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 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4607664)
    $2,995,000
    Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4607664)
    Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4607664)
    1959 Hibiscus Street, Sarasota, FL
    1959 Hibiscus Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,720 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  2. Photo of 9393 Midnight Pass Road #703, Sarasota, FL 34242 (MLS # A4606934)
    $499,900
    Photo of 9393 Midnight Pass Road #703, Sarasota, FL 34242 (MLS # A4606934)
    Photo of 9393 Midnight Pass Road #703, Sarasota, FL 34242 (MLS # A4606934)
    9393 Midnight Pass Road #703, Sarasota, FL
    9393 Midnight Pass Road #703
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 946 Home (sqft)
    • 1 Bath
    • 5.24 Lot (ac)
  3. Photo of 2181 Hillview Street, Sarasota, FL 34239 (MLS # A4607794)
    $1,659,000
    Photo of 2181 Hillview Street, Sarasota, FL 34239 (MLS # A4607794)
    Photo of 2181 Hillview Street, Sarasota, FL 34239 (MLS # A4607794)
    2181 Hillview Street, Sarasota, FL
    2181 Hillview Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,925 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  4. Photo of 2569 Prospect Street, Sarasota, FL 34239 (MLS # A4607808)
    $12,000
    Photo of 2569 Prospect Street, Sarasota, FL 34239 (MLS # A4607808)
    Photo of 2569 Prospect Street, Sarasota, FL 34239 (MLS # A4607808)
    2569 Prospect Street, Sarasota, FL
    2569 Prospect Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,241 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)
  5. Photo of 701 Hideaway Bay Drive, Longboat Key, FL 34228 (MLS # A4607011)
    $2,695,000
    Photo of 701 Hideaway Bay Drive, Longboat Key, FL 34228 (MLS # A4607011)
    Photo of 701 Hideaway Bay Drive, Longboat Key, FL 34228 (MLS # A4607011)
    701 Hideaway Bay Drive, Longboat Key, FL
    701 Hideaway Bay Drive
    Longboat Key, FL
    • 4 Beds
    • 3 Baths
    • 2,629 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
  6. Photo of 1268 11th Street #2202, Sarasota, FL 34236 (MLS # A4607744)
    $3,000
    Photo of 1268 11th Street #2202, Sarasota, FL 34236 (MLS # A4607744)
    Photo of 1268 11th Street #2202, Sarasota, FL 34236 (MLS # A4607744)
    33
     
    1268 11th Street #2202, Sarasota, FL
    1268 11th Street #2202
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,122 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  7. Photo of 313 Tarpon Street, Anna Maria, FL 34216 (MLS # A4607738)
    $4,000
    Photo of 313 Tarpon Street, Anna Maria, FL 34216 (MLS # A4607738)
    Photo of 313 Tarpon Street, Anna Maria, FL 34216 (MLS # A4607738)
    313 Tarpon Street, Anna Maria, FL
    313 Tarpon Street
    Anna Maria, FL
    • 2 Beds
    • 2 Baths
    • 908 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  8. Photo of 3210 Bayou Sound, Longboat Key, FL 34228 (MLS # A4607835)
    $12,500
    Photo of 3210 Bayou Sound, Longboat Key, FL 34228 (MLS # A4607835)
    Photo of 3210 Bayou Sound, Longboat Key, FL 34228 (MLS # A4607835)
    3210 Bayou Sound, Longboat Key, FL
    3210 Bayou Sound
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 3,171 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  9. Photo of 235 Cocoanut Avenue #101A, Sarasota, FL 34236 (MLS # A4607672)
    $1,199,999
    Photo of 235 Cocoanut Avenue #101A, Sarasota, FL 34236 (MLS # A4607672)
    Photo of 235 Cocoanut Avenue #101A, Sarasota, FL 34236 (MLS # A4607672)
    235 Cocoanut Avenue #101A, Sarasota, FL
    235 Cocoanut Avenue #101A
    Sarasota, FL
    • 2 Beds
    • 4 Baths
    • 2,116 Home (sqft)
    • 4 Baths
    • 35,720 Lot (sqft)
  10. Photo of 7000 Marina Drive, Holmes Beach, FL 34217 (MLS # A4607185)
    $1,469,000
    Photo of 7000 Marina Drive, Holmes Beach, FL 34217 (MLS # A4607185)
    Photo of 7000 Marina Drive, Holmes Beach, FL 34217 (MLS # A4607185)
    32
     
