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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'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 3806 Gulf Of Mexico Drive #C310, Longboat Key, FL 34228 (MLS # R4908708)
    $440,000
    Photo of 3806 Gulf Of Mexico Drive #C310, Longboat Key, FL 34228 (MLS # R4908708)
    Photo of 3806 Gulf Of Mexico Drive #C310, Longboat Key, FL 34228 (MLS # R4908708)
    30
     
    3806 Gulf Of Mexico Drive #C310, Longboat Key, FL
    3806 Gulf Of Mexico Drive #C310
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,056 Home (sqft)
    • 2 Baths
    • 3.00 Lot (ac)
  2. Photo of 7820 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4635246)
    $1,250,000
    Photo of 7820 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4635246)
    Photo of 7820 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4635246)
    7820 Midnight Pass Road, Sarasota, FL
    7820 Midnight Pass Road
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,557 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
  3. Photo of 475 Benjamin Franklin Drive #215, Sarasota, FL 34236 (MLS # A4636732)
    $590,000
    Photo of 475 Benjamin Franklin Drive #215, Sarasota, FL 34236 (MLS # A4636732)
    Photo of 475 Benjamin Franklin Drive #215, Sarasota, FL 34236 (MLS # A4636732)
    475 Benjamin Franklin Drive #215, Sarasota, FL
    475 Benjamin Franklin Drive #215
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 593 Home (sqft)
    • 1 Bath
    • 1.04 Lot (ac)
  4. Photo of 3990 Higel Avenue, Sarasota, FL 34242 (MLS # A4632105)
    $29,995,000
    Photo of 3990 Higel Avenue, Sarasota, FL 34242 (MLS # A4632105)
    Photo of 3990 Higel Avenue, Sarasota, FL 34242 (MLS # A4632105)
    3990 Higel Avenue, Sarasota, FL
    3990 Higel Avenue
    Sarasota, FL
    • 7 Beds
    • 11 Baths
    • 13,035 Home (sqft)
    • 11 Baths
    • 42,254 Lot (sqft)
  5. Photo of 1225 S View Drive, Sarasota, FL 34242 (MLS # A4635722)
    $1,425,000
    Photo of 1225 S View Drive, Sarasota, FL 34242 (MLS # A4635722)
    Photo of 1225 S View Drive, Sarasota, FL 34242 (MLS # A4635722)
    1225 S View Drive, Sarasota, FL
    1225 S View Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,017 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  6. Photo of 2523 Darwin Avenue, Sarasota, FL 34239 (MLS # A4636015)
    $429,500
    Photo of 2523 Darwin Avenue, Sarasota, FL 34239 (MLS # A4636015)
    Photo of 2523 Darwin Avenue, Sarasota, FL 34239 (MLS # A4636015)
    2523 Darwin Avenue, Sarasota, FL
    2523 Darwin Avenue
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,464 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  7. Photo of 2138 Floyd Street, Sarasota, FL 34239 (MLS # A4635236)
    $1,795,000
    Photo of 2138 Floyd Street, Sarasota, FL 34239 (MLS # A4635236)
    Photo of 2138 Floyd Street, Sarasota, FL 34239 (MLS # A4635236)
    2138 Floyd Street, Sarasota, FL
    2138 Floyd Street
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,545 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  8. Photo of 2502 Alpine Avenue, Sarasota, FL 34239 (MLS # A4636727)
    $665,500
    Photo of 2502 Alpine Avenue, Sarasota, FL 34239 (MLS # A4636727)
    Photo of 2502 Alpine Avenue, Sarasota, FL 34239 (MLS # A4636727)
    39
     
    2502 Alpine Avenue, Sarasota, FL
    2502 Alpine Avenue
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,068 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  9. Photo of 1188 N Tamiami Trail #203, Sarasota, FL 34236 (MLS # A4636188)
    $750,000
    Photo of 1188 N Tamiami Trail #203, Sarasota, FL 34236 (MLS # A4636188)
    Photo of 1188 N Tamiami Trail #203, Sarasota, FL 34236 (MLS # A4636188)
    27
     
    1188 N Tamiami Trail #203, Sarasota, FL
    1188 N Tamiami Trail #203
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,093 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
  10. Photo of 3015 Hillview Street, Sarasota, FL 34239 (MLS # A4636649)
    $520,000
    Photo of 3015 Hillview Street, Sarasota, FL 34239 (MLS # A4636649)
    Photo of 3015 Hillview Street, Sarasota, FL 34239 (MLS # A4636649)
    3015 Hillview Street, Sarasota, FL
    3015 Hillview Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,460 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  11. Photo of 605 Wild Turkey Lane, Sarasota, FL 34236 (MLS # A4636666)
    $2,090,000
    Photo of 605 Wild Turkey Lane, Sarasota, FL 34236 (MLS # A4636666)
    Photo of 605 Wild Turkey Lane, Sarasota, FL 34236 (MLS # A4636666)
    55
     
