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 Beach
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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 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4531109)
    $17,900,000
    Photo of 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4531109)
    Photo of 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4531109)
    5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5861 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 10,800 Home (sqft)
    • 7 Baths
    • 1.13 Lot (ac)
  2. Photo of 5442 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 (MLS # A4537763)
    $13,850,000
    Photo of 5442 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 (MLS # A4537763)
    Photo of 5442 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228 (MLS # A4537763)
    5442 GULF OF MEXICO DR, LONGBOAT KEY, FL
    5442 GULF OF MEXICO DR
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 6,000 Home (sqft)
    • 5 Baths
    • 3.14 Lot (ac)
  3. Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4527232)
    $9,900,000
    Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4527232)
    Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4527232)
    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
    • 32,235 Lot (sqft)
  4. Photo of 596 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4543167)
    $8,795,000
    Photo of 596 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4543167)
    Photo of 596 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4543167)
    596 OUTRIGGER LANE, LONGBOAT KEY, FL
    596 OUTRIGGER LANE
    LONGBOAT KEY, FL
    • 6 Beds
    • 7 Baths
    • 5,892 Home (sqft)
    • 7 Baths
    • 15,682 Lot (sqft)
  5. Photo of 5444 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4538931)
    $7,850,000
    Photo of 5444 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4538931)
    Photo of 5444 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4538931)
    5444 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5444 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 6,000 Home (sqft)
    • 5 Baths
    • 32,670 Lot (sqft)
  6. Photo of 500 HARBOR COVE CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4535024)
    $7,750,000
    Photo of 500 HARBOR COVE CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4535024)
    Photo of 500 HARBOR COVE CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4535024)
    500 HARBOR COVE CIRCLE, LONGBOAT KEY, FL
    500 HARBOR COVE CIRCLE
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 4,422 Home (sqft)
    • 6 Baths
    • 15,246 Lot (sqft)
  7. Photo of 549 SLOOP LANE, LONGBOAT KEY, FL 34228 (MLS # A4530953)
    $7,499,000
    Photo of 549 SLOOP LANE, LONGBOAT KEY, FL 34228 (MLS # A4530953)
    Photo of 549 SLOOP LANE, LONGBOAT KEY, FL 34228 (MLS # A4530953)
    549 SLOOP LANE, LONGBOAT KEY, FL
    549 SLOOP LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 4,127 Home (sqft)
    • 4 Baths
    • 12,197 Lot (sqft)
  8. Photo of 1241 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4530550)
    $6,495,000
    Photo of 1241 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4530550)
    Photo of 1241 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4530550)
    1241 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL
    1241 GULF OF MEXICO DRIVE #201
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 5,225 Home (sqft)
    • 7 Baths
    • 0 Lot (sqft)
  9. Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    $5,965,000
    Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5056 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,819 Home (sqft)
    • 3 Baths
    • 40,076 Lot (sqft)
  10. Photo of 781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # C7466398)
    $5,500,000
    Photo of 781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # C7466398)
    Photo of 781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # C7466398)
    781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL
    781 HIDEAWAY BAY DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 5,469 Home (sqft)
    • 4 Baths
    • 17,860 Lot (sqft)
  11. Photo of 572 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546142)
    $5,300,000
    Photo of 572 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546142)
    Photo of 572 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546142)
    54
     
    572 HALYARD LANE, LONGBOAT KEY, FL
    572 HALYARD LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 4,257 Home (sqft)
    • 6 Baths
    • 10,019 Lot (sqft)
  12. Photo of 3060 GRAND BAY BOULEVARD #1101, LONGBOAT KEY, FL 34228 (MLS # A4535637)
    $4,999,999
    Photo of 3060 GRAND BAY BOULEVARD #1101, LONGBOAT KEY, FL 34228 (MLS # A4535637)
    Photo of 3060 GRAND BAY BOULEVARD #1101, LONGBOAT KEY, FL 34228 (MLS # A4535637)
    3060 GRAND BAY BOULEVARD #1101, LONGBOAT KEY, FL
    3060 GRAND BAY BOULEVARD #1101
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 9,756 Home (sqft)
    • 6 Baths
    • 0 Lot (sqft)
  13. Photo of 610 YARDARM LANE, LONGBOAT KEY, FL 34228 (MLS # A4523988)
    $4,990,000
    Photo of 610 YARDARM LANE, LONGBOAT KEY, FL 34228 (MLS # A4523988)
    Photo of 610 YARDARM LANE, LONGBOAT KEY, FL 34228 (MLS # A4523988)
    610 YARDARM LANE, LONGBOAT KEY, FL
    610 YARDARM LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,138 Home (sqft)
    • 5 Baths
    • 11,326 Lot (sqft)
  14. Photo of 2333 GULF OF MEXICO DRIVE #1C2, LONGBOAT KEY, FL 34228 (MLS # A4535614)
    $4,745,000
    Photo of 2333 GULF OF MEXICO DRIVE #1C2, LONGBOAT KEY, FL 34228 (MLS # A4535614)
    Photo of 2333 GULF OF MEXICO DRIVE #1C2, LONGBOAT KEY, FL 34228 (MLS # A4535614)
    2333 GULF OF MEXICO DRIVE #1C2, LONGBOAT KEY, FL
    2333 GULF OF MEXICO DRIVE #1C2
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,895 Home (sqft)
    • 5 Baths
    • 8.24 Lot (ac)
  15. Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548328)
    $4,500,000
    Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548328)
    Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548328)
    540 HARBOR GATE WAY, LONGBOAT KEY, FL
    540 HARBOR GATE WAY
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 5,048 Home (sqft)
    • 7 Baths
    • 19,167 Lot (sqft)
  16. Photo of 991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4530239)
    $4,395,000
    Photo of 991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4530239)
    Photo of 991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4530239)
    991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL
    991 LONGBOAT CLUB ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 5,101 Home (sqft)
    • 6 Baths
    • 18,731 Lot (sqft)
  17. Photo of 700 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4542965)
    $3,895,000
    Photo of 700 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4542965)
    Photo of 700 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4542965)
    700 TARAWITT DRIVE, LONGBOAT KEY, FL
    700 TARAWITT DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,897 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  18. Photo of 540 HARBOR COVE CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4534178)
    $3,400,000
    Photo of 540 HARBOR COVE CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4534178)
    Photo of 540 HARBOR COVE CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4534178)
    540 HARBOR COVE CIRCLE, LONGBOAT KEY, FL
    540 HARBOR COVE CIRCLE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,081 Home (sqft)
    • 3 Baths
    • 16,989 Lot (sqft)
  19. Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545381)
    $3,345,000
    Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545381)
    Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545381)
    2945 PYRULA DRIVE, LONGBOAT KEY, FL
    2945 PYRULA DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 3,815 Home (sqft)
    • 5 Baths
    • 13,940 Lot (sqft)
  20. Photo of 600 DE NARVAEZ DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545926)
    $3,250,000
    Photo of 600 DE NARVAEZ DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545926)
    Photo of 600 DE NARVAEZ DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545926)
    600 DE NARVAEZ DRIVE, LONGBOAT KEY, FL
    600 DE NARVAEZ DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 1,971 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  21. Photo of 581 DE NARVAEZ DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4530441)
    $3,200,000
    Photo of 581 DE NARVAEZ DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4530441)
    Photo of 581 DE NARVAEZ DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4530441)
    10
     
