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 LONGBOAT KEY, FL 34228 (MLS # A4572396)
    $5,500
    Photo of LONGBOAT KEY, FL 34228 (MLS # A4572396)
    Photo of LONGBOAT KEY, FL 34228 (MLS # A4572396)
    MLS # A4572396, LONGBOAT KEY, FL
    MLS # A4572396
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,257 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 810 S BAY BOULEVARD #A, ANNA MARIA, FL 34216 (MLS # A4570743)
    $7,495,000
    Photo of 810 S BAY BOULEVARD #A, ANNA MARIA, FL 34216 (MLS # A4570743)
    Photo of 810 S BAY BOULEVARD #A, ANNA MARIA, FL 34216 (MLS # A4570743)
    810 S BAY BOULEVARD #A, ANNA MARIA, FL
    810 S BAY BOULEVARD #A
    ANNA MARIA, FL
    • 4 Beds
    • 5 Baths
    • 4,360 Home (sqft)
    • 5 Baths
    • 11,326 Lot (sqft)
  3. Photo of 233 COSMOPOLITAN COURT, SARASOTA, FL 34236 (MLS # A4570703)
    $925,000
    Photo of 233 COSMOPOLITAN COURT, SARASOTA, FL 34236 (MLS # A4570703)
    Photo of 233 COSMOPOLITAN COURT, SARASOTA, FL 34236 (MLS # A4570703)
    233 COSMOPOLITAN COURT, SARASOTA, FL
    233 COSMOPOLITAN COURT
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,680 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  4. Photo of 1125 W PEPPERTREE DRIVE #803, SARASOTA, FL 34242 (MLS # A4572053)
    $975,000
    Photo of 1125 W PEPPERTREE DRIVE #803, SARASOTA, FL 34242 (MLS # A4572053)
    Photo of 1125 W PEPPERTREE DRIVE #803, SARASOTA, FL 34242 (MLS # A4572053)
    1125 W PEPPERTREE DRIVE #803, SARASOTA, FL
    1125 W PEPPERTREE DRIVE #803
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  5. Photo of 8701 MIDNIGHT PASS ROAD #607A, SARASOTA, FL 34242 (MLS # A4572047)
    $975,000
    Photo of 8701 MIDNIGHT PASS ROAD #607A, SARASOTA, FL 34242 (MLS # A4572047)
    Photo of 8701 MIDNIGHT PASS ROAD #607A, SARASOTA, FL 34242 (MLS # A4572047)
    8701 MIDNIGHT PASS ROAD #607A, SARASOTA, FL
    8701 MIDNIGHT PASS ROAD #607A
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,922 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  6. Photo of 1212 BENJAMIN FRANKLIN DRIVE #308, SARASOTA, FL 34236 (MLS # A4572145)
    $1,199,000
    Photo of 1212 BENJAMIN FRANKLIN DRIVE #308, SARASOTA, FL 34236 (MLS # A4572145)
    Photo of 1212 BENJAMIN FRANKLIN DRIVE #308, SARASOTA, FL 34236 (MLS # A4572145)
    1212 BENJAMIN FRANKLIN DRIVE #308, SARASOTA, FL
    1212 BENJAMIN FRANKLIN DRIVE #308
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,421 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  7. Photo of 3017 AVENUE E, HOLMES BEACH, FL 34217 (MLS # A4572219)
    $3,985,000
    Photo of 3017 AVENUE E, HOLMES BEACH, FL 34217 (MLS # A4572219)
    Photo of 3017 AVENUE E, HOLMES BEACH, FL 34217 (MLS # A4572219)
    40
     
    3017 AVENUE E, HOLMES BEACH, FL
    3017 AVENUE E
    HOLMES BEACH, FL
    • 4 Beds
    • 5 Baths
    • 2,875 Home (sqft)
    • 5 Baths
    • 6,534 Lot (sqft)
  8. Photo of 3451 SEA VIEW STREET, SARASOTA, FL 34239 (MLS # A4572271)
    $2,600
    Photo of 3451 SEA VIEW STREET, SARASOTA, FL 34239 (MLS # A4572271)
    Photo of 3451 SEA VIEW STREET, SARASOTA, FL 34239 (MLS # A4572271)
    3451 SEA VIEW STREET, SARASOTA, FL
