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  1. Photo of 244 Countryside Key Boulevard, Oldsmar, FL 34677 (MLS # TB8465176)
    $220,000
    Photo of 244 Countryside Key Boulevard, Oldsmar, FL 34677 (MLS # TB8465176)
    Photo of 244 Countryside Key Boulevard, Oldsmar, FL 34677 (MLS # TB8465176)
    244 Countryside Key Boulevard, Oldsmar, FL
    244 Countryside Key Boulevard
    Oldsmar, FL
    • 2 Beds
    • 3 Baths
    • 1,110 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  2. Photo of 311 Washington Avenue, Oldsmar, FL 34677 (MLS # TB8465278)
    $500,000
    Photo of 311 Washington Avenue, Oldsmar, FL 34677 (MLS # TB8465278)
    Photo of 311 Washington Avenue, Oldsmar, FL 34677 (MLS # TB8465278)
    311 Washington Avenue, Oldsmar, FL
    311 Washington Avenue
    Oldsmar, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 14,811 Lot (sqft)
  3. Photo of 113 Woodlake Wynde #19, Oldsmar, FL 34677 (MLS # TB8463749)
    $215,000
    Photo of 113 Woodlake Wynde #19, Oldsmar, FL 34677 (MLS # TB8463749)
    Photo of 113 Woodlake Wynde #19, Oldsmar, FL 34677 (MLS # TB8463749)
    63
     
    113 Woodlake Wynde #19, Oldsmar, FL
    113 Woodlake Wynde #19
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 924 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  4. Photo of 291 Countryside Key Boulevard, Oldsmar, FL 34677 (MLS # TB8463435)
    $258,000
    Photo of 291 Countryside Key Boulevard, Oldsmar, FL 34677 (MLS # TB8463435)
    Photo of 291 Countryside Key Boulevard, Oldsmar, FL 34677 (MLS # TB8463435)
    291 Countryside Key Boulevard, Oldsmar, FL
    291 Countryside Key Boulevard
    Oldsmar, FL
    • 2 Beds
    • 3 Baths
    • 1,110 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  5. Photo of 110 Deerpath Drive, Oldsmar, FL 34677 (MLS # TB8462357)
    $1,199,900
    Photo of 110 Deerpath Drive, Oldsmar, FL 34677 (MLS # TB8462357)
    Photo of 110 Deerpath Drive, Oldsmar, FL 34677 (MLS # TB8462357)
    99
     
    110 Deerpath Drive, Oldsmar, FL
    110 Deerpath Drive
    Oldsmar, FL
    • 5 Beds
    • 4 Baths
    • 4,246 Home (sqft)
    • 4 Baths
    • 26,136 Lot (sqft)
  6. Photo of 83 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8465003)
    $210,000
    Photo of 83 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8465003)
    Photo of 83 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8465003)
    83 Pelican Drive N, Oldsmar, FL
    83 Pelican Drive N
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,056 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  7. Photo of 116 Brent Circle, Oldsmar, FL 34677 (MLS # TB8462407)
    $485,000
    Photo of 116 Brent Circle, Oldsmar, FL 34677 (MLS # TB8462407)
    Photo of 116 Brent Circle, Oldsmar, FL 34677 (MLS # TB8462407)
    116 Brent Circle, Oldsmar, FL
    116 Brent Circle
    Oldsmar, FL
    • 3 Beds
    • 3 Baths
    • 1,834 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  8. Photo of 219 Palmetto Court, Oldsmar, FL 34677 (MLS # TB8463698)
    $182,000
    Photo of 219 Palmetto Court, Oldsmar, FL 34677 (MLS # TB8463698)
    Photo of 219 Palmetto Court, Oldsmar, FL 34677 (MLS # TB8463698)
    219 Palmetto Court, Oldsmar, FL
    219 Palmetto Court
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,054 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  9. Photo of 2313 Sunset Wind Loop, Oldsmar, FL 34677 (MLS # TB8461950)
    $440,000
    Photo of 2313 Sunset Wind Loop, Oldsmar, FL 34677 (MLS # TB8461950)
    Photo of 2313 Sunset Wind Loop, Oldsmar, FL 34677 (MLS # TB8461950)
    2313 Sunset Wind Loop, Oldsmar, FL
    2313 Sunset Wind Loop
    Oldsmar, FL
    • 3 Beds
    • 3 Baths
    • 2,230 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  10. Photo of 3180 Curlew Road #107, Oldsmar, FL 34677 (MLS # TB8462503)
    $48,020
    Photo of 3180 Curlew Road #107, Oldsmar, FL 34677 (MLS # TB8462503)
    Photo of 3180 Curlew Road #107, Oldsmar, FL 34677 (MLS # TB8462503)
    3180 Curlew Road #107, Oldsmar, FL
    3180 Curlew Road #107
    Oldsmar, FL
    • 0 Beds
    • 0 Baths
