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 1000 LONGBOAT CLUB ROAD #506, LONGBOAT KEY, FL 34228 (MLS # A4511687)
    $1,095,000
    Photo of 1000 LONGBOAT CLUB ROAD #506, LONGBOAT KEY, FL 34228 (MLS # A4511687)
    Photo of 1000 LONGBOAT CLUB ROAD #506, LONGBOAT KEY, FL 34228 (MLS # A4511687)
    1000 LONGBOAT CLUB ROAD #506, LONGBOAT KEY, FL
    1000 LONGBOAT CLUB ROAD #506
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,409 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 2110 HARBOURSIDE DRIVE #526, LONGBOAT KEY, FL 34228 (MLS # A4514034)
    $995,000
    Photo of 2110 HARBOURSIDE DRIVE #526, LONGBOAT KEY, FL 34228 (MLS # A4514034)
    Photo of 2110 HARBOURSIDE DRIVE #526, LONGBOAT KEY, FL 34228 (MLS # A4514034)
    2110 HARBOURSIDE DRIVE #526, LONGBOAT KEY, FL
    2110 HARBOURSIDE DRIVE #526
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 2,031 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  3. Photo of 4311 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4503348)
    $964,900
    Photo of 4311 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4503348)
    Photo of 4311 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4503348)
    4311 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL
    4311 GULF OF MEXICO DRIVE #203
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,140 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  4. Photo of 1050 LONGBOAT CLUB ROAD #1005, LONGBOAT KEY, FL 34228 (MLS # A4491368)
    $925,000
    Photo of 1050 LONGBOAT CLUB ROAD #1005, LONGBOAT KEY, FL 34228 (MLS # A4491368)
    Photo of 1050 LONGBOAT CLUB ROAD #1005, LONGBOAT KEY, FL 34228 (MLS # A4491368)
    1050 LONGBOAT CLUB ROAD #1005, LONGBOAT KEY, FL
    1050 LONGBOAT CLUB ROAD #1005
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,290 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  5. Photo of 2195 HARBOURSIDE DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # O5973546)
    $849,000
    Photo of 2195 HARBOURSIDE DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # O5973546)
    Photo of 2195 HARBOURSIDE DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # O5973546)
    2195 HARBOURSIDE DRIVE #404, LONGBOAT KEY, FL
    2195 HARBOURSIDE DRIVE #404
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 1,906 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  6. Photo of 7125 GULF OF MEXICO DRIVE #11, LONGBOAT KEY, FL 34228 (MLS # A4508287)
    $799,000
    Photo of 7125 GULF OF MEXICO DRIVE #11, LONGBOAT KEY, FL 34228 (MLS # A4508287)
    Photo of 7125 GULF OF MEXICO DRIVE #11, LONGBOAT KEY, FL 34228 (MLS # A4508287)
    7125 GULF OF MEXICO DRIVE #11, LONGBOAT KEY, FL
    7125 GULF OF MEXICO DRIVE #11
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,170 Home (sqft)
    • 2 Baths
    • 2.97 Lot (ac)
  7. Photo of 1926 HARBOURSIDE DRIVE #1302, LONGBOAT KEY, FL 34228 (MLS # A4513995)
    $789,000
    Photo of 1926 HARBOURSIDE DRIVE #1302, LONGBOAT KEY, FL 34228 (MLS # A4513995)
    Photo of 1926 HARBOURSIDE DRIVE #1302, LONGBOAT KEY, FL 34228 (MLS # A4513995)
    1926 HARBOURSIDE DRIVE #1302, LONGBOAT KEY, FL
    1926 HARBOURSIDE DRIVE #1302
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 1,626 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  8. Photo of 691 BROADWAY STREET, LONGBOAT KEY, FL 34228 (MLS # A4511396)
    $749,000
