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 3105 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4499439)
    $12,900,000
    Photo of 3105 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4499439)
    Photo of 3105 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4499439)
    3105 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    3105 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 9 Baths
    • 9,947 Home (sqft)
    • 9 Baths
    • 27,106 Lot (sqft)
  2. Photo of 1620 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL 34228 (MLS # A4521086)
    $8,995,000
    Photo of 1620 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL 34228 (MLS # A4521086)
    Photo of 1620 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL 34228 (MLS # A4521086)
    22
     
    1620 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #208
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,017 Home (sqft)
    • 5 Baths
    • 17.80 Lot (ac)
  3. Photo of 1620 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # A4516610)
    $8,495,000
    Photo of 1620 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # A4516610)
    Photo of 1620 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # A4516610)
    19
     
    1620 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #303
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 4,187 Home (sqft)
    • 4 Baths
    • 17.80 Lot (ac)
  4. Photo of 1620 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4521080)
    $7,650,000
    Photo of 1620 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4521080)
    Photo of 1620 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4521080)
    22
     
    1620 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #305
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,017 Home (sqft)
    • 5 Baths
    • 17.80 Lot (ac)
  5. Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    $6,595,000
    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
    • 40,002 Lot (sqft)
  6. Photo of 25 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4503359)
    $5,200,000
    Photo of 25 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4503359)
    Photo of 25 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4503359)
    25 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL
    25 LIGHTHOUSE POINT DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 7 Baths
    • 6,025 Home (sqft)
    • 7 Baths
    • 16,942 Lot (sqft)
  7. Photo of 636 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4522823)
    $4,795,000
    Photo of 636 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4522823)
    Photo of 636 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4522823)
    636 DREAM ISLAND ROAD, LONGBOAT KEY, FL
    636 DREAM ISLAND ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 4,400 Home (sqft)
    • 6 Baths
    • 25,600 Lot (sqft)
  8. Photo of 6555 BAYOU HAMMOCK ROAD, LONGBOAT KEY, FL 34228 (MLS # A4518741)
    $3,500,000
    Photo of 6555 BAYOU HAMMOCK ROAD, LONGBOAT KEY, FL 34228 (MLS # A4518741)
    Photo of 6555 BAYOU HAMMOCK ROAD, LONGBOAT KEY, FL 34228 (MLS # A4518741)
    6555 BAYOU HAMMOCK ROAD, LONGBOAT KEY, FL
    6555 BAYOU HAMMOCK ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 3,846 Home (sqft)
    • 5 Baths
    • 35,250 Lot (sqft)
  9. Photo of 1281 GULF OF MEXICO DRIVE #302, LONGBOAT KEY, FL 34228 (MLS # A4522901)
    $3,495,000
    Photo of 1281 GULF OF MEXICO DRIVE #302, LONGBOAT KEY, FL 34228 (MLS # A4522901)
    Photo of 1281 GULF OF MEXICO DRIVE #302, LONGBOAT KEY, FL 34228 (MLS # A4522901)
    1281 GULF OF MEXICO DRIVE #302, LONGBOAT KEY, FL
    1281 GULF OF MEXICO DRIVE #302
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,435 Home (sqft)
    • 4 Baths
    • 2.11 Lot (ac)
  10. Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4504654)
    $3,195,000
    Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4504654)
    Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4504654)
    2945 PYRULA DRIVE, LONGBOAT KEY, FL
    2945 PYRULA DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 3,820 Home (sqft)
    • 5 Baths
    • 11,501 Lot (sqft)
  11. Photo of 415 L AMBIANCE DRIVE #B602, LONGBOAT KEY, FL 34228 (MLS # A4523228)
    $2,785,000
    Photo of 415 L AMBIANCE DRIVE #B602, LONGBOAT KEY, FL 34228 (MLS # A4523228)
    Photo of 415 L AMBIANCE DRIVE #B602, LONGBOAT KEY, FL 34228 (MLS # A4523228)
    415 L AMBIANCE DRIVE #B602, LONGBOAT KEY, FL
    415 L AMBIANCE DRIVE #B602
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,385 Home (sqft)
    • 3 Baths
    • 10.16 Lot (ac)
  12. Photo of 610 HIBISCUS WAY, LONGBOAT KEY, FL 34228 (MLS # A4519683)
    $2,700,000
    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
    • 3 Beds
    • 4 Baths
    • 3,124 Home (sqft)
    • 4 Baths
    • 7,336 Lot (sqft)
  13. Photo of 1620 GULF OF MEXICO DRIVE #207, LONGBOAT KEY, FL 34228 (MLS # A4516596)
    $2,490,000
    Photo of 1620 GULF OF MEXICO DRIVE #207, LONGBOAT KEY, FL 34228 (MLS # A4516596)
    Photo of 1620 GULF OF MEXICO DRIVE #207, LONGBOAT KEY, FL 34228 (MLS # A4516596)
    22
     
