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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 303 Beach Road, Sarasota, FL 34242 (MLS # A4629127)
    $2,199,000
    Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4629127)
    Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4629127)
    303 Beach Road, Sarasota, FL
    303 Beach Road
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,380 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  2. Photo of 4485 Gulf Of Mexico Drive #803, Longboat Key, FL 34228 (MLS # A4628971)
    $989,000
    Photo of 4485 Gulf Of Mexico Drive #803, Longboat Key, FL 34228 (MLS # A4628971)
    Photo of 4485 Gulf Of Mexico Drive #803, Longboat Key, FL 34228 (MLS # A4628971)
    4485 Gulf Of Mexico Drive #803, Longboat Key, FL
    4485 Gulf Of Mexico Drive #803
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,022 Home (sqft)
    • 2 Baths
    • 1.63 Lot (ac)
  3. Photo of 3112 Southgate Circle, Sarasota, FL 34239 (MLS # A4629056)
    $1,998,000
    Photo of 3112 Southgate Circle, Sarasota, FL 34239 (MLS # A4629056)
    Photo of 3112 Southgate Circle, Sarasota, FL 34239 (MLS # A4629056)
    3112 Southgate Circle, Sarasota, FL
    3112 Southgate Circle
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 8,883 Home (sqft)
    • 0 Baths
    • 13,504 Lot (sqft)
  4. Photo of 800 N Tamiami Trail #702, Sarasota, FL 34236 (MLS # A4624452)
    $3,950
    Photo of 800 N Tamiami Trail #702, Sarasota, FL 34236 (MLS # A4624452)
    Photo of 800 N Tamiami Trail #702, Sarasota, FL 34236 (MLS # A4624452)
    800 N Tamiami Trail #702, Sarasota, FL
    800 N Tamiami Trail #702
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  5. Photo of 6429 Gulfside Road, Longboat Key, FL 34228 (MLS # A4626389)
    $5,950,000
    Photo of 6429 Gulfside Road, Longboat Key, FL 34228 (MLS # A4626389)
    Photo of 6429 Gulfside Road, Longboat Key, FL 34228 (MLS # A4626389)
    6429 Gulfside Road, Longboat Key, FL
    6429 Gulfside Road
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 31,799 Lot (sqft)
  6. Photo of 3605 Fair Oaks Place, Longboat Key, FL 34228 (MLS # A4628568)
    $1,490,000
    Photo of 3605 Fair Oaks Place, Longboat Key, FL 34228 (MLS # A4628568)
    Photo of 3605 Fair Oaks Place, Longboat Key, FL 34228 (MLS # A4628568)
    3605 Fair Oaks Place, Longboat Key, FL
    3605 Fair Oaks Place
    Longboat Key, FL
    • 4 Beds
    • 4 Baths
    • 3,713 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  7. Photo of 800 N Tamiami Trail #1603, Sarasota, FL 34236 (MLS # A4627276)
    $2,950,000
    Photo of 800 N Tamiami Trail #1603, Sarasota, FL 34236 (MLS # A4627276)
    Photo of 800 N Tamiami Trail #1603, Sarasota, FL 34236 (MLS # A4627276)
    800 N Tamiami Trail #1603, Sarasota, FL
    800 N Tamiami Trail #1603
    Sarasota, FL
    • 2 Beds
    • 4 Baths
    • 2,471 Home (sqft)
    • 4 Baths
    • 2.18 Lot (ac)
  8. Photo of 467 Canal Road #467, Sarasota, FL 34242 (MLS # A4628207)
    $3,150,000
    Photo of 467 Canal Road #467, Sarasota, FL 34242 (MLS # A4628207)
    Photo of 467 Canal Road #467, Sarasota, FL 34242 (MLS # A4628207)
    467 Canal Road #467, Sarasota, FL
    467 Canal Road #467
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,036 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  9. Photo of 1315 Siesta Bayside Drive #1315B, Sarasota, FL 34242 (MLS # A4628842)
    $8,000
    Photo of 1315 Siesta Bayside Drive #1315B, Sarasota, FL 34242 (MLS # A4628842)
    Photo of 1315 Siesta Bayside Drive #1315B, Sarasota, FL 34242 (MLS # A4628842)
    1315 Siesta Bayside Drive #1315B, Sarasota, FL
    1315 Siesta Bayside Drive #1315B
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,645 Home (sqft)
    • 2 Baths
    • 1,645.00 Lot (ac)
  10. Photo of 2050 Benjamin Franklin Drive #B704, Sarasota, FL 34236 (MLS # A4629073)
    $3,695,000
    Photo of 2050 Benjamin Franklin Drive #B704, Sarasota, FL 34236 (MLS # A4629073)
    Photo of 2050 Benjamin Franklin Drive #B704, Sarasota, FL 34236 (MLS # A4629073)
    2050 Benjamin Franklin Drive #B704, Sarasota, FL
    2050 Benjamin Franklin Drive #B704
