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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 304 67th Street #A, Bradenton Beach, FL 34217 (MLS # A4637927)
    $1,395,000
    Photo of 304 67th Street #A, Bradenton Beach, FL 34217 (MLS # A4637927)
    Photo of 304 67th Street #A, Bradenton Beach, FL 34217 (MLS # A4637927)
    304 67th Street #A, Bradenton Beach, FL
    304 67th Street #A
    Bradenton Beach, FL
    • 5 Beds
    • 4 Baths
    • 3,676 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  2. Photo of 1771 Ringling Boulevard #1001, Sarasota, FL 34236 (MLS # A4640806)
    $1,230,000
    Photo of 1771 Ringling Boulevard #1001, Sarasota, FL 34236 (MLS # A4640806)
    Photo of 1771 Ringling Boulevard #1001, Sarasota, FL 34236 (MLS # A4640806)
    1771 Ringling Boulevard #1001, Sarasota, FL
    1771 Ringling Boulevard #1001
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,808 Home (sqft)
    • 2 Baths
    • 1.09 Lot (ac)
  3. Photo of 350 Golden Gate Point #11, Sarasota, FL 34236 (MLS # A4639634)
    $1,245,885
    Photo of 350 Golden Gate Point #11, Sarasota, FL 34236 (MLS # A4639634)
    Photo of 350 Golden Gate Point #11, Sarasota, FL 34236 (MLS # A4639634)
    350 Golden Gate Point #11, Sarasota, FL
    350 Golden Gate Point #11
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,693 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  4. Photo of 6790 Sarasea Circle #6790, Sarasota, FL 34242 (MLS # A4639886)
    $865,000
    Photo of 6790 Sarasea Circle #6790, Sarasota, FL 34242 (MLS # A4639886)
    Photo of 6790 Sarasea Circle #6790, Sarasota, FL 34242 (MLS # A4639886)
    6790 Sarasea Circle #6790, Sarasota, FL
    6790 Sarasea Circle #6790
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,446 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 850 S Tamiami Trail #301, Sarasota, FL 34236 (MLS # A4640584)
    $368,000
    Photo of 850 S Tamiami Trail #301, Sarasota, FL 34236 (MLS # A4640584)
    Photo of 850 S Tamiami Trail #301, Sarasota, FL 34236 (MLS # A4640584)
    850 S Tamiami Trail #301, Sarasota, FL
    850 S Tamiami Trail #301
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 980 Home (sqft)
    • 2 Baths
    • 9.11 Lot (ac)
  6. Photo of 4708 Ocean Boulevard #E2, Sarasota, FL 34242 (MLS # O6281333)
    $3,950
    Photo of 4708 Ocean Boulevard #E2, Sarasota, FL 34242 (MLS # O6281333)
    Photo of 4708 Ocean Boulevard #E2, Sarasota, FL 34242 (MLS # O6281333)
    4708 Ocean Boulevard #E2, Sarasota, FL
    4708 Ocean Boulevard #E2
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,626 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  7. Photo of 120 Maple Avenue, Anna Maria, FL 34216 (MLS # A4639417)
    $1,699,000
    Photo of 120 Maple Avenue, Anna Maria, FL 34216 (MLS # A4639417)
    Photo of 120 Maple Avenue, Anna Maria, FL 34216 (MLS # A4639417)
    120 Maple Avenue, Anna Maria, FL
    120 Maple Avenue
    Anna Maria, FL
    • 3 Beds
    • 2 Baths
    • 1,764 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  8. Photo of Sarasota, FL 34239 (MLS # A4640697)
    $174,900
    Photo of Sarasota, FL 34239 (MLS # A4640697)
    Photo of Sarasota, FL 34239 (MLS # A4640697)
    MLS # A4640697, Sarasota, FL
    MLS # A4640697
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 1,500 Home (sqft)
    • 0 Baths
    • 0 Lot (sqft)
  9. Photo of 101 S Gulfstream Avenue #5K, Sarasota, FL 34236 (MLS # A4638917)
    $1,299,000
    Photo of 101 S Gulfstream Avenue #5K, Sarasota, FL 34236 (MLS # A4638917)
    Photo of 101 S Gulfstream Avenue #5K, Sarasota, FL 34236 (MLS # A4638917)
    101 S Gulfstream Avenue #5K, Sarasota, FL
    101 S Gulfstream Avenue #5K
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,408 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  10. Photo of 710 Treasure Boat Way, Sarasota, FL 34242 (MLS # TB8350585)
    $1,369,000
    Photo of 710 Treasure Boat Way, Sarasota, FL 34242 (MLS # TB8350585)
    Photo of 710 Treasure Boat Way, Sarasota, FL 34242 (MLS # TB8350585)
    710 Treasure Boat Way, Sarasota, FL
    710 Treasure Boat Way
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,963 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  11. Photo of 4234 Gulf Of Mexico Drive #E2, Longboat Key, FL 34228 (MLS # A4640661)
    $729,000
    Photo of 4234 Gulf Of Mexico Drive #E2, Longboat Key, FL 34228 (MLS # A4640661)
    Photo of 4234 Gulf Of Mexico Drive #E2, Longboat Key, FL 34228 (MLS # A4640661)
    45
     
