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 5050 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4501274)
    $9,200,000
    Photo of 5050 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4501274)
    Photo of 5050 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4501274)
    5050 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5050 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 7,250 Home (sqft)
    • 7 Baths
    • 41,492 Lot (sqft)
  3. Photo of 1620 GULF OF MEXICO DRIVE #304, LONGBOAT KEY, FL 34228 (MLS # A4497120)
    $8,000,000
    Photo of 1620 GULF OF MEXICO DRIVE #304, LONGBOAT KEY, FL 34228 (MLS # A4497120)
    Photo of 1620 GULF OF MEXICO DRIVE #304, LONGBOAT KEY, FL 34228 (MLS # A4497120)
    18
     
    1620 GULF OF MEXICO DRIVE #304, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #304
    LONGBOAT KEY, FL
    • 3 Beds
    • 5 Baths
    • 4,967 Home (sqft)
    • 5 Baths
    • 17.80 Lot (ac)
  4. Photo of 5030 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # T3295599)
    $7,490,000
    Photo of 5030 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # T3295599)
    Photo of 5030 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # T3295599)
    5030 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5030 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 5,126 Home (sqft)
    • 5 Baths
    • 36,699 Lot (sqft)
  5. Photo of 1620 GULF OF MEXICO DRIVE #508, LONGBOAT KEY, FL 34228 (MLS # A4493481)
    $6,945,000
    Photo of 1620 GULF OF MEXICO DRIVE #508, LONGBOAT KEY, FL 34228 (MLS # A4493481)
    Photo of 1620 GULF OF MEXICO DRIVE #508, LONGBOAT KEY, FL 34228 (MLS # A4493481)
    11
     
    1620 GULF OF MEXICO DRIVE #508, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #508
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,017 Home (sqft)
    • 5 Baths
    • 17.80 Lot (ac)
  6. Photo of 1620 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL 34228 (MLS # A4498523)
    $6,670,000
    Photo of 1620 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL 34228 (MLS # A4498523)
    Photo of 1620 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL 34228 (MLS # A4498523)
    15
     
    1620 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #405
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,017 Home (sqft)
    • 5 Baths
    • 17.80 Lot (ac)
  7. Photo of 25 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4503359)
    $5,600,000
    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)
  8. Photo of 500 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4491328)
    $5,475,000
    Photo of 500 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4491328)
    Photo of 500 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228 (MLS # A4491328)
    500 HARBOR POINT ROAD, LONGBOAT KEY, FL
    500 HARBOR POINT ROAD
    LONGBOAT KEY, FL
    • 4 Beds
    • 8 Baths
    • 6,556 Home (sqft)
    • 8 Baths
    • 25,407 Lot (sqft)
  9. Photo of 591 GOLF LINKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4492669)
    $4,895,000
    Photo of 591 GOLF LINKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4492669)
    Photo of 591 GOLF LINKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4492669)
    591 GOLF LINKS LANE, LONGBOAT KEY, FL
    591 GOLF LINKS LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 4,240 Home (sqft)
    • 6 Baths
    • 13,749 Lot (sqft)
  10. Photo of 415 L AMBIANCE DRIVE #D906, LONGBOAT KEY, FL 34228 (MLS # A4503404)
    $4,400,000
    Photo of 415 L AMBIANCE DRIVE #D906, LONGBOAT KEY, FL 34228 (MLS # A4503404)
    Photo of 415 L AMBIANCE DRIVE #D906, LONGBOAT KEY, FL 34228 (MLS # A4503404)
    415 L AMBIANCE DRIVE #D906, LONGBOAT KEY, FL
    415 L AMBIANCE DRIVE #D906
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,634 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  11. Photo of 5840 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4481498)
    $4,295,000
    Photo of 5840 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4481498)
    Photo of 5840 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4481498)
    42
     
    5840 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5840 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 4,247 Home (sqft)
    • 6 Baths
    • 16,249 Lot (sqft)
  12. Photo of 636 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4500099)
    $3,995,000
    Photo of 636 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4500099)
    Photo of 636 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4500099)
    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)
  13. Photo of 500 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4484272)
    $3,990,000
    Photo of 500 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4484272)
    Photo of 500 BUTTONWOOD DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4484272)
    21
     
