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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 915 Seaside Drive #407, Sarasota, FL 34242 (MLS # A4629292)
    $3,300,000
    Photo of 915 Seaside Drive #407, Sarasota, FL 34242 (MLS # A4629292)
    Photo of 915 Seaside Drive #407, Sarasota, FL 34242 (MLS # A4629292)
    915 Seaside Drive #407, Sarasota, FL
    915 Seaside Drive #407
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,255 Home (sqft)
    • 4 Baths
    • 3.63 Lot (ac)
  2. Photo of 2746 Hibiscus Street, Sarasota, FL 34239 (MLS # TB8325139)
    $615,000
    Photo of 2746 Hibiscus Street, Sarasota, FL 34239 (MLS # TB8325139)
    Photo of 2746 Hibiscus Street, Sarasota, FL 34239 (MLS # TB8325139)
    2746 Hibiscus Street, Sarasota, FL
    2746 Hibiscus Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,819 Home (sqft)
    • 3 Baths
    • 14,375 Lot (sqft)
  3. Photo of 1340 Harbor Drive, Sarasota, FL 34239 (MLS # A4631375)
    $4,975,000
    Photo of 1340 Harbor Drive, Sarasota, FL 34239 (MLS # A4631375)
    Photo of 1340 Harbor Drive, Sarasota, FL 34239 (MLS # A4631375)
    1340 Harbor Drive, Sarasota, FL
    1340 Harbor Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 15,246 Lot (sqft)
  4. Photo of 1340 Harbor Drive, Sarasota, FL 34239 (MLS # A4631373)
    $4,975,000
    Photo of 1340 Harbor Drive, Sarasota, FL 34239 (MLS # A4631373)
    Photo of 1340 Harbor Drive, Sarasota, FL 34239 (MLS # A4631373)
    1340 Harbor Drive, Sarasota, FL
    1340 Harbor Drive
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 4,313 Home (sqft)
    • 5 Baths
    • 15,246 Lot (sqft)
  5. Photo of 2574 Hawthorne Street, Sarasota, FL 34239 (MLS # A4631679)
    $534,000
    Photo of 2574 Hawthorne Street, Sarasota, FL 34239 (MLS # A4631679)
    Photo of 2574 Hawthorne Street, Sarasota, FL 34239 (MLS # A4631679)
    2574 Hawthorne Street, Sarasota, FL
    2574 Hawthorne Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,362 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  6. Photo of 3200 Higel Avenue, Sarasota, FL 34242 (MLS # A4628374)
    $17,000,000
    Photo of 3200 Higel Avenue, Sarasota, FL 34242 (MLS # A4628374)
    Photo of 3200 Higel Avenue, Sarasota, FL 34242 (MLS # A4628374)
    3200 Higel Avenue, Sarasota, FL
    3200 Higel Avenue
    Sarasota, FL
    • 5 Beds
    • 7 Baths
    • 4,656 Home (sqft)
    • 7 Baths
    • 9,584 Lot (sqft)
  7. Photo of 1305 4th Street #402P, Sarasota, FL 34236 (MLS # A4631421)
    $1,395,000
    Photo of 1305 4th Street #402P, Sarasota, FL 34236 (MLS # A4631421)
    Photo of 1305 4th Street #402P, Sarasota, FL 34236 (MLS # A4631421)
    1305 4th Street #402P, Sarasota, FL
    1305 4th Street #402P
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,357 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  8. Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4631453)
    $2,500,000
    Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4631453)
    Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4631453)
    1647 Siesta Drive, Sarasota, FL
    1647 Siesta Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  9. Photo of 3605 S School Avenue, Sarasota, FL 34239 (MLS # A4629140)
    $3,700,000
    Photo of 3605 S School Avenue, Sarasota, FL 34239 (MLS # A4629140)
    Photo of 3605 S School Avenue, Sarasota, FL 34239 (MLS # A4629140)
    3605 S School Avenue, Sarasota, FL
    3605 S School Avenue
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 3,217 Home (sqft)
    • 0 Baths
    • 35,284 Lot (sqft)
  10. Photo of 1923 5th Street, Sarasota, FL 34236 (MLS # A4631425)
    $1,650,000
    Photo of 1923 5th Street, Sarasota, FL 34236 (MLS # A4631425)
    Photo of 1923 5th Street, Sarasota, FL 34236 (MLS # A4631425)
    1923 5th Street, Sarasota, FL
    1923 5th Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 19,024 Home (sqft)
    • 0 Baths
    • 10,455 Lot (sqft)
  11. Photo of 1923 5th Street, Sarasota, FL 34236 (MLS # A4631424)
    $1,650,000
    Photo of 1923 5th Street, Sarasota, FL 34236 (MLS # A4631424)
