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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 619 Cedars Court, Longboat Key, FL 34228 (MLS # A4629084)
    $450,000
    Photo of 619 Cedars Court, Longboat Key, FL 34228 (MLS # A4629084)
    Photo of 619 Cedars Court, Longboat Key, FL 34228 (MLS # A4629084)
    619 Cedars Court, Longboat Key, FL
    619 Cedars Court
    Longboat Key, FL
    • 1 Bed
    • 2 Baths
    • 1,244 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 230 85th Street, Holmes Beach, FL 34217 (MLS # A4629282)
    $829,000
    Photo of 230 85th Street, Holmes Beach, FL 34217 (MLS # A4629282)
    Photo of 230 85th Street, Holmes Beach, FL 34217 (MLS # A4629282)
    230 85th Street, Holmes Beach, FL
    230 85th Street
    Holmes Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,010 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  3. Photo of 2426 Calamonga Lane, Sarasota, FL 34239 (MLS # A4628209)
    $485,000
    Photo of 2426 Calamonga Lane, Sarasota, FL 34239 (MLS # A4628209)
    Photo of 2426 Calamonga Lane, Sarasota, FL 34239 (MLS # A4628209)
    2426 Calamonga Lane, Sarasota, FL
    2426 Calamonga Lane
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,611 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  4. Photo of 8625 Midnight Pass Road #304B, Sarasota, FL 34242 (MLS # A4629275)
    $925,000
    Photo of 8625 Midnight Pass Road #304B, Sarasota, FL 34242 (MLS # A4629275)
    Photo of 8625 Midnight Pass Road #304B, Sarasota, FL 34242 (MLS # A4629275)
    8625 Midnight Pass Road #304B, Sarasota, FL
    8625 Midnight Pass Road #304B
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,336 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 2425 Floyd Street, Sarasota, FL 34239 (MLS # A4629328)
    $1,875,000
    Photo of 2425 Floyd Street, Sarasota, FL 34239 (MLS # A4629328)
    Photo of 2425 Floyd Street, Sarasota, FL 34239 (MLS # A4629328)
    2425 Floyd Street, Sarasota, FL
    2425 Floyd Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,700 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)
  6. Photo of 3607 E Bay Drive #211, Holmes Beach, FL 34217 (MLS # TB8321574)
    $575,000
    Photo of 3607 E Bay Drive #211, Holmes Beach, FL 34217 (MLS # TB8321574)
    Photo of 3607 E Bay Drive #211, Holmes Beach, FL 34217 (MLS # TB8321574)
    28
     
    3607 E Bay Drive #211, Holmes Beach, FL
    3607 E Bay Drive #211
    Holmes Beach, FL
    • 2 Beds
    • 2 Baths
    • 980 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  7. Photo of 6300 Flotilla Drive #67, Holmes Beach, FL 34217 (MLS # TB8320927)
    $649,000
    Photo of 6300 Flotilla Drive #67, Holmes Beach, FL 34217 (MLS # TB8320927)
    Photo of 6300 Flotilla Drive #67, Holmes Beach, FL 34217 (MLS # TB8320927)
    6300 Flotilla Drive #67, Holmes Beach, FL
    6300 Flotilla Drive #67
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,436 Home (sqft)
    • 3 Baths
    • 436 Lot (sqft)
  8. Photo of 5855 Midnight Pass Road #722, Sarasota, FL 34242 (MLS # A4626012)
    $840,000
    Photo of 5855 Midnight Pass Road #722, Sarasota, FL 34242 (MLS # A4626012)
    Photo of 5855 Midnight Pass Road #722, Sarasota, FL 34242 (MLS # A4626012)
    5855 Midnight Pass Road #722, Sarasota, FL
    5855 Midnight Pass Road #722
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,211 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  9. Photo of 1308 Old Stickney Point Road #W41, Sarasota, FL 34242 (MLS # A4629236)
    $1,175,000
    Photo of 1308 Old Stickney Point Road #W41, Sarasota, FL 34242 (MLS # A4629236)
    Photo of 1308 Old Stickney Point Road #W41, Sarasota, FL 34242 (MLS # A4629236)
    1308 Old Stickney Point Road #W41, Sarasota, FL
    1308 Old Stickney Point Road #W41
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,512 Home (sqft)
    • 3 Baths
    • 3.50 Lot (ac)
  10. Photo of 1260 Dolphin Bay Way #403, Sarasota, FL 34242 (MLS # A4624685)
    $1,390,000
    Photo of 1260 Dolphin Bay Way #403, Sarasota, FL 34242 (MLS # A4624685)
    Photo of 1260 Dolphin Bay Way #403, Sarasota, FL 34242 (MLS # A4624685)
