Longboat Key Real Estate

Longboat Key is a 12 mile long island with white sand beaches adorning its western shore, and spectacular bay views back to the mainland on the eastern shore. With its pristine beach, waterfront, golf, fine dining, and luxury resorts, Longboat Key lives like a true luxury retreat. It is about evenly divided between Sarasota and Manatee Counties.

  • 1799
    Homes
  • 6495
    Condos
  • $1,128,100
    Median Home Price
  • $530,000
    Median Condo Price

Longboat Key

Longboat Key’s main thoroughfare, Gulf of Mexico Drive, was constructed by circus magnate John Ringling in 1925. Today Gulf of Mexico Drive is one of the most scenic drives, with glimpses to the Gulf and Bay along its length, highly manicured landscapes, and emerald colored fairways of the two championship golf courses of the Longboat Key Club.

Longboat Key has its own commercial centers, fabulous restaurants, and post office and shops. Again, you may arrive and not want or need to leave the island for days.

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Longboat Key in Sarasota, Florida area map

Longboat Key Real Estate

Much of Longboat Key is composed either single-family homes or condominium apartments. Most of the condominium associations co-own common elements which comprise pools, tennis courts, sites with water views, workout facilities, and access to beaches.


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  1. Photo of 6171 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4477467)
    $14,500,000
    Photo of 6171 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4477467)
    Photo of 6171 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4477467)
    12
     
    6171 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6171 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 7,352 Home (sqft)
    • 6 Baths
    • 33,898 Lot (sqft)
  2. Photo of 5965 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4418090)
    $11,989,000
    Photo of 5965 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4418090)
    Photo of 5965 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4418090)
    5965 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5965 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 7 Beds
    • 7 Baths
    • 10,087 Home (sqft)
    • 7 Baths
    • 1.98 Lot (ac)
  3. Photo of 5005 GULF OF MEXICO DRIVE #3, LONGBOAT KEY, FL 34228 (MLS # A4458696)
    $8,900,000
    Photo of 5005 GULF OF MEXICO DRIVE #3, LONGBOAT KEY, FL 34228 (MLS # A4458696)
    Photo of 5005 GULF OF MEXICO DRIVE #3, LONGBOAT KEY, FL 34228 (MLS # A4458696)
    5005 GULF OF MEXICO DRIVE #3, LONGBOAT KEY, FL
    5005 GULF OF MEXICO DRIVE #3
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 4,624 Home (sqft)
    • 7 Baths
    • 29,466 Lot (sqft)
  4. Photo of 5005 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL 34228 (MLS # A4454932)
    $8,100,000
    Photo of 5005 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL 34228 (MLS # A4454932)
    Photo of 5005 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL 34228 (MLS # A4454932)
    5005 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL
    5005 GULF OF MEXICO DRIVE #2
    LONGBOAT KEY, FL
    • 6 Beds
    • 8 Baths
    • 5,763 Home (sqft)
    • 8 Baths
    • 24,058 Lot (sqft)
  5. Photo of 5541 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4468729)
    $8,000,000
    Photo of 5541 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4468729)
    Photo of 5541 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4468729)
    5541 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5541 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 11 Beds
    • 14 Baths
    • 14,005 Home (sqft)
    • 14 Baths
    • 41,601 Lot (sqft)
  6. Photo of 612 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4475444)
    $7,800,000
    Photo of 612 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4475444)
    Photo of 612 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4475444)
    612 JUAN ANASCO DRIVE, LONGBOAT KEY, FL
    612 JUAN ANASCO DRIVE
    LONGBOAT KEY, FL
    • 6 Beds
    • 8 Baths
    • 8,976 Home (sqft)
    • 8 Baths
    • 1.16 Lot (ac)
  7. Photo of 1620 GULF OF MEXICO DRIVE #605, LONGBOAT KEY, FL 34228 (MLS # A4477338)
    $6,970,000
    Photo of 1620 GULF OF MEXICO DRIVE #605, LONGBOAT KEY, FL 34228 (MLS # A4477338)
    Photo of 1620 GULF OF MEXICO DRIVE #605, LONGBOAT KEY, FL 34228 (MLS # A4477338)
    15
     