    500 BUTTONWOOD DRIVE, LONGBOAT KEY, FL
    500 BUTTONWOOD DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 4,868 Home (sqft)
    • 4 Baths
    • 13,219 Lot (sqft)
  14. Photo of 531 HARBOR CAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4494952)
    $3,800,000
    Photo of 531 HARBOR CAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4494952)
    Photo of 531 HARBOR CAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4494952)
    531 HARBOR CAY DRIVE, LONGBOAT KEY, FL
    531 HARBOR CAY DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,396 Home (sqft)
    • 5 Baths
    • 15,624 Lot (sqft)
  15. Photo of 5005 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL 34228 (MLS # A4498560)
    $3,695,000
    Photo of 5005 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL 34228 (MLS # A4498560)
    Photo of 5005 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL 34228 (MLS # A4498560)
    5005 GULF OF MEXICO DRIVE #6, LONGBOAT KEY, FL
    5005 GULF OF MEXICO DRIVE #6
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,340 Home (sqft)
    • 5 Baths
    • 10,020 Lot (sqft)
  16. Photo of 3476 MISTLETOE LANE, LONGBOAT KEY, FL 34228 (MLS # A4500582)
    $2,599,900
    Photo of 3476 MISTLETOE LANE, LONGBOAT KEY, FL 34228 (MLS # A4500582)
    Photo of 3476 MISTLETOE LANE, LONGBOAT KEY, FL 34228 (MLS # A4500582)
    3476 MISTLETOE LANE, LONGBOAT KEY, FL
    3476 MISTLETOE LANE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 4,098 Home (sqft)
    • 5 Baths
    • 12,519 Lot (sqft)
  17. Photo of 614 NORTON STREET, LONGBOAT KEY, FL 34228 (MLS # A4504183)
    $2,500,000
    Photo of 614 NORTON STREET, LONGBOAT KEY, FL 34228 (MLS # A4504183)
    Photo of 614 NORTON STREET, LONGBOAT KEY, FL 34228 (MLS # A4504183)
    614 NORTON STREET, LONGBOAT KEY, FL
    614 NORTON STREET
    LONGBOAT KEY, FL
    • 6 Beds
    • 6 Baths
    • 4,676 Home (sqft)
    • 6 Baths
    • 9,840 Lot (sqft)
  18. Photo of 1620 GULF OF MEXICO DRIVE #307, LONGBOAT KEY, FL 34228 (MLS # A4498717)
    $2,195,000
    Photo of 1620 GULF OF MEXICO DRIVE #307, LONGBOAT KEY, FL 34228 (MLS # A4498717)
    Photo of 1620 GULF OF MEXICO DRIVE #307, LONGBOAT KEY, FL 34228 (MLS # A4498717)
    14
     
    1620 GULF OF MEXICO DRIVE #307, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #307
    LONGBOAT KEY, FL
    • 1 Bed
    • 2 Baths
    • 1,721 Home (sqft)
    • 2 Baths
    • 17.80 Lot (ac)
  19. Photo of 690 RUSSELL STREET, LONGBOAT KEY, FL 34228 (MLS # A4499080)
    $1,995,000
    Photo of 690 RUSSELL STREET, LONGBOAT KEY, FL 34228 (MLS # A4499080)
    Photo of 690 RUSSELL STREET, LONGBOAT KEY, FL 34228 (MLS # A4499080)
    690 RUSSELL STREET, LONGBOAT KEY, FL
    690 RUSSELL STREET
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 2,457 Home (sqft)
    • 5 Baths
    • 9,602 Lot (sqft)
  20. Photo of 647 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4503569)
    $1,950,000
    Photo of 647 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4503569)
    Photo of 647 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4503569)
    647 MARBURY LANE, LONGBOAT KEY, FL
    647 MARBURY LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 2,651 Home (sqft)
    • 5 Baths
    • 9,840 Lot (sqft)
  21. Photo of 1425 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4498301)
    $1,897,500
    Photo of 1425 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4498301)
    Photo of 1425 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4498301)
    1425 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL
    1425 GULF OF MEXICO DRIVE #201
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,107 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  22. Photo of 210 SANDS POINT ROAD #2601, LONGBOAT KEY, FL 34228 (MLS # A4504253)
    $1,750,000
    Photo of 210 SANDS POINT ROAD #2601, LONGBOAT KEY, FL 34228 (MLS # A4504253)
    Photo of 210 SANDS POINT ROAD #2601, LONGBOAT KEY, FL 34228 (MLS # A4504253)
    24
     
