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 305 TARPON STREET, ANNA MARIA, FL 34216 (MLS # A4582858)
    $8,800,000
    Photo of 305 TARPON STREET, ANNA MARIA, FL 34216 (MLS # A4582858)
    Photo of 305 TARPON STREET, ANNA MARIA, FL 34216 (MLS # A4582858)
    305 TARPON STREET, ANNA MARIA, FL
    305 TARPON STREET
    ANNA MARIA, FL
    • 5 Beds
    • 6 Baths
    • 5,074 Home (sqft)
    • 6 Baths
    • 12,633 Lot (sqft)
  2. Photo of 340 W Royal Flamingo Drive, Sarasota, FL 34236 (MLS # A4601285)
    $8,750,000
    Photo of 340 W Royal Flamingo Drive, Sarasota, FL 34236 (MLS # A4601285)
    Photo of 340 W Royal Flamingo Drive, Sarasota, FL 34236 (MLS # A4601285)
    340 W Royal Flamingo Drive, Sarasota, FL
    340 W Royal Flamingo Drive
    Sarasota, FL
    • 4 Beds
    • 7 Baths
    • 6,067 Home (sqft)
    • 7 Baths
    • 15,246 Lot (sqft)
  3. Photo of 555 Quay Common #1803, Sarasota, FL 34236 (MLS # A4596638)
    $8,499,000
    Photo of 555 Quay Common #1803, Sarasota, FL 34236 (MLS # A4596638)
    Photo of 555 Quay Common #1803, Sarasota, FL 34236 (MLS # A4596638)
    555 Quay Common #1803, Sarasota, FL
    555 Quay Common #1803
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 4,360 Home (sqft)
    • 4 Baths
    • 42,689 Lot (sqft)
  4. Photo of 518 Blue Heron Drive, Anna Maria, FL 34216 (MLS # A4594598)
    $8,495,000
    Photo of 518 Blue Heron Drive, Anna Maria, FL 34216 (MLS # A4594598)
    Photo of 518 Blue Heron Drive, Anna Maria, FL 34216 (MLS # A4594598)
    100
     
    518 Blue Heron Drive, Anna Maria, FL
    518 Blue Heron Drive
    Anna Maria, FL
    • 5 Beds
    • 7 Baths
    • 5,098 Home (sqft)
    • 7 Baths
    • 14,375 Lot (sqft)
  5. Photo of 316 Beach Road, Sarasota, FL 34242 (MLS # A4571947)
    $8,450,000
    Photo of 316 Beach Road, Sarasota, FL 34242 (MLS # A4571947)
    Photo of 316 Beach Road, Sarasota, FL 34242 (MLS # A4571947)
    316 Beach Road, Sarasota, FL
    316 Beach Road
    Sarasota, FL
    • 8 Beds
    • 10 Baths
    • 4,681 Home (sqft)
    • 10 Baths
    • 5,663 Lot (sqft)
  6. Photo of 609 Norsota Way, Sarasota, FL 34242 (MLS # A4602572)
    $8,250,000
    Photo of 609 Norsota Way, Sarasota, FL 34242 (MLS # A4602572)
    Photo of 609 Norsota Way, Sarasota, FL 34242 (MLS # A4602572)
    609 Norsota Way, Sarasota, FL
    609 Norsota Way
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,701 Home (sqft)
    • 3 Baths
    • 24,830 Lot (sqft)
  7. Photo of 65 Lighthouse Point Drive, Longboat Key, FL 34228 (MLS # A4593518)
    $8,150,000
    Photo of 65 Lighthouse Point Drive, Longboat Key, FL 34228 (MLS # A4593518)
    Photo of 65 Lighthouse Point Drive, Longboat Key, FL 34228 (MLS # A4593518)
    65 Lighthouse Point Drive, Longboat Key, FL
    65 Lighthouse Point Drive
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 4,941 Home (sqft)
    • 5 Baths
    • 16,118 Lot (sqft)
  8. Photo of 759 N Shore Drive, Anna Maria, FL 34216 (MLS # T3500755)
    $8,000,000
    Photo of 759 N Shore Drive, Anna Maria, FL 34216 (MLS # T3500755)
