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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 3320 Gulf Of Mexico Drive #307C, Longboat Key, FL 34228 (MLS # A4625446)
    $595,000
    Photo of 3320 Gulf Of Mexico Drive #307C, Longboat Key, FL 34228 (MLS # A4625446)
    Photo of 3320 Gulf Of Mexico Drive #307C, Longboat Key, FL 34228 (MLS # A4625446)
    3320 Gulf Of Mexico Drive #307C, Longboat Key, FL
    3320 Gulf Of Mexico Drive #307C
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,187 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 219 Cosmopolitan Court, Sarasota, FL 34236 (MLS # A4626901)
    $1,475,000
    Photo of 219 Cosmopolitan Court, Sarasota, FL 34236 (MLS # A4626901)
    Photo of 219 Cosmopolitan Court, Sarasota, FL 34236 (MLS # A4626901)
    219 Cosmopolitan Court, Sarasota, FL
    219 Cosmopolitan Court
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,588 Home (sqft)
    • 4 Baths
    • 1,307 Lot (sqft)
  3. Photo of 990 Blvd Of The Arts #404, Sarasota, FL 34236 (MLS # A4625530)
    $2,495,000
    Photo of 990 Blvd Of The Arts #404, Sarasota, FL 34236 (MLS # A4625530)
    Photo of 990 Blvd Of The Arts #404, Sarasota, FL 34236 (MLS # A4625530)
    990 Blvd Of The Arts #404, Sarasota, FL
    990 Blvd Of The Arts #404
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 3,135 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  4. Photo of 33 S Gulfstream Avenue #1007, Sarasota, FL 34236 (MLS # A4625812)
    $649,000
    Photo of 33 S Gulfstream Avenue #1007, Sarasota, FL 34236 (MLS # A4625812)
    Photo of 33 S Gulfstream Avenue #1007, Sarasota, FL 34236 (MLS # A4625812)
    33 S Gulfstream Avenue #1007, Sarasota, FL
    33 S Gulfstream Avenue #1007
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 820 Home (sqft)
    • 1 Bath
    • 32,670 Lot (sqft)
  5. Photo of 750 N Tamiami Trail #416, Sarasota, FL 34236 (MLS # A4625772)
    $739,000
    Photo of 750 N Tamiami Trail #416, Sarasota, FL 34236 (MLS # A4625772)
    Photo of 750 N Tamiami Trail #416, Sarasota, FL 34236 (MLS # A4625772)
    750 N Tamiami Trail #416, Sarasota, FL
    750 N Tamiami Trail #416
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  6. Photo of 1919 Irving Street, Sarasota, FL 34236 (MLS # A4624889)
    $3,495,000
    Photo of 1919 Irving Street, Sarasota, FL 34236 (MLS # A4624889)
    Photo of 1919 Irving Street, Sarasota, FL 34236 (MLS # A4624889)
    1919 Irving Street, Sarasota, FL
    1919 Irving Street
    Sarasota, FL
    • 5 Beds
    • 6 Baths
    • 4,956 Home (sqft)
    • 6 Baths
    • 14,811 Lot (sqft)
  7. Photo of 5518 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4625736)
    $6,500
    Photo of 5518 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4625736)
    Photo of 5518 Shadow Lawn Drive, Sarasota, FL 34242 (MLS # A4625736)
    5518 Shadow Lawn Drive, Sarasota, FL
    5518 Shadow Lawn Drive
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,790 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  8. Photo of 4380 Exeter Drive #303, Longboat Key, FL 34228 (MLS # A4625662)
    $554,900
    Photo of 4380 Exeter Drive #303, Longboat Key, FL 34228 (MLS # A4625662)
    Photo of 4380 Exeter Drive #303, Longboat Key, FL 34228 (MLS # A4625662)
    4380 Exeter Drive #303, Longboat Key, FL
    4380 Exeter Drive #303
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,152 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  9. Photo of 1519 Harbor Drive, Sarasota, FL 34239 (MLS # A4625720)
    $2,000,000
    Photo of 1519 Harbor Drive, Sarasota, FL 34239 (MLS # A4625720)
    Photo of 1519 Harbor Drive, Sarasota, FL 34239 (MLS # A4625720)
    1519 Harbor Drive, Sarasota, FL
    1519 Harbor Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 13,940 Lot (sqft)
  10. Photo of 3806 Gulf Of Mexico Drive #C112, Longboat Key, FL 34228 (MLS # A4625663)
    $399,900
    Photo of 3806 Gulf Of Mexico Drive #C112, Longboat Key, FL 34228 (MLS # A4625663)
    Photo of 3806 Gulf Of Mexico Drive #C112, Longboat Key, FL 34228 (MLS # A4625663)
    3806 Gulf Of Mexico Drive #C112, Longboat Key, FL
    3806 Gulf Of Mexico Drive #C112
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,027 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  11. Photo of 2200 Bahia Vista Street #B3, Sarasota, FL 34239 (MLS # A4625576)
    $2,500
    Photo of 2200 Bahia Vista Street #B3, Sarasota, FL 34239 (MLS # A4625576)
    Photo of 2200 Bahia Vista Street #B3, Sarasota, FL 34239 (MLS # A4625576)
    2200 Bahia Vista Street #B3, Sarasota, FL
    2200 Bahia Vista Street #B3
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 982 Home (sqft)
    • 2 Baths
    • 1.31 Lot (ac)
  12. Photo of 2516 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4625581)
    $599,000
    Photo of 2516 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4625581)
    Photo of 2516 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4625581)
    2516 Tanglewood Drive, Sarasota, FL
    2516 Tanglewood Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 14,811 Lot (sqft)
  13. Photo of 2208 Bahia Vista Street #F1, Sarasota, FL 34239 (MLS # A4625574)
    $2,900
    Photo of 2208 Bahia Vista Street #F1, Sarasota, FL 34239 (MLS # A4625574)
    Photo of 2208 Bahia Vista Street #F1, Sarasota, FL 34239 (MLS # A4625574)
    2208 Bahia Vista Street #F1, Sarasota, FL
    2208 Bahia Vista Street #F1
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,313 Home (sqft)
    • 3 Baths
    • 1.31 Lot (ac)
  14. Photo of 2251 Gulf Of Mexico Drive #203, Longboat Key, FL 34228 (MLS # O6247566)
    $8,495,000
    Photo of 2251 Gulf Of Mexico Drive #203, Longboat Key, FL 34228 (MLS # O6247566)
    Photo of 2251 Gulf Of Mexico Drive #203, Longboat Key, FL 34228 (MLS # O6247566)
    2251 Gulf Of Mexico Drive #203, Longboat Key, FL
    2251 Gulf Of Mexico Drive #203
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 3,961 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
  15. Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4625429)
    $2,895,000
    Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4625429)
    Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4625429)
    42
     