    1260 Dolphin Bay Way #403, Sarasota, FL
    1260 Dolphin Bay Way #403
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,915 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  11. Photo of 1243 Starboard Lane, Sarasota, FL 34242 (MLS # A4627883)
    $4,950,000
    Photo of 1243 Starboard Lane, Sarasota, FL 34242 (MLS # A4627883)
    Photo of 1243 Starboard Lane, Sarasota, FL 34242 (MLS # A4627883)
    1243 Starboard Lane, Sarasota, FL
    1243 Starboard Lane
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 5,142 Home (sqft)
    • 5 Baths
    • 18,296 Lot (sqft)
  12. Photo of 401 Quay #1404, Sarasota, FL 34236 (MLS # A4629759)
    $4,999,000
    Photo of 401 Quay #1404, Sarasota, FL 34236 (MLS # A4629759)
    Photo of 401 Quay #1404, Sarasota, FL 34236 (MLS # A4629759)
    401 Quay #1404, Sarasota, FL
    401 Quay #1404
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,984 Home (sqft)
    • 4 Baths
    • 1.87 Lot (ac)
  13. Photo of 301 Quay Commons #1807, Sarasota, FL 34236 (MLS # A4626911)
    $1,675,000
    Photo of 301 Quay Commons #1807, Sarasota, FL 34236 (MLS # A4626911)
    Photo of 301 Quay Commons #1807, Sarasota, FL 34236 (MLS # A4626911)
    301 Quay Commons #1807, Sarasota, FL
    301 Quay Commons #1807
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,589 Home (sqft)
    • 3 Baths
    • 42,689 Lot (sqft)
  14. Photo of 755 S Palm Avenue #404, Sarasota, FL 34236 (MLS # A4627636)
    $899,900
    Photo of 755 S Palm Avenue #404, Sarasota, FL 34236 (MLS # A4627636)
    Photo of 755 S Palm Avenue #404, Sarasota, FL 34236 (MLS # A4627636)
    755 S Palm Avenue #404, Sarasota, FL
    755 S Palm Avenue #404
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,421 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  15. Photo of 5770 Midnight Pass Road #301, Sarasota, FL 34242 (MLS # A4629233)
    $1,099,000
    Photo of 5770 Midnight Pass Road #301, Sarasota, FL 34242 (MLS # A4629233)
    Photo of 5770 Midnight Pass Road #301, Sarasota, FL 34242 (MLS # A4629233)
    79
     
    5770 Midnight Pass Road #301, Sarasota, FL
    5770 Midnight Pass Road #301
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,337 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 3605 S School Avenue, Sarasota, FL 34239 (MLS # A4628563)
    $3,700,000
    Photo of 3605 S School Avenue, Sarasota, FL 34239 (MLS # A4628563)
    Photo of 3605 S School Avenue, Sarasota, FL 34239 (MLS # A4628563)
    3605 S School Avenue, Sarasota, FL
    3605 S School Avenue
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 3,217 Home (sqft)
    • 0 Baths
    • 35,284 Lot (sqft)
  17. Photo of 5624 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4628681)
    $1,250,000
    Photo of 5624 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4628681)
    Photo of 5624 Cape Leyte Drive, Sarasota, FL 34242 (MLS # A4628681)
    5624 Cape Leyte Drive, Sarasota, FL
    5624 Cape Leyte Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,550 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  18. Photo of 2055 Arlington Street #106, Sarasota, FL 34239 (MLS # A4629228)
    $1,800
    Photo of 2055 Arlington Street #106, Sarasota, FL 34239 (MLS # A4629228)
    Photo of 2055 Arlington Street #106, Sarasota, FL 34239 (MLS # A4629228)
    2055 Arlington Street #106, Sarasota, FL
    2055 Arlington Street #106
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 856 Home (sqft)
    • 2 Baths
    • 24,830 Lot (sqft)
  19. Photo of 800 N Tamiami Trail #307, Sarasota, FL 34236 (MLS # A4629201)
    $1,100,000
    Photo of 800 N Tamiami Trail #307, Sarasota, FL 34236 (MLS # A4629201)
    Photo of 800 N Tamiami Trail #307, Sarasota, FL 34236 (MLS # A4629201)
    65
     
    800 N Tamiami Trail #307, Sarasota, FL
    800 N Tamiami Trail #307
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,911 Home (sqft)
    • 3 Baths
    • 2.18 Lot (ac)
  20. Photo of 11101 Gulf Drive, Anna Maria, FL 34216 (MLS # A4628792)
    $2,250,000
    Photo of 11101 Gulf Drive, Anna Maria, FL 34216 (MLS # A4628792)
    Photo of 11101 Gulf Drive, Anna Maria, FL 34216 (MLS # A4628792)
    10
     
