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 6201 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4549851)
    $22,000,000
    Photo of 6201 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4549851)
    Photo of 6201 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4549851)
    6201 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6201 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 8 Baths
    • 6,820 Home (sqft)
    • 8 Baths
    • 34,413 Lot (sqft)
  2. Photo of 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # O6080850)
    $18,500,000
    Photo of 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # O6080850)
    Photo of 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # O6080850)
    16
     
    5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5861 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 10,800 Home (sqft)
    • 7 Baths
    • 1.13 Lot (ac)
  3. Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4527232)
    $9,800,000
    Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4527232)
    Photo of 6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4527232)
    6877 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    6877 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,820 Home (sqft)
    • 5 Baths
    • 32,235 Lot (sqft)
  4. Photo of 596 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4543167)
    $8,295,000
    Photo of 596 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4543167)
    Photo of 596 OUTRIGGER LANE, LONGBOAT KEY, FL 34228 (MLS # A4543167)
    596 OUTRIGGER LANE, LONGBOAT KEY, FL
    596 OUTRIGGER LANE
    LONGBOAT KEY, FL
    • 6 Beds
    • 7 Baths
    • 5,892 Home (sqft)
    • 7 Baths
    • 15,682 Lot (sqft)
  5. Photo of 6565 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4556728)
    $7,775,000
    Photo of 6565 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4556728)
    Photo of 6565 GULFSIDE ROAD, LONGBOAT KEY, FL 34228 (MLS # A4556728)
    24
     
    6565 GULFSIDE ROAD, LONGBOAT KEY, FL
    6565 GULFSIDE ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 4 Baths
    • 5,572 Home (sqft)
    • 4 Baths
    • 16,989 Lot (sqft)
  6. Photo of 520 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4553676)
    $6,600,000
    Photo of 520 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4553676)
    Photo of 520 CHIPPING LANE, LONGBOAT KEY, FL 34228 (MLS # A4553676)
    520 CHIPPING LANE, LONGBOAT KEY, FL
    520 CHIPPING LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,412 Home (sqft)
    • 5 Baths
    • 11,326 Lot (sqft)
  7. Photo of 781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4554268)
    $6,500,000
    Photo of 781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4554268)
    Photo of 781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4554268)
    781 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL
    781 HIDEAWAY BAY DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 5,469 Home (sqft)
    • 4 Baths
    • 17,860 Lot (sqft)
  8. Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    $5,965,000
    Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    Photo of 5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4516289)
    5056 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    5056 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 3,819 Home (sqft)
    • 3 Baths
    • 40,076 Lot (sqft)
  9. Photo of 4975 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4557519)
    $5,495,000
    Photo of 4975 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4557519)
    Photo of 4975 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL 34228 (MLS # A4557519)
    4975 GULF OF MEXICO DRIVE #305, LONGBOAT KEY, FL
    4975 GULF OF MEXICO DRIVE #305
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 3,122 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  10. Photo of 545 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4553162)
    $4,995,000
    Photo of 545 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4553162)
    Photo of 545 KINGFISHER LANE, LONGBOAT KEY, FL 34228 (MLS # A4553162)
    545 KINGFISHER LANE, LONGBOAT KEY, FL
    545 KINGFISHER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,646 Home (sqft)
    • 5 Baths
    • 11,762 Lot (sqft)
  11. Photo of 610 YARDARM LANE, LONGBOAT KEY, FL 34228 (MLS # A4523988)
    $4,940,000
    Photo of 610 YARDARM LANE, LONGBOAT KEY, FL 34228 (MLS # A4523988)
    Photo of 610 YARDARM LANE, LONGBOAT KEY, FL 34228 (MLS # A4523988)
    610 YARDARM LANE, LONGBOAT KEY, FL
    610 YARDARM LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,138 Home (sqft)
    • 5 Baths
    • 11,326 Lot (sqft)
  12. Photo of 672 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4559316)
    $4,850,000
    Photo of 672 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4559316)
    Photo of 672 DREAM ISLAND ROAD, LONGBOAT KEY, FL 34228 (MLS # A4559316)
    672 DREAM ISLAND ROAD, LONGBOAT KEY, FL
    672 DREAM ISLAND ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 3,312 Home (sqft)
    • 5 Baths
    • 22,216 Lot (sqft)
  13. Photo of 572 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546142)
    $4,800,000
    Photo of 572 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546142)
    Photo of 572 HALYARD LANE, LONGBOAT KEY, FL 34228 (MLS # A4546142)
    572 HALYARD LANE, LONGBOAT KEY, FL
    572 HALYARD LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 4,257 Home (sqft)
    • 6 Baths
    • 10,019 Lot (sqft)
  14. Photo of 7147 E LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4549674)
    $4,500,000
    Photo of 7147 E LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4549674)
    Photo of 7147 E LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4549674)
    7147 E LA LENAIRE DRIVE, LONGBOAT KEY, FL
    7147 E LA LENAIRE DRIVE
    LONGBOAT KEY, FL
    • 6 Beds
    • 6 Baths
    • 3,503 Home (sqft)
    • 6 Baths
    • 1.35 Lot (ac)
  15. Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548501)
    $4,500,000
    Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548501)
    Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548501)
    540 HARBOR GATE WAY, LONGBOAT KEY, FL
    540 HARBOR GATE WAY
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 19,167 Lot (sqft)
  16. Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548328)
    $4,500,000
    Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548328)
    Photo of 540 HARBOR GATE WAY, LONGBOAT KEY, FL 34228 (MLS # A4548328)
    540 HARBOR GATE WAY, LONGBOAT KEY, FL
    540 HARBOR GATE WAY
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 5,048 Home (sqft)
    • 7 Baths
    • 19,167 Lot (sqft)
  17. Photo of 551 BROADWAY, LONGBOAT KEY, FL 34228 (MLS # A4555735)
    $4,450,000
    Photo of 551 BROADWAY, LONGBOAT KEY, FL 34228 (MLS # A4555735)
    Photo of 551 BROADWAY, LONGBOAT KEY, FL 34228 (MLS # A4555735)
    551 BROADWAY, LONGBOAT KEY, FL
    551 BROADWAY
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,738 Home (sqft)
    • 5 Baths
    • 6,099 Lot (sqft)
  18. Photo of 3970 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4533244)
    $3,995,000
    Photo of 3970 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4533244)
    Photo of 3970 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4533244)
    29
     
