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 2425 GULF OF MEXICO DRIVE #14B, LONGBOAT KEY, FL 34228 (MLS # A4534144)
    $1,899,000
    Photo of 2425 GULF OF MEXICO DRIVE #14B, LONGBOAT KEY, FL 34228 (MLS # A4534144)
    Photo of 2425 GULF OF MEXICO DRIVE #14B, LONGBOAT KEY, FL 34228 (MLS # A4534144)
    2425 GULF OF MEXICO DRIVE #14B, LONGBOAT KEY, FL
    2425 GULF OF MEXICO DRIVE #14B
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 714 NORTON STREET, LONGBOAT KEY, FL 34228 (MLS # A4534056)
    $1,890,000
    Photo of 714 NORTON STREET, LONGBOAT KEY, FL 34228 (MLS # A4534056)
    Photo of 714 NORTON STREET, LONGBOAT KEY, FL 34228 (MLS # A4534056)
    100
     
    714 NORTON STREET, LONGBOAT KEY, FL
    714 NORTON STREET
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,109 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  3. Photo of 1465 GULF OF MEXICO DRIVE #504, LONGBOAT KEY, FL 34228 (MLS # A4534263)
    $1,875,000
    Photo of 1465 GULF OF MEXICO DRIVE #504, LONGBOAT KEY, FL 34228 (MLS # A4534263)
    Photo of 1465 GULF OF MEXICO DRIVE #504, LONGBOAT KEY, FL 34228 (MLS # A4534263)
    1465 GULF OF MEXICO DRIVE #504, LONGBOAT KEY, FL
    1465 GULF OF MEXICO DRIVE #504
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,262 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  4. Photo of 575 SANCTUARY DRIVE #A302, LONGBOAT KEY, FL 34228 (MLS # A4534942)
    $1,799,000
    Photo of 575 SANCTUARY DRIVE #A302, LONGBOAT KEY, FL 34228 (MLS # A4534942)
    Photo of 575 SANCTUARY DRIVE #A302, LONGBOAT KEY, FL 34228 (MLS # A4534942)
    575 SANCTUARY DRIVE #A302, LONGBOAT KEY, FL
    575 SANCTUARY DRIVE #A302
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 1,823 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 603 LONGBOAT CLUB ROAD #604N, LONGBOAT KEY, FL 34228 (MLS # A4534863)
    $1,798,000
    Photo of 603 LONGBOAT CLUB ROAD #604N, LONGBOAT KEY, FL 34228 (MLS # A4534863)
    Photo of 603 LONGBOAT CLUB ROAD #604N, LONGBOAT KEY, FL 34228 (MLS # A4534863)
    603 LONGBOAT CLUB ROAD #604N, LONGBOAT KEY, FL
    603 LONGBOAT CLUB ROAD #604N
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 2,210 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  6. Photo of 2525 GULF OF MEXICO DRIVE #6B, LONGBOAT KEY, FL 34228 (MLS # A4533416)
    $1,790,000
    Photo of 2525 GULF OF MEXICO DRIVE #6B, LONGBOAT KEY, FL 34228 (MLS # A4533416)
    Photo of 2525 GULF OF MEXICO DRIVE #6B, LONGBOAT KEY, FL 34228 (MLS # A4533416)
    2525 GULF OF MEXICO DRIVE #6B, LONGBOAT KEY, FL
    2525 GULF OF MEXICO DRIVE #6B
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,616 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  7. Photo of 3750 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4522103)
    $1,750,000
    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
    • 4,356 Lot (sqft)
  8. Photo of 2425 GULF OF MEXICO DRIVE #2A, LONGBOAT KEY, FL 34228 (MLS # A4519776)
    $1,595,000
    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)
  9. Photo of 775 LONGBOAT CLUB ROAD #306, LONGBOAT KEY, FL 34228 (MLS # A4534841)
    $1,395,000
    Photo of 775 LONGBOAT CLUB ROAD #306, LONGBOAT KEY, FL 34228 (MLS # A4534841)