    4234 Gulf Of Mexico Drive #E2, Longboat Key, FL
    4234 Gulf Of Mexico Drive #E2
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,150 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  12. Photo of 100 Central Avenue #D509, Sarasota, FL 34236 (MLS # N6137234)
    $1,575,000
    Photo of 100 Central Avenue #D509, Sarasota, FL 34236 (MLS # N6137234)
    Photo of 100 Central Avenue #D509, Sarasota, FL 34236 (MLS # N6137234)
    100 Central Avenue #D509, Sarasota, FL
    100 Central Avenue #D509
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,273 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  13. Photo of 522 Pine Avenue #6A, Anna Maria, FL 34216 (MLS # TB8350656)
    $549,900
    Photo of 522 Pine Avenue #6A, Anna Maria, FL 34216 (MLS # TB8350656)
    Photo of 522 Pine Avenue #6A, Anna Maria, FL 34216 (MLS # TB8350656)
    522 Pine Avenue #6A, Anna Maria, FL
    522 Pine Avenue #6A
    Anna Maria, FL
    • 2 Beds
    • 1 Bath
    • 822 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
  14. Photo of 111 S Pineapple Avenue #1206, Sarasota, FL 34236 (MLS # A4640521)
    $2,770,000
    Photo of 111 S Pineapple Avenue #1206, Sarasota, FL 34236 (MLS # A4640521)
    Photo of 111 S Pineapple Avenue #1206, Sarasota, FL 34236 (MLS # A4640521)
    44
     
    111 S Pineapple Avenue #1206, Sarasota, FL
    111 S Pineapple Avenue #1206
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,507 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  15. Photo of 1331 14th Street, Sarasota, FL 34236 (MLS # O6281131)
    $21,000
    Photo of 1331 14th Street, Sarasota, FL 34236 (MLS # O6281131)
    Photo of 1331 14th Street, Sarasota, FL 34236 (MLS # O6281131)
    1331 14th Street, Sarasota, FL
    1331 14th Street
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 884 Home (sqft)
    • 1 Bath
    • 6,099 Lot (sqft)
  16. Photo of 6701 Gulf Of Mexico Drive #311, Longboat Key, FL 34228 (MLS # A4640305)
    $849,900
    Photo of 6701 Gulf Of Mexico Drive #311, Longboat Key, FL 34228 (MLS # A4640305)
    Photo of 6701 Gulf Of Mexico Drive #311, Longboat Key, FL 34228 (MLS # A4640305)
    6701 Gulf Of Mexico Drive #311, Longboat Key, FL
    6701 Gulf Of Mexico Drive #311
    Longboat Key, FL
    • 1 Bed
    • 1 Bath
    • 936 Home (sqft)
    • 1 Bath
    • 4.25 Lot (ac)
  17. Photo of 448 Gulf Of Mexico Drive #A204, Longboat Key, FL 34228 (MLS # A4639143)
    $695,000
    Photo of 448 Gulf Of Mexico Drive #A204, Longboat Key, FL 34228 (MLS # A4639143)
    Photo of 448 Gulf Of Mexico Drive #A204, Longboat Key, FL 34228 (MLS # A4639143)
    448 Gulf Of Mexico Drive #A204, Longboat Key, FL
    448 Gulf Of Mexico Drive #A204
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,194 Home (sqft)
    • 2 Baths
    • 3.42 Lot (ac)
  18. Photo of 231 Hourglass Way #V5, Sarasota, FL 34242 (MLS # A4640327)
    $1,350,000
    Photo of 231 Hourglass Way #V5, Sarasota, FL 34242 (MLS # A4640327)
    Photo of 231 Hourglass Way #V5, Sarasota, FL 34242 (MLS # A4640327)
    231 Hourglass Way #V5, Sarasota, FL
    231 Hourglass Way #V5
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,662 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 3220 Southfield Lane #810, Sarasota, FL 34239 (MLS # D6140780)
    $314,900
    Photo of 3220 Southfield Lane #810, Sarasota, FL 34239 (MLS # D6140780)
    Photo of 3220 Southfield Lane #810, Sarasota, FL 34239 (MLS # D6140780)
    3220 Southfield Lane #810, Sarasota, FL
    3220 Southfield Lane #810
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,547 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  20. Photo of 2613 Temple Street, Sarasota, FL 34239 (MLS # A4640522)
    $1,680,000
    Photo of 2613 Temple Street, Sarasota, FL 34239 (MLS # A4640522)
    Photo of 2613 Temple Street, Sarasota, FL 34239 (MLS # A4640522)
    2613 Temple Street, Sarasota, FL
    2613 Temple Street
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 3,308 Home (sqft)
    • 4 Baths
    • 13,940 Lot (sqft)
  21. Photo of 1808 Flower Drive, Sarasota, FL 34239 (MLS # A4640544)
    $10,500,000
    Photo of 1808 Flower Drive, Sarasota, FL 34239 (MLS # A4640544)
    Photo of 1808 Flower Drive, Sarasota, FL 34239 (MLS # A4640544)
    1808 Flower Drive, Sarasota, FL
    1808 Flower Drive
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 5,609 Home (sqft)
    • 6 Baths
    • 24,394 Lot (sqft)
  22. Photo of 3278 Village Green Drive #1024, Sarasota, FL 34239 (MLS # A4639953)
    $279,900
    Photo of 3278 Village Green Drive #1024, Sarasota, FL 34239 (MLS # A4639953)
    Photo of 3278 Village Green Drive #1024, Sarasota, FL 34239 (MLS # A4639953)
    68
     
