Homes under $500K in Windermere, FL
41 for sale · 102 homes listed · Updated November 9, 2026 · Page 1 of 3
- 14442 Desert Haven Street #4305, Windermere 34786 $359,000 · 3 bd · 3 ba · 1,534 sqft
- 8860 Herencia Alley, Windermere 34786 $398,000 · 3 bd · 3 ba · 1,547 sqft
- 8866 Herencia Alley, Windermere 34786 $415,000 · 3 bd · 3 ba · 1,577 sqft
- 7712 Fordson Lane, Windermere 34786 $345,000 · 3 bd · 3 ba · 1,644 sqft
- 11425 Brownstone Street, Windermere 34786 $410,000 · 3 bd · 3 ba · 1,881 sqft
- 8168 Boat Hook Loop #303, Windermere 34786 $320,000 · 3 bd · 2 ba · 1,442 sqft
- 12417 Cruxbury Drive, Windermere 34786 $359,000 · 2 bd · 3 ba · 1,311 sqft
- 12353 Via Derna Place, Windermere 34786 $445,900 · 3 bd · 3 ba · 1,974 sqft
- 11938 Silverlake Park Drive, Windermere 34786 $499,999 · 4 bd · 3 ba · 2,074 sqft
- 12333 Via Derna Place, Windermere 34786 $445,000 · 3 bd · 3 ba · 1,919 sqft
- 9764 Gotha Road, Windermere 34786 $425,000 · 2 bd · 1 ba · 1,216 sqft
- 11429 Brownstone Street, Windermere 34786 $429,000 · 4 bd · 3 ba · 1,910 sqft
- 7430 Bentonshire Avenue, Windermere 34786 $354,000 · 2 bd · 3 ba · 1,412 sqft
- 8180 Boat Hook Loop #102, Windermere 34786 $295,000 · 2 bd · 2 ba · 1,161 sqft
- 7752 Rigby Street, Windermere 34786 $385,000 · 3 bd · 3 ba · 1,335 sqft
- 14030 Sparkling Cove Lane #603, Windermere 34786 $324,900 · 2 bd · 3 ba · 1,232 sqft
- 8218 Mystic View Way #2801, Windermere 34786 $397,500 · 3 bd · 3 ba · 1,840 sqft
- 11446 Jasper Kay Terrace #202, Windermere 34786 $290,000 · 2 bd · 2 ba · 1,161 sqft
- 13712 Summerport Village Parkway, Windermere 34786 $444,900 · 3 bd · 3 ba · 1,997 sqft
- 7867 Berkshire Oak Alley, Windermere 34786 $499,990 · 4 bd · 3 ba · 2,221 sqft
- 8180 Boat Hook Loop #109, Windermere 34786 $299,500 · 2 bd · 2 ba · 1,161 sqft
- 12744 Langstaff Drive, Windermere 34786 $394,900 · 3 bd · 3 ba · 1,369 sqft
- 7060 Ventnor Drive, Windermere 34786 $444,900 · 3 bd · 3 ba · 1,642 sqft
- 8386 Iron Mountain Trail, Windermere 34786 $438,000 · 4 bd · 3 ba · 1,631 sqft
- 13535 Bramham Lane, Windermere 34786 $489,900 · 3 bd · 2 ba · 1,820 sqft
- 8608 Brookvale Drive, Windermere 34786 $379,900 · 3 bd · 3 ba · 1,480 sqft
- 8168 Boat Hook Loop #302, Windermere 34786 $294,997 · 2 bd · 2 ba · 1,161 sqft
- 8179 Maritime Flag Street #206, Windermere 34786 $350,000 · 3 bd · 2 ba · 1,332 sqft
- 8634 Danforth Drive, Windermere 34786 $365,000 · 2 bd · 3 ba · 1,380 sqft
- 11963 Vermillion Avenue, Windermere 34786 $430,000 · 3 bd · 3 ba · 1,676 sqft
- 8276 Maritime Flag Street #1204, Windermere 34786 $324,900 · 3 bd · 2 ba · 1,455 sqft
- 8867 Herencia Alley, Windermere 34786 $405,000 · 3 bd · 3 ba · 1,382 sqft
- 12930 Vennetta Way, Windermere 34786 $349,000 · 3 bd · 3 ba · 1,644 sqft
- 11267 Grander Drive, Windermere 34786 $435,000 · 3 bd · 3 ba · 1,743 sqft
- 14500 Bridgewater Crossings Boulevard, Windermere 34786 $400,000 · 4 bd · 3 ba · 1,706 sqft
- 8516 Danforth Drive, Windermere 34786 $350,000 · 2 bd · 3 ba · 1,280 sqft
- 13731 Calera Alley, Windermere 34786 $465,000 · 3 bd · 3 ba · 2,113 sqft
- 7663 Bramwell Street, Windermere 34786 $369,990 · 3 bd · 3 ba · 1,398 sqft
- 8214 Serenity Spring Drive #2405, Windermere 34786 $350,000 · 3 bd · 3 ba · 1,512 sqft
- 7129 Thicket Branch Alley, Windermere 34786 $450,000 · 3 bd · 3 ba · 1,588 sqft
- 10628 Reams Road, Windermere 34786 $479,000 · 4 bd · 3 ba · 1,892 sqft
- 8905 Newmarket Drive, Windermere 34786 Pending $359,900 · 2 bd · 3 ba · 1,429 sqft
- 7330 Brightland Street, Windermere 34786 Pending $449,000 · 3 bd · 3 ba · 1,881 sqft
- 11951 Vermillion Avenue, Windermere 34786 Pending $459,000 · 3 bd · 3 ba · 1,539 sqft
- 11434 Jasper Kay Terrace 106, Windermere 34786 Pending $320,000 · 3 bd · 2 ba · 1,455 sqft
- 13743 Calera Alley, Windermere 34786 Pending $439,500 · 3 bd · 3 ba · 1,997 sqft
- 11564 Mizzon Drive 923, Windermere 34786 Pending $325,000 · 3 bd · 2 ba · 1,442 sqft
- 5451 Kumquat Loop, Windermere 34786 Pending $384,900 · 2 bd · 2 ba · 1,298 sqft
- 929 Lascala Drive, Windermere 34786 Pending $349,900 · 3 bd · 2 ba · 1,852 sqft
- 8641 Brookvale Drive, Windermere 34786 Pending $410,000 · 3 bd · 3 ba · 1,526 sqft