    Photo of 775 LONGBOAT CLUB ROAD #306, LONGBOAT KEY, FL 34228 (MLS # A4534841)
    775 LONGBOAT CLUB ROAD #306, LONGBOAT KEY, FL
    775 LONGBOAT CLUB ROAD #306
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,714 Home (sqft)
    • 2 Baths
    • 5.54 Lot (ac)
  10. Photo of 1075 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4528613)
    $1,395,000
    Photo of 1075 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4528613)
    Photo of 1075 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4528613)
    1075 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL
    1075 GULF OF MEXICO DRIVE #202
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,392 Home (sqft)
    • 2 Baths
    • 31.00 Lot (ac)
  11. Photo of 4545 GULF OF MEXICO DRIVE #210, LONGBOAT KEY, FL 34228 (MLS # A4534719)
    $1,375,000
    Photo of 4545 GULF OF MEXICO DRIVE #210, LONGBOAT KEY, FL 34228 (MLS # A4534719)
    Photo of 4545 GULF OF MEXICO DRIVE #210, LONGBOAT KEY, FL 34228 (MLS # A4534719)
    4545 GULF OF MEXICO DRIVE #210, LONGBOAT KEY, FL
    4545 GULF OF MEXICO DRIVE #210
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,460 Home (sqft)
    • 2 Baths
    • 5.90 Lot (ac)
  12. 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)
  13. Photo of 2525 GULF OF MEXICO DRIVE #5B, LONGBOAT KEY, FL 34228 (MLS # A4534602)
    $1,349,000
    Photo of 2525 GULF OF MEXICO DRIVE #5B, LONGBOAT KEY, FL 34228 (MLS # A4534602)
    Photo of 2525 GULF OF MEXICO DRIVE #5B, LONGBOAT KEY, FL 34228 (MLS # A4534602)
    2525 GULF OF MEXICO DRIVE #5B, LONGBOAT KEY, FL
    2525 GULF OF MEXICO DRIVE #5B
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,491 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  14. Photo of 775 LONGBOAT CLUB ROAD #906, LONGBOAT KEY, FL 34228 (MLS # A4527843)
    $1,299,000
    Photo of 775 LONGBOAT CLUB ROAD #906, LONGBOAT KEY, FL 34228 (MLS # A4527843)
    Photo of 775 LONGBOAT CLUB ROAD #906, LONGBOAT KEY, FL 34228 (MLS # A4527843)
    775 LONGBOAT CLUB ROAD #906, LONGBOAT KEY, FL
    775 LONGBOAT CLUB ROAD #906
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,714 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  15. Photo of 3808 GULF OF MEXICO DRIVE #E112, LONGBOAT KEY, FL 34228 (MLS # T3367603)
    $1,250,000
    Photo of 3808 GULF OF MEXICO DRIVE #E112, LONGBOAT KEY, FL 34228 (MLS # T3367603)
    Photo of 3808 GULF OF MEXICO DRIVE #E112, LONGBOAT KEY, FL 34228 (MLS # T3367603)
    3808 GULF OF MEXICO DRIVE #E112, LONGBOAT KEY, FL
    3808 GULF OF MEXICO DRIVE #E112
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,273 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  16. Photo of 2109 GULF OF MEXICO DRIVE #1103, LONGBOAT KEY, FL 34228 (MLS # A4530863)
    $1,250,000
    Photo of 2109 GULF OF MEXICO DRIVE #1103, LONGBOAT KEY, FL 34228 (MLS # A4530863)
    Photo of 2109 GULF OF MEXICO DRIVE #1103, LONGBOAT KEY, FL 34228 (MLS # A4530863)
    2109 GULF OF MEXICO DRIVE #1103, LONGBOAT KEY, FL
    2109 GULF OF MEXICO DRIVE #1103
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,843 Home (sqft)
    • 2 Baths
    • 4.26 Lot (ac)
