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  1. Photo of 7143 La Lenaire Drive, Longboat Key, FL 34228 (MLS # A4694196)
    $5,895,000
    Photo of 7143 La Lenaire Drive, Longboat Key, FL 34228 (MLS # A4694196)
    Photo of 7143 La Lenaire Drive, Longboat Key, FL 34228 (MLS # A4694196)
    7143 La Lenaire Drive, Longboat Key, FL
    7143 La Lenaire Drive
    Longboat Key, FL
    • 4 Beds
    • 4 Baths
    • 2,721 Home (sqft)
    • 4 Baths
    • 1.24 Lot (ac)
  2. Photo of 3606 Fair Oaks Place, Longboat Key, FL 34228 (MLS # A4694394)
    $4,999,000
    Photo of 3606 Fair Oaks Place, Longboat Key, FL 34228 (MLS # A4694394)
    Photo of 3606 Fair Oaks Place, Longboat Key, FL 34228 (MLS # A4694394)
    3606 Fair Oaks Place, Longboat Key, FL
    3606 Fair Oaks Place
    Longboat Key, FL
    • 5 Beds
    • 3 Baths
    • 3,842 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  3. Photo of 1211 Gulf Of Mexico Drive #105, Longboat Key, FL 34228 (MLS # A4694733)
    $1,648,000
    Photo of 1211 Gulf Of Mexico Drive #105, Longboat Key, FL 34228 (MLS # A4694733)
    Photo of 1211 Gulf Of Mexico Drive #105, Longboat Key, FL 34228 (MLS # A4694733)
    1211 Gulf Of Mexico Drive #105, Longboat Key, FL
    1211 Gulf Of Mexico Drive #105
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,598 Home (sqft)
    • 2 Baths
    • 7.87 Lot (ac)
  4. Photo of 2185 Gulf Of Mexico Drive #212, Longboat Key, FL 34228 (MLS # A4694656)
    $1,895,000
    Photo of 2185 Gulf Of Mexico Drive #212, Longboat Key, FL 34228 (MLS # A4694656)
    Photo of 2185 Gulf Of Mexico Drive #212, Longboat Key, FL 34228 (MLS # A4694656)
    54
     
    2185 Gulf Of Mexico Drive #212, Longboat Key, FL
    2185 Gulf Of Mexico Drive #212
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,448 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 523 Juan Anasco Drive, Longboat Key, FL 34228 (MLS # A4694601)
    $1,690,000
    Photo of 523 Juan Anasco Drive, Longboat Key, FL 34228 (MLS # A4694601)
    Photo of 523 Juan Anasco Drive, Longboat Key, FL 34228 (MLS # A4694601)
    58
     
    523 Juan Anasco Drive, Longboat Key, FL
    523 Juan Anasco Drive
    Longboat Key, FL
    • 4 Beds
    • 3 Baths
    • 2,899 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  6. Photo of 3527 Fair Oaks Lane, Longboat Key, FL 34228 (MLS # A4694532)
    $2,300,000
    Photo of 3527 Fair Oaks Lane, Longboat Key, FL 34228 (MLS # A4694532)
    Photo of 3527 Fair Oaks Lane, Longboat Key, FL 34228 (MLS # A4694532)
    3527 Fair Oaks Lane, Longboat Key, FL
    3527 Fair Oaks Lane
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 4,154 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  7. Photo of 591 Russell Street, Longboat Key, FL 34228 (MLS # A4694355)
    $995,000
    Photo of 591 Russell Street, Longboat Key, FL 34228 (MLS # A4694355)
    Photo of 591 Russell Street, Longboat Key, FL 34228 (MLS # A4694355)
    591 Russell Street, Longboat Key, FL
    591 Russell Street
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 13,068 Lot (sqft)
  8. Photo of 2600 Harbourside Dr #H-04, Longboat Key, FL 34228 (MLS # A4694327)
    $275,000
    Photo of 2600 Harbourside Dr #H-04, Longboat Key, FL 34228 (MLS # A4694327)
    Photo of 2600 Harbourside Dr #H-04, Longboat Key, FL 34228 (MLS # A4694327)
    2600 Harbourside Dr #H-04, Longboat Key, FL
    2600 Harbourside Dr #H-04
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 0 Lot (sqft)
  9. Photo of 791 Broadway Street, Longboat Key, FL 34228 (MLS # A4694059)
    $1,525,000
    Photo of 791 Broadway Street, Longboat Key, FL 34228 (MLS # A4694059)
    Photo of 791 Broadway Street, Longboat Key, FL 34228 (MLS # A4694059)
    59
     
