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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 888 S Orange Avenue #PH-C, Sarasota, FL 34236 (MLS # A4630214)
    $2,650,000
    Photo of 888 S Orange Avenue #PH-C, Sarasota, FL 34236 (MLS # A4630214)
    Photo of 888 S Orange Avenue #PH-C, Sarasota, FL 34236 (MLS # A4630214)
    888 S Orange Avenue #PH-C, Sarasota, FL
    888 S Orange Avenue #PH-C
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,511 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  2. Photo of 2110 Harbourside Drive #547, Longboat Key, FL 34228 (MLS # A4628918)
    $929,000
    Photo of 2110 Harbourside Drive #547, Longboat Key, FL 34228 (MLS # A4628918)
    Photo of 2110 Harbourside Drive #547, Longboat Key, FL 34228 (MLS # A4628918)
    2110 Harbourside Drive #547, Longboat Key, FL
    2110 Harbourside Drive #547
    Longboat Key, FL
    • 3 Beds
    • 2 Baths
    • 2,105 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  3. Photo of 5537 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4630208)
    $1,650,000
    Photo of 5537 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4630208)
    Photo of 5537 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4630208)
    5537 Cape Leyte Drive, Sarasota, FL
    5537 Cape Leyte Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,095 Home (sqft)
    • 2 Baths
    • 15,246 Lot (sqft)
  4. Photo of 350 S Polk Drive #303, Sarasota, FL 34236 (MLS # A4625971)
    $565,000
    Photo of 350 S Polk Drive #303, Sarasota, FL 34236 (MLS # A4625971)
    Photo of 350 S Polk Drive #303, Sarasota, FL 34236 (MLS # A4625971)
    350 S Polk Drive #303, Sarasota, FL
    350 S Polk Drive #303
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,036 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  5. Photo of 8750 Midnight Pass Road #202, Sarasota, FL 34242 (MLS # C7500987)
    $539,000
    Photo of 8750 Midnight Pass Road #202, Sarasota, FL 34242 (MLS # C7500987)
    Photo of 8750 Midnight Pass Road #202, Sarasota, FL 34242 (MLS # C7500987)
    85
     
    8750 Midnight Pass Road #202, Sarasota, FL
    8750 Midnight Pass Road #202
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 800 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  6. Photo of 2909 Gulf Drive #A, Bradenton Beach, FL 34217 (MLS # A4630162)
    $970,999
    Photo of 2909 Gulf Drive #A, Bradenton Beach, FL 34217 (MLS # A4630162)
    Photo of 2909 Gulf Drive #A, Bradenton Beach, FL 34217 (MLS # A4630162)
    2909 Gulf Drive #A, Bradenton Beach, FL
    2909 Gulf Drive #A
    Bradenton Beach, FL
    • 0 Beds
    • 0 Baths
    • 1,512 Home (sqft)
    • 0 Baths
    • 4,792 Lot (sqft)
  7. Photo of 1623 North Drive, Sarasota, FL 34239 (MLS # A4628861)
    $4,650,000
    Photo of 1623 North Drive, Sarasota, FL 34239 (MLS # A4628861)
    Photo of 1623 North Drive, Sarasota, FL 34239 (MLS # A4628861)
    1623 North Drive, Sarasota, FL
    1623 North Drive
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 4,215 Home (sqft)
    • 5 Baths
    • 14,811 Lot (sqft)
  8. Photo of 1350 Main Street #502, Sarasota, FL 34236 (MLS # TB8323355)
    $675,000
    Photo of 1350 Main Street #502, Sarasota, FL 34236 (MLS # TB8323355)
    Photo of 1350 Main Street #502, Sarasota, FL 34236 (MLS # TB8323355)
    14
     