    Photo of 759 N Shore Drive, Anna Maria, FL 34216 (MLS # T3500755)
    759 N Shore Drive, Anna Maria, FL
    759 N Shore Drive
    Anna Maria, FL
    • 4 Beds
    • 4 Baths
    • 1,760 Home (sqft)
    • 4 Baths
    • 40,947 Lot (sqft)
  9. Photo of 102 Sunset Lane, Holmes Beach, FL 34217 (MLS # A4556016)
    $7,995,000
    Photo of 102 Sunset Lane, Holmes Beach, FL 34217 (MLS # A4556016)
    Photo of 102 Sunset Lane, Holmes Beach, FL 34217 (MLS # A4556016)
    102 Sunset Lane, Holmes Beach, FL
    102 Sunset Lane
    Holmes Beach, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 25,701 Lot (sqft)
  10. Photo of 515 Canal Road, Sarasota, FL 34242 (MLS # A4564885)
    $7,985,000
    Photo of 515 Canal Road, Sarasota, FL 34242 (MLS # A4564885)
    Photo of 515 Canal Road, Sarasota, FL 34242 (MLS # A4564885)
    515 Canal Road, Sarasota, FL
    515 Canal Road
    Sarasota, FL
    • 12 Beds
    • 10 Baths
    • 5,835 Home (sqft)
    • 10 Baths
    • 9,584 Lot (sqft)
  11. Photo of 11101 Gulf Drive, Anna Maria, FL 34216 (MLS # A4601324)
    $7,950,000
    Photo of 11101 Gulf Drive, Anna Maria, FL 34216 (MLS # A4601324)
    Photo of 11101 Gulf Drive, Anna Maria, FL 34216 (MLS # A4601324)
    11101 Gulf Drive, Anna Maria, FL
    11101 Gulf Drive
    Anna Maria, FL
    • 6 Beds
    • 7 Baths
    • 4,280 Home (sqft)
    • 7 Baths
    • 10,890 Lot (sqft)
  12. Photo of 709 Key Royale Drive, Holmes Beach, FL 34217 (MLS # A4592827)
    $7,890,000
    Photo of 709 Key Royale Drive, Holmes Beach, FL 34217 (MLS # A4592827)
    Photo of 709 Key Royale Drive, Holmes Beach, FL 34217 (MLS # A4592827)
    709 Key Royale Drive, Holmes Beach, FL
    709 Key Royale Drive
    Holmes Beach, FL
    • 4 Beds
    • 4 Baths
    • 4,600 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  13. Photo of 89 Avenida Messina, Sarasota, FL 34242 (MLS # A4599873)
    $7,750,000
    Photo of 89 Avenida Messina, Sarasota, FL 34242 (MLS # A4599873)
    Photo of 89 Avenida Messina, Sarasota, FL 34242 (MLS # A4599873)
    89 Avenida Messina, Sarasota, FL
    89 Avenida Messina
    Sarasota, FL
    • 7 Beds
    • 8 Baths
    • 3,388 Home (sqft)
    • 8 Baths
    • 6,099 Lot (sqft)
  14. Photo of 1515 Hillview Drive, Sarasota, FL 34239 (MLS # A4592554)
    $7,650,000
    Photo of 1515 Hillview Drive, Sarasota, FL 34239 (MLS # A4592554)
    Photo of 1515 Hillview Drive, Sarasota, FL 34239 (MLS # A4592554)
    1515 Hillview Drive, Sarasota, FL
    1515 Hillview Drive
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 5,424 Home (sqft)
    • 6 Baths
    • 21,780 Lot (sqft)
  15. Photo of 528 72nd Street, Holmes Beach, FL 34217 (MLS # A4597657)
    $7,595,000
    Photo of 528 72nd Street, Holmes Beach, FL 34217 (MLS # A4597657)
    Photo of 528 72nd Street, Holmes Beach, FL 34217 (MLS # A4597657)
    528 72nd Street, Holmes Beach, FL
    528 72nd Street
    Holmes Beach, FL
    • 4 Beds
    • 5 Baths
    • 4,014 Home (sqft)
    • 5 Baths
    • 11,762 Lot (sqft)
  16. Photo of 2113 Avenue B #A, Bradenton Beach, FL 34217 (MLS # A4586931)