    605 Wild Turkey Lane, Sarasota, FL
    605 Wild Turkey Lane
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  12. Photo of 206 Church Avenue, Bradenton Beach, FL 34217 (MLS # TB8338971)
    $3,200,000
    Photo of 206 Church Avenue, Bradenton Beach, FL 34217 (MLS # TB8338971)
    Photo of 206 Church Avenue, Bradenton Beach, FL 34217 (MLS # TB8338971)
    206 Church Avenue, Bradenton Beach, FL
    206 Church Avenue
    Bradenton Beach, FL
    • 5 Beds
    • 6 Baths
    • 3,308 Home (sqft)
    • 6 Baths
    • 4,792 Lot (sqft)
  13. Photo of 1350 Main Street #304, Sarasota, FL 34236 (MLS # A4636634)
    $3,500
    Photo of 1350 Main Street #304, Sarasota, FL 34236 (MLS # A4636634)
    Photo of 1350 Main Street #304, Sarasota, FL 34236 (MLS # A4636634)
    1350 Main Street #304, Sarasota, FL
    1350 Main Street #304
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 760 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  14. Photo of 402 29th Street #A, Holmes Beach, FL 34217 (MLS # O6272923)
    $750,000
    Photo of 402 29th Street #A, Holmes Beach, FL 34217 (MLS # O6272923)
    Photo of 402 29th Street #A, Holmes Beach, FL 34217 (MLS # O6272923)
    402 29th Street #A, Holmes Beach, FL
    402 29th Street #A
    Holmes Beach, FL
    • 4 Beds
    • 2 Baths
    • 1,464 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  15. Photo of 4839 Primrose Path, Sarasota, FL 34242 (MLS # A4635980)
    $1,848,000
    Photo of 4839 Primrose Path, Sarasota, FL 34242 (MLS # A4635980)
    Photo of 4839 Primrose Path, Sarasota, FL 34242 (MLS # A4635980)
    11
     