    3970 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL
    3970 GULF OF MEXICO DRIVE
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,038 Lot (sqft)
  19. Photo of 3614 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4559314)
    $3,900,000
    Photo of 3614 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4559314)
    Photo of 3614 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4559314)
    3614 FAIR OAKS PLACE, LONGBOAT KEY, FL
    3614 FAIR OAKS PLACE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 4,050 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  20. Photo of 3533 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4550611)
    $3,895,000
    Photo of 3533 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4550611)
    Photo of 3533 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4550611)
    3533 FAIR OAKS LANE, LONGBOAT KEY, FL
    3533 FAIR OAKS LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 3,909 Home (sqft)
    • 6 Baths
    • 9,584 Lot (sqft)
  21. Photo of 991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4530239)
    $3,800,000
    Photo of 991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4530239)
    Photo of 991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL 34228 (MLS # A4530239)
    991 LONGBOAT CLUB ROAD, LONGBOAT KEY, FL
    991 LONGBOAT CLUB ROAD
    LONGBOAT KEY, FL
    • 5 Beds
    • 6 Baths
    • 5,101 Home (sqft)
    • 6 Baths
    • 18,731 Lot (sqft)
  22. Photo of 700 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4542965)
    $3,695,000
    Photo of 700 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4542965)
    Photo of 700 TARAWITT DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4542965)
    700 TARAWITT DRIVE, LONGBOAT KEY, FL
    700 TARAWITT DRIVE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 3,897 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  23. Photo of 3606 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4555331)
    $3,600,000
    Photo of 3606 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4555331)
    Photo of 3606 FAIR OAKS PLACE, LONGBOAT KEY, FL 34228 (MLS # A4555331)
    3606 FAIR OAKS PLACE, LONGBOAT KEY, FL
    3606 FAIR OAKS PLACE
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 3,842 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  24. Photo of 554 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4557138)
    $3,499,900
    Photo of 554 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4557138)
    Photo of 554 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4557138)
    554 JESSMYTH DRIVE, LONGBOAT KEY, FL
    554 JESSMYTH DRIVE
    LONGBOAT KEY, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,909 Lot (sqft)
  25. Photo of 554 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4557120)
    $3,499,900
    Photo of 554 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4557120)
    Photo of 554 JESSMYTH DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4557120)
    554 JESSMYTH DRIVE, LONGBOAT KEY, FL
    554 JESSMYTH DRIVE
    LONGBOAT KEY, FL
    • 3 Beds
    • 4 Baths
    • 4,700 Home (sqft)
    • 4 Baths
    • 20,909 Lot (sqft)
  26. Photo of 562 RANGER LANE, LONGBOAT KEY, FL 34228 (MLS # T3413859)
    $3,350,000
    Photo of 562 RANGER LANE, LONGBOAT KEY, FL 34228 (MLS # T3413859)
    Photo of 562 RANGER LANE, LONGBOAT KEY, FL 34228 (MLS # T3413859)
    562 RANGER LANE, LONGBOAT KEY, FL
    562 RANGER LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 3,149 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  27. Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545381)
    $3,345,000
    Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545381)
    Photo of 2945 PYRULA DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4545381)
    2945 PYRULA DRIVE, LONGBOAT KEY, FL
    2945 PYRULA DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 5 Baths
    • 3,815 Home (sqft)
    • 5 Baths
    • 13,940 Lot (sqft)
  28. Photo of 760 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4551328)
    $3,314,000
    Photo of 760 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4551328)
    Photo of 760 MARBURY LANE, LONGBOAT KEY, FL 34228 (MLS # A4551328)
    760 MARBURY LANE, LONGBOAT KEY, FL
    760 MARBURY LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 3 Baths
    • 2,575 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  29. Photo of 3621 BAYOU CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4553519)
    $3,250,000
    Photo of 3621 BAYOU CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4553519)
    Photo of 3621 BAYOU CIRCLE, LONGBOAT KEY, FL 34228 (MLS # A4553519)
    3621 BAYOU CIRCLE, LONGBOAT KEY, FL
    3621 BAYOU CIRCLE
    LONGBOAT KEY, FL
    • 4 Beds
    • 4 Baths
    • 4,322 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  30. Photo of 3527 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4554063)
    $3,149,000
    Photo of 3527 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4554063)
    Photo of 3527 FAIR OAKS LANE, LONGBOAT KEY, FL 34228 (MLS # A4554063)
    3527 FAIR OAKS LANE, LONGBOAT KEY, FL
    3527 FAIR OAKS LANE
    LONGBOAT KEY, FL
    • 4 Beds
    • 5 Baths
    • 4,154 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 2/2/23 11:40 PM PST.

This IDX Solution is (c) Diverse Solutions 2023. Privacy | Terms & Conditions

 
 

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