  17. Photo of 1000 LONGBOAT CLUB ROAD #702, LONGBOAT KEY, FL 34228 (MLS # A4533257)
    $1,200,000
    Photo of 1000 LONGBOAT CLUB ROAD #702, LONGBOAT KEY, FL 34228 (MLS # A4533257)
    Photo of 1000 LONGBOAT CLUB ROAD #702, LONGBOAT KEY, FL 34228 (MLS # A4533257)
    1000 LONGBOAT CLUB ROAD #702, LONGBOAT KEY, FL
    1000 LONGBOAT CLUB ROAD #702
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,390 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  18. Photo of 7135 GULF OF MEXICO DRIVE #12, LONGBOAT KEY, FL 34228 (MLS # A4532632)
    $1,190,000
    Photo of 7135 GULF OF MEXICO DRIVE #12, LONGBOAT KEY, FL 34228 (MLS # A4532632)
    Photo of 7135 GULF OF MEXICO DRIVE #12, LONGBOAT KEY, FL 34228 (MLS # A4532632)
    7135 GULF OF MEXICO DRIVE #12, LONGBOAT KEY, FL
    7135 GULF OF MEXICO DRIVE #12
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,404 Home (sqft)
    • 2 Baths
    • 2.90 Lot (ac)
  19. Photo of 2004 N HARBOURSIDE DRIVE #1701, LONGBOAT KEY, FL 34228 (MLS # R4905948)
    $1,045,000
    Photo of 2004 N HARBOURSIDE DRIVE #1701, LONGBOAT KEY, FL 34228 (MLS # R4905948)
    Photo of 2004 N HARBOURSIDE DRIVE #1701, LONGBOAT KEY, FL 34228 (MLS # R4905948)
    54
     
    2004 N HARBOURSIDE DRIVE #1701, LONGBOAT KEY, FL
    2004 N HARBOURSIDE DRIVE #1701
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 3,075 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  20. Photo of 2089 GULF OF MEXICO DRIVE #G1-302, LONGBOAT KEY, FL 34228 (MLS # A4531491)
    $995,000
    Photo of 2089 GULF OF MEXICO DRIVE #G1-302, LONGBOAT KEY, FL 34228 (MLS # A4531491)
    Photo of 2089 GULF OF MEXICO DRIVE #G1-302, LONGBOAT KEY, FL 34228 (MLS # A4531491)
    2089 GULF OF MEXICO DRIVE #G1-302, LONGBOAT KEY, FL
    2089 GULF OF MEXICO DRIVE #G1-302
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,257 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 1926 HARBOURSIDE DRIVE #1304, LONGBOAT KEY, FL 34228 (MLS # A4528490)
    $995,000
    Photo of 1926 HARBOURSIDE DRIVE #1304, LONGBOAT KEY, FL 34228 (MLS # A4528490)
    Photo of 1926 HARBOURSIDE DRIVE #1304, LONGBOAT KEY, FL 34228 (MLS # A4528490)
    1926 HARBOURSIDE DRIVE #1304, LONGBOAT KEY, FL
    1926 HARBOURSIDE DRIVE #1304
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 4,049 Home (sqft)
    • 3 Baths
    • 10.83 Lot (ac)
  22. Photo of 525 CHANNEL LANE, LONGBOAT KEY, FL 34228 (MLS # A4535621)
    $925,000
    Photo of 525 CHANNEL LANE, LONGBOAT KEY, FL 34228 (MLS # A4535621)
    Photo of 525 CHANNEL LANE, LONGBOAT KEY, FL 34228 (MLS # A4535621)
    525 CHANNEL LANE, LONGBOAT KEY, FL
    525 CHANNEL LANE
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 988 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  23. Photo of 4485 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL 34228 (MLS # W7842568)
    $899,000
    Photo of 4485 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL 34228 (MLS # W7842568)
    Photo of 4485 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL 34228 (MLS # W7842568)
    4485 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL
    4485 GULF OF MEXICO DRIVE #204
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,175 Home (sqft)
