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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 111 S Pineapple Avenue #903, Sarasota, FL 34236 (MLS # A4624999)
    $1,479,000
    Photo of 111 S Pineapple Avenue #903, Sarasota, FL 34236 (MLS # A4624999)
    Photo of 111 S Pineapple Avenue #903, Sarasota, FL 34236 (MLS # A4624999)
    111 S Pineapple Avenue #903, Sarasota, FL
    111 S Pineapple Avenue #903
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,600 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  2. Photo of 1569 7th Street, Sarasota, FL 34236 (MLS # A4625551)
    $3,099,000
    Photo of 1569 7th Street, Sarasota, FL 34236 (MLS # A4625551)
    Photo of 1569 7th Street, Sarasota, FL 34236 (MLS # A4625551)
    1569 7th Street, Sarasota, FL
    1569 7th Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 860 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  3. Photo of 3280 Southfield Lane #804, Sarasota, FL 34239 (MLS # TB8309229)
    $289,900
    Photo of 3280 Southfield Lane #804, Sarasota, FL 34239 (MLS # TB8309229)
    Photo of 3280 Southfield Lane #804, Sarasota, FL 34239 (MLS # TB8309229)
    3280 Southfield Lane #804, Sarasota, FL
    3280 Southfield Lane #804
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  4. Photo of 915 Seaside Drive #410, Weeks 14-15, Sarasota, FL 34242 (MLS # A4624655)
    $78,000
    Photo of 915 Seaside Drive #410, Weeks 14-15, Sarasota, FL 34242 (MLS # A4624655)
    Photo of 915 Seaside Drive #410, Weeks 14-15, Sarasota, FL 34242 (MLS # A4624655)
    915 Seaside Drive #410, Weeks 14-15, Sarasota, FL
    915 Seaside Drive #410, Weeks 14-15
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,900 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 128 Golden Gate Point #501B, Sarasota, FL 34236 (MLS # A4623038)
    $2,995,000
    Photo of 128 Golden Gate Point #501B, Sarasota, FL 34236 (MLS # A4623038)
    Photo of 128 Golden Gate Point #501B, Sarasota, FL 34236 (MLS # A4623038)
    128 Golden Gate Point #501B, Sarasota, FL
    128 Golden Gate Point #501B
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 3,000 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  6. Photo of 3153 Jennings Drive, Sarasota, FL 34239 (MLS # A4624964)
    $425,000
    Photo of 3153 Jennings Drive, Sarasota, FL 34239 (MLS # A4624964)
    Photo of 3153 Jennings Drive, Sarasota, FL 34239 (MLS # A4624964)
    3153 Jennings Drive, Sarasota, FL
    3153 Jennings Drive
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,373 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  7. Photo of 1542 Oak Street #6, Sarasota, FL 34236 (MLS # A4624938)
    $490,000
    Photo of 1542 Oak Street #6, Sarasota, FL 34236 (MLS # A4624938)
    Photo of 1542 Oak Street #6, Sarasota, FL 34236 (MLS # A4624938)
    1542 Oak Street #6, Sarasota, FL
    1542 Oak Street #6
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 990 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  8. Photo of 1160 Morningside Place, Sarasota, FL 34236 (MLS # A4624903)
    $9,000
    Photo of 1160 Morningside Place, Sarasota, FL 34236 (MLS # A4624903)
    Photo of 1160 Morningside Place, Sarasota, FL 34236 (MLS # A4624903)
    1160 Morningside Place, Sarasota, FL
    1160 Morningside Place
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,346 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  9. Photo of 1270 5th Street, Sarasota, FL 34236 (MLS # A4624901)
    $4,200
    Photo of 1270 5th Street, Sarasota, FL 34236 (MLS # A4624901)
    Photo of 1270 5th Street, Sarasota, FL 34236 (MLS # A4624901)
    1270 5th Street, Sarasota, FL
    1270 5th Street
    Sarasota, FL
    • 4 Beds
    • 2 Baths
    • 2,100 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  10. Photo of 2425 Temple Street, Sarasota, FL 34239 (MLS # A4624829)
    $1,829,000
    Photo of 2425 Temple Street, Sarasota, FL 34239 (MLS # A4624829)
    Photo of 2425 Temple Street, Sarasota, FL 34239 (MLS # A4624829)
    2425 Temple Street, Sarasota, FL
    2425 Temple Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,915 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  11. Photo of 2055 Arlington Street #204, Sarasota, FL 34239 (MLS # A4624791)