    Photo of 1923 5th Street, Sarasota, FL 34236 (MLS # A4631424)
    1923 5th Street, Sarasota, FL
    1923 5th Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 10,455 Lot (sqft)
  12. Photo of 404 S Bay Boulevard, Anna Maria, FL 34216 (MLS # A4630955)
    $2,995,000
    Photo of 404 S Bay Boulevard, Anna Maria, FL 34216 (MLS # A4630955)
    Photo of 404 S Bay Boulevard, Anna Maria, FL 34216 (MLS # A4630955)
    404 S Bay Boulevard, Anna Maria, FL
    404 S Bay Boulevard
    Anna Maria, FL
    • 3 Beds
    • 3 Baths
    • 990 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  13. Photo of 237 S Harbor Drive, Holmes Beach, FL 34217 (MLS # A4631402)
    $999,000
    Photo of 237 S Harbor Drive, Holmes Beach, FL 34217 (MLS # A4631402)
    Photo of 237 S Harbor Drive, Holmes Beach, FL 34217 (MLS # A4631402)
    237 S Harbor Drive, Holmes Beach, FL
    237 S Harbor Drive
    Holmes Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,261 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  14. Photo of 750 N Tamiami Trail #719, Sarasota, FL 34236 (MLS # A4631389)
    $990,000
    Photo of 750 N Tamiami Trail #719, Sarasota, FL 34236 (MLS # A4631389)
    Photo of 750 N Tamiami Trail #719, Sarasota, FL 34236 (MLS # A4631389)
    750 N Tamiami Trail #719, Sarasota, FL
    750 N Tamiami Trail #719
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,460 Home (sqft)
    • 2 Baths
    • 2.72 Lot (ac)
  15. Photo of 601 Gulf Drive N #209, Bradenton Beach, FL 34217 (MLS # A4629921)
    $599,000
    Photo of 601 Gulf Drive N #209, Bradenton Beach, FL 34217 (MLS # A4629921)
    Photo of 601 Gulf Drive N #209, Bradenton Beach, FL 34217 (MLS # A4629921)
    601 Gulf Drive N #209, Bradenton Beach, FL
    601 Gulf Drive N #209
    Bradenton Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,122 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 1265 5th Street, Sarasota, FL 34236 (MLS # A4631357)
    $940
    Photo of 1265 5th Street, Sarasota, FL 34236 (MLS # A4631357)
    Photo of 1265 5th Street, Sarasota, FL 34236 (MLS # A4631357)
    1265 5th Street, Sarasota, FL
    1265 5th Street
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 600 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
  17. Photo of 4307 Gulf Drive #103, Holmes Beach, FL 34217 (MLS # A4631337)
    $695,000
    Photo of 4307 Gulf Drive #103, Holmes Beach, FL 34217 (MLS # A4631337)
    Photo of 4307 Gulf Drive #103, Holmes Beach, FL 34217 (MLS # A4631337)
    4307 Gulf Drive #103, Holmes Beach, FL
    4307 Gulf Drive #103
    Holmes Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,027 Home (sqft)
    • 2 Baths
    • 1.14 Lot (ac)
  18. Photo of 1485 Gulf Of Mexico Drive #201, Longboat Key, FL 34228 (MLS # A4625837)
    $1,095,000
    Photo of 1485 Gulf Of Mexico Drive #201, Longboat Key, FL 34228 (MLS # A4625837)
    Photo of 1485 Gulf Of Mexico Drive #201, Longboat Key, FL 34228 (MLS # A4625837)
    1485 Gulf Of Mexico Drive #201, Longboat Key, FL
    1485 Gulf Of Mexico Drive #201
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 1,551 Home (sqft)
    • 3 Baths
    • 2.74 Lot (ac)
  19. Photo of 530 Freeling Drive, Sarasota, FL 34242 (MLS # A4630576)
    $1,750,000
    Photo of 530 Freeling Drive, Sarasota, FL 34242 (MLS # A4630576)
    Photo of 530 Freeling Drive, Sarasota, FL 34242 (MLS # A4630576)
    530 Freeling Drive, Sarasota, FL
    530 Freeling Drive
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 2,152 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  20. Photo of 796 Jacaranda Road, Anna Maria, FL 34216 (MLS # A4631029)
    $2,925,000
    Photo of 796 Jacaranda Road, Anna Maria, FL 34216 (MLS # A4631029)
    Photo of 796 Jacaranda Road, Anna Maria, FL 34216 (MLS # A4631029)
    796 Jacaranda Road, Anna Maria, FL
    796 Jacaranda Road
    Anna Maria, FL
    • 4 Beds
    • 3 Baths
    • 2,412 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  21. Photo of 4440 Exeter Drive #104, Longboat Key, FL 34228 (MLS # A4631274)
    $525,000
    Photo of 4440 Exeter Drive #104, Longboat Key, FL 34228 (MLS # A4631274)