    1959 Hibiscus Street, Sarasota, FL
    1959 Hibiscus Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,720 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  16. Photo of 8030 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4625440)
    $3,750,000
    Photo of 8030 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4625440)
    Photo of 8030 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4625440)
    21
     
    8030 Midnight Pass Road, Sarasota, FL
    8030 Midnight Pass Road
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 3,720 Home (sqft)
    • 6 Baths
    • 8,277 Lot (sqft)
  17. Photo of 988 Blvd Of The Arts #1712, Sarasota, FL 34236 (MLS # A4625434)
    $1,350,000
    Photo of 988 Blvd Of The Arts #1712, Sarasota, FL 34236 (MLS # A4625434)
    Photo of 988 Blvd Of The Arts #1712, Sarasota, FL 34236 (MLS # A4625434)
    988 Blvd Of The Arts #1712, Sarasota, FL
    988 Blvd Of The Arts #1712
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,729 Home (sqft)
    • 2 Baths
    • 2.80 Lot (ac)
  18. Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4624670)
    $2,275,000
    Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4624670)
    Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4624670)
    1690 Arlington Street, Sarasota, FL
    1690 Arlington Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 2,965 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  19. Photo of 3977 Roberts Point Road, Sarasota, FL 34242 (MLS # A4625343)
    $3,900,000
    Photo of 3977 Roberts Point Road, Sarasota, FL 34242 (MLS # A4625343)
    Photo of 3977 Roberts Point Road, Sarasota, FL 34242 (MLS # A4625343)
    3977 Roberts Point Road, Sarasota, FL
    3977 Roberts Point Road
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 7,060 Home (sqft)
    • 6 Baths
    • 15,682 Lot (sqft)
  20. Photo of 800 N Tamiami Trail #1111, Sarasota, FL 34236 (MLS # A4625324)
    $1,299,000
    Photo of 800 N Tamiami Trail #1111, Sarasota, FL 34236 (MLS # A4625324)
    Photo of 800 N Tamiami Trail #1111, Sarasota, FL 34236 (MLS # A4625324)
    800 N Tamiami Trail #1111, Sarasota, FL
    800 N Tamiami Trail #1111
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 3920 Roberts Point Road, Sarasota, FL 34242 (MLS # A4625300)
    $3,795,000
    Photo of 3920 Roberts Point Road, Sarasota, FL 34242 (MLS # A4625300)
    Photo of 3920 Roberts Point Road, Sarasota, FL 34242 (MLS # A4625300)
    42
     
