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
  • $2,562,500
    Median Home Price
  • $968,200
    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 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4617809)
    $2,298,000
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4617809)
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4617809)
    65356537 Peacock Road, Sarasota, FL
    65356537 Peacock Road
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 3,000 Home (sqft)
    • 6 Baths
    • 6,099 Lot (sqft)
  2. Photo of 722 Siesta Key Circle, Sarasota, FL 34242 (MLS # A4617797)
    $3,650,000
    Photo of 722 Siesta Key Circle, Sarasota, FL 34242 (MLS # A4617797)
    Photo of 722 Siesta Key Circle, Sarasota, FL 34242 (MLS # A4617797)
    83
     
    722 Siesta Key Circle, Sarasota, FL
    722 Siesta Key Circle
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,488 Home (sqft)
    • 5 Baths
    • 12,197 Lot (sqft)
  3. Photo of 508 65th Street, Holmes Beach, FL 34217 (MLS # A4617789)
    $1,500,000
    Photo of 508 65th Street, Holmes Beach, FL 34217 (MLS # A4617789)
    Photo of 508 65th Street, Holmes Beach, FL 34217 (MLS # A4617789)
    508 65th Street, Holmes Beach, FL
    508 65th Street
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,985 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  4. Photo of 830 Tarawitt Drive, Longboat Key, FL 34228 (MLS # A4617446)
    $17,000
    Photo of 830 Tarawitt Drive, Longboat Key, FL 34228 (MLS # A4617446)
    Photo of 830 Tarawitt Drive, Longboat Key, FL 34228 (MLS # A4617446)
    830 Tarawitt Drive, Longboat Key, FL
    830 Tarawitt Drive
    Longboat Key, FL
    • 4 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  5. Photo of 6250 Holmes Boulevard #34, Holmes Beach, FL 34217 (MLS # A4616846)
    $849,000
    Photo of 6250 Holmes Boulevard #34, Holmes Beach, FL 34217 (MLS # A4616846)
    Photo of 6250 Holmes Boulevard #34, Holmes Beach, FL 34217 (MLS # A4616846)
    6250 Holmes Boulevard #34, Holmes Beach, FL
    6250 Holmes Boulevard #34
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,512 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  6. Photo of 630 Companion Way, Longboat Key, FL 34228 (MLS # A4617730)
    $11,000
    Photo of 630 Companion Way, Longboat Key, FL 34228 (MLS # A4617730)
    Photo of 630 Companion Way, Longboat Key, FL 34228 (MLS # A4617730)
    630 Companion Way, Longboat Key, FL
    630 Companion Way
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 2,900 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  7. Photo of 1125 Lake House Circle #C112, Sarasota, FL 34242 (MLS # A4617715)
    $725,000
    Photo of 1125 Lake House Circle #C112, Sarasota, FL 34242 (MLS # A4617715)
    Photo of 1125 Lake House Circle #C112, Sarasota, FL 34242 (MLS # A4617715)
    1125 Lake House Circle #C112, Sarasota, FL
    1125 Lake House Circle #C112
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,352 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  8. Photo of 4822 Ocean Boulevard #4D, Sarasota, FL 34242 (MLS # A4617651)
    $850,000
    Photo of 4822 Ocean Boulevard #4D, Sarasota, FL 34242 (MLS # A4617651)
    Photo of 4822 Ocean Boulevard #4D, Sarasota, FL 34242 (MLS # A4617651)
    4822 Ocean Boulevard #4D, Sarasota, FL
    4822 Ocean Boulevard #4D
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,440 Home (sqft)
    • 2 Baths
    • 40,076 Lot (sqft)
  9. Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617702)
    $11,000
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617702)
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617702)
    53
     
    1255 N Gulfstream Avenue #402, Sarasota, FL
    1255 N Gulfstream Avenue #402
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,269 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  10. Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617698)
    $1,975,000
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617698)
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617698)
    41
     