    1350 Main Street #502, Sarasota, FL
    1350 Main Street #502
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 705 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  9. Photo of 4310 Falmouth Drive #A302, Longboat Key, FL 34228 (MLS # A4629995)
    $619,000
    Photo of 4310 Falmouth Drive #A302, Longboat Key, FL 34228 (MLS # A4629995)
    Photo of 4310 Falmouth Drive #A302, Longboat Key, FL 34228 (MLS # A4629995)
    4310 Falmouth Drive #A302, Longboat Key, FL
    4310 Falmouth Drive #A302
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,072 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  10. Photo of 4241 Gulf Of Mexico Drive #201, Longboat Key, FL 34228 (MLS # A4627999)
    $1,675,000
    Photo of 4241 Gulf Of Mexico Drive #201, Longboat Key, FL 34228 (MLS # A4627999)
    Photo of 4241 Gulf Of Mexico Drive #201, Longboat Key, FL 34228 (MLS # A4627999)
    4241 Gulf Of Mexico Drive #201, Longboat Key, FL
    4241 Gulf Of Mexico Drive #201
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 1,660 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  11. Photo of 4660 Ocean Boulevard #G1, Sarasota, FL 34242 (MLS # A4630013)
    $3,900
    Photo of 4660 Ocean Boulevard #G1, Sarasota, FL 34242 (MLS # A4630013)
    Photo of 4660 Ocean Boulevard #G1, Sarasota, FL 34242 (MLS # A4630013)
    4660 Ocean Boulevard #G1, Sarasota, FL
    4660 Ocean Boulevard #G1
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 4.23 Lot (ac)
  12. Photo of 990 Bogey Lane, Longboat Key, FL 34228 (MLS # A4630108)
    $7,500
    Photo of 990 Bogey Lane, Longboat Key, FL 34228 (MLS # A4630108)
    Photo of 990 Bogey Lane, Longboat Key, FL 34228 (MLS # A4630108)
    990 Bogey Lane, Longboat Key, FL
    990 Bogey Lane
    Longboat Key, FL
    • 3 Beds
    • 2 Baths
    • 1,962 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  13. Photo of 2800 Harbourside Dr #M-03, Longboat Key, FL 34228 (MLS # A4629626)
    $269,000
    Photo of 2800 Harbourside Dr #M-03, Longboat Key, FL 34228 (MLS # A4629626)
    Photo of 2800 Harbourside Dr #M-03, Longboat Key, FL 34228 (MLS # A4629626)
    2800 Harbourside Dr #M-03, Longboat Key, FL
    2800 Harbourside Dr #M-03
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 21,780 Lot (sqft)
  14. Photo of 893 N Shore Drive, Anna Maria, FL 34216 (MLS # A4630085)
    $3,250,000
    Photo of 893 N Shore Drive, Anna Maria, FL 34216 (MLS # A4630085)
    Photo of 893 N Shore Drive, Anna Maria, FL 34216 (MLS # A4630085)
    893 N Shore Drive, Anna Maria, FL
    893 N Shore Drive
    Anna Maria, FL
    • 4 Beds
    • 3 Baths
    • 2,933 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  15. Photo of 585 Gunwale Lane, Longboat Key, FL 34228 (MLS # A4629742)
    $5,995,000
    Photo of 585 Gunwale Lane, Longboat Key, FL 34228 (MLS # A4629742)
    Photo of 585 Gunwale Lane, Longboat Key, FL 34228 (MLS # A4629742)
    585 Gunwale Lane, Longboat Key, FL
    585 Gunwale Lane
    Longboat Key, FL
    • 3 Beds
    • 4 Baths
    • 4,733 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  16. Photo of 5026 Calle Minorga, Sarasota, FL 34242 (MLS # A4630032)
    $990,000
    Photo of 5026 Calle Minorga, Sarasota, FL 34242 (MLS # A4630032)
    Photo of 5026 Calle Minorga, Sarasota, FL 34242 (MLS # A4630032)
    5026 Calle Minorga, Sarasota, FL
    5026 Calle Minorga
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 1,240 Home (sqft)
    • 0 Baths
    • 7,406 Lot (sqft)
  17. Photo of 5026 Calle Minorga, Sarasota, FL 34242 (MLS # A4630037)
    $990,000
    Photo of 5026 Calle Minorga, Sarasota, FL 34242 (MLS # A4630037)
    Photo of 5026 Calle Minorga, Sarasota, FL 34242 (MLS # A4630037)
    5026 Calle Minorga, Sarasota, FL
    5026 Calle Minorga
    Sarasota, FL
    • 3 Beds
    • 1 Bath
    • 1,240 Home (sqft)
    • 1 Bath
    • 7,406 Lot (sqft)
  18. Photo of 4534 Banan Place, Siesta Key, FL 34242 (MLS # A4630024)
    $1,200,000
    Photo of 4534 Banan Place, Siesta Key, FL 34242 (MLS # A4630024)
    Photo of 4534 Banan Place, Siesta Key, FL 34242 (MLS # A4630024)
    4534 Banan Place, Siesta Key, FL
    4534 Banan Place
    Siesta Key, FL
    • 5 Beds
    • 3 Baths
    • 3,119 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  19. Photo of 301 Quay Commons #509, Sarasota, FL 34236 (MLS # A4629650)
    $10,000
    Photo of 301 Quay Commons #509, Sarasota, FL 34236 (MLS # A4629650)
    Photo of 301 Quay Commons #509, Sarasota, FL 34236 (MLS # A4629650)
    31
     