    Photo of 691 BROADWAY STREET, LONGBOAT KEY, FL 34228 (MLS # A4511396)
    Photo of 691 BROADWAY STREET, LONGBOAT KEY, FL 34228 (MLS # A4511396)
    691 BROADWAY STREET, LONGBOAT KEY, FL
    691 BROADWAY STREET
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,189 Home (sqft)
    • 2 Baths
    • 6,000 Lot (sqft)
  9. Photo of 3240 GULF OF MEXICO DRIVE #B207, LONGBOAT KEY, FL 34228 (MLS # A4515467)
    $719,000
    Photo of 3240 GULF OF MEXICO DRIVE #B207, LONGBOAT KEY, FL 34228 (MLS # A4515467)
    Photo of 3240 GULF OF MEXICO DRIVE #B207, LONGBOAT KEY, FL 34228 (MLS # A4515467)
    3240 GULF OF MEXICO DRIVE #B207, LONGBOAT KEY, FL
    3240 GULF OF MEXICO DRIVE #B207
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,290 Home (sqft)
    • 2 Baths
    • 4.84 Lot (ac)
  10. Photo of 4600 GULF OF MEXICO DRIVE #206, LONGBOAT KEY, FL 34228 (MLS # A4510128)
    $710,000
    Photo of 4600 GULF OF MEXICO DRIVE #206, LONGBOAT KEY, FL 34228 (MLS # A4510128)
    Photo of 4600 GULF OF MEXICO DRIVE #206, LONGBOAT KEY, FL 34228 (MLS # A4510128)
    4600 GULF OF MEXICO DRIVE #206, LONGBOAT KEY, FL
    4600 GULF OF MEXICO DRIVE #206
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,523 Home (sqft)
    • 2 Baths
    • 26.67 Lot (ac)
  11. Photo of 4725 GULF OF MEXICO DRIVE #111, LONGBOAT KEY, FL 34228 (MLS # A4509689)
    $700,000
    Photo of 4725 GULF OF MEXICO DRIVE #111, LONGBOAT KEY, FL 34228 (MLS # A4509689)
    Photo of 4725 GULF OF MEXICO DRIVE #111, LONGBOAT KEY, FL 34228 (MLS # A4509689)
    30
     
    4725 GULF OF MEXICO DRIVE #111, LONGBOAT KEY, FL
    4725 GULF OF MEXICO DRIVE #111
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,032 Home (sqft)
    • 2 Baths
    • 4.93 Lot (ac)
  12. Photo of 5611 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL 34228 (MLS # A4503673)
    $699,000
    Photo of 5611 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL 34228 (MLS # A4503673)
    Photo of 5611 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL 34228 (MLS # A4503673)
    5611 GULF OF MEXICO DRIVE #2, LONGBOAT KEY, FL
    5611 GULF OF MEXICO DRIVE #2
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,207 Home (sqft)
    • 3 Baths
    • 1.02 Lot (ac)
  13. Photo of 4725 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL 34228 (MLS # A4514992)
    $695,000
    Photo of 4725 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL 34228 (MLS # A4514992)
    Photo of 4725 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL 34228 (MLS # A4514992)
    4725 GULF OF MEXICO DRIVE #208, LONGBOAT KEY, FL
    4725 GULF OF MEXICO DRIVE #208
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,071 Home (sqft)
    • 2 Baths
    • 4.93 Lot (ac)
  14. Photo of 4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL 34228 (MLS # A4512361)
    $675,000
    Photo of 4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL 34228 (MLS # A4512361)
    Photo of 4600 GULF OF MEXICO DRIVE #205, LONGBOAT KEY, FL 34228 (MLS # A4512361)
    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)
  15. Photo of 4401 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # T3318597)
    $625,000
    Photo of 4401 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # T3318597)
    Photo of 4401 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # T3318597)
    4401 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL