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,936 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  11. Photo of 2125 Datura Street, Sarasota, FL 34239 (MLS # A4629542)
    $3,325,000
    Photo of 2125 Datura Street, Sarasota, FL 34239 (MLS # A4629542)
    Photo of 2125 Datura Street, Sarasota, FL 34239 (MLS # A4629542)
    2125 Datura Street, Sarasota, FL
    2125 Datura Street
    Sarasota, FL
    • 6 Beds
    • 6 Baths
    • 3,900 Home (sqft)
    • 6 Baths
    • 8,712 Lot (sqft)
  12. Photo of 1712 S. Shade, Sarasota, FL 34239 (MLS # A4629288)
    $1,870,000
    Photo of 1712 S. Shade, Sarasota, FL 34239 (MLS # A4629288)
    Photo of 1712 S. Shade, Sarasota, FL 34239 (MLS # A4629288)
    1712 S. Shade, Sarasota, FL
    1712 S. Shade
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,300 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  13. Photo of 2915 Lynnhurst Street, Sarasota, FL 34239 (MLS # A4628893)
    $524,999
    Photo of 2915 Lynnhurst Street, Sarasota, FL 34239 (MLS # A4628893)
    Photo of 2915 Lynnhurst Street, Sarasota, FL 34239 (MLS # A4628893)
    2915 Lynnhurst Street, Sarasota, FL
    2915 Lynnhurst Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 1,632 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  14. Photo of 111 Golden Gate Point #402, Sarasota, FL 34236 (MLS # A4628715)
    $3,250,000
    Photo of 111 Golden Gate Point #402, Sarasota, FL 34236 (MLS # A4628715)
    Photo of 111 Golden Gate Point #402, Sarasota, FL 34236 (MLS # A4628715)
    111 Golden Gate Point #402, Sarasota, FL
    111 Golden Gate Point #402
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,314 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  15. Photo of 850 S Tamiami Trail #704, Sarasota, FL 34236 (MLS # A4626948)
    $389,900
    Photo of 850 S Tamiami Trail #704, Sarasota, FL 34236 (MLS # A4626948)
    Photo of 850 S Tamiami Trail #704, Sarasota, FL 34236 (MLS # A4626948)
    850 S Tamiami Trail #704, Sarasota, FL
    850 S Tamiami Trail #704
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 980 Home (sqft)
    • 2 Baths
    • 9.00 Lot (ac)
  16. Photo of 2121 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4627869)
    $795,000
    Photo of 2121 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4627869)
    Photo of 2121 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4627869)
    2121 Tanglewood Drive, Sarasota, FL
    2121 Tanglewood Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,321 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  17. Photo of 144 Garden Lane, Sarasota, FL 34242 (MLS # A4628245)
    $999,000
    Photo of 144 Garden Lane, Sarasota, FL 34242 (MLS # A4628245)
    Photo of 144 Garden Lane, Sarasota, FL 34242 (MLS # A4628245)
    144 Garden Lane, Sarasota, FL
    144 Garden Lane
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 1,702 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  18. Photo of 750 N Tamiami Trail #912, Sarasota, FL 34236 (MLS # A4628826)
    $449,000
    Photo of 750 N Tamiami Trail #912, Sarasota, FL 34236 (MLS # A4628826)
    Photo of 750 N Tamiami Trail #912, Sarasota, FL 34236 (MLS # A4628826)
    750 N Tamiami Trail #912, Sarasota, FL
    750 N Tamiami Trail #912
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 810 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  19. Photo of 808 N Bay Boulevard, Anna Maria, FL 34216 (MLS # A4628820)
    $4,800,000
    Photo of 808 N Bay Boulevard, Anna Maria, FL 34216 (MLS # A4628820)
    Photo of 808 N Bay Boulevard, Anna Maria, FL 34216 (MLS # A4628820)
    808 N Bay Boulevard, Anna Maria, FL
    808 N Bay Boulevard
    Anna Maria, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 22,652 Lot (sqft)
  20. Photo of 3012 Gulf Drive, Bradenton Beach, FL 34217 (MLS # A4628781)
    $725,000
    Photo of 3012 Gulf Drive, Bradenton Beach, FL 34217 (MLS # A4628781)
    Photo of 3012 Gulf Drive, Bradenton Beach, FL 34217 (MLS # A4628781)
    3012 Gulf Drive, Bradenton Beach, FL
    3012 Gulf Drive
    Bradenton Beach, FL
    • 0 Beds
    • 0 Baths
    • 1,224 Home (sqft)
    • 0 Baths
    • 5,228 Lot (sqft)
  21. Photo of 2425 Calamonga Lane, Sarasota, FL 34239 (MLS # A4625610)
    $560,000
    Photo of 2425 Calamonga Lane, Sarasota, FL 34239 (MLS # A4625610)