    301 Quay Commons #509, Sarasota, FL
    301 Quay Commons #509
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,869 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  20. Photo of 569 Channel Lane, Longboat Key, FL 34228 (MLS # A4630246)
    $1,050,000
    Photo of 569 Channel Lane, Longboat Key, FL 34228 (MLS # A4630246)
    Photo of 569 Channel Lane, Longboat Key, FL 34228 (MLS # A4630246)
    569 Channel Lane, Longboat Key, FL
    569 Channel Lane
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 9,584 Lot (sqft)
  21. Photo of 569 Channel Lane, Longboat Key, FL 34228 (MLS # A4630233)
    $1,050,000
    Photo of 569 Channel Lane, Longboat Key, FL 34228 (MLS # A4630233)
    Photo of 569 Channel Lane, Longboat Key, FL 34228 (MLS # A4630233)
    569 Channel Lane, Longboat Key, FL
    569 Channel Lane
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 2,381 Home (sqft)
    • 0 Baths
    • 9,584 Lot (sqft)
  22. Photo of 3320 Gulf Of Mexico Drive #302C, Longboat Key, FL 34228 (MLS # A4630138)
    $489,000
    Photo of 3320 Gulf Of Mexico Drive #302C, Longboat Key, FL 34228 (MLS # A4630138)
    Photo of 3320 Gulf Of Mexico Drive #302C, Longboat Key, FL 34228 (MLS # A4630138)
    3320 Gulf Of Mexico Drive #302C, Longboat Key, FL
    3320 Gulf Of Mexico Drive #302C
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,187 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 523 72nd Street, Holmes Beach, FL 34217 (MLS # A4630232)
    $1,500,000
    Photo of 523 72nd Street, Holmes Beach, FL 34217 (MLS # A4630232)
    Photo of 523 72nd Street, Holmes Beach, FL 34217 (MLS # A4630232)
    523 72nd Street, Holmes Beach, FL
    523 72nd Street
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 2,588 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  24. Photo of 475 Benjamin Franklin Drive #209, Sarasota, FL 34236 (MLS # A4629671)
    $590,000
    Photo of 475 Benjamin Franklin Drive #209, Sarasota, FL 34236 (MLS # A4629671)
    Photo of 475 Benjamin Franklin Drive #209, Sarasota, FL 34236 (MLS # A4629671)
    475 Benjamin Franklin Drive #209, Sarasota, FL
    475 Benjamin Franklin Drive #209
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 593 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  25. Photo of 767 John Ringling Boulevard #34, Sarasota, FL 34236 (MLS # TB8323358)
    $399,000
    Photo of 767 John Ringling Boulevard #34, Sarasota, FL 34236 (MLS # TB8323358)
    Photo of 767 John Ringling Boulevard #34, Sarasota, FL 34236 (MLS # TB8323358)
    767 John Ringling Boulevard #34, Sarasota, FL
    767 John Ringling Boulevard #34
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 816 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  26. Photo of 225 Hourglass Way #303, Sarasota, FL 34242 (MLS # TB8323153)
    $599,000
    Photo of 225 Hourglass Way #303, Sarasota, FL 34242 (MLS # TB8323153)
    Photo of 225 Hourglass Way #303, Sarasota, FL 34242 (MLS # TB8323153)
    76
     
    225 Hourglass Way #303, Sarasota, FL
    225 Hourglass Way #303
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  27. Photo of 1350 Main Street #600, Sarasota, FL 34236 (MLS # A4629947)
    $7,500
    Photo of 1350 Main Street #600, Sarasota, FL 34236 (MLS # A4629947)
    Photo of 1350 Main Street #600, Sarasota, FL 34236 (MLS # A4629947)
    1350 Main Street #600, Sarasota, FL
    1350 Main Street #600
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,338 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  28. Photo of 475 Benjamin Franklin Drive #202, Sarasota, FL 34236 (MLS # A4629453)
    $675,000
    Photo of 475 Benjamin Franklin Drive #202, Sarasota, FL 34236 (MLS # A4629453)
    Photo of 475 Benjamin Franklin Drive #202, Sarasota, FL 34236 (MLS # A4629453)
    475 Benjamin Franklin Drive #202, Sarasota, FL
    475 Benjamin Franklin Drive #202
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 784 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  29. Photo of 244 Gladiolus Street, Anna Maria, FL 34216 (MLS # A4629672)
    $995,000
    Photo of 244 Gladiolus Street, Anna Maria, FL 34216 (MLS # A4629672)
    Photo of 244 Gladiolus Street, Anna Maria, FL 34216 (MLS # A4629672)
    244 Gladiolus Street, Anna Maria, FL
    244 Gladiolus Street
    Anna Maria, FL
    • 3 Beds
    • 2 Baths
    • 1,350 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  30. Photo of 307 68th St, Holmes Beach, FL 34217 (MLS # A4629474)
    $1,495,000
    Photo of 307 68th St, Holmes Beach, FL 34217 (MLS # A4629474)
    Photo of 307 68th St, Holmes Beach, FL 34217 (MLS # A4629474)
    48
     
    307 68th St, Holmes Beach, FL
    307 68th St
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,829 Home (sqft)
    • 3 Baths
    • 10,019 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 11/25/24 6:13 PM PST.

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