    4839 Primrose Path, Sarasota, FL
    4839 Primrose Path
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 15,682 Lot (sqft)
  16. Photo of 1211 Gulf Of Mexico Drive #211, Longboat Key, FL 34228 (MLS # A4636155)
    $2,300,000
    Photo of 1211 Gulf Of Mexico Drive #211, Longboat Key, FL 34228 (MLS # A4636155)
    Photo of 1211 Gulf Of Mexico Drive #211, Longboat Key, FL 34228 (MLS # A4636155)
    1211 Gulf Of Mexico Drive #211, Longboat Key, FL
    1211 Gulf Of Mexico Drive #211
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,273 Home (sqft)
    • 3 Baths
    • 7.87 Lot (ac)
  17. Photo of 2203 Avenue B, Bradenton Beach, FL 34217 (MLS # TB8340132)
    $3,350,000
    Photo of 2203 Avenue B, Bradenton Beach, FL 34217 (MLS # TB8340132)
    Photo of 2203 Avenue B, Bradenton Beach, FL 34217 (MLS # TB8340132)
    2203 Avenue B, Bradenton Beach, FL
    2203 Avenue B
    Bradenton Beach, FL
    • 5 Beds
    • 5 Baths
    • 2,796 Home (sqft)
    • 5 Baths
    • 4,792 Lot (sqft)
  18. Photo of 1212 Benjamin Franklin Drive #701, Sarasota, FL 34236 (MLS # A4636324)
    $11,000
    Photo of 1212 Benjamin Franklin Drive #701, Sarasota, FL 34236 (MLS # A4636324)
    Photo of 1212 Benjamin Franklin Drive #701, Sarasota, FL 34236 (MLS # A4636324)
    1212 Benjamin Franklin Drive #701, Sarasota, FL
    1212 Benjamin Franklin Drive #701
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,532 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 2110 Harbourside Drive #522, Longboat Key, FL 34228 (MLS # A4636284)
    $948,750
    Photo of 2110 Harbourside Drive #522, Longboat Key, FL 34228 (MLS # A4636284)
    Photo of 2110 Harbourside Drive #522, Longboat Key, FL 34228 (MLS # A4636284)
    2110 Harbourside Drive #522, Longboat Key, FL
    2110 Harbourside Drive #522
    Longboat Key, FL
    • 3 Beds
    • 2 Baths
    • 2,039 Home (sqft)
    • 2 Baths
    • 6.31 Lot (ac)
  20. Photo of 1111 N Gulfstream Avenue #3E, Sarasota, FL 34236 (MLS # A4636309)
    $825,000
    Photo of 1111 N Gulfstream Avenue #3E, Sarasota, FL 34236 (MLS # A4636309)
    Photo of 1111 N Gulfstream Avenue #3E, Sarasota, FL 34236 (MLS # A4636309)
    1111 N Gulfstream Avenue #3E, Sarasota, FL
    1111 N Gulfstream Avenue #3E
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,575 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 601 Ambassador Lane, Holmes Beach, FL 34217 (MLS # TB8340397)
    $1,000,000
    Photo of 601 Ambassador Lane, Holmes Beach, FL 34217 (MLS # TB8340397)
    Photo of 601 Ambassador Lane, Holmes Beach, FL 34217 (MLS # TB8340397)
    601 Ambassador Lane, Holmes Beach, FL
    601 Ambassador Lane
    Holmes Beach, FL
    • 4 Beds
    • 2 Baths
    • 2,067 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  22. Photo of 250 Robin Drive, Sarasota, FL 34236 (MLS # A4636327)
    $1,900,000
    Photo of 250 Robin Drive, Sarasota, FL 34236 (MLS # A4636327)
    Photo of 250 Robin Drive, Sarasota, FL 34236 (MLS # A4636327)
    250 Robin Drive, Sarasota, FL
    250 Robin Drive
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,548 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  23. Photo of 214 85th Street, Holmes Beach, FL 34217 (MLS # TB8340183)
    $750,000
    Photo of 214 85th Street, Holmes Beach, FL 34217 (MLS # TB8340183)
    Photo of 214 85th Street, Holmes Beach, FL 34217 (MLS # TB8340183)
    214 85th Street, Holmes Beach, FL
    214 85th Street
    Holmes Beach, FL
    • 3 Beds
    • 2 Baths
    • 1,398 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  24. Photo of 727 Holly Road, Anna Maria, FL 34216 (MLS # A4636265)
    $2,600,000
    Photo of 727 Holly Road, Anna Maria, FL 34216 (MLS # A4636265)
    Photo of 727 Holly Road, Anna Maria, FL 34216 (MLS # A4636265)
    727 Holly Road, Anna Maria, FL
    727 Holly Road
    Anna Maria, FL
    • 3 Beds
    • 3 Baths
    • 2,321 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  25. Photo of 536 Ketch Lane, Longboat Key, FL 34228 (MLS # A4634879)
    $3,999,999
    Photo of 536 Ketch Lane, Longboat Key, FL 34228 (MLS # A4634879)
    Photo of 536 Ketch Lane, Longboat Key, FL 34228 (MLS # A4634879)
    536 Ketch Lane, Longboat Key, FL
    536 Ketch Lane
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,960 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
  26. Photo of 1800 Benjamin Franklin Drive #A801, Sarasota, FL 34236 (MLS # A4636503)
    $2,400,000
    Photo of 1800 Benjamin Franklin Drive #A801, Sarasota, FL 34236 (MLS # A4636503)
    Photo of 1800 Benjamin Franklin Drive #A801, Sarasota, FL 34236 (MLS # A4636503)
    1800 Benjamin Franklin Drive #A801, Sarasota, FL
    1800 Benjamin Franklin Drive #A801
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 2,070 Home (sqft)
    • 3 Baths
    • 5.09 Lot (ac)
  27. Photo of 650 Golden Gate Point #401, Sarasota, FL 34236 (MLS # A4636416)
    $2,200,000
    Photo of 650 Golden Gate Point #401, Sarasota, FL 34236 (MLS # A4636416)
    Photo of 650 Golden Gate Point #401, Sarasota, FL 34236 (MLS # A4636416)
    50
     
    650 Golden Gate Point #401, Sarasota, FL
    650 Golden Gate Point #401
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,837 Home (sqft)
    • 3 Baths
    • 22,652 Lot (sqft)
  28. Photo of 624 Goodrich Avenue, Sarasota, FL 34236 (MLS # A4635887)
    $1,600,000
    Photo of 624 Goodrich Avenue, Sarasota, FL 34236 (MLS # A4635887)
    Photo of 624 Goodrich Avenue, Sarasota, FL 34236 (MLS # A4635887)
    624 Goodrich Avenue, Sarasota, FL
    624 Goodrich Avenue
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 1,596 Home (sqft)
    • 0 Baths
    • 10,455 Lot (sqft)
  29. Photo of 1705 6th Street, Sarasota, FL 34236 (MLS # A4635694)
    $1,600,000
    Photo of 1705 6th Street, Sarasota, FL 34236 (MLS # A4635694)
    Photo of 1705 6th Street, Sarasota, FL 34236 (MLS # A4635694)
    1705 6th Street, Sarasota, FL
    1705 6th Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 12,197 Lot (sqft)
  30. Photo of 624 Goodrich Avenue, Sarasota, FL 34236 (MLS # A4635693)
    $1,600,000
    Photo of 624 Goodrich Avenue, Sarasota, FL 34236 (MLS # A4635693)
    Photo of 624 Goodrich Avenue, Sarasota, FL 34236 (MLS # A4635693)
    624 Goodrich Avenue, Sarasota, FL
    624 Goodrich Avenue
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 10,455 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 1/20/25 10:28 AM PST.

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