    791 Broadway Street, Longboat Key, FL
    791 Broadway Street
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 2,236 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  10. Photo of 6664 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4694502)
    $18,500,000
    Photo of 6664 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4694502)
    Photo of 6664 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4694502)
    26
     
    6664 Gulf Of Mexico Drive, Longboat Key, FL
    6664 Gulf Of Mexico Drive
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 10,298 Home (sqft)
    • 2 Baths
    • 5.50 Lot (ac)
  11. Photo of 6660 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4693760)
    $18,500,000
    Photo of 6660 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4693760)
    Photo of 6660 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4693760)
    6660 Gulf Of Mexico Drive, Longboat Key, FL
    6660 Gulf Of Mexico Drive
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 5.50 Lot (ac)
  12. Photo of 3710 Gulf Of Mexico Drive #G20, Longboat Key, FL 34228 (MLS # A4693944)
    $349,900
    Photo of 3710 Gulf Of Mexico Drive #G20, Longboat Key, FL 34228 (MLS # A4693944)
    Photo of 3710 Gulf Of Mexico Drive #G20, Longboat Key, FL 34228 (MLS # A4693944)
    3710 Gulf Of Mexico Drive #G20, Longboat Key, FL
    3710 Gulf Of Mexico Drive #G20
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,052 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  13. Photo of 2600 Harbourside Drive #H06, Longboat Key, FL 34228 (MLS # A4694669)
    $250,000
    Photo of 2600 Harbourside Drive #H06, Longboat Key, FL 34228 (MLS # A4694669)
    Photo of 2600 Harbourside Drive #H06, Longboat Key, FL 34228 (MLS # A4694669)
    31
     
