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 4651 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4451632)
    $15,900,000
    Photo of 4651 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4451632)
    Photo of 4651 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4451632)
    4651 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    4651 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 23 Beds
    • 20 Baths
    • 23,595 Home (sqft)
    • 20 Baths
    • 3.40 Lot (ac)
  3. Photo of 6021 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4448650)
    $13,950,000
    Photo of 6021 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4448650)
    Photo of 6021 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4448650)
    6021 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6021 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 8 Baths
    • 7,174 Home (sqft)
    • 8 Baths
    • 1.06 Lot (ac)
  4. 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)
  5. Photo of 6685 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4198676)
    $12,500,000
    Photo of 6685 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4198676)
    Photo of 6685 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4198676)
    6685 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6685 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 6 Beds
    • 8 Baths
    • 12,752 Home (sqft)
    • 8 Baths
    • 1.58 Lot (ac)
  6. Photo of 5965 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4418090)
    $11,995,000
    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)
  7. 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
    • 4,903 Home (sqft)
    • 8 Baths
    • 24,058 Lot (sqft)
  8. Photo of 3475 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4445990)
    $8,100,000
    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)
  9. Photo of 5005 GULF OF MEXICO DRIVE #9, LONGBOAT KEY, FL 34228 (MLS # A4454912)
    $4,950,000
    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
    • 3,490 Home (sqft)
    • 4 Baths
    • 9,255 Lot (sqft)
  10. Photo of 6529 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4452411)
    $4,395,000
    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)
  11. Photo of 530 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4435590)
    $3,900,000
    Photo of 530 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4435590)
    Photo of 530 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4435590)
    530 HARBOR GATE WAY, LONGBOAT KEY, FL
    530 HARBOR GATE WAY
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 5,011 Home (sqft)
    • 5 Baths
    • 18,256 Lot (sqft)
  12. 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)
  13. Photo of 65 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4438181)
    $3,795,000
    Photo of 65 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4438181)
    Photo of 65 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4438181)
    65 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL
    65 LIGHTHOUSE POINT DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,933 Home (sqft)
    • 5 Baths
    • 15,899 Lot (sqft)
  14. Photo of 2923 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4448679)
    $3,650,000
    Photo of 2923 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4448679)
    Photo of 2923 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4448679)
    2923 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    2923 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 2 Beds
    • 1 Bath
    • 1,325 Home (sqft)
    • 1 Bath
    • 21,001 Lot (sqft)
  15. Photo of 3040 GRAND BAY BOULEVARD #PH2102, LONGBOAT KEY, FL 34228 (MLS # A4445142)
    $3,500,000
    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
    • 3 Beds
    • 6 Baths
    • 4,413 Home (sqft)
    • 6 Baths
    • 0 Lot (sqft)
  16. Photo of 545 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4454908)
    $3,450,000
    Photo of 545 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4454908)
    Photo of 545 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4454908)
    13
     
    545 KINGFISHER LANE, LONGBOAT KEY, FL
    545 KINGFISHER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,646 Home (sqft)
    • 5 Baths
    • 11,751 Lot (sqft)
  17. 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)
  18. Photo of 581 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4449066)
    $3,229,000
    Photo of 581 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4449066)