    Photo of 4440 Exeter Drive #104, Longboat Key, FL 34228 (MLS # A4631274)
    22
     
    4440 Exeter Drive #104, Longboat Key, FL
    4440 Exeter Drive #104
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 992 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  22. Photo of 518 Bird Key Drive, Sarasota, FL 34236 (MLS # A4630646)
    $7,900
    Photo of 518 Bird Key Drive, Sarasota, FL 34236 (MLS # A4630646)
    Photo of 518 Bird Key Drive, Sarasota, FL 34236 (MLS # A4630646)
    518 Bird Key Drive, Sarasota, FL
    518 Bird Key Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,065 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  23. Photo of 308 56th Street #B, Holmes Beach, FL 34217 (MLS # A4631067)
    $1,850,000
    Photo of 308 56th Street #B, Holmes Beach, FL 34217 (MLS # A4631067)
    Photo of 308 56th Street #B, Holmes Beach, FL 34217 (MLS # A4631067)
    308 56th Street #B, Holmes Beach, FL
    308 56th Street #B
    Holmes Beach, FL
    • 2 Beds
    • 3 Baths
    • 1,703 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  24. Photo of 8767 Midnight Pass Road #203F, Sarasota, FL 34242 (MLS # A4630239)
    $665,000
    Photo of 8767 Midnight Pass Road #203F, Sarasota, FL 34242 (MLS # A4630239)
    Photo of 8767 Midnight Pass Road #203F, Sarasota, FL 34242 (MLS # A4630239)
    8767 Midnight Pass Road #203F, Sarasota, FL
    8767 Midnight Pass Road #203F
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,303 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 4820 Higel Avenue, Sarasota, FL 34242 (MLS # A4631341)
    $1,850,000
    Photo of 4820 Higel Avenue, Sarasota, FL 34242 (MLS # A4631341)
    Photo of 4820 Higel Avenue, Sarasota, FL 34242 (MLS # A4631341)
    4820 Higel Avenue, Sarasota, FL
    4820 Higel Avenue
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,672 Home (sqft)
    • 3 Baths
    • 16,118 Lot (sqft)
  26. Photo of 5911 Midnight Pass Road #504, Sarasota, FL 34242 (MLS # A4631004)
    $750,000
    Photo of 5911 Midnight Pass Road #504, Sarasota, FL 34242 (MLS # A4631004)
    Photo of 5911 Midnight Pass Road #504, Sarasota, FL 34242 (MLS # A4631004)
    5911 Midnight Pass Road #504, Sarasota, FL
    5911 Midnight Pass Road #504
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,447 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  27. Photo of 5300 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4631229)
    $4,500,000
    Photo of 5300 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4631229)
    Photo of 5300 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4631229)
    5300 Avenida Del Mare, Sarasota, FL
    5300 Avenida Del Mare
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 3,234 Home (sqft)
    • 6 Baths
    • 7,841 Lot (sqft)
  28. Photo of 1667 Laurel Street, Sarasota, FL 34236 (MLS # A4631217)
    $1,975,000
    Photo of 1667 Laurel Street, Sarasota, FL 34236 (MLS # A4631217)
    Photo of 1667 Laurel Street, Sarasota, FL 34236 (MLS # A4631217)
    1667 Laurel Street, Sarasota, FL
    1667 Laurel Street
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 3,245 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  29. Photo of 675 Avenida Del Norte, Sarasota, FL 34242 (MLS # TB8326703)
    $779,900
    Photo of 675 Avenida Del Norte, Sarasota, FL 34242 (MLS # TB8326703)
    Photo of 675 Avenida Del Norte, Sarasota, FL 34242 (MLS # TB8326703)
    675 Avenida Del Norte, Sarasota, FL
    675 Avenida Del Norte
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  30. Photo of 1305 4th Street #402, Sarasota, FL 34236 (MLS # A4631109)
    $1,795,000
    Photo of 1305 4th Street #402, Sarasota, FL 34236 (MLS # A4631109)
    Photo of 1305 4th Street #402, Sarasota, FL 34236 (MLS # A4631109)
    1305 4th Street #402, Sarasota, FL
    1305 4th Street #402
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,823 Home (sqft)
    • 3 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 12/8/24 10:16 AM PST.

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