    2600 Harbourside Drive #H06, Longboat Key, FL
    2600 Harbourside Drive #H06
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 15,246 Lot (sqft)
  14. Photo of 4325 Gulf Of Mexico Drive #103, Longboat Key, FL 34228 (MLS # A4693621)
    $950,000
    Photo of 4325 Gulf Of Mexico Drive #103, Longboat Key, FL 34228 (MLS # A4693621)
    Photo of 4325 Gulf Of Mexico Drive #103, Longboat Key, FL 34228 (MLS # A4693621)
    4325 Gulf Of Mexico Drive #103, Longboat Key, FL
    4325 Gulf Of Mexico Drive #103
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,336 Home (sqft)
    • 2 Baths
    • 3.50 Lot (ac)
  15. Photo of 1095 Gulf Of Mexico Drive #102, Longboat Key, FL 34228 (MLS # A4693425)
    $575,000
    Photo of 1095 Gulf Of Mexico Drive #102, Longboat Key, FL 34228 (MLS # A4693425)
    Photo of 1095 Gulf Of Mexico Drive #102, Longboat Key, FL 34228 (MLS # A4693425)
    1095 Gulf Of Mexico Drive #102, Longboat Key, FL
    1095 Gulf Of Mexico Drive #102
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,392 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 617 Rountree Drive, Longboat Key, FL 34228 (MLS # A4692822)
    $2,150,000
    Photo of 617 Rountree Drive, Longboat Key, FL 34228 (MLS # A4692822)
    Photo of 617 Rountree Drive, Longboat Key, FL 34228 (MLS # A4692822)
    617 Rountree Drive, Longboat Key, FL
    617 Rountree Drive
    Longboat Key, FL
    • 3 Beds
    • 2 Baths
    • 1,972 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  17. Photo of 6441 Gulfside Road, Longboat Key, FL 34228 (MLS # A4692771)
    $5,600,000
    Photo of 6441 Gulfside Road, Longboat Key, FL 34228 (MLS # A4692771)
    Photo of 6441 Gulfside Road, Longboat Key, FL 34228 (MLS # A4692771)
    6441 Gulfside Road, Longboat Key, FL
    6441 Gulfside Road
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 30,928 Lot (sqft)
  18. Photo of 524 Hornblower Lane, Longboat Key, FL 34228 (MLS # A4692210)
    $2,700,000
    Photo of 524 Hornblower Lane, Longboat Key, FL 34228 (MLS # A4692210)
    Photo of 524 Hornblower Lane, Longboat Key, FL 34228 (MLS # A4692210)
    524 Hornblower Lane, Longboat Key, FL
    524 Hornblower Lane
    Longboat Key, FL
    • 3 Beds
    • 4 Baths
    • 3,045 Home (sqft)
    • 4 Baths
    • 12,197 Lot (sqft)
  19. Photo of 3040 Gulf Of Mexico Drive #3, Longboat Key, FL 34228 (MLS # A4692587)
    $1,899,000
    Photo of 3040 Gulf Of Mexico Drive #3, Longboat Key, FL 34228 (MLS # A4692587)
    Photo of 3040 Gulf Of Mexico Drive #3, Longboat Key, FL 34228 (MLS # A4692587)
    92
     
