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 1661 7TH STREET, SARASOTA, FL 34236 (MLS # A4582904)
    $947,000
    Photo of 1661 7TH STREET, SARASOTA, FL 34236 (MLS # A4582904)
    Photo of 1661 7TH STREET, SARASOTA, FL 34236 (MLS # A4582904)
    1661 7TH STREET, SARASOTA, FL
    1661 7TH STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,222 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  2. Photo of 915 SEASIDE DRIVE #511, Weeks 16-17, SARASOTA, FL 34242 (MLS # A4582913)
    $110,000
    Photo of 915 SEASIDE DRIVE #511, Weeks 16-17, SARASOTA, FL 34242 (MLS # A4582913)
    Photo of 915 SEASIDE DRIVE #511, Weeks 16-17, SARASOTA, FL 34242 (MLS # A4582913)
    50
     
    915 SEASIDE DRIVE #511, Weeks 16-17, SARASOTA, FL
    915 SEASIDE DRIVE #511, Weeks 16-17
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,625 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  3. Photo of 365 AVENIDA DE PARADISIO, SARASOTA, FL 34242 (MLS # A4583156)
    $1,799,000
    Photo of 365 AVENIDA DE PARADISIO, SARASOTA, FL 34242 (MLS # A4583156)
    Photo of 365 AVENIDA DE PARADISIO, SARASOTA, FL 34242 (MLS # A4583156)
    365 AVENIDA DE PARADISIO, SARASOTA, FL
    365 AVENIDA DE PARADISIO
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,542 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  4. Photo of 104 29TH STREET #1, HOLMES BEACH, FL 34217 (MLS # A4583478)
    $1,200,000
    Photo of 104 29TH STREET #1, HOLMES BEACH, FL 34217 (MLS # A4583478)
    Photo of 104 29TH STREET #1, HOLMES BEACH, FL 34217 (MLS # A4583478)
    104 29TH STREET #1, HOLMES BEACH, FL
    104 29TH STREET #1
    HOLMES BEACH, FL
    • 3 Beds
    • 2 Baths
    • 1,616 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  5. Photo of 1127 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # T3474611)
    $1,600,000
    Photo of 1127 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # T3474611)
    Photo of 1127 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # T3474611)
    1127 S OSPREY AVENUE, SARASOTA, FL
    1127 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,200 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  6. Photo of 111 PINEAPPLE AVENUE S #1002, SARASOTA, FL 34236 (MLS # A4583433)
    $8,000
    Photo of 111 PINEAPPLE AVENUE S #1002, SARASOTA, FL 34236 (MLS # A4583433)
    Photo of 111 PINEAPPLE AVENUE S #1002, SARASOTA, FL 34236 (MLS # A4583433)
    111 PINEAPPLE AVENUE S #1002, SARASOTA, FL
    111 PINEAPPLE AVENUE S #1002
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,535 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  7. Photo of 1912 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4583425)
    $1,995,000
    Photo of 1912 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4583425)
    Photo of 1912 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4583425)
    1912 HIGH POINT DRIVE, SARASOTA, FL
    1912 HIGH POINT DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,941 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  8. Photo of 1801 GULF DRIVE N #187, BRADENTON BEACH, FL 34217 (MLS # A4583532)
    $675,000
    Photo of 1801 GULF DRIVE N #187, BRADENTON BEACH, FL 34217 (MLS # A4583532)