    3451 SEA VIEW STREET
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,565 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  9. Photo of 5325 MARINA DRIVE #423, HOLMES BEACH, FL 34217 (MLS # A4572264)
    $699,000
    Photo of 5325 MARINA DRIVE #423, HOLMES BEACH, FL 34217 (MLS # A4572264)
    Photo of 5325 MARINA DRIVE #423, HOLMES BEACH, FL 34217 (MLS # A4572264)
    5325 MARINA DRIVE #423, HOLMES BEACH, FL
    5325 MARINA DRIVE #423
    HOLMES BEACH, FL
    • 2 Beds
    • 2 Baths
    • 1,023 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  10. Photo of 223 GOLDEN GATE POINT #5A, SARASOTA, FL 34236 (MLS # A4572253)
    $3,400,000
    Photo of 223 GOLDEN GATE POINT #5A, SARASOTA, FL 34236 (MLS # A4572253)
    Photo of 223 GOLDEN GATE POINT #5A, SARASOTA, FL 34236 (MLS # A4572253)
    223 GOLDEN GATE POINT #5A, SARASOTA, FL
    223 GOLDEN GATE POINT #5A
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,832 Home (sqft)
    • 4 Baths
    • 43,560 Lot (sqft)
  11. Photo of 223 GOLDEN GATE POINT #8C, SARASOTA, FL 34236 (MLS # A4572252)
    $5,800,000
    Photo of 223 GOLDEN GATE POINT #8C, SARASOTA, FL 34236 (MLS # A4572252)
    Photo of 223 GOLDEN GATE POINT #8C, SARASOTA, FL 34236 (MLS # A4572252)
    223 GOLDEN GATE POINT #8C, SARASOTA, FL
    223 GOLDEN GATE POINT #8C
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,068 Home (sqft)
    • 4 Baths
    • 43,560 Lot (sqft)
  12. Photo of 2737 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570967)
    $699,000
    Photo of 2737 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570967)
    Photo of 2737 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570967)
    2737 SIESTA DRIVE, SARASOTA, FL
    2737 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,941 Home (sqft)
    • 3 Baths
    • 15,246 Lot (sqft)
  13. Photo of 113 CEDAR AVENUE, ANNA MARIA, FL 34216 (MLS # A4572085)
    $1,900,000
    Photo of 113 CEDAR AVENUE, ANNA MARIA, FL 34216 (MLS # A4572085)
    Photo of 113 CEDAR AVENUE, ANNA MARIA, FL 34216 (MLS # A4572085)
    113 CEDAR AVENUE, ANNA MARIA, FL
    113 CEDAR AVENUE
    ANNA MARIA, FL
    • 2 Beds
    • 2 Baths
    • 964 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  14. Photo of 2208 BOUGAINVILLEA STREET, SARASOTA, FL 34239 (MLS # A4571424)
    $2,275,000
    Photo of 2208 BOUGAINVILLEA STREET, SARASOTA, FL 34239 (MLS # A4571424)
    Photo of 2208 BOUGAINVILLEA STREET, SARASOTA, FL 34239 (MLS # A4571424)
    16
     
    2208 BOUGAINVILLEA STREET, SARASOTA, FL
    2208 BOUGAINVILLEA STREET
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,220 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  15. Photo of 3240 GULF OF MEXICO DRIVE #603, LONGBOAT KEY, FL 34228 (MLS # A4571215)
    $2,300
    Photo of 3240 GULF OF MEXICO DRIVE #603, LONGBOAT KEY, FL 34228 (MLS # A4571215)
    Photo of 3240 GULF OF MEXICO DRIVE #603, LONGBOAT KEY, FL 34228 (MLS # A4571215)
    3240 GULF OF MEXICO DRIVE #603, LONGBOAT KEY, FL
    3240 GULF OF MEXICO DRIVE #603
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 4651 GULF OF MEXICO DRIVE #102, LONGBOAT KEY, FL 34228 (MLS # A4571454)
    $7,200,000