    1620 GULF OF MEXICO DRIVE #207, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #207
    LONGBOAT KEY, FL
    • 1 Bed
    • 2 Baths
    • 1,721 Home (sqft)
    • 2 Baths
    • 17.80 Lot (ac)
  14. Photo of 3750 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4522103)
    $2,300,000
    Photo of 3750 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4522103)
    Photo of 3750 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4522103)
    56
     
    3750 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    3750 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 6 Beds
    • 5 Baths
    • 3,470 Home (sqft)
    • 5 Baths
    • 4,379 Lot (sqft)
  15. Photo of 545 SANCTUARY DRIVE #A303, LONGBOAT KEY, FL 34228 (MLS # A4522671)
    $2,175,000
    Photo of 545 SANCTUARY DRIVE #A303, LONGBOAT KEY, FL 34228 (MLS # A4522671)
    Photo of 545 SANCTUARY DRIVE #A303, LONGBOAT KEY, FL 34228 (MLS # A4522671)
    545 SANCTUARY DRIVE #A303, LONGBOAT KEY, FL
    545 SANCTUARY DRIVE #A303
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,375 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  16. Photo of 3421 BAYOU COURT, LONGBOAT KEY, FL 34228 (MLS # A4520723)
    $2,145,000
    Photo of 3421 BAYOU COURT, LONGBOAT KEY, FL 34228 (MLS # A4520723)
    Photo of 3421 BAYOU COURT, LONGBOAT KEY, FL 34228 (MLS # A4520723)
    3421 BAYOU COURT, LONGBOAT KEY, FL
    3421 BAYOU COURT
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,504 Home (sqft)
    • 4 Baths
    • 16,252 Lot (sqft)
  17. Photo of 3395 BAYOU LANE, LONGBOAT KEY, FL 34228 (MLS # A4520879)
    $1,970,000
    Photo of 3395 BAYOU LANE, LONGBOAT KEY, FL 34228 (MLS # A4520879)
    Photo of 3395 BAYOU LANE, LONGBOAT KEY, FL 34228 (MLS # A4520879)
    3395 BAYOU LANE, LONGBOAT KEY, FL
    3395 BAYOU LANE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,436 Home (sqft)
    • 4 Baths
    • 12,193 Lot (sqft)
  18. Photo of 2425 GULF OF MEXICO DRIVE #2A, LONGBOAT KEY, FL 34228 (MLS # A4519776)
    $1,895,000
    Photo of 2425 GULF OF MEXICO DRIVE #2A, LONGBOAT KEY, FL 34228 (MLS # A4519776)
    Photo of 2425 GULF OF MEXICO DRIVE #2A, LONGBOAT KEY, FL 34228 (MLS # A4519776)
    2425 GULF OF MEXICO DRIVE #2A, LONGBOAT KEY, FL
    2425 GULF OF MEXICO DRIVE #2A
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,513 Home (sqft)
    • 2 Baths
    • 4.26 Lot (ac)
  19. Photo of 3261 BAYOU WAY, LONGBOAT KEY, FL 34228 (MLS # A4518648)
    $1,750,000
    Photo of 3261 BAYOU WAY, LONGBOAT KEY, FL 34228 (MLS # A4518648)
    Photo of 3261 BAYOU WAY, LONGBOAT KEY, FL 34228 (MLS # A4518648)
    3261 BAYOU WAY, LONGBOAT KEY, FL
    3261 BAYOU WAY
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 2,523 Home (sqft)
    • 4 Baths
    • 16,627 Lot (sqft)
  20. Photo of 3060 GRAND BAY BOULEVARD #174, LONGBOAT KEY, FL 34228 (MLS # A4522696)
    $1,700,000
    Photo of 3060 GRAND BAY BOULEVARD #174, LONGBOAT KEY, FL 34228 (MLS # A4522696)
    Photo of 3060 GRAND BAY BOULEVARD #174, LONGBOAT KEY, FL 34228 (MLS # A4522696)
    3060 GRAND BAY BOULEVARD #174, LONGBOAT KEY, FL
    3060 GRAND BAY BOULEVARD #174
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,369 Home (sqft)
    • 3 Baths
    • 1.23 Lot (ac)
  21. Photo of 601 LONGBOAT CLUB ROAD #203S, LONGBOAT KEY, FL 34228 (MLS # O5994816)
    $1,475,000
    Photo of 601 LONGBOAT CLUB ROAD #203S, LONGBOAT KEY, FL 34228 (MLS # O5994816)
    Photo of 601 LONGBOAT CLUB ROAD #203S, LONGBOAT KEY, FL 34228 (MLS # O5994816)
    601 LONGBOAT CLUB ROAD #203S, LONGBOAT KEY, FL
    601 LONGBOAT CLUB ROAD #203S
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,458 Home (sqft)
    • 2 Baths
    • 4.97 Lot (ac)
  22. Photo of 1445 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4522200)
    $1,450,000
    Photo of 1445 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4522200)
    Photo of 1445 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4522200)
    1445 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL
    1445 GULF OF MEXICO DRIVE #305
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 1,957 Home (sqft)
    • 3 Baths
    • 1.16 Lot (ac)
  23. Photo of 3060 GRAND BAY BOULEVARD #112, LONGBOAT KEY, FL 34228 (MLS # A4520251)
    $1,450,000
    Photo of 3060 GRAND BAY BOULEVARD #112, LONGBOAT KEY, FL 34228 (MLS # A4520251)
    Photo of 3060 GRAND BAY BOULEVARD #112, LONGBOAT KEY, FL 34228 (MLS # A4520251)
    3060 GRAND BAY BOULEVARD #112, LONGBOAT KEY, FL
    3060 GRAND BAY BOULEVARD #112
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,250 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  24. Photo of 711 RUSSELL STREET, LONGBOAT KEY, FL 34228 (MLS # A4520114)
    $1,400,000
    Photo of 711 RUSSELL STREET, LONGBOAT KEY, FL 34228 (MLS # A4520114)
    Photo of 711 RUSSELL STREET, LONGBOAT KEY, FL 34228 (MLS # A4520114)
    28
     