    4401 GULF OF MEXICO DRIVE #303
    LONGBOAT KEY, FL
    • 1 Bed
    • 1 Bath
    • 725 Home (sqft)
    • 1 Bath
    • 2.16 Lot (ac)
  16. Photo of 4960 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL 34228 (MLS # A4510679)
    $615,000
    Photo of 4960 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL 34228 (MLS # A4510679)
    Photo of 4960 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL 34228 (MLS # A4510679)
    4960 GULF OF MEXICO DRIVE #204, LONGBOAT KEY, FL
    4960 GULF OF MEXICO DRIVE #204
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,312 Home (sqft)
    • 2 Baths
    • 26.67 Lot (ac)
  17. Photo of 225 SANDS POINT ROAD #6104, LONGBOAT KEY, FL 34228 (MLS # A4505298)
    $599,000
    Photo of 225 SANDS POINT ROAD #6104, LONGBOAT KEY, FL 34228 (MLS # A4505298)
    Photo of 225 SANDS POINT ROAD #6104, LONGBOAT KEY, FL 34228 (MLS # A4505298)
    225 SANDS POINT ROAD #6104, LONGBOAT KEY, FL
    225 SANDS POINT ROAD #6104
    LONGBOAT KEY, FL
    • 1 Bed
    • 1 Bath
    • 642 Home (sqft)
    • 1 Bath
    • 1.76 Lot (ac)
  18. Photo of 3806 GULF OF MEXICO #C109, LONGBOAT KEY, FL 34228 (MLS # A4507523)
    $524,999
    Photo of 3806 GULF OF MEXICO #C109, LONGBOAT KEY, FL 34228 (MLS # A4507523)
    Photo of 3806 GULF OF MEXICO #C109, LONGBOAT KEY, FL 34228 (MLS # A4507523)
    3806 GULF OF MEXICO #C109, LONGBOAT KEY, FL
    3806 GULF OF MEXICO #C109
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,027 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 4320 FALMOUTH DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4514592)
    $495,000
    Photo of 4320 FALMOUTH DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4514592)
    Photo of 4320 FALMOUTH DRIVE #202, LONGBOAT KEY, FL 34228 (MLS # A4514592)
    4320 FALMOUTH DRIVE #202, LONGBOAT KEY, FL
    4320 FALMOUTH DRIVE #202
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,150 Home (sqft)
    • 2 Baths
    • 20.68 Lot (ac)
  20. Photo of 2600 HARBOURSIDE DRIVE #B-4, LONGBOAT KEY, FL 34228 (MLS # A4510855)
    $475,000
    Photo of 2600 HARBOURSIDE DRIVE #B-4, LONGBOAT KEY, FL 34228 (MLS # A4510855)
    Photo of 2600 HARBOURSIDE DRIVE #B-4, LONGBOAT KEY, FL 34228 (MLS # A4510855)
    2600 HARBOURSIDE DRIVE #B-4, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #B-4
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 1.06 Lot (ac)
  21. Photo of 3804 GULF OF MEXICO DRIVE #B106, LONGBOAT KEY, FL 34228 (MLS # A4509123)
    $450,000
    Photo of 3804 GULF OF MEXICO DRIVE #B106, LONGBOAT KEY, FL 34228 (MLS # A4509123)
    Photo of 3804 GULF OF MEXICO DRIVE #B106, LONGBOAT KEY, FL 34228 (MLS # A4509123)
    3804 GULF OF MEXICO DRIVE #B106, LONGBOAT KEY, FL
    3804 GULF OF MEXICO DRIVE #B106
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 976 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  22. Photo of 4380 EXETER DR #303, LONGBOAT KEY, FL 34228 (MLS # A4507230)
    $444,900
    Photo of 4380 EXETER DR #303, LONGBOAT KEY, FL 34228 (MLS # A4507230)
    Photo of 4380 EXETER DR #303, LONGBOAT KEY, FL 34228 (MLS # A4507230)
    4380 EXETER DR #303, LONGBOAT KEY, FL
    4380 EXETER DR #303
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,152 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 2600 HARBOURSIDE DRIVE #L-06, LONGBOAT KEY, FL 34228 (MLS # A4515253)
    $349,000