    7000 Marina Drive, Holmes Beach, FL
    7000 Marina Drive
    Holmes Beach, FL
    • 3 Beds
    • 2 Baths
    • 1,778 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  11. Photo of 1753 Hillview Street #3, Sarasota, FL 34239 (MLS # A4607663)
    $2,100
    Photo of 1753 Hillview Street #3, Sarasota, FL 34239 (MLS # A4607663)
    Photo of 1753 Hillview Street #3, Sarasota, FL 34239 (MLS # A4607663)
    1753 Hillview Street #3, Sarasota, FL
    1753 Hillview Street #3
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 743 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  12. Photo of 1132 Crescent Street, Sarasota, FL 34242 (MLS # A4607696)
    $1,490,000
    Photo of 1132 Crescent Street, Sarasota, FL 34242 (MLS # A4607696)
    Photo of 1132 Crescent Street, Sarasota, FL 34242 (MLS # A4607696)
    93
     
    1132 Crescent Street, Sarasota, FL
    1132 Crescent Street
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,261 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  13. Photo of 120 Maple Avenue, Anna Maria, FL 34216 (MLS # A4606699)
    $1,799,500
    Photo of 120 Maple Avenue, Anna Maria, FL 34216 (MLS # A4606699)
    Photo of 120 Maple Avenue, Anna Maria, FL 34216 (MLS # A4606699)
    120 Maple Avenue, Anna Maria, FL
    120 Maple Avenue
    Anna Maria, FL
    • 3 Beds
    • 2 Baths
    • 1,506 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  14. Photo of 1280 Dolphin Bay Way #504, Sarasota, FL 34242 (MLS # A4607725)
    $7,500
    Photo of 1280 Dolphin Bay Way #504, Sarasota, FL 34242 (MLS # A4607725)
    Photo of 1280 Dolphin Bay Way #504, Sarasota, FL 34242 (MLS # A4607725)
    1280 Dolphin Bay Way #504, Sarasota, FL
    1280 Dolphin Bay Way #504
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,840 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  15. Photo of 1800 Benjamin Franklin Drive #A403, Sarasota, FL 34236 (MLS # A4606780)
    $1,118,000
    Photo of 1800 Benjamin Franklin Drive #A403, Sarasota, FL 34236 (MLS # A4606780)
    Photo of 1800 Benjamin Franklin Drive #A403, Sarasota, FL 34236 (MLS # A4606780)
    1800 Benjamin Franklin Drive #A403, Sarasota, FL
    1800 Benjamin Franklin Drive #A403
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,350 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 1754 10th Street, Sarasota, FL 34236 (MLS # A4606611)
    $699,000
    Photo of 1754 10th Street, Sarasota, FL 34236 (MLS # A4606611)
    Photo of 1754 10th Street, Sarasota, FL 34236 (MLS # A4606611)
    1754 10th Street, Sarasota, FL
    1754 10th Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 6,534 Lot (sqft)
  17. Photo of 111 Golden Gate Point #201, Sarasota, FL 34236 (MLS # A4607687)
    $2,550,000
    Photo of 111 Golden Gate Point #201, Sarasota, FL 34236 (MLS # A4607687)
    Photo of 111 Golden Gate Point #201, Sarasota, FL 34236 (MLS # A4607687)
    111 Golden Gate Point #201, Sarasota, FL
    111 Golden Gate Point #201
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,505 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  18. Photo of 1250 N Portofino Drive #305MAR, Sarasota, FL 34242 (MLS # A4606532)
    $2,000
    Photo of 1250 N Portofino Drive #305MAR, Sarasota, FL 34242 (MLS # A4606532)
    Photo of 1250 N Portofino Drive #305MAR, Sarasota, FL 34242 (MLS # A4606532)
    1250 N Portofino Drive #305MAR, Sarasota, FL
    1250 N Portofino Drive #305MAR
    Sarasota, FL
    • 1 Bed
    • 2 Baths
    • 780 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 5216 Calle De Costa Rica, Sarasota, FL 34242 (MLS # A4607652)
    $6,800
    Photo of 5216 Calle De Costa Rica, Sarasota, FL 34242 (MLS # A4607652)
    Photo of 5216 Calle De Costa Rica, Sarasota, FL 34242 (MLS # A4607652)
    35
     
