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 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 500 KETCH LANE, LONGBOAT KEY, FL 34228 (MLS # A4443417)
    $2,395,000
    Photo of 500 KETCH LANE, LONGBOAT KEY, FL 34228 (MLS # A4443417)
    Photo of 500 KETCH LANE, LONGBOAT KEY, FL 34228 (MLS # A4443417)
    500 KETCH LANE, LONGBOAT KEY, FL
    500 KETCH LANE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,172 Home (sqft)
    • 4 Baths
    • 15,246 Lot (sqft)
  2. Photo of 3616 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4449455)
    $2,225,000
    Photo of 3616 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4449455)
    Photo of 3616 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4449455)
    3616 FAIR OAKS PLACE, LONGBOAT KEY, FL
    3616 FAIR OAKS PLACE
    LONGBOAT KEY, FL
    • 4 Beds
    • 7 Baths
    • 4,621 Home (sqft)
    • 7 Baths
    • 10,660 Lot (sqft)
  3. Photo of 771 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4434573)
    $2,199,000
    Photo of 771 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4434573)
    Photo of 771 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4434573)
    771 EMERALD HARBOR DRIVE, LONGBOAT KEY, FL
    771 EMERALD HARBOR DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,750 Home (sqft)
    • 3 Baths
    • 15,001 Lot (sqft)
  4. Photo of 435 L AMBIANCE DRIVE #J403, LONGBOAT KEY, FL 34228 (MLS # A4430073)
    $2,195,000
    Photo of 435 L AMBIANCE DRIVE #J403, LONGBOAT KEY, FL 34228 (MLS # A4430073)
    Photo of 435 L AMBIANCE DRIVE #J403, LONGBOAT KEY, FL 34228 (MLS # A4430073)
    435 L AMBIANCE DRIVE #J403, LONGBOAT KEY, FL
    435 L AMBIANCE DRIVE #J403
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,820 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 536 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4421242)
    $2,100,000
    Photo of 536 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4421242)
    Photo of 536 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4421242)
    536 OUTRIGGER LANE, LONGBOAT KEY, FL
    536 OUTRIGGER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,229 Home (sqft)
    • 5 Baths
    • 12,918 Lot (sqft)
  6. Photo of 3560 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4451697)
    $2,095,000
    Photo of 3560 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4451697)
    Photo of 3560 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4451697)
    3560 FAIR OAKS LANE, LONGBOAT KEY, FL
    3560 FAIR OAKS LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,894 Home (sqft)
    • 5 Baths
    • 10,486 Lot (sqft)
  7. Photo of 798 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 (MLS # A4438448)
    $1,999,000
    Photo of 798 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 (MLS # A4438448)
    Photo of 798 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 (MLS # A4438448)
    798 JUNGLE QUEEN WAY, LONGBOAT KEY, FL
    798 JUNGLE QUEEN WAY
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 4,210 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  8. Photo of 573 CUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4436812)
    $1,999,000
    Photo of 573 CUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4436812)
    Photo of 573 CUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4436812)
    573 CUTTER LANE, LONGBOAT KEY, FL
    573 CUTTER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,629 Home (sqft)
    • 5 Baths
    • 12,052 Lot (sqft)
  9. Photo of 560 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4445252)
    $1,998,000
    Photo of 560 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4445252)
    Photo of 560 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4445252)
    560 CHIPPING LANE, LONGBOAT KEY, FL
    560 CHIPPING LANE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 4,315 Home (sqft)
    • 5 Baths
    • 11,248 Lot (sqft)
  10. Photo of 1281 GULF OF MEXICO DRIVE #804, LONGBOAT KEY, FL 34228 (MLS # A4450333)
    $1,995,000
    Photo of 1281 GULF OF MEXICO DRIVE #804, LONGBOAT KEY, FL 34228 (MLS # A4450333)
    Photo of 1281 GULF OF MEXICO DRIVE #804, LONGBOAT KEY, FL 34228 (MLS # A4450333)
    1281 GULF OF MEXICO DRIVE #804, LONGBOAT KEY, FL
    1281 GULF OF MEXICO DRIVE #804
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,054 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  11. Photo of 1241 GULF OF MEXICO DRIVE #PH08, LONGBOAT KEY, FL 34228 (MLS # A4449751)