    Photo of 2600 HARBOURSIDE DRIVE #L-06, LONGBOAT KEY, FL 34228 (MLS # A4515253)
    Photo of 2600 HARBOURSIDE DRIVE #L-06, LONGBOAT KEY, FL 34228 (MLS # A4515253)
    2600 HARBOURSIDE DRIVE #L-06, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #L-06
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 36,962 Lot (sqft)
  24. Photo of 2800 HARBOURSIDE DRIVE #D-05, LONGBOAT KEY, FL 34228 (MLS # A4515251)
    $349,000
    Photo of 2800 HARBOURSIDE DRIVE #D-05, LONGBOAT KEY, FL 34228 (MLS # A4515251)
    Photo of 2800 HARBOURSIDE DRIVE #D-05, LONGBOAT KEY, FL 34228 (MLS # A4515251)
    2800 HARBOURSIDE DRIVE #D-05, LONGBOAT KEY, FL
    2800 HARBOURSIDE DRIVE #D-05
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 40,290 Lot (sqft)
  25. Photo of 2600 HARBOURSIDE DRIVE #I-16, LONGBOAT KEY, FL 34228 (MLS # A4515247)
    $349,000
    Photo of 2600 HARBOURSIDE DRIVE #I-16, LONGBOAT KEY, FL 34228 (MLS # A4515247)
    Photo of 2600 HARBOURSIDE DRIVE #I-16, LONGBOAT KEY, FL 34228 (MLS # A4515247)
    2600 HARBOURSIDE DRIVE #I-16, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #I-16
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 24,055 Lot (sqft)
  26. Photo of 717 SAINT JUDES DRIVE S #2, LONGBOAT KEY, FL 34228 (MLS # A4511040)
    $325,000
    Photo of 717 SAINT JUDES DRIVE S #2, LONGBOAT KEY, FL 34228 (MLS # A4511040)
    Photo of 717 SAINT JUDES DRIVE S #2, LONGBOAT KEY, FL 34228 (MLS # A4511040)
    717 SAINT JUDES DRIVE S #2, LONGBOAT KEY, FL
    717 SAINT JUDES DRIVE S #2
    LONGBOAT KEY, FL
    • 1 Bed
    • 1 Bath
    • 630 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  27. Photo of 2600 HARBOURSIDE DRIVE #C-17, LONGBOAT KEY, FL 34228 (MLS # A4510851)
    $325,000
    Photo of 2600 HARBOURSIDE DRIVE #C-17, LONGBOAT KEY, FL 34228 (MLS # A4510851)
    Photo of 2600 HARBOURSIDE DRIVE #C-17, LONGBOAT KEY, FL 34228 (MLS # A4510851)
    2600 HARBOURSIDE DRIVE #C-17, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #C-17
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 34,719 Lot (sqft)
  28. Photo of 2600 HARBOURSIDE DRIVE #C-13, LONGBOAT KEY, FL 34228 (MLS # A4510845)
    $325,000
    Photo of 2600 HARBOURSIDE DRIVE #C-13, LONGBOAT KEY, FL 34228 (MLS # A4510845)
    Photo of 2600 HARBOURSIDE DRIVE #C-13, LONGBOAT KEY, FL 34228 (MLS # A4510845)
    2600 HARBOURSIDE DRIVE #C-13, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #C-13
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 34,719 Lot (sqft)
  29. Photo of 2600 HARBOURSIDE DRIVE #C-15, LONGBOAT KEY, FL 34228 (MLS # A4510841)
    $325,000
    Photo of 2600 HARBOURSIDE DRIVE #C-15, LONGBOAT KEY, FL 34228 (MLS # A4510841)
    Photo of 2600 HARBOURSIDE DRIVE #C-15, LONGBOAT KEY, FL 34228 (MLS # A4510841)
    2600 HARBOURSIDE DRIVE #C-15, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #C-15
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 34,719 Lot (sqft)
  30. Photo of 2600 HARBOURSIDE DRIVE #G-17, LONGBOAT KEY, FL 34228 (MLS # A4511337)
    $298,000
    Photo of 2600 HARBOURSIDE DRIVE #G-17, LONGBOAT KEY, FL 34228 (MLS # A4511337)
    Photo of 2600 HARBOURSIDE DRIVE #G-17, LONGBOAT KEY, FL 34228 (MLS # A4511337)
    2600 HARBOURSIDE DRIVE #G-17, LONGBOAT KEY, FL
    2600 HARBOURSIDE DRIVE #G-17
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 21,837 Lot (sqft)
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