    5216 Calle De Costa Rica, Sarasota, FL
    5216 Calle De Costa Rica
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,290 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  20. Photo of 8630 Midnight Pass Road #405A, Sarasota, FL 34242 (MLS # A4607681)
    $10,500
    Photo of 8630 Midnight Pass Road #405A, Sarasota, FL 34242 (MLS # A4607681)
    Photo of 8630 Midnight Pass Road #405A, Sarasota, FL 34242 (MLS # A4607681)
    8630 Midnight Pass Road #405A, Sarasota, FL
    8630 Midnight Pass Road #405A
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,222 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 5683 Midnight Pass Road #109, Sarasota, FL 34242 (MLS # A4607677)
    $5,400
    Photo of 5683 Midnight Pass Road #109, Sarasota, FL 34242 (MLS # A4607677)
    Photo of 5683 Midnight Pass Road #109, Sarasota, FL 34242 (MLS # A4607677)
    41
     
    5683 Midnight Pass Road #109, Sarasota, FL
    5683 Midnight Pass Road #109
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 797 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  22. Photo of 301 Quay Commons #1007, Sarasota, FL 34236 (MLS # A4607651)
    $1,600,000
    Photo of 301 Quay Commons #1007, Sarasota, FL 34236 (MLS # A4607651)
    Photo of 301 Quay Commons #1007, Sarasota, FL 34236 (MLS # A4607651)
    301 Quay Commons #1007, Sarasota, FL
    301 Quay Commons #1007
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,578 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  23. Photo of 1055 Beach Road #B203, Sarasota, FL 34242 (MLS # A4607669)
    $8,700
    Photo of 1055 Beach Road #B203, Sarasota, FL 34242 (MLS # A4607669)
    Photo of 1055 Beach Road #B203, Sarasota, FL 34242 (MLS # A4607669)
    38
     
    1055 Beach Road #B203, Sarasota, FL
    1055 Beach Road #B203
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,204 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  24. Photo of 3700 S Osprey Avenue #121, Sarasota, FL 34239 (MLS # A4607447)
    $269,000
    Photo of 3700 S Osprey Avenue #121, Sarasota, FL 34239 (MLS # A4607447)
    Photo of 3700 S Osprey Avenue #121, Sarasota, FL 34239 (MLS # A4607447)
    3700 S Osprey Avenue #121, Sarasota, FL
    3700 S Osprey Avenue #121
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,053 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 1703 Main Street #1203, Sarasota, FL 34236 (MLS # A4607642)
    $2,245,000
    Photo of 1703 Main Street #1203, Sarasota, FL 34236 (MLS # A4607642)
    Photo of 1703 Main Street #1203, Sarasota, FL 34236 (MLS # A4607642)
    1703 Main Street #1203, Sarasota, FL
    1703 Main Street #1203
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,160 Home (sqft)
    • 4 Baths
    • 18,731 Lot (sqft)
  26. Photo of 306 Beach Road #306, Sarasota, FL 34242 (MLS # A4607636)
    $13,200
    Photo of 306 Beach Road #306, Sarasota, FL 34242 (MLS # A4607636)
    Photo of 306 Beach Road #306, Sarasota, FL 34242 (MLS # A4607636)
    48
     
    306 Beach Road #306, Sarasota, FL
    306 Beach Road #306
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,041 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 5640 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4607612)
    $10,500
    Photo of 5640 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4607612)
    Photo of 5640 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4607612)
    58
     
    5640 Cape Leyte Drive, Sarasota, FL
    5640 Cape Leyte Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,002 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  28. Photo of 338 Avenida De Paradisio, Sarasota, FL 34242 (MLS # A4607598)
    $6,500
    Photo of 338 Avenida De Paradisio, Sarasota, FL 34242 (MLS # A4607598)
    Photo of 338 Avenida De Paradisio, Sarasota, FL 34242 (MLS # A4607598)
    45
     
    338 Avenida De Paradisio, Sarasota, FL
    338 Avenida De Paradisio
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,735 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  29. Photo of 4255 Gulf Drive #116, Holmes Beach, FL 34217 (MLS # A4607469)
    $620,000
    Photo of 4255 Gulf Drive #116, Holmes Beach, FL 34217 (MLS # A4607469)
    Photo of 4255 Gulf Drive #116, Holmes Beach, FL 34217 (MLS # A4607469)
    4255 Gulf Drive #116, Holmes Beach, FL
    4255 Gulf Drive #116
    Holmes Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,220 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 5129 Sandy Cove Avenue, Sarasota, FL 34242 (MLS # A4607518)
    $15,000
    Photo of 5129 Sandy Cove Avenue, Sarasota, FL 34242 (MLS # A4607518)
    Photo of 5129 Sandy Cove Avenue, Sarasota, FL 34242 (MLS # A4607518)
    65
     
    5129 Sandy Cove Avenue, Sarasota, FL
    5129 Sandy Cove Avenue
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,823 Home (sqft)
    • 3 Baths
    • 14,375 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 4/22/24 12:04 PM PDT.

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