    Photo of 1801 GULF DRIVE N #187, BRADENTON BEACH, FL 34217 (MLS # A4583532)
    1801 GULF DRIVE N #187, BRADENTON BEACH, FL
    1801 GULF DRIVE N #187
    BRADENTON BEACH, FL
    • 2 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  9. Photo of 2185 GULF OF MEXICO DRIVE #211, LONGBOAT KEY, FL 34228 (MLS # A4581194)
    $2,095,000
    Photo of 2185 GULF OF MEXICO DRIVE #211, LONGBOAT KEY, FL 34228 (MLS # A4581194)
    Photo of 2185 GULF OF MEXICO DRIVE #211, LONGBOAT KEY, FL 34228 (MLS # A4581194)
    2185 GULF OF MEXICO DRIVE #211, LONGBOAT KEY, FL
    2185 GULF OF MEXICO DRIVE #211
    LONGBOAT KEY, FL
    • 3 Beds
    • 3 Baths
    • 2,485 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  10. Photo of 136 GOLDEN GATE POINT #401, SARASOTA, FL 34236 (MLS # A4583039)
    $3,350,000
    Photo of 136 GOLDEN GATE POINT #401, SARASOTA, FL 34236 (MLS # A4583039)
    Photo of 136 GOLDEN GATE POINT #401, SARASOTA, FL 34236 (MLS # A4583039)
    136 GOLDEN GATE POINT #401, SARASOTA, FL
    136 GOLDEN GATE POINT #401
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,785 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  11. Photo of 2369 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214695)
    $1,300,000
    Photo of 2369 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214695)
    Photo of 2369 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214695)
    2369 BAHIA VISTA STREET, SARASOTA, FL
    2369 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,048 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  12. Photo of 4380 EXETER DRIVE #103, LONGBOAT KEY, FL 34228 (MLS # A4583498)
    $6,500
    Photo of 4380 EXETER DRIVE #103, LONGBOAT KEY, FL 34228 (MLS # A4583498)
    Photo of 4380 EXETER DRIVE #103, LONGBOAT KEY, FL 34228 (MLS # A4583498)
    4380 EXETER DRIVE #103, LONGBOAT KEY, FL
    4380 EXETER DRIVE #103
    LONGBOAT KEY, FL
    • 2 Beds
    • 1 Bath
    • 992 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  13. Photo of 2365 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214691)
    $1,300,000
    Photo of 2365 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214691)
    Photo of 2365 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214691)
    2365 BAHIA VISTA STREET, SARASOTA, FL
    2365 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,048 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  14. Photo of 2355 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214678)
    $1,300,000
    Photo of 2355 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214678)
    Photo of 2355 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # U8214678)
    2355 BAHIA VISTA STREET, SARASOTA, FL
    2355 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,048 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  15. Photo of 1750 BENJAMIN FRANKLIN DRIVE #3C, SARASOTA, FL 34236 (MLS # A4582822)
    $1,350,000
    Photo of 1750 BENJAMIN FRANKLIN DRIVE #3C, SARASOTA, FL 34236 (MLS # A4582822)
    Photo of 1750 BENJAMIN FRANKLIN DRIVE #3C, SARASOTA, FL 34236 (MLS # A4582822)
    1750 BENJAMIN FRANKLIN DRIVE #3C, SARASOTA, FL
    1750 BENJAMIN FRANKLIN DRIVE #3C