    581 DE NARVAEZ DRIVE, LONGBOAT KEY, FL
    581 DE NARVAEZ DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,134 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  22. Photo of 830 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545868)
    $3,100,000
    Photo of 830 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545868)
    Photo of 830 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545868)
    830 TARAWITT DRIVE, LONGBOAT KEY, FL
    830 TARAWITT DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  23. Photo of 6821 HUGHES STREET, LONGBOAT KEY, FL 34228 (MLS # A4534334)
    $2,999,000
    Photo of 6821 HUGHES STREET, LONGBOAT KEY, FL 34228 (MLS # A4534334)
    Photo of 6821 HUGHES STREET, LONGBOAT KEY, FL 34228 (MLS # A4534334)
    6821 HUGHES STREET, LONGBOAT KEY, FL
    6821 HUGHES STREET
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 1,804 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  24. Photo of 500 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4527024)
    $2,995,000
    Photo of 500 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4527024)
    Photo of 500 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4527024)
    10
     
    500 GENERAL HARRIS STREET, LONGBOAT KEY, FL
    500 GENERAL HARRIS STREET
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 3,743 Home (sqft)
    • 5 Baths
    • 10,455 Lot (sqft)
  25. Photo of 609 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546210)
    $2,950,000
    Photo of 609 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546210)
    Photo of 609 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546210)
    609 HALYARD LANE, LONGBOAT KEY, FL
    609 HALYARD LANE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,069 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  26. Photo of 3030 GRAND BAY BOULEVARD #316, LONGBOAT KEY, FL 34228 (MLS # A4543951)
    $2,895,000
    Photo of 3030 GRAND BAY BOULEVARD #316, LONGBOAT KEY, FL 34228 (MLS # A4543951)
    Photo of 3030 GRAND BAY BOULEVARD #316, LONGBOAT KEY, FL 34228 (MLS # A4543951)
    3030 GRAND BAY BOULEVARD #316, LONGBOAT KEY, FL
    3030 GRAND BAY BOULEVARD #316
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,925 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 2929 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4548600)
    $2,750,000
    Photo of 2929 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4548600)
    Photo of 2929 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4548600)
    2929 PYRULA DRIVE, LONGBOAT KEY, FL
    2929 PYRULA DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 3,014 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  28. Photo of 610 HIBISCUS WAY, LONGBOAT KEY, FL 34228 (MLS # A4519683)
    $2,695,000
    Photo of 610 HIBISCUS WAY, LONGBOAT KEY, FL 34228 (MLS # A4519683)
    Photo of 610 HIBISCUS WAY, LONGBOAT KEY, FL 34228 (MLS # A4519683)
    610 HIBISCUS WAY, LONGBOAT KEY, FL
    610 HIBISCUS WAY
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 2,788 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  29. Photo of 569 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4526082)
    $2,590,000
    Photo of 569 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4526082)
    Photo of 569 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4526082)
    569 JUAN ANASCO DRIVE, LONGBOAT KEY, FL
    569 JUAN ANASCO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,804 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  30. Photo of 6840 LONGBOAT DRIVE S, LONGBOAT KEY, FL 34228 (MLS # A4534091)
    $2,550,000
    Photo of 6840 LONGBOAT DRIVE S, LONGBOAT KEY, FL 34228 (MLS # A4534091)
    Photo of 6840 LONGBOAT DRIVE S, LONGBOAT KEY, FL 34228 (MLS # A4534091)
    6840 LONGBOAT DRIVE S, LONGBOAT KEY, FL
    6840 LONGBOAT DRIVE S
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 2,665 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
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