    • 2 Baths
    • 1.63 Lot (ac)
  24. Photo of 4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL 34228 (MLS # A4529849)
    $875,000
    Photo of 4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL 34228 (MLS # A4529849)
    Photo of 4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL 34228 (MLS # A4529849)
    36
     
    4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL
    4600 GULF OF MEXICO DRIVE #205
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,312 Home (sqft)
    • 2 Baths
    • 26.67 Lot (ac)
  25. Photo of 3240 GULF OF MEXICO DRIVE #B404, LONGBOAT KEY, FL 34228 (MLS # A4534057)
    $675,000
    Photo of 3240 GULF OF MEXICO DRIVE #B404, LONGBOAT KEY, FL 34228 (MLS # A4534057)
    Photo of 3240 GULF OF MEXICO DRIVE #B404, LONGBOAT KEY, FL 34228 (MLS # A4534057)
    3240 GULF OF MEXICO DRIVE #B404, LONGBOAT KEY, FL
    3240 GULF OF MEXICO DRIVE #B404
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  26. Photo of 2630 HARBOURSIDE DRIVE #L-05, LONGBOAT KEY, FL 34228 (MLS # A4521991)
    $649,000
    Photo of 2630 HARBOURSIDE DRIVE #L-05, LONGBOAT KEY, FL 34228 (MLS # A4521991)
    Photo of 2630 HARBOURSIDE DRIVE #L-05, LONGBOAT KEY, FL 34228 (MLS # A4521991)
    2630 HARBOURSIDE DRIVE #L-05, LONGBOAT KEY, FL
    2630 HARBOURSIDE DRIVE #L-05
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 0 Lot (sqft)
  27. Photo of 4320 FALMOUTH DRIVE #103, LONGBOAT KEY, FL 34228 (MLS # A4532570)
    $610,000
    Photo of 4320 FALMOUTH DRIVE #103, LONGBOAT KEY, FL 34228 (MLS # A4532570)
    Photo of 4320 FALMOUTH DRIVE #103, LONGBOAT KEY, FL 34228 (MLS # A4532570)
    4320 FALMOUTH DRIVE #103, LONGBOAT KEY, FL
    4320 FALMOUTH DRIVE #103
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,072 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  28. Photo of 573 SUTTON PLACE, LONGBOAT KEY, FL 34228 (MLS # A4529073)
    $599,900
    Photo of 573 SUTTON PLACE, LONGBOAT KEY, FL 34228 (MLS # A4529073)
    Photo of 573 SUTTON PLACE, LONGBOAT KEY, FL 34228 (MLS # A4529073)
    573 SUTTON PLACE, LONGBOAT KEY, FL
    573 SUTTON PLACE
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,608 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  29. Photo of 4400 EXETER DRIVE #J106, LONGBOAT KEY, FL 34228 (MLS # A4534112)
    $595,000
    Photo of 4400 EXETER DRIVE #J106, LONGBOAT KEY, FL 34228 (MLS # A4534112)
    Photo of 4400 EXETER DRIVE #J106, LONGBOAT KEY, FL 34228 (MLS # A4534112)
    63
     
    4400 EXETER DRIVE #J106, LONGBOAT KEY, FL
    4400 EXETER DRIVE #J106
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,152 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 2600 HARBOURSIDE DRIVE #G-19 & G-20, LONGBOAT KEY, FL 34228 (MLS # A4517804)
    $595,000
    Photo of 2600 HARBOURSIDE DRIVE #G-19 & G-20, LONGBOAT KEY, FL 34228 (MLS # A4517804)
    Photo of 2600 HARBOURSIDE DRIVE #G-19 & G-20, LONGBOAT KEY, FL 34228 (MLS # A4517804)
    2600 HARBOURSIDE DRIVE #G-19 & G-20, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #G-19 & G-20
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 21,837 Lot (sqft)
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