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,364 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 3311 GULF DRIVE #3, HOLMES BEACH, FL 34217 (MLS # A4582251)
    $979,000
    Photo of 3311 GULF DRIVE #3, HOLMES BEACH, FL 34217 (MLS # A4582251)
    Photo of 3311 GULF DRIVE #3, HOLMES BEACH, FL 34217 (MLS # A4582251)
    3311 GULF DRIVE #3, HOLMES BEACH, FL
    3311 GULF DRIVE #3
    HOLMES BEACH, FL
    • 2 Beds
    • 2 Baths
    • 1,331 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  17. Photo of 5164 WINDWARD AVENUE, SARASOTA, FL 34242 (MLS # A4583537)
    $7,400
    Photo of 5164 WINDWARD AVENUE, SARASOTA, FL 34242 (MLS # A4583537)
    Photo of 5164 WINDWARD AVENUE, SARASOTA, FL 34242 (MLS # A4583537)
    5164 WINDWARD AVENUE, SARASOTA, FL
    5164 WINDWARD AVENUE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,972 Home (sqft)
    • 2 Baths
    • 17,424 Lot (sqft)
  18. Photo of 420 ADELIA AVENUE, SARASOTA, FL 34236 (MLS # A4583450)
    $1,350
    Photo of 420 ADELIA AVENUE, SARASOTA, FL 34236 (MLS # A4583450)
    Photo of 420 ADELIA AVENUE, SARASOTA, FL 34236 (MLS # A4583450)
    420 ADELIA AVENUE, SARASOTA, FL
    420 ADELIA AVENUE
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 500 Home (sqft)
    • 1 Bath
    • 4,792 Lot (sqft)
  19. Photo of 804 N SHORE DRIVE, ANNA MARIA, FL 34216 (MLS # A4583175)
    $6,875,000
    Photo of 804 N SHORE DRIVE, ANNA MARIA, FL 34216 (MLS # A4583175)
    Photo of 804 N SHORE DRIVE, ANNA MARIA, FL 34216 (MLS # A4583175)
    804 N SHORE DRIVE, ANNA MARIA, FL
    804 N SHORE DRIVE
    ANNA MARIA, FL
    • 7 Beds
    • 3 Baths
    • 5,462 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  20. Photo of 3636 MINEOLA DRIVE, SARASOTA, FL 34239 (MLS # A4582111)
    $1,457,363
    Photo of 3636 MINEOLA DRIVE, SARASOTA, FL 34239 (MLS # A4582111)
    Photo of 3636 MINEOLA DRIVE, SARASOTA, FL 34239 (MLS # A4582111)
    30
     
    3636 MINEOLA DRIVE, SARASOTA, FL
    3636 MINEOLA DRIVE
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 2,000 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  21. Photo of 5400 GULF DRIVE #32, HOLMES BEACH, FL 34217 (MLS # A4583454)
    $975,000
    Photo of 5400 GULF DRIVE #32, HOLMES BEACH, FL 34217 (MLS # A4583454)
    Photo of 5400 GULF DRIVE #32, HOLMES BEACH, FL 34217 (MLS # A4583454)
    5400 GULF DRIVE #32, HOLMES BEACH, FL
    5400 GULF DRIVE #32
    HOLMES BEACH, FL
    • 2 Beds
    • 2 Baths
    • 1,188 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  22. Photo of 101 S GULFSTREAM AVENUE #15E, SARASOTA, FL 34236 (MLS # A4583420)
    $649,000
    Photo of 101 S GULFSTREAM AVENUE #15E, SARASOTA, FL 34236 (MLS # A4583420)
    Photo of 101 S GULFSTREAM AVENUE #15E, SARASOTA, FL 34236 (MLS # A4583420)
    101 S GULFSTREAM AVENUE #15E, SARASOTA, FL
    101 S GULFSTREAM AVENUE #15E
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 1.01 Lot (ac)
  23. Photo of 11 SUNSET DRIVE #805, SARASOTA, FL 34236 (MLS # A4579278)
    $12,500
    Photo of 11 SUNSET DRIVE #805, SARASOTA, FL 34236 (MLS # A4579278)
    Photo of 11 SUNSET DRIVE #805, SARASOTA, FL 34236 (MLS # A4579278)
    11 SUNSET DRIVE #805, SARASOTA, FL
    11 SUNSET DRIVE #805
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,433 Home (sqft)