    711 RUSSELL STREET, LONGBOAT KEY, FL
    711 RUSSELL STREET
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 1,862 Home (sqft)
    • 2 Baths
    • 11,812 Lot (sqft)
  25. Photo of 536 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4505565)
    $1,350,000
    Photo of 536 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4505565)
    Photo of 536 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4505565)
    536 GENERAL HARRIS STREET, LONGBOAT KEY, FL
    536 GENERAL HARRIS STREET
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 2,336 Home (sqft)
    • 3 Baths
    • 19,999 Lot (sqft)
  26. Photo of 1701 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # A4520048)
    $1,200,000
    Photo of 1701 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # A4520048)
    Photo of 1701 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # A4520048)
    1701 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL
    1701 GULF OF MEXICO DRIVE #404
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,551 Home (sqft)
    • 2 Baths
    • 4.15 Lot (ac)
  27. Photo of 741 FOX STREET, LONGBOAT KEY, FL 34228 (MLS # A4520104)
    $1,195,000
    Photo of 741 FOX STREET, LONGBOAT KEY, FL 34228 (MLS # A4520104)
    Photo of 741 FOX STREET, LONGBOAT KEY, FL 34228 (MLS # A4520104)
    55
     
    741 FOX STREET, LONGBOAT KEY, FL
    741 FOX STREET
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 2,390 Home (sqft)
    • 3 Baths
    • 7,350 Lot (sqft)
  28. Photo of 4401 GULF OF MEXICO DRIVE #606, LONGBOAT KEY, FL 34228 (MLS # A4523061)
    $1,100,000
    Photo of 4401 GULF OF MEXICO DRIVE #606, LONGBOAT KEY, FL 34228 (MLS # A4523061)
    Photo of 4401 GULF OF MEXICO DRIVE #606, LONGBOAT KEY, FL 34228 (MLS # A4523061)
    4401 GULF OF MEXICO DRIVE #606, LONGBOAT KEY, FL
    4401 GULF OF MEXICO DRIVE #606
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,251 Home (sqft)
    • 2 Baths
    • 5.50 Lot (ac)
  29. Photo of 4311 GULF OF MEXICO DRIVE #401, LONGBOAT KEY, FL 34228 (MLS # A4522542)
    $1,100,000
    Photo of 4311 GULF OF MEXICO DRIVE #401, LONGBOAT KEY, FL 34228 (MLS # A4522542)
    Photo of 4311 GULF OF MEXICO DRIVE #401, LONGBOAT KEY, FL 34228 (MLS # A4522542)
    29
     
    4311 GULF OF MEXICO DRIVE #401, LONGBOAT KEY, FL
    4311 GULF OF MEXICO DRIVE #401
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,293 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 680 FOX STREET, LONGBOAT KEY, FL 34228 (MLS # A4520803)
    $995,000
    Photo of 680 FOX STREET, LONGBOAT KEY, FL 34228 (MLS # A4520803)
    Photo of 680 FOX STREET, LONGBOAT KEY, FL 34228 (MLS # A4520803)
    46
     
    680 FOX STREET, LONGBOAT KEY, FL
    680 FOX STREET
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 1,544 Home (sqft)
    • 2 Baths
    • 10,499 Lot (sqft)
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