    Photo of 581 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4449066)
    48
     
    581 KINGFISHER LANE, LONGBOAT KEY, FL
    581 KINGFISHER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,783 Home (sqft)
    • 5 Baths
    • 15,001 Lot (sqft)
  19. Photo of 435 L AMBIANCE DRIVE #K306, LONGBOAT KEY, FL 34228 (MLS # A4456747)
    $3,195,000
    Photo of 435 L AMBIANCE DRIVE #K306, LONGBOAT KEY, FL 34228 (MLS # A4456747)
    Photo of 435 L AMBIANCE DRIVE #K306, LONGBOAT KEY, FL 34228 (MLS # A4456747)
    435 L AMBIANCE DRIVE #K306, LONGBOAT KEY, FL
    435 L AMBIANCE DRIVE #K306
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,820 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  20. Photo of 591 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4427895)
    $3,100,000
    Photo of 591 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4427895)
    Photo of 591 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4427895)
    591 PUTTER LANE, LONGBOAT KEY, FL
    591 PUTTER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,159 Home (sqft)
    • 5 Baths
    • 12,646 Lot (sqft)
  21. Photo of 537 YAWL LANE, LONGBOAT KEY, FL 34228 (MLS # A4428503)
    $2,995,000
    Photo of 537 YAWL LANE, LONGBOAT KEY, FL 34228 (MLS # A4428503)
    Photo of 537 YAWL LANE, LONGBOAT KEY, FL 34228 (MLS # A4428503)
    537 YAWL LANE, LONGBOAT KEY, FL
    537 YAWL LANE
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 4,142 Home (sqft)
    • 7 Baths
    • 12,197 Lot (sqft)
  22. Photo of 1281 GULF OF MEXICO DRIVE #1007, LONGBOAT KEY, FL 34228 (MLS # A4448214)
    $2,975,000
    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)
  23. Photo of 501 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4438974)
    $2,975,000
    Photo of 501 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4438974)
    Photo of 501 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4438974)
    501 HARBOR POINT ROAD, LONGBOAT KEY, FL
    501 HARBOR POINT ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 6,125 Home (sqft)
    • 6 Baths
    • 24,202 Lot (sqft)
  24. Photo of 590 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4452503)
    $2,850,000
    Photo of 590 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4452503)
    Photo of 590 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4452503)
    590 CHIPPING LANE, LONGBOAT KEY, FL
    590 CHIPPING LANE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,374 Home (sqft)
    • 4 Baths
    • 16,930 Lot (sqft)
  25. Photo of 550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4441702)
    $2,800,300
    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
    • 3,551 Home (sqft)
    • 3 Baths
    • 11,525 Lot (sqft)
  26. Photo of 655 LONGBOAT CLUB ROAD #15B, LONGBOAT KEY, FL 34228 (MLS # A4428715)
    $2,790,000
    Photo of 655 LONGBOAT CLUB ROAD #15B, LONGBOAT KEY, FL 34228 (MLS # A4428715)
    Photo of 655 LONGBOAT CLUB ROAD #15B, LONGBOAT KEY, FL 34228 (MLS # A4428715)
    655 LONGBOAT CLUB ROAD #15B, LONGBOAT KEY, FL
    655 LONGBOAT CLUB ROAD #15B
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,139 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  27. 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)
  28. Photo of 2151 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL 34228 (MLS # A4448967)
    $2,698,000
    Photo of 2151 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL 34228 (MLS # A4448967)
    Photo of 2151 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL 34228 (MLS # A4448967)
    2151 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL
    2151 GULF OF MEXICO DRIVE #6
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,800 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  29. Photo of 581 WEDGE LANE, LONGBOAT KEY, FL 34228 (MLS # A4456340)
    $2,650,000
    Photo of 581 WEDGE LANE, LONGBOAT KEY, FL 34228 (MLS # A4456340)
    Photo of 581 WEDGE LANE, LONGBOAT KEY, FL 34228 (MLS # A4456340)
    581 WEDGE LANE, LONGBOAT KEY, FL
    581 WEDGE LANE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,127 Home (sqft)
    • 4 Baths
    • 11,985 Lot (sqft)
  30. Photo of 511 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4431877)
    $2,650,000
    Photo of 511 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4431877)
    Photo of 511 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4431877)
    511 HARBOR POINT ROAD, LONGBOAT KEY, FL
    511 HARBOR POINT ROAD
    LONGBOAT KEY, FL
    • 3 Beds
    • 5 Baths
    • 3,667 Home (sqft)
    • 5 Baths
    • 16,177 Lot (sqft)
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