    $7,570,000
    Photo of 2113 Avenue B #A, Bradenton Beach, FL 34217 (MLS # A4586931)
    Photo of 2113 Avenue B #A, Bradenton Beach, FL 34217 (MLS # A4586931)
    2113 Avenue B #A, Bradenton Beach, FL
    2113 Avenue B #A
    Bradenton Beach, FL
    • 10 Beds
    • 11 Baths
    • 4,241 Home (sqft)
    • 11 Baths
    • 7,406 Lot (sqft)
  17. Photo of 119 Mckinley Drive, Sarasota, FL 34236 (MLS # A4602803)
    $7,500,000
    Photo of 119 Mckinley Drive, Sarasota, FL 34236 (MLS # A4602803)
    Photo of 119 Mckinley Drive, Sarasota, FL 34236 (MLS # A4602803)
    119 Mckinley Drive, Sarasota, FL
    119 Mckinley Drive
    Sarasota, FL
    • 10 Beds
    • 12 Baths
    • 4,443 Home (sqft)
    • 12 Baths
    • 8,712 Lot (sqft)
  18. Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4546764)
    $7,500,000
    Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4546764)
    Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4546764)
    11
     
    1490 Hillview Drive, Sarasota, FL
    1490 Hillview Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,474 Lot (sqft)
  19. Photo of 107 Maple Avenue, Anna Maria, FL 34216 (MLS # A4588760)
    $7,385,000
    Photo of 107 Maple Avenue, Anna Maria, FL 34216 (MLS # A4588760)
    Photo of 107 Maple Avenue, Anna Maria, FL 34216 (MLS # A4588760)
    107 Maple Avenue, Anna Maria, FL
    107 Maple Avenue
    Anna Maria, FL
    • 6 Beds
    • 7 Baths
    • 3,675 Home (sqft)
    • 7 Baths
    • 7,406 Lot (sqft)
  20. Photo of 808 N Bay Blvd, Anna Maria, FL 34216 (MLS # T3500255)
    $7,300,000
    Photo of 808 N Bay Blvd, Anna Maria, FL 34216 (MLS # T3500255)
    Photo of 808 N Bay Blvd, Anna Maria, FL 34216 (MLS # T3500255)
    808 N Bay Blvd, Anna Maria, FL
    808 N Bay Blvd
    Anna Maria, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 22,652 Lot (sqft)
  21. Photo of 808 N Bay Blvd, Anna Maria, FL 34216 (MLS # T3499199)
    $7,300,000
    Photo of 808 N Bay Blvd, Anna Maria, FL 34216 (MLS # T3499199)
    Photo of 808 N Bay Blvd, Anna Maria, FL 34216 (MLS # T3499199)
    808 N Bay Blvd, Anna Maria, FL
    808 N Bay Blvd
    Anna Maria, FL
    • 0 Beds
    • 0 Baths
    • 4,321 Home (sqft)
    • 0 Baths
    • 22,652 Lot (sqft)
  22. Photo of 214 Little Pond Lane, Sarasota, FL 34242 (MLS # A4600180)
    $7,250,000
    Photo of 214 Little Pond Lane, Sarasota, FL 34242 (MLS # A4600180)
    Photo of 214 Little Pond Lane, Sarasota, FL 34242 (MLS # A4600180)
    214 Little Pond Lane, Sarasota, FL
    214 Little Pond Lane
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 5,661 Home (sqft)
    • 4 Baths
    • 33,106 Lot (sqft)
  23. Photo of 118 N Warbler Lane, Sarasota, FL 34236 (MLS # A4557763)
    $7,250,000
    Photo of 118 N Warbler Lane, Sarasota, FL 34236 (MLS # A4557763)
    Photo of 118 N Warbler Lane, Sarasota, FL 34236 (MLS # A4557763)
    118 N Warbler Lane, Sarasota, FL
    118 N Warbler Lane
    Sarasota, FL
    • 4 Beds
    • 7 Baths
    • 4,594 Home (sqft)
    • 7 Baths
    • 14,811 Lot (sqft)
