores | $620,000 | $352 | 1d |
| 330 W Morse Blvd #104 1,790 sf · Medical Office | Winter Park Comm | $93,080 | $52 | 1d |
| 1631 Hillcrest Avenue 5 bd · 5.5 ba · 4,754 sf · Single Family Residence | Ellno Willo | $4,500,000 | $947 | 2d |
| 1884 Jessica Court 3 bd · 2 ba · 1,666 sf · Single Family Residence | Waterbridge | $699,900 | $420 | 2d |
| 808 Densmore Drive 3 bd · 2 ba · 1,460 sf · Single Family Residence | Winter Park Estates | $509,999 | $349 | 2d |
| 1825 Whitehall Drive 4 bd · 5 ba · 4,311 sf · Single Family Residence | Kenilworth Shores | $3,195,000 | $741 | 3d |
| 4832 Tangerine Avenue #4832 2 bd · 2 ba · 1,058 sf · Condominium | Wrenwood Condominium | $188,800 | $178 | 3d |
| 2887 Temple Trail 2 bd · 2.5 ba · 1,801 sf · Townhouse | — | $695,000 | $386 | 4d |
| 1458 Lone Feather Trail 4 bd · 2.5 ba · 1,770 sf · Single Family Residence | — | $650,000 | $367 | 4d |
| 239 Orange Terrace Drive 4 bd · 2.5 ba · 1,866 sf · Single Family Residence | — | $450,000 | $241 | 4d |
| 5468 Bracken Court 3 bd · 2.5 ba · 1,602 sf · Townhouse | — | $299,000 | $187 | 4d |
| 4786 Tangerine Avenue #4786 2 bd · 1.5 ba · 1,281 sf · Townhouse | Wrenwood Condominium | $220,000 | $172 | 4d |
| 7307 Sandscove Court #5 23,760 sf · Warehouse | North Goldenrod Commerce Park | $42,000 | $2 | 4d |
| 617 N Interlachen Avenue 11 bd · 7.5 ba · 3,615 sf · Single Family Residence | Winter Park Villas | $4,695,000 | $1,299 | 5d |
| 1600 Legion Drive 5 bd · 5.5 ba · 4,483 sf · Single Family Residence | Green Oaks | $3,495,000 | $780 | 5d |
| 1681 Woodland Avenue 5 bd · 4.5 ba · 3,682 sf · Single Family Residence | Comstock Park | $2,629,000 | $714 | 5d |
| 7536 Village Green Drive 3 bd · 2 ba · 1,647 sf · Single Family Residence | — | $479,900 | $291 | 5d |
| 1939 Woodcrest Drive 4 bd · 3.5 ba · 2,575 sf · Single Family Residence | — | $1,349,000 | $524 | 7d |
| 8061 Pleasant Pine Circle 5 bd · 3.5 ba · 3,496 sf · Single Family Residence | Enclave At Aloma | $750,000 | $215 | 7d |
| 2640 Beverly Avenue 3 bd · 1 ba · 1,216 sf · Single Family Residence | Killarney Circle | $305,000 | $251 | 7d |
Where the new listings are
| Community | City | New this week | Median asking |
|---|---|---|---|
| Kenilworth Shores | Winter Park | 2 | $1,907,500 |
| Wrenwood Condominium | Winter Park | 2 | $204,400 |
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 24, 2026. and this week’s Winter Park price reductions.