New Listings in Windermere, 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 Windermere listing from the last week, newest first, with price, size and community, refreshed every night from the live MLS record.
54 homes came on the market in Windermere, FL in the last 7 days — about 8 a day — at a median asking price of $1,494,000 ($409,900 to $6,950,000 for the middle 80%). That is 23% of the 230 homes currently for sale. The most new listings are in Isleworth (10) and ZIP 34786 (54).
New listings in Windermere this week
| Listing | Community | Asking | $ / sq ft | Listed |
|---|---|---|---|---|
| 11532 Waterstone Loop Drive 4 bd · 5 ba · 4,169 sf · Single Family Residence | Waterstone | $2,350,000 | $564 | 0d |
| 104 E 1St Avenue 4 bd · 2.5 ba · 2,441 sf · Single Family Residence | Windermere Town | $1,280,000 | $524 | 0d |
| 9609 Westover Club Circle 5 bd · 4.5 ba · 3,797 sf · Single Family Residence | — | $969,000 | $255 | 0d |
| 5603 Marleon Drive 7 bd · 9 ba · 22,108 sf · Single Family Residence | — | $27,000,000 | $1,221 | 1d |
| 5192 Vardon Drive 6 bd · 9 ba · 13,494 sf · Single Family Residence | — | $19,500,000 | $1,445 | 1d |
| 5092 Isleworth Country Club Drive 4 bd · 5 ba · 7,100 sf · Single Family Residence | Isleworth | $8,500,000 | $1,197 | 1d |
| 5373 Isleworth Country Club Drive 5 bd · 5.5 ba · 5,993 sf · Single Family Residence | Isleworth | $7,200,000 | $1,201 | 1d |
| 1330 Lake Olivia 6 bd · 7 ba · 6,442 sf · Single Family Residence | Lake Olivia Reserve | $5,500,000 | $854 | 1d |
| 5186 Vardon Drive 6 bd · 6 ba · 4,739 sf · Single Family Residence | Isleworth | $4,395,000 | $927 | 1d |
| 6120 Greatwater Drive 5 bd · 5 ba · 5,580 sf · Single Family Residence | Keenes Pointe | $3,999,000 | $717 | 1d |
| 4906 Aviva Garden Court 4 bd · 4.5 ba · 6,605 sf · Single Family Residence | Isleworth | $3,850,000 | $583 | 1d |
| 9960 6Th Street 5 bd · 5.5 ba · 6,182 sf · Single Family Residence | Gotha Town | $3,750,000 | $607 | 1d |
| 9310 Isleworth Gardens Drive 3 bd · 4 ba · 4,333 sf · Single Family Residence | Isleworth | $3,595,000 | $830 | 1d |
| 5524 Worsham Court 4 bd · 6 ba · 7,669 sf · Single Family Residence | Isleworth | $3,500,000 | $456 | 1d |
| 6126 Payne Stewart Drive 3 bd · 3.5 ba · 2,848 sf · Single Family Residence | Isleworth | $3,250,000 | $1,141 | 1d |
| 5050 Isleworth Country Club Drive 4 bd · 4.5 ba · 3,365 sf · Single Family Residence | Isleworth | $3,189,000 | $948 | 1d |
| 12722 S Lake Sawyer Lane 5 bd · 4 ba · 5,139 sf · Single Family Residence | — | $2,400,000 | $467 | 1d |
| 6102 S Hampshire Ct 4 bd · 5.5 ba · 4,812 sf · Single Family Residence | Keenes Pointe | $2,240,000 | $466 | 1d |
| 7467 Lake Albert Drive 6 bd · 6.5 ba · 5,140 sf · Single Family Residence | lake burden south | $1,870,000 | $364 | 1d |
| 11035 Schooner Way 4 bd · 3 ba · 3,517 sf · Single Family Residence | Marina Bay Estates | $1,500,000 | $426 | 1d |
| 17526 Black Rail Street 5 bd · 4 ba · 3,656 sf · Single Family Residence | Enclave | $1,500,000 | $410 | 1d |
| 12721 Jacob Grace Court 4 bd · 4 ba · 3,763 sf · Single Family Residence | Tildens Grove | $1,488,000 | $395 | 1d |
| 11768 Hampstead Street 6 bd · 4 ba · 3,900 sf · Single Family Residence | Enclave | $1,318,000 | $338 | 1d |
| 8524 Vivaro Isle Way 4 bd · 3 ba · 2,680 sf · Single Family Residence | windermere isle | $950,000 | $354 | 1d |
| 11727 Delwick Drive 4 bd · 3 ba · 2,704 sf · Single Family Residence | reserve at belmere | $875,000 | $324 | 1d |
| 7252 Backwoods Trail 4 bd · 3 ba · 2,214 sf · Single Family Residence | ashlin park | $645,000 | $291 | 1d |
| 11543 Charnock Drive 4 bd · 2.5 ba · 2,214 sf · Single Family Residence | Westside Village | $560,000 | $253 | 1d |