    1620 GULF OF MEXICO DRIVE #605, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #605
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,017 Home (sqft)
    • 5 Baths
    • 17.80 Lot (ac)
  8. Photo of 771 OLD COMPASS ROAD, LONGBOAT KEY, FL 34228 (MLS # A4476818)
    $6,950,000
    Photo of 771 OLD COMPASS ROAD, LONGBOAT KEY, FL 34228 (MLS # A4476818)
    Photo of 771 OLD COMPASS ROAD, LONGBOAT KEY, FL 34228 (MLS # A4476818)
    771 OLD COMPASS ROAD, LONGBOAT KEY, FL
    771 OLD COMPASS ROAD
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 5,259 Home (sqft)
    • 6 Baths
    • 16,898 Lot (sqft)
  9. Photo of 4651 GULF OF MEXICO DRIVE #PH A, LONGBOAT KEY, FL 34228 (MLS # A4479087)
    $6,240,000
    Photo of 4651 GULF OF MEXICO DRIVE #PH A, LONGBOAT KEY, FL 34228 (MLS # A4479087)
    Photo of 4651 GULF OF MEXICO DRIVE #PH A, LONGBOAT KEY, FL 34228 (MLS # A4479087)
    4651 GULF OF MEXICO DRIVE #PH A, LONGBOAT KEY, FL
    4651 GULF OF MEXICO DRIVE #PH A
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,000 Home (sqft)
    • 5 Baths
    • 3.40 Lot (ac)
  10. Photo of 4651 GULF OF MEXICO DRIVE #3 C, LONGBOAT KEY, FL 34228 (MLS # A4479191)
    $5,260,000
    Photo of 4651 GULF OF MEXICO DRIVE #3 C, LONGBOAT KEY, FL 34228 (MLS # A4479191)
    Photo of 4651 GULF OF MEXICO DRIVE #3 C, LONGBOAT KEY, FL 34228 (MLS # A4479191)
    4651 GULF OF MEXICO DRIVE #3 C, LONGBOAT KEY, FL
    4651 GULF OF MEXICO DRIVE #3 C
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,100 Home (sqft)
    • 5 Baths
    • 3.40 Lot (ac)
  11. Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460731)
    $4,995,000
    Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460731)
    Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460731)
    6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6877 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,820 Home (sqft)
    • 5 Baths
    • 32,130 Lot (sqft)
  12. Photo of 4651 GULF OF MEXICO DRIVE #2B, LONGBOAT KEY, FL 34228 (MLS # A4479178)
    $4,845,000
    Photo of 4651 GULF OF MEXICO DRIVE #2B, LONGBOAT KEY, FL 34228 (MLS # A4479178)
    Photo of 4651 GULF OF MEXICO DRIVE #2B, LONGBOAT KEY, FL 34228 (MLS # A4479178)
    4651 GULF OF MEXICO DRIVE #2B, LONGBOAT KEY, FL
    4651 GULF OF MEXICO DRIVE #2B
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,900 Home (sqft)
    • 5 Baths
    • 3.40 Lot (ac)
  13. Photo of 6525 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460038)
    $4,295,000
    Photo of 6525 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460038)
    Photo of 6525 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460038)
    6525 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6525 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 5,740 Home (sqft)
    • 6 Baths
    • 18,501 Lot (sqft)
  14. Photo of 5005 GULF OF MEXICO DRIVE #9, LONGBOAT KEY, FL 34228 (MLS # A4454912)
    $4,250,000
    Photo of 5005 GULF OF MEXICO DRIVE #9, LONGBOAT KEY, FL 34228 (MLS # A4454912)
    Photo of 5005 GULF OF MEXICO DRIVE #9, LONGBOAT KEY, FL 34228 (MLS # A4454912)
    50
     