    1255 N Gulfstream Avenue #402, Sarasota, FL
    1255 N Gulfstream Avenue #402
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,269 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  11. Photo of 300 Bay Dr S, Bradenton Beach, FL 34217 (MLS # A4617625)
    $595,000
    Photo of 300 Bay Dr S, Bradenton Beach, FL 34217 (MLS # A4617625)
    Photo of 300 Bay Dr S, Bradenton Beach, FL 34217 (MLS # A4617625)
    300 Bay Dr S, Bradenton Beach, FL
    300 Bay Dr S
    Bradenton Beach, FL
    • 0 Beds
    • 0 Baths
    • 1,226 Home (sqft)
    • 0 Baths
    • 0 Lot (sqft)
  12. Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4616843)
    $2,298,000
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4616843)
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4616843)
    65356537 Peacock Road, Sarasota, FL
    65356537 Peacock Road
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,000 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  13. Photo of 5858 Midnight Pass Road #27, Sarasota, FL 34242 (MLS # A4616738)
    $659,000
    Photo of 5858 Midnight Pass Road #27, Sarasota, FL 34242 (MLS # A4616738)
    Photo of 5858 Midnight Pass Road #27, Sarasota, FL 34242 (MLS # A4616738)
    5858 Midnight Pass Road #27, Sarasota, FL
    5858 Midnight Pass Road #27
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 531 Home (sqft)
    • 1 Bath
    • 5.02 Lot (ac)
  14. Photo of 525 Rawls Avenue #5, Sarasota, FL 34236 (MLS # A4617618)
    $1,255
    Photo of 525 Rawls Avenue #5, Sarasota, FL 34236 (MLS # A4617618)
    Photo of 525 Rawls Avenue #5, Sarasota, FL 34236 (MLS # A4617618)
    525 Rawls Avenue #5, Sarasota, FL
    525 Rawls Avenue #5
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 250 Home (sqft)
    • 1 Bath
    • 3,921 Lot (sqft)
  15. Photo of 771 Marbury Lane, Longboat Key, FL 34228 (MLS # A4617465)
    $2,100,000
    Photo of 771 Marbury Lane, Longboat Key, FL 34228 (MLS # A4617465)
    Photo of 771 Marbury Lane, Longboat Key, FL 34228 (MLS # A4617465)
    771 Marbury Lane, Longboat Key, FL
    771 Marbury Lane
    Longboat Key, FL
    • 5 Beds
    • 4 Baths
    • 3,016 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  16. Photo of 1221 N Palm Avenue #305, Sarasota, FL 34236 (MLS # A4616972)
    $495,000
    Photo of 1221 N Palm Avenue #305, Sarasota, FL 34236 (MLS # A4616972)
    Photo of 1221 N Palm Avenue #305, Sarasota, FL 34236 (MLS # A4616972)
    1221 N Palm Avenue #305, Sarasota, FL
    1221 N Palm Avenue #305
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 676 Home (sqft)
    • 1 Bath
    • 21,345 Lot (sqft)
  17. Photo of 408 Clark Drive, Holmes Beach, FL 34217 (MLS # A4617184)
    $1,650,000
    Photo of 408 Clark Drive, Holmes Beach, FL 34217 (MLS # A4617184)
    Photo of 408 Clark Drive, Holmes Beach, FL 34217 (MLS # A4617184)
    408 Clark Drive, Holmes Beach, FL
    408 Clark Drive
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,362 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  18. Photo of 562 Juan Anasco Drive, Longboat Key, FL 34228 (MLS # A4617251)
    $1,250,000
    Photo of 562 Juan Anasco Drive, Longboat Key, FL 34228 (MLS # A4617251)
    Photo of 562 Juan Anasco Drive, Longboat Key, FL 34228 (MLS # A4617251)
    40
     
    562 Juan Anasco Drive, Longboat Key, FL
    562 Juan Anasco Drive
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 10,019 Lot (sqft)
  19. Photo of 100 Central Avenue #K622, Sarasota, FL 34236 (MLS # A4617126)
    $1,050,000
    Photo of 100 Central Avenue #K622, Sarasota, FL 34236 (MLS # A4617126)
    Photo of 100 Central Avenue #K622, Sarasota, FL 34236 (MLS # A4617126)
    100 Central Avenue #K622, Sarasota, FL
    100 Central Avenue #K622
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,707 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  20. Photo of 1681 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4616816)
    $998,000
    Photo of 1681 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4616816)
    Photo of 1681 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4616816)
    1681 Bahia Vista Street, Sarasota, FL
    1681 Bahia Vista Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,568 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  21. Photo of 6171 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4616520)
    $19,900,000
    Photo of 6171 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4616520)
    Photo of 6171 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4616520)
    61
     