    $1,995,000
    Photo of 1241 GULF OF MEXICO DRIVE #PH08, LONGBOAT KEY, FL 34228 (MLS # A4449751)
    Photo of 1241 GULF OF MEXICO DRIVE #PH08, LONGBOAT KEY, FL 34228 (MLS # A4449751)
    1241 GULF OF MEXICO DRIVE #PH08, LONGBOAT KEY, FL
    1241 GULF OF MEXICO DRIVE #PH08
    LONGBOAT KEY, FL
    • 2 Beds
    • 4 Baths
    • 2,965 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  12. Photo of 501 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4448468)
    $1,995,000
    Photo of 501 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4448468)
    Photo of 501 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4448468)
    501 HALYARD LANE, LONGBOAT KEY, FL
    501 HALYARD LANE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,340 Home (sqft)
    • 4 Baths
    • 13,680 Lot (sqft)
  13. Photo of 510 BOWSPRIT LANE, LONGBOAT KEY, FL 34228 (MLS # A4440699)
    $1,950,000
    Photo of 510 BOWSPRIT LANE, LONGBOAT KEY, FL 34228 (MLS # A4440699)
    Photo of 510 BOWSPRIT LANE, LONGBOAT KEY, FL 34228 (MLS # A4440699)
    510 BOWSPRIT LANE, LONGBOAT KEY, FL
    510 BOWSPRIT LANE
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 4,389 Home (sqft)
    • 7 Baths
    • 10,014 Lot (sqft)
  14. Photo of 1001 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4414365)
    $1,950,000
    Photo of 1001 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4414365)
    Photo of 1001 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4414365)
    1001 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL
    1001 LONGBOAT CLUB ROAD
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,050 Home (sqft)
    • 5 Baths
    • 18,751 Lot (sqft)
  15. Photo of 524 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4449639)
    $1,925,000
    Photo of 524 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4449639)
    Photo of 524 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4449639)
    524 OUTRIGGER LANE, LONGBOAT KEY, FL
    524 OUTRIGGER LANE
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 4,664 Home (sqft)
    • 6 Baths
    • 12,758 Lot (sqft)
  16. Photo of 1485 GULF OF MEXICO DRIVE #A503, LONGBOAT KEY, FL 34228 (MLS # A4451587)
    $1,895,000
    Photo of 1485 GULF OF MEXICO DRIVE #A503, LONGBOAT KEY, FL 34228 (MLS # A4451587)
    Photo of 1485 GULF OF MEXICO DRIVE #A503, LONGBOAT KEY, FL 34228 (MLS # A4451587)
    1485 GULF OF MEXICO DRIVE #A503, LONGBOAT KEY, FL
    1485 GULF OF MEXICO DRIVE #A503
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,188 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  17. Photo of 3010 GRAND BAY BOULEVARD #461, LONGBOAT KEY, FL 34228 (MLS # A4445962)
    $1,895,000
    Photo of 3010 GRAND BAY BOULEVARD #461, LONGBOAT KEY, FL 34228 (MLS # A4445962)
    Photo of 3010 GRAND BAY BOULEVARD #461, LONGBOAT KEY, FL 34228 (MLS # A4445962)
    3010 GRAND BAY BOULEVARD #461, LONGBOAT KEY, FL
    3010 GRAND BAY BOULEVARD #461
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,925 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  18. Photo of 3612 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4426931)
    $1,895,000
    Photo of 3612 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4426931)
    Photo of 3612 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4426931)
    3612 FAIR OAKS PLACE, LONGBOAT KEY, FL
    3612 FAIR OAKS PLACE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,144 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  19. Photo of 6540 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4430933)
    $1,796,000
    Photo of 6540 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4430933)
    Photo of 6540 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4430933)
    6540 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6540 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,292 Home (sqft)
    • 3 Baths
    • 20,474 Lot (sqft)
  20. Photo of 4325 GULF OF MEXICO DRIVE #604, LONGBOAT KEY, FL 34228 (MLS # A4447042)
    $1,795,000
    Photo of 4325 GULF OF MEXICO DRIVE #604, LONGBOAT KEY, FL 34228 (MLS # A4447042)
    Photo of 4325 GULF OF MEXICO DRIVE #604, LONGBOAT KEY, FL 34228 (MLS # A4447042)
    4325 GULF OF MEXICO DRIVE #604, LONGBOAT KEY, FL
    4325 GULF OF MEXICO DRIVE #604
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 2,907 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  21. Photo of 525 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4440664)