    3040 Gulf Of Mexico Drive #3, Longboat Key, FL
    3040 Gulf Of Mexico Drive #3
    Longboat Key, FL
    • 4 Beds
    • 3 Baths
    • 3,009 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  20. Photo of 6700 Gulf Of Mexico Drive #143, Longboat Key, FL 34228 (MLS # A4692139)
    $410,000
    Photo of 6700 Gulf Of Mexico Drive #143, Longboat Key, FL 34228 (MLS # A4692139)
    Photo of 6700 Gulf Of Mexico Drive #143, Longboat Key, FL 34228 (MLS # A4692139)
    6700 Gulf Of Mexico Drive #143, Longboat Key, FL
    6700 Gulf Of Mexico Drive #143
    Longboat Key, FL
    • 1 Bed
    • 1 Bath
    • 936 Home (sqft)
    • 1 Bath
    • 10.16 Lot (ac)
  21. Photo of 530 Jessmyth Drive, Longboat Key, FL 34228 (MLS # A4691731)
    $5,985,000
    Photo of 530 Jessmyth Drive, Longboat Key, FL 34228 (MLS # A4691731)
    Photo of 530 Jessmyth Drive, Longboat Key, FL 34228 (MLS # A4691731)
    530 Jessmyth Drive, Longboat Key, FL
    530 Jessmyth Drive
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 12,197 Lot (sqft)
  22. Photo of 1600 Harbor Sound Drive, Longboat Key, FL 34228 (MLS # A4692027)
    $11,900,000
    Photo of 1600 Harbor Sound Drive, Longboat Key, FL 34228 (MLS # A4692027)
    Photo of 1600 Harbor Sound Drive, Longboat Key, FL 34228 (MLS # A4692027)
    1600 Harbor Sound Drive, Longboat Key, FL
    1600 Harbor Sound Drive
    Longboat Key, FL
    • 5 Beds
    • 6 Baths
    • 5,689 Home (sqft)
    • 6 Baths
    • 17,860 Lot (sqft)
  23. Photo of 610 Hibiscus Way, Longboat Key, FL 34228 (MLS # A4691880)
    $2,650,000
    Photo of 610 Hibiscus Way, Longboat Key, FL 34228 (MLS # A4691880)
    Photo of 610 Hibiscus Way, Longboat Key, FL 34228 (MLS # A4691880)
    610 Hibiscus Way, Longboat Key, FL
    610 Hibiscus Way
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 2,788 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
  24. Photo of 720 Broadway Street, Longboat Key, FL 34228 (MLS # A4690381)
    $760,000
    Photo of 720 Broadway Street, Longboat Key, FL 34228 (MLS # A4690381)
    Photo of 720 Broadway Street, Longboat Key, FL 34228 (MLS # A4690381)
    720 Broadway Street, Longboat Key, FL
    720 Broadway Street
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  25. Photo of 5311 Gulf Of Mexico Drive #5, Longboat Key, FL 34228 (MLS # A4691314)
    $799,000
    Photo of 5311 Gulf Of Mexico Drive #5, Longboat Key, FL 34228 (MLS # A4691314)
    Photo of 5311 Gulf Of Mexico Drive #5, Longboat Key, FL 34228 (MLS # A4691314)
    5311 Gulf Of Mexico Drive #5, Longboat Key, FL
    5311 Gulf Of Mexico Drive #5
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,110 Home (sqft)
    • 2 Baths
    • 1.01 Lot (ac)
  26. Photo of 4325 Gulf Of Mexico Drive #305, Longboat Key, FL 34228 (MLS # A4690883)
    $999,000
    Photo of 4325 Gulf Of Mexico Drive #305, Longboat Key, FL 34228 (MLS # A4690883)
    Photo of 4325 Gulf Of Mexico Drive #305, Longboat Key, FL 34228 (MLS # A4690883)
    4325 Gulf Of Mexico Drive #305, Longboat Key, FL
    4325 Gulf Of Mexico Drive #305
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,336 Home (sqft)
    • 2 Baths
    • 3.50 Lot (ac)
  27. Photo of 448 Gulf Of Mexico Drive #A205, Longboat Key, FL 34228 (MLS # A4690875)
    $569,000
    Photo of 448 Gulf Of Mexico Drive #A205, Longboat Key, FL 34228 (MLS # A4690875)
    Photo of 448 Gulf Of Mexico Drive #A205, Longboat Key, FL 34228 (MLS # A4690875)
    448 Gulf Of Mexico Drive #A205, Longboat Key, FL
    448 Gulf Of Mexico Drive #A205
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,306 Home (sqft)
    • 2 Baths
    • 3.42 Lot (ac)
  28. Photo of 900 Spanish Drive N, Longboat Key, FL 34228 (MLS # A4690879)
    $750,000
    Photo of 900 Spanish Drive N, Longboat Key, FL 34228 (MLS # A4690879)
    Photo of 900 Spanish Drive N, Longboat Key, FL 34228 (MLS # A4690879)
    69
     
    900 Spanish Drive N, Longboat Key, FL
    900 Spanish Drive N
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,423 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  29. Photo of 581 Rountree Drive, Longboat Key, FL 34228 (MLS # O6400352)
    $2,500,000
    Photo of 581 Rountree Drive, Longboat Key, FL 34228 (MLS # O6400352)
    Photo of 581 Rountree Drive, Longboat Key, FL 34228 (MLS # O6400352)
    581 Rountree Drive, Longboat Key, FL
    581 Rountree Drive
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 11,762 Lot (sqft)
  30. Photo of 615 Dream Island Place #105, Longboat Key, FL 34228 (MLS # A4689957)
    $949,000
    Photo of 615 Dream Island Place #105, Longboat Key, FL 34228 (MLS # A4689957)
    Photo of 615 Dream Island Place #105, Longboat Key, FL 34228 (MLS # A4689957)
    615 Dream Island Place #105, Longboat Key, FL
    615 Dream Island Place #105
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,293 Home (sqft)
    • 2 Baths
    • 4.76 Lot (ac)
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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 11/8/26 1:01 PM PST.

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