    5005 GULF OF MEXICO DRIVE #9, LONGBOAT KEY, FL
    5005 GULF OF MEXICO DRIVE #9
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 3,922 Home (sqft)
    • 4 Baths
    • 9,255 Lot (sqft)
  15. Photo of 4651 GULF OF MEXICO DRIVE #1 D, LONGBOAT KEY, FL 34228 (MLS # A4479112)
    $4,180,000
    Photo of 4651 GULF OF MEXICO DRIVE #1 D, LONGBOAT KEY, FL 34228 (MLS # A4479112)
    Photo of 4651 GULF OF MEXICO DRIVE #1 D, LONGBOAT KEY, FL 34228 (MLS # A4479112)
    4651 GULF OF MEXICO DRIVE #1 D, LONGBOAT KEY, FL
    4651 GULF OF MEXICO DRIVE #1 D
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,900 Home (sqft)
    • 5 Baths
    • 3.40 Lot (ac)
  16. Photo of 1620 GULF OF MEXICO DRIVE #411, LONGBOAT KEY, FL 34228 (MLS # A4480034)
    $3,920,000
    Photo of 1620 GULF OF MEXICO DRIVE #411, LONGBOAT KEY, FL 34228 (MLS # A4480034)
    Photo of 1620 GULF OF MEXICO DRIVE #411, LONGBOAT KEY, FL 34228 (MLS # A4480034)
    15
     
    1620 GULF OF MEXICO DRIVE #411, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #411
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 3,130 Home (sqft)
    • 3 Baths
    • 17.80 Lot (ac)
  17. Photo of 35 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4477572)
    $3,875,000
    Photo of 35 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4477572)
    Photo of 35 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4477572)
    35 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL
    35 LIGHTHOUSE POINT DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,430 Home (sqft)
    • 5 Baths
    • 17,521 Lot (sqft)
  18. Photo of 4965 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4448678)
    $3,875,000
    Photo of 4965 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4448678)
    Photo of 4965 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4448678)
    4965 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL
    4965 GULF OF MEXICO DRIVE #202
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,344 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  19. Photo of 5372 SANDHAMN PLACE, LONGBOAT KEY, FL 34228 (MLS # A4458496)
    $3,850,000
    Photo of 5372 SANDHAMN PLACE, LONGBOAT KEY, FL 34228 (MLS # A4458496)
    Photo of 5372 SANDHAMN PLACE, LONGBOAT KEY, FL 34228 (MLS # A4458496)
    35
     