    3278 Village Green Drive #1024, Sarasota, FL
    3278 Village Green Drive #1024
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 1035 Seaside Drive #503, Sarasota, FL 34242 (MLS # A4639170)
    $5,150,000
    Photo of 1035 Seaside Drive #503, Sarasota, FL 34242 (MLS # A4639170)
    Photo of 1035 Seaside Drive #503, Sarasota, FL 34242 (MLS # A4639170)
    1035 Seaside Drive #503, Sarasota, FL
    1035 Seaside Drive #503
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,518 Home (sqft)
    • 4 Baths
    • 2.47 Lot (ac)
  24. Photo of 542 67th Street, Holmes Beach, FL 34217 (MLS # A4639601)
    $4,750,000
    Photo of 542 67th Street, Holmes Beach, FL 34217 (MLS # A4639601)
    Photo of 542 67th Street, Holmes Beach, FL 34217 (MLS # A4639601)
    542 67th Street, Holmes Beach, FL
    542 67th Street
    Holmes Beach, FL
    • 4 Beds
    • 4 Baths
    • 2,909 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  25. Photo of 301 Quay Commons #1811, Sarasota, FL 34236 (MLS # A4640537)
    $2,850,000
    Photo of 301 Quay Commons #1811, Sarasota, FL 34236 (MLS # A4640537)
    Photo of 301 Quay Commons #1811, Sarasota, FL 34236 (MLS # A4640537)
    301 Quay Commons #1811, Sarasota, FL
    301 Quay Commons #1811
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 2,079 Home (sqft)
    • 3 Baths
    • 42,689 Lot (sqft)
  26. Photo of 1241 Gulf Of Mexico Drive #1005, Longboat Key, FL 34228 (MLS # A4640586)
    $3,995,000
    Photo of 1241 Gulf Of Mexico Drive #1005, Longboat Key, FL 34228 (MLS # A4640586)
    Photo of 1241 Gulf Of Mexico Drive #1005, Longboat Key, FL 34228 (MLS # A4640586)
    1241 Gulf Of Mexico Drive #1005, Longboat Key, FL
    1241 Gulf Of Mexico Drive #1005
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,650 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 33 S Palm Avenue #901, Sarasota, FL 34236 (MLS # A4640484)
    $12,000
    Photo of 33 S Palm Avenue #901, Sarasota, FL 34236 (MLS # A4640484)
    Photo of 33 S Palm Avenue #901, Sarasota, FL 34236 (MLS # A4640484)
    33 S Palm Avenue #901, Sarasota, FL
    33 S Palm Avenue #901
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,045 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
  28. Photo of 301 Quay Commons #1411, Sarasota, FL 34236 (MLS # A4639075)
    $2,795,000
    Photo of 301 Quay Commons #1411, Sarasota, FL 34236 (MLS # A4639075)
    Photo of 301 Quay Commons #1411, Sarasota, FL 34236 (MLS # A4639075)
    63
     
    301 Quay Commons #1411, Sarasota, FL
    301 Quay Commons #1411
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 2,072 Home (sqft)
    • 3 Baths
    • 42,689 Lot (sqft)
  29. Photo of 2424 Webber Street, Sarasota, FL 34239 (MLS # TB8345824)
    $315,000
    Photo of 2424 Webber Street, Sarasota, FL 34239 (MLS # TB8345824)
    Photo of 2424 Webber Street, Sarasota, FL 34239 (MLS # TB8345824)
    2424 Webber Street, Sarasota, FL
    2424 Webber Street
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 772 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  30. Photo of 344 Monroe Drive, Sarasota, FL 34236 (MLS # A4639827)
    $1,200,000
    Photo of 344 Monroe Drive, Sarasota, FL 34236 (MLS # A4639827)
    Photo of 344 Monroe Drive, Sarasota, FL 34236 (MLS # A4639827)
    344 Monroe Drive, Sarasota, FL
    344 Monroe Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,247 Home (sqft)
    • 2 Baths
    • 9,148 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 2/16/25 8:33 AM PST.

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