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.

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 845 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4440615)
    $19,750,000
    Photo of 845 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4440615)
    Photo of 845 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4440615)
    845 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL
    845 LONGBOAT CLUB ROAD
    LONGBOAT KEY, FL
    • 6 Beds
    • 8 Baths
    • 19,300 Home (sqft)
    • 8 Baths
    • 1.18 Lot (ac)
  2. Photo of 825 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452670)
    $12,850,000
    Photo of 825 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452670)
    Photo of 825 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452670)
    825 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL
    825 LONGBOAT CLUB ROAD
    LONGBOAT KEY, FL
    • 6 Beds
    • 7 Baths
    • 12,619 Home (sqft)
    • 7 Baths
    • 1.35 Lot (ac)
  3. 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)
  4. 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
    • 4,808 Home (sqft)
    • 7 Baths
    • 29,466 Lot (sqft)
  5. 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)
  6. 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)
  7. Photo of 3475 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4445990)
    $7,445,000
    Photo of 3475 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4445990)
    Photo of 3475 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4445990)
    3475 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    3475 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 7,608 Home (sqft)
    • 6 Baths
    • 25,127 Lot (sqft)
  8. Photo of 2837 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4471077)
    $7,200,000
    Photo of 2837 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4471077)
    Photo of 2837 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4471077)
    2837 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    2837 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 5,089 Home (sqft)
    • 6 Baths
    • 9,901 Lot (sqft)
  9. 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)
  10. Photo of 1580 HARBOR CAY LANE, LONGBOAT KEY, FL 34228 (MLS # A4460976)
    $4,900,000
    Photo of 1580 HARBOR CAY LANE, LONGBOAT KEY, FL 34228 (MLS # A4460976)
    Photo of 1580 HARBOR CAY LANE, LONGBOAT KEY, FL 34228 (MLS # A4460976)
    1580 HARBOR CAY LANE, LONGBOAT KEY, FL
    1580 HARBOR CAY LANE
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 6,349 Home (sqft)
    • 6 Baths
    • 15,001 Lot (sqft)
  11. Photo of 5005 GULF OF MEXICO DRIVE #9, LONGBOAT KEY, FL 34228 (MLS # A4454912)
    $4,585,000
    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)
  12. Photo of 6525 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4460038)
    $4,495,000
    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)
  13. Photo of 4051 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4470796)
    $4,000,000
    Photo of 4051 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4470796)
    Photo of 4051 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4470796)
    4051 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    4051 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,648 Home (sqft)
    • 3 Baths
    • 27,352 Lot (sqft)
  14. Photo of 6529 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452411)
    $3,995,000
    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)
  15. 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)
  16. 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)
    10
     