  24. Photo of 33 S Palm Avenue #1501, Sarasota, FL 34236 (MLS # A4596347)
    $7,200,000
    Photo of 33 S Palm Avenue #1501, Sarasota, FL 34236 (MLS # A4596347)
    Photo of 33 S Palm Avenue #1501, Sarasota, FL 34236 (MLS # A4596347)
    33 S Palm Avenue #1501, Sarasota, FL
    33 S Palm Avenue #1501
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  25. Photo of 7153 LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4576991)
    $7,200,000
    Photo of 7153 LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4576991)
    Photo of 7153 LA LENAIRE DRIVE, LONGBOAT KEY, FL 34228 (MLS # A4576991)
    7153 LA LENAIRE DRIVE, LONGBOAT KEY, FL
    7153 LA LENAIRE DRIVE
    LONGBOAT KEY, FL
    • 5 Beds
    • 7 Baths
    • 4,231 Home (sqft)
    • 7 Baths
    • 1.26 Lot (ac)
  26. Photo of 360 N Washington Drive, Sarasota, FL 34236 (MLS # A4599067)
    $6,999,000
    Photo of 360 N Washington Drive, Sarasota, FL 34236 (MLS # A4599067)
    Photo of 360 N Washington Drive, Sarasota, FL 34236 (MLS # A4599067)
    360 N Washington Drive, Sarasota, FL
    360 N Washington Drive
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,951 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
  27. Photo of 241 Willow Avenue, Anna Maria, FL 34216 (MLS # A4602699)
    $6,995,000
    Photo of 241 Willow Avenue, Anna Maria, FL 34216 (MLS # A4602699)
    Photo of 241 Willow Avenue, Anna Maria, FL 34216 (MLS # A4602699)
    241 Willow Avenue, Anna Maria, FL
    241 Willow Avenue
    Anna Maria, FL
    • 6 Beds
    • 7 Baths
    • 4,439 Home (sqft)
    • 7 Baths
    • 10,890 Lot (sqft)
  28. Photo of 361 Benjamin Franklin Drive #A, Sarasota, FL 34236 (MLS # N6131634)
    $6,995,000
    Photo of 361 Benjamin Franklin Drive #A, Sarasota, FL 34236 (MLS # N6131634)
    Photo of 361 Benjamin Franklin Drive #A, Sarasota, FL 34236 (MLS # N6131634)
    361 Benjamin Franklin Drive #A, Sarasota, FL
    361 Benjamin Franklin Drive #A
    Sarasota, FL
    • 5 Beds
    • 6 Baths
    • 5,405 Home (sqft)
    • 6 Baths
    • 6,970 Lot (sqft)
  29. Photo of 2514 Avenue C #A, Bradenton Beach, FL 34217 (MLS # A4596315)
    $6,995,000
    Photo of 2514 Avenue C #A, Bradenton Beach, FL 34217 (MLS # A4596315)
    Photo of 2514 Avenue C #A, Bradenton Beach, FL 34217 (MLS # A4596315)
    2514 Avenue C #A, Bradenton Beach, FL
    2514 Avenue C #A
    Bradenton Beach, FL
    • 14 Beds
    • 14 Baths
    • 5,852 Home (sqft)
    • 14 Baths
    • 9,148 Lot (sqft)
  30. Photo of 12126 Center Place, Sarasota, FL 34236 (MLS # A4593015)
    $6,995,000
    Photo of 12126 Center Place, Sarasota, FL 34236 (MLS # A4593015)
    Photo of 12126 Center Place, Sarasota, FL 34236 (MLS # A4593015)
    12126 Center Place, Sarasota, FL
    12126 Center Place
    Sarasota, FL
    • 5 Beds
    • 7 Baths
    • 4,750 Home (sqft)
    • 7 Baths
    • 12,197 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 3/28/24 11:59 AM PDT.

This MLS IDX is (c) Diverse Solutions 2024.

 
 

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