    • 34,576 Home (sqft)
    • 0 Baths
    • 2.66 Lot (ac)
  11. Photo of 107 Mary Drive #107, Oldsmar, FL 34677 (MLS # TB8462887)
    $189,000
    Photo of 107 Mary Drive #107, Oldsmar, FL 34677 (MLS # TB8462887)
    Photo of 107 Mary Drive #107, Oldsmar, FL 34677 (MLS # TB8462887)
    107 Mary Drive #107, Oldsmar, FL
    107 Mary Drive #107
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,094 Home (sqft)
    • 2 Baths
    • 8.00 Lot (ac)
  12. Photo of 118 Lakeview Way #118, Oldsmar, FL 34677 (MLS # A4677135)
    $150,000
    Photo of 118 Lakeview Way #118, Oldsmar, FL 34677 (MLS # A4677135)
    Photo of 118 Lakeview Way #118, Oldsmar, FL 34677 (MLS # A4677135)
    118 Lakeview Way #118, Oldsmar, FL
    118 Lakeview Way #118
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,148 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  13. Photo of 9009 Palm Key Avenue, Oldsmar, FL 34677 (MLS # TB8461356)
    $674,900
    Photo of 9009 Palm Key Avenue, Oldsmar, FL 34677 (MLS # TB8461356)
    Photo of 9009 Palm Key Avenue, Oldsmar, FL 34677 (MLS # TB8461356)
    9009 Palm Key Avenue, Oldsmar, FL
    9009 Palm Key Avenue
    Oldsmar, FL
    • 4 Beds
    • 3 Baths
    • 2,587 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  14. Photo of 112 Brent Circle, Oldsmar, FL 34677 (MLS # TB8461018)
    $499,000
    Photo of 112 Brent Circle, Oldsmar, FL 34677 (MLS # TB8461018)
    Photo of 112 Brent Circle, Oldsmar, FL 34677 (MLS # TB8461018)
    112 Brent Circle, Oldsmar, FL
    112 Brent Circle
    Oldsmar, FL
    • 3 Beds
    • 3 Baths
    • 1,834 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  15. Photo of 475 Woods Landing Trail, Oldsmar, FL 34677 (MLS # A4676723)
    $255,000
    Photo of 475 Woods Landing Trail, Oldsmar, FL 34677 (MLS # A4676723)
    Photo of 475 Woods Landing Trail, Oldsmar, FL 34677 (MLS # A4676723)
    475 Woods Landing Trail, Oldsmar, FL
    475 Woods Landing Trail
    Oldsmar, FL
    • 2 Beds
    • 3 Baths
    • 1,200 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  16. Photo of 405 Woods Landing Trail, Oldsmar, FL 34677 (MLS # A4676677)
    $255,000
    Photo of 405 Woods Landing Trail, Oldsmar, FL 34677 (MLS # A4676677)
    Photo of 405 Woods Landing Trail, Oldsmar, FL 34677 (MLS # A4676677)
    405 Woods Landing Trail, Oldsmar, FL
    405 Woods Landing Trail
    Oldsmar, FL
    • 2 Beds
    • 3 Baths
    • 1,200 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  17. Photo of 4738 Pebble Brook Drive, Oldsmar, FL 34677 (MLS # TB8460875)
    $549,000
    Photo of 4738 Pebble Brook Drive, Oldsmar, FL 34677 (MLS # TB8460875)
    Photo of 4738 Pebble Brook Drive, Oldsmar, FL 34677 (MLS # TB8460875)
    4738 Pebble Brook Drive, Oldsmar, FL
    4738 Pebble Brook Drive
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,938 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  18. Photo of 440 Lakeview Drive, Oldsmar, FL 34677 (MLS # TB8454195)
    $460,000
    Photo of 440 Lakeview Drive, Oldsmar, FL 34677 (MLS # TB8454195)
    Photo of 440 Lakeview Drive, Oldsmar, FL 34677 (MLS # TB8454195)
    440 Lakeview Drive, Oldsmar, FL
    440 Lakeview Drive
    Oldsmar, FL
    • 3 Beds
    • 2 Baths
    • 1,554 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  19. Photo of 278 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8453637)
    $179,999
    Photo of 278 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8453637)
    Photo of 278 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8453637)
    278 Pelican Drive N, Oldsmar, FL
    278 Pelican Drive N
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,128 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  20. Photo of 215 Clays Trail #215, Oldsmar, FL 34677 (MLS # TB8452814)
    $305,000
    Photo of 215 Clays Trail #215, Oldsmar, FL 34677 (MLS # TB8452814)
    Photo of 215 Clays Trail #215, Oldsmar, FL 34677 (MLS # TB8452814)
    215 Clays Trail #215, Oldsmar, FL
    215 Clays Trail #215
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,237 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 283 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8453169)