    Photo of 2425 Calamonga Lane, Sarasota, FL 34239 (MLS # A4625610)
    2425 Calamonga Lane, Sarasota, FL
    2425 Calamonga Lane
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,885 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  22. Photo of 1561 Gulf Of Mexico Drive #403, Longboat Key, FL 34228 (MLS # A4627926)
    $13,250,000
    Photo of 1561 Gulf Of Mexico Drive #403, Longboat Key, FL 34228 (MLS # A4627926)
    Photo of 1561 Gulf Of Mexico Drive #403, Longboat Key, FL 34228 (MLS # A4627926)
    90
     
    1561 Gulf Of Mexico Drive #403, Longboat Key, FL
    1561 Gulf Of Mexico Drive #403
    Longboat Key, FL
    • 3 Beds
    • 4 Baths
    • 4,187 Home (sqft)
    • 4 Baths
    • 17.80 Lot (ac)
  23. Photo of 5400 Ocean Boulevard #1-5, Sarasota, FL 34242 (MLS # A4628649)
    $5,000
    Photo of 5400 Ocean Boulevard #1-5, Sarasota, FL 34242 (MLS # A4628649)
    Photo of 5400 Ocean Boulevard #1-5, Sarasota, FL 34242 (MLS # A4628649)
    5400 Ocean Boulevard #1-5, Sarasota, FL
    5400 Ocean Boulevard #1-5
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 698 Home (sqft)
    • 1 Bath
    • 2.08 Lot (ac)
  24. Photo of 642 Lafayette Court, Sarasota, FL 34236 (MLS # A4628290)
    $579,000
    Photo of 642 Lafayette Court, Sarasota, FL 34236 (MLS # A4628290)
    Photo of 642 Lafayette Court, Sarasota, FL 34236 (MLS # A4628290)
    642 Lafayette Court, Sarasota, FL
    642 Lafayette Court
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,180 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  25. Photo of 1521 Siesta Drive, Sarasota, FL 34239 (MLS # A4628696)
    $1,625,000
    Photo of 1521 Siesta Drive, Sarasota, FL 34239 (MLS # A4628696)
    Photo of 1521 Siesta Drive, Sarasota, FL 34239 (MLS # A4628696)
    1521 Siesta Drive, Sarasota, FL
    1521 Siesta Drive
    Sarasota, FL
    • 3 Beds
    • 5 Baths
    • 3,057 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
  26. Photo of 1762 Bay Street #401, Sarasota, FL 34236 (MLS # A4628691)
    $5,500
    Photo of 1762 Bay Street #401, Sarasota, FL 34236 (MLS # A4628691)
    Photo of 1762 Bay Street #401, Sarasota, FL 34236 (MLS # A4628691)
    1762 Bay Street #401, Sarasota, FL
    1762 Bay Street #401
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,183 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 1259 5th Street, Sarasota, FL 34236 (MLS # A4628697)
    $1,395
    Photo of 1259 5th Street, Sarasota, FL 34236 (MLS # A4628697)
    Photo of 1259 5th Street, Sarasota, FL 34236 (MLS # A4628697)
    1259 5th Street, Sarasota, FL
    1259 5th Street
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 900 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
  28. Photo of 1591 Gulf Of Mexico Drive #316, Longboat Key, FL 34228 (MLS # A4628607)
    $3,400,000
    Photo of 1591 Gulf Of Mexico Drive #316, Longboat Key, FL 34228 (MLS # A4628607)
    Photo of 1591 Gulf Of Mexico Drive #316, Longboat Key, FL 34228 (MLS # A4628607)
    1591 Gulf Of Mexico Drive #316, Longboat Key, FL
    1591 Gulf Of Mexico Drive #316
    Longboat Key, FL
    • 1 Bed
    • 2 Baths
    • 1,556 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  29. Photo of 1581 Gulf Of Mexico Dr #407, Longboat Key, FL 34228 (MLS # A4627871)
    $3,770,000
    Photo of 1581 Gulf Of Mexico Dr #407, Longboat Key, FL 34228 (MLS # A4627871)
    Photo of 1581 Gulf Of Mexico Dr #407, Longboat Key, FL 34228 (MLS # A4627871)
    1581 Gulf Of Mexico Dr #407, Longboat Key, FL
    1581 Gulf Of Mexico Dr #407
    Longboat Key, FL
    • 1 Bed
    • 2 Baths
    • 1,721 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 1591 Gulf Of Mexico Drive #515, Longboat Key, FL 34228 (MLS # A4628048)
    $3,975,000
    Photo of 1591 Gulf Of Mexico Drive #515, Longboat Key, FL 34228 (MLS # A4628048)
    Photo of 1591 Gulf Of Mexico Drive #515, Longboat Key, FL 34228 (MLS # A4628048)
    1591 Gulf Of Mexico Drive #515, Longboat Key, FL
    1591 Gulf Of Mexico Drive #515
    Longboat Key, FL
    • 1 Bed
    • 2 Baths
    • 1,556 Home (sqft)
    • 2 Baths
    • 0 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 11/21/24 4:12 PM PST.

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