| 8225 Bryce Canyon Avenue 4 bd · 2.5 ba · 1,840 sf · Single Family Residence | windermere trails | $560,000 | $304 | 1d |
| 8470 Iron Mountain Trail 3 bd · 2.5 ba · 1,664 sf · Townhouse | windermere trails | $449,900 | $270 | 1d |
| 12333 Via Derna Place 3 bd · 2.5 ba · 1,919 sf · Townhouse | Carrington | $449,000 | $234 | 1d |
| 8860 Herencia Alley 3 bd · 2.5 ba · 1,547 sf · Townhouse | — | $409,900 | $265 | 1d |
| 14350 Bridgewater Crossings Boulevard 4 bd · 2.5 ba · 2,294 sf · Townhouse | Tennyson Park Summerport | $405,000 | $177 | 1d |
| 12417 Cruxbury Drive 2 bd · 2.5 ba · 1,311 sf · Townhouse | Lakes Windermere Lake Reams Twhm | $360,000 | $275 | 1d |
| 8168 Boat Hook Loop #303 3 bd · 2 ba · 1,442 sf · Condominium | — | $320,000 | $222 | 1d |
| 11446 Jasper Kay Terrace #202 2 bd · 2 ba · 1,161 sf · Condominium | lakeside lakes windermere windermere | $295,000 | $254 | 1d |
| 5036 Latrobe Drive 6 bd · 8 ba · 15,337 sf · Single Family Residence | Isleworth | $18,750,000 | $1,223 | 2d |
| 4243 Isabella Circle 5 bd · 6 ba · 5,502 sf · Single Family Residence | Casabella | $3,290,000 | $598 | 2d |
| 8142 Tibet Butler Drive 5 bd · 6.5 ba · 5,747 sf · Single Family Residence | Keenes Pointe | $2,685,000 | $467 | 2d |
| 9043 Horizon Pointe Trail 4 bd · 3 ba · 3,746 sf · Single Family Residence | windermere trails | $870,000 | $232 | 2d |
| 6828 Helmsley Circle 4 bd · 3 ba · 2,064 sf · Single Family Residence | Preston Square | $575,000 | $279 | 2d |
| 13535 Bramham Lane 3 bd · 2 ba · 1,820 sf · Single Family Residence | Lakes Windermere Peachtree | $489,900 | $269 | 2d |
| 9010 Reflection Pointe Drive 4 bd · 3.5 ba · 3,264 sf · Single Family Residence | windermere trails | $945,000 | $290 | 3d |
| 8180 Boat Hook Loop #109 2 bd · 2 ba · 1,161 sf · Condominium | Lakeside Lakes | $299,500 | $258 | 3d |
| 6113 Grosvenor Shore Drive 7 bd · 7 ba · 8,722 sf · Single Family Residence | Keenes Pointe | $6,950,000 | $797 | 4d |
| 4201 Isabella Circle 6 bd · 7 ba · 6,896 sf · Single Family Residence | Casabella | $3,990,000 | $579 | 4d |
| 3986 Isabella Circle 5 bd · 6 ba · 5,342 sf · Single Family Residence | Casabella | $3,599,000 | $674 | 4d |
| 1243 Dingens Avenue 4 bd · 3 ba · 2,728 sf · Single Family Residence | Gotha Town | $990,000 | $363 | 4d |
| 6679 Duncaster Street 3 bd · 2 ba · 1,926 sf · Single Family Residence | lakes windermere windermere | $525,000 | $273 | 4d |
| 9921 Lake Louise Drive 5 bd · 6 ba · 6,970 sf · Single Family Residence | Isleworth | $6,650,000 | $954 | 5d |
| 12809 Holdenbury Lane 4 bd · 2.5 ba · 2,683 sf · Single Family Residence | lakes windermere windermere | $625,000 | $233 | 5d |
| 7271 Londale Boulevard 3 bd · 2 ba · 2,147 sf · Single Family Residence | Enclave Berkshire Park B G H | $565,000 | $263 | 6d |
| 515 W 2Nd Avenue 4 bd · 5.5 ba · 3,966 sf · Single Family Residence | Windermere Town | $3,300,000 | $832 | 7d |
| 6309 Earthgold Drive 4 bd · 2.5 ba · 2,648 sf · Single Family Residence | West Point Commons | $880,000 | $332 | 7d |
| 11861 Vermillion Avenue 3 bd · 2.5 ba · 1,600 sf · Townhouse | windermere trails | $475,000 | $297 | 7d |
Where the new listings are
| Community | City | New this week | Median asking |
|---|---|---|---|
| Isleworth | Windermere | 10 | $4,122,500 |
| Keenes Pointe | Windermere | 4 | $3,342,000 |
| windermere trails | Windermere | 3 | $870,000 |
| Casabella | Windermere | 3 | $3,599,000 |
| windermere trails | Windermere | 2 | $462,450 |
| Windermere Town | Windermere | 2 | $2,290,000 |
| Enclave | Windermere | 2 | $1,409,000 |
| Gotha Town | Windermere | 2 | $2,370,000 |
| lakes windermere windermere | Windermere | 2 | $575,000 |
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 Windermere price reductions.