    $1,800
    Photo of 2055 Arlington Street #204, Sarasota, FL 34239 (MLS # A4624791)
    Photo of 2055 Arlington Street #204, Sarasota, FL 34239 (MLS # A4624791)
    2055 Arlington Street #204, Sarasota, FL
    2055 Arlington Street #204
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 856 Home (sqft)
    • 2 Baths
    • 24,830 Lot (sqft)
  12. Photo of 737 Tropical Circle, Sarasota, FL 34242 (MLS # A4623913)
    $1,500,000
    Photo of 737 Tropical Circle, Sarasota, FL 34242 (MLS # A4623913)
    Photo of 737 Tropical Circle, Sarasota, FL 34242 (MLS # A4623913)
    737 Tropical Circle, Sarasota, FL
    737 Tropical Circle
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,512 Home (sqft)
    • 3 Baths
    • 16,553 Lot (sqft)
  13. Photo of 301 Quay Commons #1209, Sarasota, FL 34236 (MLS # A4624806)
    $1,950,000
    Photo of 301 Quay Commons #1209, Sarasota, FL 34236 (MLS # A4624806)
    Photo of 301 Quay Commons #1209, Sarasota, FL 34236 (MLS # A4624806)
    301 Quay Commons #1209, Sarasota, FL
    301 Quay Commons #1209
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,869 Home (sqft)
    • 3 Baths
    • 42,689 Lot (sqft)
  14. Photo of 1677 4th Street, Sarasota, FL 34236 (MLS # A4624136)
    $1,125,000
    Photo of 1677 4th Street, Sarasota, FL 34236 (MLS # A4624136)
    Photo of 1677 4th Street, Sarasota, FL 34236 (MLS # A4624136)
    64
     
    1677 4th Street, Sarasota, FL
    1677 4th Street
    Sarasota, FL
    • 5 Beds
    • 4 Baths
    • 2,690 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  15. Photo of 1663 4th Street, Sarasota, FL 34236 (MLS # A4623779)
    $849,500
    Photo of 1663 4th Street, Sarasota, FL 34236 (MLS # A4623779)
    Photo of 1663 4th Street, Sarasota, FL 34236 (MLS # A4623779)
    72
     
    1663 4th Street, Sarasota, FL
    1663 4th Street
    Sarasota, FL
    • 4 Beds
    • 2 Baths
    • 1,859 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  16. Photo of 8911 Midnight Pass Road #110, Sarasota, FL 34242 (MLS # A4624485)
    $649,900
    Photo of 8911 Midnight Pass Road #110, Sarasota, FL 34242 (MLS # A4624485)
    Photo of 8911 Midnight Pass Road #110, Sarasota, FL 34242 (MLS # A4624485)
    8911 Midnight Pass Road #110, Sarasota, FL
    8911 Midnight Pass Road #110
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,093 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  17. Photo of 1064 N Tamiami Trail #1324, Sarasota, FL 34236 (MLS # TB8306564)
    $2,200
    Photo of 1064 N Tamiami Trail #1324, Sarasota, FL 34236 (MLS # TB8306564)
    Photo of 1064 N Tamiami Trail #1324, Sarasota, FL 34236 (MLS # TB8306564)
    1064 N Tamiami Trail #1324, Sarasota, FL
    1064 N Tamiami Trail #1324
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 804 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
  18. Photo of 1255 N Gulfstream Avenue #1003, Sarasota, FL 34236 (MLS # A4624160)
    $1,400,000
    Photo of 1255 N Gulfstream Avenue #1003, Sarasota, FL 34236 (MLS # A4624160)
    Photo of 1255 N Gulfstream Avenue #1003, Sarasota, FL 34236 (MLS # A4624160)
    1255 N Gulfstream Avenue #1003, Sarasota, FL
    1255 N Gulfstream Avenue #1003
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,565 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 4105 4th Avenue, Holmes Beach, FL 34217 (MLS # A4622759)
    $3,495,000
    Photo of 4105 4th Avenue, Holmes Beach, FL 34217 (MLS # A4622759)
    Photo of 4105 4th Avenue, Holmes Beach, FL 34217 (MLS # A4622759)
    4105 4th Avenue, Holmes Beach, FL
    4105 4th Avenue
    Holmes Beach, FL
    • 6 Beds
    • 7 Baths
    • 2,453 Home (sqft)
    • 7 Baths
    • 5,228 Lot (sqft)
  20. Photo of 915 Seaside Drive #312, Weeks 8-9, Sarasota, FL 34242 (MLS # A4624333)
    $80,000
    Photo of 915 Seaside Drive #312, Weeks 8-9, Sarasota, FL 34242 (MLS # A4624333)
    Photo of 915 Seaside Drive #312, Weeks 8-9, Sarasota, FL 34242 (MLS # A4624333)
    915 Seaside Drive #312, Weeks 8-9, Sarasota, FL
    915 Seaside Drive #312, Weeks 8-9
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,750 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 6157 Midnight Pass Road #A51, Sarasota, FL 34242 (MLS # A4623461)