    6171 Gulf Of Mexico Drive, Longboat Key, FL
    6171 Gulf Of Mexico Drive
    Longboat Key, FL
    • 4 Beds
    • 6 Baths
    • 7,352 Home (sqft)
    • 6 Baths
    • 33,977 Lot (sqft)
  22. Photo of 7700 Marina Drive, Holmes Beach, FL 34217 (MLS # A4617552)
    $2,200,000
    Photo of 7700 Marina Drive, Holmes Beach, FL 34217 (MLS # A4617552)
    Photo of 7700 Marina Drive, Holmes Beach, FL 34217 (MLS # A4617552)
    7700 Marina Drive, Holmes Beach, FL
    7700 Marina Drive
    Holmes Beach, FL
    • 3 Beds
    • 2 Baths
    • 2,046 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 800 Benjamin Franklin Drive #107, Sarasota, FL 34236 (MLS # A4616596)
    $1,100,000
    Photo of 800 Benjamin Franklin Drive #107, Sarasota, FL 34236 (MLS # A4616596)
    Photo of 800 Benjamin Franklin Drive #107, Sarasota, FL 34236 (MLS # A4616596)
    800 Benjamin Franklin Drive #107, Sarasota, FL
    800 Benjamin Franklin Drive #107
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,150 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  24. Photo of 2632 Hawthorne Street, Sarasota, FL 34239 (MLS # A4617528)
    $599,000
    Photo of 2632 Hawthorne Street, Sarasota, FL 34239 (MLS # A4617528)
    Photo of 2632 Hawthorne Street, Sarasota, FL 34239 (MLS # A4617528)
    25
     
    2632 Hawthorne Street, Sarasota, FL
    2632 Hawthorne Street
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 625 Home (sqft)
    • 1 Bath
    • 14,375 Lot (sqft)
  25. Photo of 2314 Prospect Street, Sarasota, FL 34239 (MLS # A4617182)
    $1,985,000
    Photo of 2314 Prospect Street, Sarasota, FL 34239 (MLS # A4617182)
    Photo of 2314 Prospect Street, Sarasota, FL 34239 (MLS # A4617182)
    2314 Prospect Street, Sarasota, FL
    2314 Prospect Street
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 3,651 Home (sqft)
    • 6 Baths
    • 6,970 Lot (sqft)
  26. Photo of 5400 Gulf Drive #28, Holmes Beach, FL 34217 (MLS # A4616590)
    $585,000
    Photo of 5400 Gulf Drive #28, Holmes Beach, FL 34217 (MLS # A4616590)
    Photo of 5400 Gulf Drive #28, Holmes Beach, FL 34217 (MLS # A4616590)
    5400 Gulf Drive #28, Holmes Beach, FL
    5400 Gulf Drive #28
    Holmes Beach, FL
    • 1 Bed
    • 1 Bath
    • 810 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  27. Photo of 5215 Calle De Costa Rica, Sarasota, FL 34242 (MLS # A4617305)
    $1,100,000
    Photo of 5215 Calle De Costa Rica, Sarasota, FL 34242 (MLS # A4617305)
    Photo of 5215 Calle De Costa Rica, Sarasota, FL 34242 (MLS # A4617305)
    5215 Calle De Costa Rica, Sarasota, FL
    5215 Calle De Costa Rica
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,762 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  28. Photo of 1350 Main Street #709, Sarasota, FL 34236 (MLS # O6224136)
    $3,500
    Photo of 1350 Main Street #709, Sarasota, FL 34236 (MLS # O6224136)
    Photo of 1350 Main Street #709, Sarasota, FL 34236 (MLS # O6224136)
    1350 Main Street #709, Sarasota, FL
    1350 Main Street #709
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 895 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  29. Photo of 1350 Main Street #709, Sarasota, FL 34236 (MLS # O6212942)
    $615,000
    Photo of 1350 Main Street #709, Sarasota, FL 34236 (MLS # O6212942)
    Photo of 1350 Main Street #709, Sarasota, FL 34236 (MLS # O6212942)
    1350 Main Street #709, Sarasota, FL
    1350 Main Street #709
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 895 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  30. Photo of 102 75th Street, Holmes Beach, FL 34217 (MLS # A4617275)
    $6,895,000
    Photo of 102 75th Street, Holmes Beach, FL 34217 (MLS # A4617275)
    Photo of 102 75th Street, Holmes Beach, FL 34217 (MLS # A4617275)
    64
     
    102 75th Street, Holmes Beach, FL
    102 75th Street
    Holmes Beach, FL
    • 4 Beds
    • 5 Baths
    • 2,803 Home (sqft)
    • 5 Baths
    • 8,277 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 7/21/24 5:31 AM PDT.

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