Homes under $500K in Windermere, FL
31 for sale · 110 homes listed · Updated September 27, 2026 · Page 2 of 3
- 13736 summerport village parkway, Windermere 34786 Active Under Contract $440,000 · 3 bd · 3 ba · 1,976 sqft
- 13449 carroway street, Windermere 34786 Active Under Contract $409,900 · 3 bd · 3 ba · 1,387 sqft
- 9017 woodbreeze boulevard, Windermere 34786 Active Under Contract $464,000 · 3 bd · 2 ba · 1,723 sqft
- 13006 sunkiss loop, Windermere 34786 Active Under Contract $379,900 · 2 bd · 2 ba · 1,155 sqft
- 14125 oasis cove boulevard 206, Windermere 34786 Active Under Contract $399,900 · 3 bd · 3 ba · 1,647 sqft
- 12303 langstaff drive, Windermere 34786 Active Under Contract $400,000 · 3 bd · 3 ba · 1,545 sqft
- 14077 ancilla boulevard, Windermere 34786 Active Under Contract $399,000 · 3 bd · 3 ba · 1,651 sqft
- 13730 lensdale lane, Windermere 34786 Active Under Contract $375,000 · 4 bd · 3 ba · 1,640 sqft
- 5426 kumquat loop, Windermere 34786 Active Under Contract $400,000 · 2 bd · 2 ba · 1,155 sqft
- 12930 vennetta way, Windermere 34786 Off market since Sep 2026 $350,000 · 3 bd · 3 ba · 1,644 sqft
- 12333 via derna place, Windermere 34786 Off market since Jul 2026 $449,000 · 3 bd · 3 ba · 1,919 sqft
- 12305 via derna place, Windermere 34786 Off market since Sep 2026 $450,000 · 3 bd · 3 ba · 1,891 sqft
- 13712 summerport village parkway, Windermere 34786 Off market since Sep 2026 $444,900 · 3 bd · 3 ba · 1,997 sqft
- 13755 bravante alley, Windermere 34786 Off market since Sep 2026 $455,000 · 3 bd · 3 ba · 2,091 sqft
- 12353 via derna place, Windermere 34786 Off market since Sep 2026 $460,000 · 3 bd · 3 ba · 1,974 sqft
- 12405 cruxbury drive, Windermere 34786 Off market since Sep 2026 $399,000 · 2 bd · 3 ba · 1,429 sqft
- 7327 millstone street, Windermere 34786 Off market since Sep 2026 $449,000 · 3 bd · 3 ba · 1,531 sqft
- 14422 desert haven street 4206, Windermere 34786 Off market since Jul 2026 $385,000 · 3 bd · 3 ba · 1,840 sqft
- 12966 vennetta way, Windermere 34786 Off market since Sep 2026 $349,000 · 3 bd · 3 ba · 1,644 sqft
- 7612 fairgrove avenue, Windermere 34786 Off market since Sep 2026 $440,000 · 3 bd · 3 ba · 1,742 sqft
- 8866 herencia alley, Windermere 34786 Off market since Sep 2026 $415,000 · 3 bd · 3 ba · 1,577 sqft
- 8180 boat hook loop 109, Windermere 34786 Off market since Sep 2026 $299,500 · 2 bd · 2 ba · 1,161 sqft
- 14442 desert haven street 4305, Windermere 34786 Off market since Sep 2026 $359,900 · 3 bd · 3 ba · 1,534 sqft
- 7867 berkshire oak alley, Windermere 34786 Off market since Sep 2026 $499,990 · 4 bd · 3 ba · 2,221 sqft
- 11822 silverlake park drive, Windermere 34786 Off market since Aug 2026 $485,000 · 3 bd · 3 ba · 1,829 sqft
- 11861 vermillion avenue, Windermere 34786 Off market since Sep 2026 $475,000 · 3 bd · 3 ba · 1,600 sqft
- 8266 bryce canyon avenue, Windermere 34786 Off market since Sep 2026 $470,000 · 3 bd · 3 ba · 1,825 sqft
- 12357 via derna place, Windermere 34786 Off market since Sep 2026 $430,000 · 3 bd · 3 ba · 1,919 sqft
- 11933 water run alley, Windermere 34786 Off market since Jul 2026 $414,000 · 3 bd · 3 ba · 1,569 sqft
- 12988 borland street, Windermere 34786 Off market since Sep 2026 $435,000 · 3 bd · 3 ba · 1,460 sqft
- 8218 mystic view way 2801, Windermere 34786 Off market since Sep 2026 $399,999 · 3 bd · 3 ba · 1,840 sqft
- 7723 fairgrove avenue, Windermere 34786 Off market since Sep 2026 $380,000 · 3 bd · 3 ba · 1,680 sqft
- 8470 iron mountain trail, Windermere 34786 Off market since Jul 2026 $449,900 · 3 bd · 3 ba · 1,664 sqft
- 8180 boat hook loop 102, Windermere 34786 Off market since Sep 2026 $295,000 · 2 bd · 2 ba · 1,161 sqft
- 8168 boat hook loop 724, Windermere 34786 Off market since Sep 2026 $325,000 · 3 bd · 2 ba · 1,455 sqft
- 11446 jasper kay terrace 103, Windermere 34786 Off market since Sep 2026 $330,000 · 3 bd · 2 ba · 1,442 sqft
- 7060 ventnor drive, Windermere 34786 Off market since Sep 2026 $444,900 · 3 bd · 3 ba · 1,642 sqft
- 14030 sparkling cove lane 603, Windermere 34786 Off market since Sep 2026 $330,000 · 2 bd · 3 ba · 1,232 sqft
- 11429 brownstone street, Windermere 34786 Off market since Sep 2026 $439,000 · 4 bd · 3 ba · 1,910 sqft
- 5579 somersby road, Windermere 34786 Off market since Sep 2026 $375,000 · 3 bd · 3 ba · 1,579 sqft
- 7712 fordson lane, Windermere 34786 Off market since Sep 2026 $350,000 · 3 bd · 3 ba · 1,644 sqft
- 8386 iron mountain trail, Windermere 34786 Off market since Sep 2026 $438,000 · 4 bd · 3 ba · 1,631 sqft
- 12914 vennetta way, Windermere 34786 Off market since Sep 2026 $379,900 · 3 bd · 3 ba · 1,644 sqft
- 12744 langstaff drive, Windermere 34786 Off market since Sep 2026 $404,990 · 3 bd · 3 ba · 1,369 sqft
- 7752 rigby street, Windermere 34786 Off market since Sep 2026 $415,000 · 3 bd · 3 ba · 1,335 sqft
- 7668 fairgrove avenue, Windermere 34786 Off market since Sep 2026 $485,000 · 4 bd · 3 ba · 1,866 sqft
- 8860 herencia alley, Windermere 34786 Off market since Sep 2026 $409,900 · 3 bd · 3 ba · 1,547 sqft
- 11425 brownstone street, Windermere 34786 Off market since Sep 2026 $420,000 · 3 bd · 3 ba · 1,881 sqft
- 7430 bentonshire avenue, Windermere 34786 Off market since Sep 2026 $354,900 · 2 bd · 3 ba · 1,412 sqft
- 11734 water run alley, Windermere 34786 Off market since Sep 2026 $445,000 · 3 bd · 3 ba · 1,727 sqft