    $164,900
    Photo of 283 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8453169)
    Photo of 283 Pelican Drive N, Oldsmar, FL 34677 (MLS # TB8453169)
    283 Pelican Drive N, Oldsmar, FL
    283 Pelican Drive N
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,048 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  22. Photo of 3684 Tampa Road #101, Oldsmar, FL 34677 (MLS # TB8452564)
    $1,795,000
    Photo of 3684 Tampa Road #101, Oldsmar, FL 34677 (MLS # TB8452564)
    Photo of 3684 Tampa Road #101, Oldsmar, FL 34677 (MLS # TB8452564)
    3684 Tampa Road #101, Oldsmar, FL
    3684 Tampa Road #101
    Oldsmar, FL
    • 0 Beds
    • 0 Baths
    • 3,850 Home (sqft)
    • 0 Baths
    • 0 Lot (sqft)
  23. Photo of 311 Vista Cruiser Lane, Oldsmar, FL 34677 (MLS # TB8450597)
    $355,000
    Photo of 311 Vista Cruiser Lane, Oldsmar, FL 34677 (MLS # TB8450597)
    Photo of 311 Vista Cruiser Lane, Oldsmar, FL 34677 (MLS # TB8450597)
    311 Vista Cruiser Lane, Oldsmar, FL
    311 Vista Cruiser Lane
    Oldsmar, FL
    • 3 Beds
    • 3 Baths
    • 1,547 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  24. Photo of 395 Wingate Circle, Oldsmar, FL 34677 (MLS # TB8450027)
    $590,000
    Photo of 395 Wingate Circle, Oldsmar, FL 34677 (MLS # TB8450027)
    Photo of 395 Wingate Circle, Oldsmar, FL 34677 (MLS # TB8450027)
    395 Wingate Circle, Oldsmar, FL
    395 Wingate Circle
    Oldsmar, FL
    • 5 Beds
    • 3 Baths
    • 2,827 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  25. Photo of 1820 Driftwood Circle N, Oldsmar, FL 34677 (MLS # TB8447176)
    $379,900
    Photo of 1820 Driftwood Circle N, Oldsmar, FL 34677 (MLS # TB8447176)
    Photo of 1820 Driftwood Circle N, Oldsmar, FL 34677 (MLS # TB8447176)
    1820 Driftwood Circle N, Oldsmar, FL
    1820 Driftwood Circle N
    Oldsmar, FL
    • 3 Beds
    • 2 Baths
    • 1,528 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  26. Photo of 123 Dolphin Drive S, Oldsmar, FL 34677 (MLS # TB8447450)
    $270,000
    Photo of 123 Dolphin Drive S, Oldsmar, FL 34677 (MLS # TB8447450)
    Photo of 123 Dolphin Drive S, Oldsmar, FL 34677 (MLS # TB8447450)
    123 Dolphin Drive S, Oldsmar, FL
    123 Dolphin Drive S
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,248 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  27. Photo of 101 Dolphin Drive N, Oldsmar, FL 34677 (MLS # TB8444809)
    $244,900
    Photo of 101 Dolphin Drive N, Oldsmar, FL 34677 (MLS # TB8444809)
    Photo of 101 Dolphin Drive N, Oldsmar, FL 34677 (MLS # TB8444809)
    101 Dolphin Drive N, Oldsmar, FL
    101 Dolphin Drive N
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,573 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  28. Photo of 645 Timber Bay Circle E, Oldsmar, FL 34677 (MLS # TB8443970)
    $295,000
    Photo of 645 Timber Bay Circle E, Oldsmar, FL 34677 (MLS # TB8443970)
    Photo of 645 Timber Bay Circle E, Oldsmar, FL 34677 (MLS # TB8443970)
    29
     
    645 Timber Bay Circle E, Oldsmar, FL
    645 Timber Bay Circle E
    Oldsmar, FL
    • 3 Beds
    • 2 Baths
    • 1,274 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  29. Photo of 117 E Cypress Court #117, Oldsmar, FL 34677 (MLS # TB8443086)
    $239,000
    Photo of 117 E Cypress Court #117, Oldsmar, FL 34677 (MLS # TB8443086)
    Photo of 117 E Cypress Court #117, Oldsmar, FL 34677 (MLS # TB8443086)
    117 E Cypress Court #117, Oldsmar, FL
    117 E Cypress Court #117
    Oldsmar, FL
    • 2 Beds
    • 2 Baths
    • 1,054 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 140 Brent Circle, Oldsmar, FL 34677 (MLS # O6357016)
    $565,000
    Photo of 140 Brent Circle, Oldsmar, FL 34677 (MLS # O6357016)
    Photo of 140 Brent Circle, Oldsmar, FL 34677 (MLS # O6357016)
    140 Brent Circle, Oldsmar, FL
    140 Brent Circle
    Oldsmar, FL
    • 3 Beds
    • 3 Baths
    • 1,791 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 4/16/26 6:04 PM PDT.

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