    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)
  17. 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)
  18. Photo of 6609 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4450141)
    $3,395,000
    Photo of 6609 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4450141)
    Photo of 6609 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4450141)
    6609 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6609 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 4,132 Home (sqft)
    • 4 Baths
    • 15,160 Lot (sqft)
  19. Photo of 3040 GRAND BAY BOULEVARD #PH2102, LONGBOAT KEY, FL 34228 (MLS # A4445142)
    $3,200,000
    Photo of 3040 GRAND BAY BOULEVARD #PH2102, LONGBOAT KEY, FL 34228 (MLS # A4445142)
    Photo of 3040 GRAND BAY BOULEVARD #PH2102, LONGBOAT KEY, FL 34228 (MLS # A4445142)
    3040 GRAND BAY BOULEVARD #PH2102, LONGBOAT KEY, FL
    3040 GRAND BAY BOULEVARD #PH2102
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 4,413 Home (sqft)
    • 6 Baths
    • 0 Lot (sqft)
  20. Photo of 602 RANGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4470520)
    $3,195,000
    Photo of 602 RANGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4470520)
    Photo of 602 RANGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4470520)
    602 RANGER LANE, LONGBOAT KEY, FL
    602 RANGER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,018 Home (sqft)
    • 5 Baths
    • 10,014 Lot (sqft)
  21. Photo of 1241 GULF OF MEXICO DRIVE #701, LONGBOAT KEY, FL 34228 (MLS # A4460348)
    $3,195,000
    Photo of 1241 GULF OF MEXICO DRIVE #701, LONGBOAT KEY, FL 34228 (MLS # A4460348)
    Photo of 1241 GULF OF MEXICO DRIVE #701, LONGBOAT KEY, FL 34228 (MLS # A4460348)
    1241 GULF OF MEXICO DRIVE #701, LONGBOAT KEY, FL
    1241 GULF OF MEXICO DRIVE #701
    LONGBOAT KEY, FL
    • 3 Beds
    • 5 Baths
    • 3,400 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
  22. Photo of 580 PUTTING GREEN LANE, LONGBOAT KEY, FL 34228 (MLS # A4468094)
    $2,997,000
    Photo of 580 PUTTING GREEN LANE, LONGBOAT KEY, FL 34228 (MLS # A4468094)
    Photo of 580 PUTTING GREEN LANE, LONGBOAT KEY, FL 34228 (MLS # A4468094)
    580 PUTTING GREEN LANE, LONGBOAT KEY, FL
    580 PUTTING GREEN LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,586 Home (sqft)
    • 5 Baths
    • 10,014 Lot (sqft)
  23. Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    $2,900,000
    Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    31
     
    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)
  24. 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)
  25. Photo of 1590 HARBOR SOUND DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4463437)
    $2,750,000
    Photo of 1590 HARBOR SOUND DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4463437)
    Photo of 1590 HARBOR SOUND DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4463437)
    1590 HARBOR SOUND DRIVE, LONGBOAT KEY, FL
    1590 HARBOR SOUND DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 5,591 Home (sqft)
    • 5 Baths
    • 18,119 Lot (sqft)
  26. 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)
  27. Photo of 7147 LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4457127)
    $2,600,000
    Photo of 7147 LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4457127)
    Photo of 7147 LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4457127)
    7147 LA LENAIRE DRIVE, LONGBOAT KEY, FL
    7147 LA LENAIRE DRIVE
    LONGBOAT KEY, FL
    • 6 Beds
    • 6 Baths
    • 3,503 Home (sqft)
    • 6 Baths
    • 1.35 Lot (ac)
  28. Photo of 435 L AMBIANCE DRIVE #J703, LONGBOAT KEY, FL 34228 (MLS # A4470430)
    $2,495,000
    Photo of 435 L AMBIANCE DRIVE #J703, LONGBOAT KEY, FL 34228 (MLS # A4470430)
    Photo of 435 L AMBIANCE DRIVE #J703, LONGBOAT KEY, FL 34228 (MLS # A4470430)
    435 L AMBIANCE DRIVE #J703, LONGBOAT KEY, FL
    435 L AMBIANCE DRIVE #J703
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,820 Home (sqft)
    • 3 Baths
    • 7.01 Lot (ac)
  29. Photo of 560 HORNBLOWER LANE, LONGBOAT KEY, FL 34228 (MLS # A4462103)
    $2,375,000
    Photo of 560 HORNBLOWER LANE, LONGBOAT KEY, FL 34228 (MLS # A4462103)
    Photo of 560 HORNBLOWER LANE, LONGBOAT KEY, FL 34228 (MLS # A4462103)
    560 HORNBLOWER LANE, LONGBOAT KEY, FL
    560 HORNBLOWER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,206 Home (sqft)
    • 5 Baths
    • 12,354 Lot (sqft)
  30. Photo of 5950 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4450545)
    $2,340,000
    Photo of 5950 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4450545)
    Photo of 5950 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4450545)
    5950 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5950 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,464 Home (sqft)
    • 4 Baths
    • 31,500 Lot (sqft)
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