    Photo of 4651 GULF OF MEXICO DRIVE #102, LONGBOAT KEY, FL 34228 (MLS # A4571454)
    Photo of 4651 GULF OF MEXICO DRIVE #102, LONGBOAT KEY, FL 34228 (MLS # A4571454)
    4651 GULF OF MEXICO DRIVE #102, LONGBOAT KEY, FL
    4651 GULF OF MEXICO DRIVE #102
    LONGBOAT KEY, FL
    • 4 Beds
    • 6 Baths
    • 4,007 Home (sqft)
    • 6 Baths
    • 3.40 Lot (ac)
  17. Photo of 101 S GULFSTREAM AVENUE #16C, SARASOTA, FL 34236 (MLS # A4572168)
    $594,500
    Photo of 101 S GULFSTREAM AVENUE #16C, SARASOTA, FL 34236 (MLS # A4572168)
    Photo of 101 S GULFSTREAM AVENUE #16C, SARASOTA, FL 34236 (MLS # A4572168)
    101 S GULFSTREAM AVENUE #16C, SARASOTA, FL
    101 S GULFSTREAM AVENUE #16C
    SARASOTA, FL
    • 1 Bed
    • 2 Baths
    • 1,002 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  18. Photo of 538 CANAL ROAD, SARASOTA, FL 34242 (MLS # A4571945)
    $6,850,000
    Photo of 538 CANAL ROAD, SARASOTA, FL 34242 (MLS # A4571945)
    Photo of 538 CANAL ROAD, SARASOTA, FL 34242 (MLS # A4571945)
    538 CANAL ROAD, SARASOTA, FL
    538 CANAL ROAD
    SARASOTA, FL
    • 8 Beds
    • 7 Baths
    • 4,094 Home (sqft)
    • 7 Baths
    • 6,534 Lot (sqft)
  19. Photo of 3330 GULF OF MEXICO DRIVE #106-D, LONGBOAT KEY, FL 34228 (MLS # T3449781)
    $749,000
    Photo of 3330 GULF OF MEXICO DRIVE #106-D, LONGBOAT KEY, FL 34228 (MLS # T3449781)
    Photo of 3330 GULF OF MEXICO DRIVE #106-D, LONGBOAT KEY, FL 34228 (MLS # T3449781)
    3330 GULF OF MEXICO DRIVE #106-D, LONGBOAT KEY, FL
    3330 GULF OF MEXICO DRIVE #106-D
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,106 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  20. Photo of 1188 N TAMIAMI TRAIL #205-B, SARASOTA, FL 34236 (MLS # A4572090)
    $5,940
    Photo of 1188 N TAMIAMI TRAIL #205-B, SARASOTA, FL 34236 (MLS # A4572090)
    Photo of 1188 N TAMIAMI TRAIL #205-B, SARASOTA, FL 34236 (MLS # A4572090)
    1188 N TAMIAMI TRAIL #205-B, SARASOTA, FL
    1188 N TAMIAMI TRAIL #205-B
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 87 Home (sqft)
    • 0 Baths
    • 41,382 Lot (sqft)
  21. Photo of 1508 DOLPHIN STREET #4, SARASOTA, FL 34236 (MLS # A4572127)
    $1,850
    Photo of 1508 DOLPHIN STREET #4, SARASOTA, FL 34236 (MLS # A4572127)
    Photo of 1508 DOLPHIN STREET #4, SARASOTA, FL 34236 (MLS # A4572127)
    1508 DOLPHIN STREET #4, SARASOTA, FL
    1508 DOLPHIN STREET #4
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 412 Home (sqft)
    • 1 Bath
    • 8,610.00 Lot (ac)
  22. Photo of 3751 S SCHOOL AVENUE #26, SARASOTA, FL 34239 (MLS # A4572120)
    $1,950
    Photo of 3751 S SCHOOL AVENUE #26, SARASOTA, FL 34239 (MLS # A4572120)
    Photo of 3751 S SCHOOL AVENUE #26, SARASOTA, FL 34239 (MLS # A4572120)
    3751 S SCHOOL AVENUE #26, SARASOTA, FL
    3751 S SCHOOL AVENUE #26
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 964 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 3484 HAMILTON AVENUE, SARASOTA, FL 34242 (MLS # A4571423)
    $1,500,000
    Photo of 3484 HAMILTON AVENUE, SARASOTA, FL 34242 (MLS # A4571423)
    Photo of 3484 HAMILTON AVENUE, SARASOTA, FL 34242 (MLS # A4571423)
    3484 HAMILTON AVENUE, SARASOTA, FL