    $1,795,000
    Photo of 525 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4440664)
    Photo of 525 PUTTER LANE, LONGBOAT KEY, FL 34228 (MLS # A4440664)
    525 PUTTER LANE, LONGBOAT KEY, FL
    525 PUTTER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,280 Home (sqft)
    • 5 Baths
    • 18,728 Lot (sqft)
  22. Photo of 3322 BAYOU ROAD, LONGBOAT KEY, FL 34228 (MLS # A4431965)
    $1,790,000
    Photo of 3322 BAYOU ROAD, LONGBOAT KEY, FL 34228 (MLS # A4431965)
    Photo of 3322 BAYOU ROAD, LONGBOAT KEY, FL 34228 (MLS # A4431965)
    3322 BAYOU ROAD, LONGBOAT KEY, FL
    3322 BAYOU ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 4 Baths
    • 3,441 Home (sqft)
    • 4 Baths
    • 12,699 Lot (sqft)
  23. Photo of 3271 BAYOU ROAD, LONGBOAT KEY, FL 34228 (MLS # N6107295)
    $1,750,000
    Photo of 3271 BAYOU ROAD, LONGBOAT KEY, FL 34228 (MLS # N6107295)
    Photo of 3271 BAYOU ROAD, LONGBOAT KEY, FL 34228 (MLS # N6107295)
    3271 BAYOU ROAD, LONGBOAT KEY, FL
    3271 BAYOU ROAD
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 3,059 Home (sqft)
    • 4 Baths
    • 12,197 Lot (sqft)
  24. Photo of 3315 SABAL COVE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4449634)
    $1,749,000
    Photo of 3315 SABAL COVE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4449634)
    Photo of 3315 SABAL COVE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4449634)
    3315 SABAL COVE DRIVE, LONGBOAT KEY, FL
    3315 SABAL COVE DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 3,755 Home (sqft)
    • 6 Baths
    • 22,908 Lot (sqft)
  25. Photo of 811 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 (MLS # A4438987)
    $1,695,000
    Photo of 811 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 (MLS # A4438987)
    Photo of 811 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228 (MLS # A4438987)
    811 JUNGLE QUEEN WAY, LONGBOAT KEY, FL
    811 JUNGLE QUEEN WAY
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 3,414 Home (sqft)
    • 3 Baths
    • 20,001 Lot (sqft)
  26. Photo of 1241 GULF OF MEXICO DRIVE #906, LONGBOAT KEY, FL 34228 (MLS # O5769948)
    $1,695,000
    Photo of 1241 GULF OF MEXICO DRIVE #906, LONGBOAT KEY, FL 34228 (MLS # O5769948)
    Photo of 1241 GULF OF MEXICO DRIVE #906, LONGBOAT KEY, FL 34228 (MLS # O5769948)
    23
     
    1241 GULF OF MEXICO DRIVE #906, LONGBOAT KEY, FL
    1241 GULF OF MEXICO DRIVE #906
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,650 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 590 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4431434)
    $1,599,000
    Photo of 590 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4431434)
    Photo of 590 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4431434)
    590 JESSMYTH DRIVE, LONGBOAT KEY, FL
    590 JESSMYTH DRIVE
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,318 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  28. Photo of 6820 LONGBOAT DR S, LONGBOAT KEY, FL 34228 (MLS # A4426635)
    $1,595,000
    Photo of 6820 LONGBOAT DR S, LONGBOAT KEY, FL 34228 (MLS # A4426635)
    Photo of 6820 LONGBOAT DR S, LONGBOAT KEY, FL 34228 (MLS # A4426635)
    6820 LONGBOAT DR S, LONGBOAT KEY, FL
    6820 LONGBOAT DR S
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,900 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  29. Photo of 525 RECLINATA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4433098)
    $1,590,000
    Photo of 525 RECLINATA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4433098)
    Photo of 525 RECLINATA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4433098)
    525 RECLINATA DRIVE, LONGBOAT KEY, FL
    525 RECLINATA DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 3,070 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  30. Photo of 350 GULF OF MEXICO DRIVE #233, LONGBOAT KEY, FL 34228 (MLS # A4447913)
    $1,565,000
    Photo of 350 GULF OF MEXICO DRIVE #233, LONGBOAT KEY, FL 34228 (MLS # A4447913)
    Photo of 350 GULF OF MEXICO DRIVE #233, LONGBOAT KEY, FL 34228 (MLS # A4447913)
    350 GULF OF MEXICO DRIVE #233, LONGBOAT KEY, FL
    350 GULF OF MEXICO DRIVE #233
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 2,880 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
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Listing information is deemed reliable, but not guaranteed.

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