    $485,000
    Photo of 6157 Midnight Pass Road #A51, Sarasota, FL 34242 (MLS # A4623461)
    Photo of 6157 Midnight Pass Road #A51, Sarasota, FL 34242 (MLS # A4623461)
    6157 Midnight Pass Road #A51, Sarasota, FL
    6157 Midnight Pass Road #A51
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 690 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  22. Photo of 306 Island Circle, Sarasota, FL 34242 (MLS # A4624278)
    $7,500
    Photo of 306 Island Circle, Sarasota, FL 34242 (MLS # A4624278)
    Photo of 306 Island Circle, Sarasota, FL 34242 (MLS # A4624278)
    306 Island Circle, Sarasota, FL
    306 Island Circle
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,392 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  23. Photo of 2923 Marshall Drive, Sarasota, FL 34239 (MLS # A4624820)
    $435,000
    Photo of 2923 Marshall Drive, Sarasota, FL 34239 (MLS # A4624820)
    Photo of 2923 Marshall Drive, Sarasota, FL 34239 (MLS # A4624820)
    2923 Marshall Drive, Sarasota, FL
    2923 Marshall Drive
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 894 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  24. Photo of 1904 S Shade Avenue, Sarasota, FL 34239 (MLS # A4624214)
    $2,900
    Photo of 1904 S Shade Avenue, Sarasota, FL 34239 (MLS # A4624214)
    Photo of 1904 S Shade Avenue, Sarasota, FL 34239 (MLS # A4624214)
    1904 S Shade Avenue, Sarasota, FL
    1904 S Shade Avenue
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,744 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  25. Photo of 702 Treasure Boat Way, Sarasota, FL 34242 (MLS # A4623892)
    $1,599,000
    Photo of 702 Treasure Boat Way, Sarasota, FL 34242 (MLS # A4623892)
    Photo of 702 Treasure Boat Way, Sarasota, FL 34242 (MLS # A4623892)
    702 Treasure Boat Way, Sarasota, FL
    702 Treasure Boat Way
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,299 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  26. Photo of 1065 Gulf Of Mexico Drive #302, Longboat Key, FL 34228 (MLS # A4624142)
    $849,000
    Photo of 1065 Gulf Of Mexico Drive #302, Longboat Key, FL 34228 (MLS # A4624142)
    Photo of 1065 Gulf Of Mexico Drive #302, Longboat Key, FL 34228 (MLS # A4624142)
    1065 Gulf Of Mexico Drive #302, Longboat Key, FL
    1065 Gulf Of Mexico Drive #302
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,392 Home (sqft)
    • 2 Baths
    • 7.98 Lot (ac)
  27. Photo of 2431 Loma Linda Street, Sarasota, FL 34239 (MLS # A4624205)
    $4,250
    Photo of 2431 Loma Linda Street, Sarasota, FL 34239 (MLS # A4624205)
    Photo of 2431 Loma Linda Street, Sarasota, FL 34239 (MLS # A4624205)
    2431 Loma Linda Street, Sarasota, FL
    2431 Loma Linda Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,254 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  28. Photo of 750 N Tamiami Trail #421, Sarasota, FL 34236 (MLS # A4624036)
    $465,000
    Photo of 750 N Tamiami Trail #421, Sarasota, FL 34236 (MLS # A4624036)
    Photo of 750 N Tamiami Trail #421, Sarasota, FL 34236 (MLS # A4624036)
    750 N Tamiami Trail #421, Sarasota, FL
    750 N Tamiami Trail #421
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 1,020 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  29. Photo of 1500 State Street #401, Sarasota, FL 34236 (MLS # A4624093)
    $885,000
    Photo of 1500 State Street #401, Sarasota, FL 34236 (MLS # A4624093)
    Photo of 1500 State Street #401, Sarasota, FL 34236 (MLS # A4624093)
    30
     
    1500 State Street #401, Sarasota, FL
    1500 State Street #401
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,028 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 453 E Royal Flamingo Drive, Sarasota, FL 34236 (MLS # A4624049)
    $8,495,000
    Photo of 453 E Royal Flamingo Drive, Sarasota, FL 34236 (MLS # A4624049)
    Photo of 453 E Royal Flamingo Drive, Sarasota, FL 34236 (MLS # A4624049)
    453 E Royal Flamingo Drive, Sarasota, FL
    453 E Royal Flamingo Drive
    Sarasota, FL
    • 5 Beds
    • 6 Baths
    • 4,500 Home (sqft)
    • 6 Baths
    • 14,811 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 11/23/24 8:13 AM PST.

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