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 #405, LONGBOAT KEY, FL 34228 (MLS # A4498523)
    $6,945,000
    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)
  3. Photo of 5030 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # T3295599)
    $6,900,000
    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)
  4. 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)
  5. 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)
  6. 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)
  7. 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)
  8. 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)
  9. Photo of 591 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4506675)
    $4,200,000
    Photo of 591 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4506675)
    Photo of 591 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4506675)
    591 PUTTER LANE, LONGBOAT KEY, FL
    591 PUTTER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,191 Home (sqft)
    • 5 Baths
    • 12,646 Lot (sqft)
  10. 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)
  11. 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)
  12. 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)
  13. 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)
  14. Photo of 1281 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # A4504264)
    $2,695,000
    Photo of 1281 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # A4504264)
    Photo of 1281 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL 34228 (MLS # A4504264)
    1281 GULF OF MEXICO DRIVE #404, LONGBOAT KEY, FL
    1281 GULF OF MEXICO DRIVE #404
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,054 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  15. 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)
  16. Photo of 1620 GULF OF MEXICO DRIVE #315, LONGBOAT KEY, FL 34228 (MLS # A4506084)
    $2,335,000
    Photo of 1620 GULF OF MEXICO DRIVE #315, LONGBOAT KEY, FL 34228 (MLS # A4506084)
    Photo of 1620 GULF OF MEXICO DRIVE #315, LONGBOAT KEY, FL 34228 (MLS # A4506084)
    20
     
    1620 GULF OF MEXICO DRIVE #315, LONGBOAT KEY, FL
    1620 GULF OF MEXICO DRIVE #315
    LONGBOAT KEY, FL
    • 1 Bed
    • 2 Baths
    • 1,556 Home (sqft)
    • 2 Baths
    • 17.80 Lot (ac)
  17. Photo of 595 DREAM ISLAND ROAD #31, LONGBOAT KEY, FL 34228 (MLS # A4504997)
    $2,295,000
    Photo of 595 DREAM ISLAND ROAD #31, LONGBOAT KEY, FL 34228 (MLS # A4504997)
    Photo of 595 DREAM ISLAND ROAD #31, LONGBOAT KEY, FL 34228 (MLS # A4504997)
    74
     
    595 DREAM ISLAND ROAD #31, LONGBOAT KEY, FL
    595 DREAM ISLAND ROAD #31
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,928 Home (sqft)
    • 4 Baths
    • 1.90 Lot (ac)
  18. 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)
  19. Photo of 600 WESTON POINTE COURT, LONGBOAT KEY, FL 34228 (MLS # D6120333)
    $1,895,000
    Photo of 600 WESTON POINTE COURT, LONGBOAT KEY, FL 34228 (MLS # D6120333)
    Photo of 600 WESTON POINTE COURT, LONGBOAT KEY, FL 34228 (MLS # D6120333)
    600 WESTON POINTE COURT, LONGBOAT KEY, FL
    600 WESTON POINTE COURT
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,649 Home (sqft)
    • 4 Baths
    • 15,926 Lot (sqft)
  20. Photo of 647 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4503569)
    $1,799,000
    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 651 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4505807)
    $1,695,000
    Photo of 651 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4505807)
    Photo of 651 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4505807)
    29
     
    651 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL
    651 EMERALD HARBOR DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,860 Home (sqft)
    • 4 Baths
    • 15,003 Lot (sqft)
  22. Photo of 1425 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4498301)
    $1,695,000
    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)
  23. Photo of 2550 HARBOURSIDE DRIVE #312, LONGBOAT KEY, FL 34228 (MLS # A4504914)
    $1,649,000
    Photo of 2550 HARBOURSIDE DRIVE #312, LONGBOAT KEY, FL 34228 (MLS # A4504914)
    Photo of 2550 HARBOURSIDE DRIVE #312, LONGBOAT KEY, FL 34228 (MLS # A4504914)
    2550 HARBOURSIDE DRIVE #312, LONGBOAT KEY, FL
    2550 HARBOURSIDE DRIVE #312
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,197 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  24. Photo of 1085 GULF OF MEXICO DRIVE #505, LONGBOAT KEY, FL 34228 (MLS # A4505864)
    $1,599,000
    Photo of 1085 GULF OF MEXICO DRIVE #505, LONGBOAT KEY, FL 34228 (MLS # A4505864)
    Photo of 1085 GULF OF MEXICO DRIVE #505, LONGBOAT KEY, FL 34228 (MLS # A4505864)
    1085 GULF OF MEXICO DRIVE #505, LONGBOAT KEY, FL
    1085 GULF OF MEXICO DRIVE #505
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 1,819 Home (sqft)
    • 2 Baths
    • 30.00 Lot (ac)
  25. Photo of 536 GENERAL HARRIS STREET, LONGBOAT KEY, FL 34228 (MLS # A4505565)
    $1,500,000
    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 1095 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL 34228 (MLS # A4502691)
    $1,495,000
    Photo of 1095 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL 34228 (MLS # A4502691)
    Photo of 1095 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL 34228 (MLS # A4502691)
    1095 GULF OF MEXICO DRIVE #405, LONGBOAT KEY, FL
    1095 GULF OF MEXICO DRIVE #405
    LONGBOAT KEY, FL
    • 3 Beds
    • 2 Baths
    • 1,819 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  27. 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)
  28. Photo of 1145 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4505900)
    $1,449,000
    Photo of 1145 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4505900)
    Photo of 1145 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL 34228 (MLS # A4505900)
    1145 GULF OF MEXICO DRIVE #201, LONGBOAT KEY, FL
    1145 GULF OF MEXICO DRIVE #201
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,172 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  29. Photo of 1045 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4506199)
    $1,349,900
    Photo of 1045 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4506199)
    Photo of 1045 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228 (MLS # A4506199)
    1045 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL
    1045 GULF OF MEXICO DRIVE #203
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,503 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 1701 GULF OF MEXICO DRIVE #608, LONGBOAT KEY, FL 34228 (MLS # A4504835)
    $1,285,000
    Photo of 1701 GULF OF MEXICO DRIVE #608, LONGBOAT KEY, FL 34228 (MLS # A4504835)
    Photo of 1701 GULF OF MEXICO DRIVE #608, LONGBOAT KEY, FL 34228 (MLS # A4504835)
    1701 GULF OF MEXICO DRIVE #608, LONGBOAT KEY, FL
    1701 GULF OF MEXICO DRIVE #608
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,551 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
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