    5372 SANDHAMN PLACE, LONGBOAT KEY, FL
    5372 SANDHAMN PLACE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 5,484 Home (sqft)
    • 5 Baths
    • 15,290 Lot (sqft)
  20. Photo of 6529 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452411)
    $3,795,000
    Photo of 6529 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452411)
    Photo of 6529 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452411)
    6529 GULFSIDE ROAD, LONGBOAT KEY, FL
    6529 GULFSIDE ROAD
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 4,524 Home (sqft)
    • 4 Baths
    • 22,901 Lot (sqft)
  21. Photo of 5005 GULF OF MEXICO DRIVE #8, LONGBOAT KEY, FL 34228 (MLS # A4471664)
    $3,788,000
    Photo of 5005 GULF OF MEXICO DRIVE #8, LONGBOAT KEY, FL 34228 (MLS # A4471664)
    Photo of 5005 GULF OF MEXICO DRIVE #8, LONGBOAT KEY, FL 34228 (MLS # A4471664)
    5005 GULF OF MEXICO DRIVE #8, LONGBOAT KEY, FL
    5005 GULF OF MEXICO DRIVE #8
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 4,115 Home (sqft)
    • 6 Baths
    • 9,148 Lot (sqft)
  22. Photo of 6603 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4480258)
    $3,750,000
    Photo of 6603 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4480258)
    Photo of 6603 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4480258)
    6603 GULFSIDE ROAD, LONGBOAT KEY, FL
    6603 GULFSIDE ROAD
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,051 Home (sqft)
    • 3 Baths
    • 16,894 Lot (sqft)
  23. Photo of 5005 GULF OF MEXICO DRIVE #5, LONGBOAT KEY, FL 34228 (MLS # A4480202)
    $3,650,000
    Photo of 5005 GULF OF MEXICO DRIVE #5, LONGBOAT KEY, FL 34228 (MLS # A4480202)
    Photo of 5005 GULF OF MEXICO DRIVE #5, LONGBOAT KEY, FL 34228 (MLS # A4480202)
    5005 GULF OF MEXICO DRIVE #5, LONGBOAT KEY, FL
    5005 GULF OF MEXICO DRIVE #5
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,595 Home (sqft)
    • 5 Baths
    • 10,070 Lot (sqft)
  24. Photo of 8 WINSLOW PLACE, LONGBOAT KEY, FL 34228 (MLS # A4472608)
    $3,345,000
    Photo of 8 WINSLOW PLACE, LONGBOAT KEY, FL 34228 (MLS # A4472608)
    Photo of 8 WINSLOW PLACE, LONGBOAT KEY, FL 34228 (MLS # A4472608)
    8 WINSLOW PLACE, LONGBOAT KEY, FL
    8 WINSLOW PLACE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 4,169 Home (sqft)
    • 4 Baths
    • 20,388 Lot (sqft)
  25. Photo of 1511 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4481414)
    $3,200,000
    Photo of 1511 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4481414)
    Photo of 1511 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4481414)
    1511 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL
    1511 GULF OF MEXICO DRIVE #202
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,940 Home (sqft)
    • 4 Baths
    • 3.40 Lot (ac)
  26. Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    $2,990,000
    Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    24
     
    550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL
    550 BUTTONWOOD DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 4,390 Home (sqft)
    • 3 Baths
    • 11,525 Lot (sqft)
  27. Photo of 1281 GULF OF MEXICO DRIVE #1007, LONGBOAT KEY, FL 34228 (MLS # A4448214)
    $2,875,000
    Photo of 1281 GULF OF MEXICO DRIVE #1007, LONGBOAT KEY, FL 34228 (MLS # A4448214)
    Photo of 1281 GULF OF MEXICO DRIVE #1007, LONGBOAT KEY, FL 34228 (MLS # A4448214)
    1281 GULF OF MEXICO DRIVE #1007, LONGBOAT KEY, FL
    1281 GULF OF MEXICO DRIVE #1007
    LONGBOAT KEY, FL
    • 3 Beds
    • 5 Baths
    • 3,273 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
  28. Photo of 6321 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4455431)
    $2,700,000
    Photo of 6321 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4455431)
    Photo of 6321 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4455431)
    6321 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6321 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 1,620 Home (sqft)
    • 3 Baths
    • 21,001 Lot (sqft)
  29. Photo of 541 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4479481)
    $2,695,000
    Photo of 541 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4479481)
    Photo of 541 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4479481)
    541 HARBOR POINT ROAD, LONGBOAT KEY, FL
    541 HARBOR POINT ROAD
    LONGBOAT KEY, FL
    • 4 Beds
    • 7 Baths
    • 5,114 Home (sqft)
    • 7 Baths
    • 15,514 Lot (sqft)
  30. Photo of 435 L AMBIANCE DRIVE #K405, LONGBOAT KEY, FL 34228 (MLS # A4481335)
    $2,599,000
    Photo of 435 L AMBIANCE DRIVE #K405, LONGBOAT KEY, FL 34228 (MLS # A4481335)
    Photo of 435 L AMBIANCE DRIVE #K405, LONGBOAT KEY, FL 34228 (MLS # A4481335)
    435 L AMBIANCE DRIVE #K405, LONGBOAT KEY, FL
    435 L AMBIANCE DRIVE #K405
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,820 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
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Listing information is deemed reliable, but not guaranteed.

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