    3920 Roberts Point Road, Sarasota, FL
    3920 Roberts Point Road
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,070 Home (sqft)
    • 5 Baths
    • 12,197 Lot (sqft)
  22. Photo of 800 N Tamiami Trail #1412, Sarasota, FL 34236 (MLS # A4625292)
    $749,000
    Photo of 800 N Tamiami Trail #1412, Sarasota, FL 34236 (MLS # A4625292)
    Photo of 800 N Tamiami Trail #1412, Sarasota, FL 34236 (MLS # A4625292)
    800 N Tamiami Trail #1412, Sarasota, FL
    800 N Tamiami Trail #1412
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 3257 Southfield Lane #918, Sarasota, FL 34239 (MLS # A4624841)
    $249,900
    Photo of 3257 Southfield Lane #918, Sarasota, FL 34239 (MLS # A4624841)
    Photo of 3257 Southfield Lane #918, Sarasota, FL 34239 (MLS # A4624841)
    3257 Southfield Lane #918, Sarasota, FL
    3257 Southfield Lane #918
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  24. Photo of 111 S Pineapple Avenue #1021, Sarasota, FL 34236 (MLS # A4624898)
    $1,599,000
    Photo of 111 S Pineapple Avenue #1021, Sarasota, FL 34236 (MLS # A4624898)
    Photo of 111 S Pineapple Avenue #1021, Sarasota, FL 34236 (MLS # A4624898)
    111 S Pineapple Avenue #1021, Sarasota, FL
    111 S Pineapple Avenue #1021
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,575 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  25. Photo of 382 Bob White Drive, Sarasota, FL 34236 (MLS # A4623115)
    $4,500,000
    Photo of 382 Bob White Drive, Sarasota, FL 34236 (MLS # A4623115)
    Photo of 382 Bob White Drive, Sarasota, FL 34236 (MLS # A4623115)
    382 Bob White Drive, Sarasota, FL
    382 Bob White Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,875 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
  26. Photo of 501 Harbor Point Road, Longboat Key, FL 34228 (MLS # A4625287)
    $10,500,000
    Photo of 501 Harbor Point Road, Longboat Key, FL 34228 (MLS # A4625287)
    Photo of 501 Harbor Point Road, Longboat Key, FL 34228 (MLS # A4625287)
    79
     
    501 Harbor Point Road, Longboat Key, FL
    501 Harbor Point Road
    Longboat Key, FL
    • 5 Beds
    • 6 Baths
    • 6,125 Home (sqft)
    • 6 Baths
    • 24,394 Lot (sqft)
  27. Photo of 2522 Fruit Tree Drive, Sarasota, FL 34239 (MLS # A4625162)
    $674,900
    Photo of 2522 Fruit Tree Drive, Sarasota, FL 34239 (MLS # A4625162)
    Photo of 2522 Fruit Tree Drive, Sarasota, FL 34239 (MLS # A4625162)
    2522 Fruit Tree Drive, Sarasota, FL
    2522 Fruit Tree Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,072 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  28. Photo of 1773 Harmony Lane, Sarasota, FL 34239 (MLS # A4625278)
    $949,000
    Photo of 1773 Harmony Lane, Sarasota, FL 34239 (MLS # A4625278)
    Photo of 1773 Harmony Lane, Sarasota, FL 34239 (MLS # A4625278)
    1773 Harmony Lane, Sarasota, FL
    1773 Harmony Lane
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,098 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  29. Photo of 2155 Oriole Drive, Sarasota, FL 34239 (MLS # A4624997)
    $1,595,000
    Photo of 2155 Oriole Drive, Sarasota, FL 34239 (MLS # A4624997)
    Photo of 2155 Oriole Drive, Sarasota, FL 34239 (MLS # A4624997)
    2155 Oriole Drive, Sarasota, FL
    2155 Oriole Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 14,375 Lot (sqft)
  30. Photo of 2234 Hibiscus Street, Sarasota, FL 34239 (MLS # A4617991)
    $1,880,000
    Photo of 2234 Hibiscus Street, Sarasota, FL 34239 (MLS # A4617991)
    Photo of 2234 Hibiscus Street, Sarasota, FL 34239 (MLS # A4617991)
    2234 Hibiscus Street, Sarasota, FL
    2234 Hibiscus Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,692 Home (sqft)
    • 4 Baths
    • 8,712 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 4:13 AM PST.

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