    210 SANDS POINT ROAD #2601, LONGBOAT KEY, FL
    210 SANDS POINT ROAD #2601
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,380 Home (sqft)
    • 2 Baths
    • 14.14 Lot (ac)
  23. Photo of 200 SANDS POINT ROAD #1207, LONGBOAT KEY, FL 34228 (MLS # A4496250)
    $1,679,000
    Photo of 200 SANDS POINT ROAD #1207, LONGBOAT KEY, FL 34228 (MLS # A4496250)
    Photo of 200 SANDS POINT ROAD #1207, LONGBOAT KEY, FL 34228 (MLS # A4496250)
    200 SANDS POINT ROAD #1207, LONGBOAT KEY, FL
    200 SANDS POINT ROAD #1207
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,619 Home (sqft)
    • 2 Baths
    • 14.14 Lot (ac)
  24. Photo of 5650 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4118777)
    $1,495,000
    Photo of 5650 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4118777)
    Photo of 5650 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4118777)
    5650 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5650 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 2,009 Home (sqft)
    • 0 Baths
    • 32,192 Lot (sqft)
  25. Photo of 1445 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4504369)
    $1,200,000
    Photo of 1445 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4504369)
    Photo of 1445 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4504369)
    12
     
    1445 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL
    1445 GULF OF MEXICO DRIVE #201
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,274 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  26. Photo of 380 GULF OF MEXICO DRIVE #511, LONGBOAT KEY, FL 34228 (MLS # A4503819)
    $1,195,000
    Photo of 380 GULF OF MEXICO DRIVE #511, LONGBOAT KEY, FL 34228 (MLS # A4503819)
    Photo of 380 GULF OF MEXICO DRIVE #511, LONGBOAT KEY, FL 34228 (MLS # A4503819)
    380 GULF OF MEXICO DRIVE #511, LONGBOAT KEY, FL
    380 GULF OF MEXICO DRIVE #511
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,476 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  27. Photo of 2525 GULF OF MEXICO DRIVE #14C, LONGBOAT KEY, FL 34228 (MLS # A4502195)
    $1,095,000
    Photo of 2525 GULF OF MEXICO DRIVE #14C, LONGBOAT KEY, FL 34228 (MLS # A4502195)
    Photo of 2525 GULF OF MEXICO DRIVE #14C, LONGBOAT KEY, FL 34228 (MLS # A4502195)
    2525 GULF OF MEXICO DRIVE #14C, LONGBOAT KEY, FL
    2525 GULF OF MEXICO DRIVE #14C
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,468 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  28. Photo of 4311 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4503348)
    $979,000
    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)
  29. Photo of 1701 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # A4503585)
    $950,000
    Photo of 1701 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # A4503585)
    Photo of 1701 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL 34228 (MLS # A4503585)
    21
     
    1701 GULF OF MEXICO DRIVE #303, LONGBOAT KEY, FL
    1701 GULF OF MEXICO DRIVE #303
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,551 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 670 LANDS END DRIVE #5, LONGBOAT KEY, FL 34228 (MLS # A4499495)
    $943,000
    Photo of 670 LANDS END DRIVE #5, LONGBOAT KEY, FL 34228 (MLS # A4499495)
    Photo of 670 LANDS END DRIVE #5, LONGBOAT KEY, FL 34228 (MLS # A4499495)
    670 LANDS END DRIVE #5, LONGBOAT KEY, FL
    670 LANDS END DRIVE #5
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 1,803 Home (sqft)
    • 3 Baths
    • 2,277 Lot (sqft)
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