    3484 HAMILTON AVENUE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 2,658 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  24. Photo of 2107 ORCHID STREET, SARASOTA, FL 34239 (MLS # A4572088)
    $675,000
    Photo of 2107 ORCHID STREET, SARASOTA, FL 34239 (MLS # A4572088)
    Photo of 2107 ORCHID STREET, SARASOTA, FL 34239 (MLS # A4572088)
    2107 ORCHID STREET, SARASOTA, FL
    2107 ORCHID STREET
    SARASOTA, FL
    • 2 Beds
    • 1 Bath
    • 1,032 Home (sqft)
    • 1 Bath
    • 9,148 Lot (sqft)
  25. Photo of 831 SIESTA DRIVE, SARASOTA, FL 34242 (MLS # A4572070)
    $1,200,000
    Photo of 831 SIESTA DRIVE, SARASOTA, FL 34242 (MLS # A4572070)
    Photo of 831 SIESTA DRIVE, SARASOTA, FL 34242 (MLS # A4572070)
    31
     
    831 SIESTA DRIVE, SARASOTA, FL
    831 SIESTA DRIVE
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 16,989 Lot (sqft)
  26. Photo of 3520 MINEOLA DRIVE, SARASOTA, FL 34239 (MLS # A4572066)
    $6,000
    Photo of 3520 MINEOLA DRIVE, SARASOTA, FL 34239 (MLS # A4572066)
    Photo of 3520 MINEOLA DRIVE, SARASOTA, FL 34239 (MLS # A4572066)
    3520 MINEOLA DRIVE, SARASOTA, FL
    3520 MINEOLA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,652 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  27. Photo of 2055 ARLINGTON STREET #201, SARASOTA, FL 34239 (MLS # A4568748)
    $2,050
    Photo of 2055 ARLINGTON STREET #201, SARASOTA, FL 34239 (MLS # A4568748)
    Photo of 2055 ARLINGTON STREET #201, SARASOTA, FL 34239 (MLS # A4568748)
    2055 ARLINGTON STREET #201, SARASOTA, FL
    2055 ARLINGTON STREET #201
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,100 Home (sqft)
    • 2 Baths
    • 24,830 Lot (sqft)
  28. Photo of 3001 BEE RIDGE ROAD #210, SARASOTA, FL 34239 (MLS # A4570621)
    $1,575
    Photo of 3001 BEE RIDGE ROAD #210, SARASOTA, FL 34239 (MLS # A4570621)
    Photo of 3001 BEE RIDGE ROAD #210, SARASOTA, FL 34239 (MLS # A4570621)
    3001 BEE RIDGE ROAD #210, SARASOTA, FL
    3001 BEE RIDGE ROAD #210
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 560 Home (sqft)
    • 1 Bath
    • 1.24 Lot (ac)
  29. Photo of 3001 BEE RIDGE ROAD #110, SARASOTA, FL 34239 (MLS # A4569942)
    $1,650
    Photo of 3001 BEE RIDGE ROAD #110, SARASOTA, FL 34239 (MLS # A4569942)
    Photo of 3001 BEE RIDGE ROAD #110, SARASOTA, FL 34239 (MLS # A4569942)
    3001 BEE RIDGE ROAD #110, SARASOTA, FL
    3001 BEE RIDGE ROAD #110
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 560 Home (sqft)
    • 1 Bath
    • 1.24 Lot (ac)
  30. Photo of 1801 GULF DRIVE N #279, BRADENTON BEACH, FL 34217 (MLS # A4571889)
    $495,000
    Photo of 1801 GULF DRIVE N #279, BRADENTON BEACH, FL 34217 (MLS # A4571889)
    Photo of 1801 GULF DRIVE N #279, BRADENTON BEACH, FL 34217 (MLS # A4571889)
    1801 GULF DRIVE N #279, BRADENTON BEACH, FL
    1801 GULF DRIVE N #279
    BRADENTON BEACH, FL
    • 1 Bed
    • 1 Bath
    • 691 Home (sqft)
    • 1 Bath
    • 0 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 6/3/23 12:32 PM PDT.

This MLS IDX is (c) Diverse Solutions 2023. Privacy | Terms & Conditions

 
 

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