    • 2 Baths
    • 1.89 Lot (ac)
  24. Photo of 101 BENJAMIN FRANKLIN DRIVE #26, SARASOTA, FL 34236 (MLS # W7858068)
    $1,500,000
    Photo of 101 BENJAMIN FRANKLIN DRIVE #26, SARASOTA, FL 34236 (MLS # W7858068)
    Photo of 101 BENJAMIN FRANKLIN DRIVE #26, SARASOTA, FL 34236 (MLS # W7858068)
    101 BENJAMIN FRANKLIN DRIVE #26, SARASOTA, FL
    101 BENJAMIN FRANKLIN DRIVE #26
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,275 Home (sqft)
    • 2 Baths
    • 1.42 Lot (ac)
  25. Photo of 3060 GRAND BAY BOULEVARD #153, LONGBOAT KEY, FL 34228 (MLS # A4581210)
    $1,999,500
    Photo of 3060 GRAND BAY BOULEVARD #153, LONGBOAT KEY, FL 34228 (MLS # A4581210)
    Photo of 3060 GRAND BAY BOULEVARD #153, LONGBOAT KEY, FL 34228 (MLS # A4581210)
    3060 GRAND BAY BOULEVARD #153, LONGBOAT KEY, FL
    3060 GRAND BAY BOULEVARD #153
    LONGBOAT KEY, FL
    • 2 Beds
    • 3 Baths
    • 2,550 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  26. Photo of 847 HUDSON AVENUE, SARASOTA, FL 34236 (MLS # A4583404)
    $14,000
    Photo of 847 HUDSON AVENUE, SARASOTA, FL 34236 (MLS # A4583404)
    Photo of 847 HUDSON AVENUE, SARASOTA, FL 34236 (MLS # A4583404)
    847 HUDSON AVENUE, SARASOTA, FL
    847 HUDSON AVENUE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,142 Home (sqft)
    • 3 Baths
    • 17,424 Lot (sqft)
  27. Photo of 1155 N GULFSTREAM AVENUE #508, SARASOTA, FL 34236 (MLS # A4582622)
    $8,300
    Photo of 1155 N GULFSTREAM AVENUE #508, SARASOTA, FL 34236 (MLS # A4582622)
    Photo of 1155 N GULFSTREAM AVENUE #508, SARASOTA, FL 34236 (MLS # A4582622)
    1155 N GULFSTREAM AVENUE #508, SARASOTA, FL
    1155 N GULFSTREAM AVENUE #508
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,710 Home (sqft)
    • 3 Baths
    • 436 Lot (sqft)
  28. Photo of 413 63RD STREET, HOLMES BEACH, FL 34217 (MLS # A4582922)
    $675,000
    Photo of 413 63RD STREET, HOLMES BEACH, FL 34217 (MLS # A4582922)
    Photo of 413 63RD STREET, HOLMES BEACH, FL 34217 (MLS # A4582922)
    413 63RD STREET, HOLMES BEACH, FL
    413 63RD STREET
    HOLMES BEACH, FL
    • 2 Beds
    • 2 Baths
    • 900 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  29. Photo of 411 63RD STREET, HOLMES BEACH, FL 34217 (MLS # A4582921)
    $650,000
    Photo of 411 63RD STREET, HOLMES BEACH, FL 34217 (MLS # A4582921)
    Photo of 411 63RD STREET, HOLMES BEACH, FL 34217 (MLS # A4582921)
    411 63RD STREET, HOLMES BEACH, FL
    411 63RD STREET
    HOLMES BEACH, FL
    • 2 Beds
    • 2 Baths
    • 972 Home (sqft)
    • 2 Baths
    • 3,485 Lot (sqft)
  30. Photo of 3001 BEE RIDGE ROAD #213, SARASOTA, FL 34239 (MLS # A4583352)
    $1,600
    Photo of 3001 BEE RIDGE ROAD #213, SARASOTA, FL 34239 (MLS # A4583352)
    Photo of 3001 BEE RIDGE ROAD #213, SARASOTA, FL 34239 (MLS # A4583352)
    3001 BEE RIDGE ROAD #213, SARASOTA, FL
    3001 BEE RIDGE ROAD #213
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 560 Home (sqft)
    • 1 Bath
    • 1.24 Lot (ac)
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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 9/24/23 9:51 PM PDT.

This Custom IDX is (c) Diverse Solutions 2023.

 
 

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