    11101 Gulf Drive, Anna Maria, FL
    11101 Gulf Drive
    Anna Maria, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 10,890 Lot (sqft)
  21. Photo of 1250 Point Crisp Road, Sarasota, FL 34242 (MLS # A4629191)
    $825,000
    Photo of 1250 Point Crisp Road, Sarasota, FL 34242 (MLS # A4629191)
    Photo of 1250 Point Crisp Road, Sarasota, FL 34242 (MLS # A4629191)
    1250 Point Crisp Road, Sarasota, FL
    1250 Point Crisp Road
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,050 Home (sqft)
    • 2 Baths
    • 18,296 Lot (sqft)
  22. Photo of 6901 Poinsettia Avenue, Longboat Key, FL 34228 (MLS # A4629158)
    $799,000
    Photo of 6901 Poinsettia Avenue, Longboat Key, FL 34228 (MLS # A4629158)
    Photo of 6901 Poinsettia Avenue, Longboat Key, FL 34228 (MLS # A4629158)
    6901 Poinsettia Avenue, Longboat Key, FL
    6901 Poinsettia Avenue
    Longboat Key, FL
    • 4 Beds
    • 3 Baths
    • 2,173 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  23. Photo of 1 Benjamin Franklin Drive #104, Sarasota, FL 34236 (MLS # A4629185)
    $5,500
    Photo of 1 Benjamin Franklin Drive #104, Sarasota, FL 34236 (MLS # A4629185)
    Photo of 1 Benjamin Franklin Drive #104, Sarasota, FL 34236 (MLS # A4629185)
    1 Benjamin Franklin Drive #104, Sarasota, FL
    1 Benjamin Franklin Drive #104
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,389 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  24. Photo of 6901 Poinsettia Avenue, Longboat Key, FL 34228 (MLS # A4629170)
    $799,000
    Photo of 6901 Poinsettia Avenue, Longboat Key, FL 34228 (MLS # A4629170)
    Photo of 6901 Poinsettia Avenue, Longboat Key, FL 34228 (MLS # A4629170)
    6901 Poinsettia Avenue, Longboat Key, FL
    6901 Poinsettia Avenue
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 9,148 Lot (sqft)
  25. Photo of 1102 Benjamin Franklin Drive #409, Sarasota, FL 34236 (MLS # A4628710)
    $629,000
    Photo of 1102 Benjamin Franklin Drive #409, Sarasota, FL 34236 (MLS # A4628710)
    Photo of 1102 Benjamin Franklin Drive #409, Sarasota, FL 34236 (MLS # A4628710)
    1102 Benjamin Franklin Drive #409, Sarasota, FL
    1102 Benjamin Franklin Drive #409
    Sarasota, FL
    • 1 Bed
    • 2 Baths
    • 918 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  26. Photo of 1808 Flower Drive, Sarasota, FL 34239 (MLS # A4627235)
    $11,995,000
    Photo of 1808 Flower Drive, Sarasota, FL 34239 (MLS # A4627235)
    Photo of 1808 Flower Drive, Sarasota, FL 34239 (MLS # A4627235)
    1808 Flower Drive, Sarasota, FL
    1808 Flower Drive
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 5,609 Home (sqft)
    • 6 Baths
    • 24,394 Lot (sqft)
  27. Photo of 4906 Primrose Path, Sarasota, FL 34242 (MLS # A4629047)
    $1,794,000
    Photo of 4906 Primrose Path, Sarasota, FL 34242 (MLS # A4629047)
    Photo of 4906 Primrose Path, Sarasota, FL 34242 (MLS # A4629047)
    4906 Primrose Path, Sarasota, FL
    4906 Primrose Path
    Sarasota, FL
    • 5 Beds
    • 4 Baths
    • 3,120 Home (sqft)
    • 4 Baths
    • 20,038 Lot (sqft)
  28. Photo of 1955 Gulf Of Mexico Drive #G6-311, Longboat Key, FL 34228 (MLS # A4629074)
    $1,165,000
    Photo of 1955 Gulf Of Mexico Drive #G6-311, Longboat Key, FL 34228 (MLS # A4629074)
    Photo of 1955 Gulf Of Mexico Drive #G6-311, Longboat Key, FL 34228 (MLS # A4629074)
    1955 Gulf Of Mexico Drive #G6-311, Longboat Key, FL
    1955 Gulf Of Mexico Drive #G6-311
    Longboat Key, FL
    • 3 Beds
    • 2 Baths
    • 1,492 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  29. Photo of 100 Sands Point Road #223, Longboat Key, FL 34228 (MLS # A4629111)
    $1,285,000
    Photo of 100 Sands Point Road #223, Longboat Key, FL 34228 (MLS # A4629111)
    Photo of 100 Sands Point Road #223, Longboat Key, FL 34228 (MLS # A4629111)
    100 Sands Point Road #223, Longboat Key, FL
    100 Sands Point Road #223
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,941 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  30. Photo of 800 N Tamiami Trail #321, Sarasota, FL 34236 (MLS # A4629105)
    $1,050,000
    Photo of 800 N Tamiami Trail #321, Sarasota, FL 34236 (MLS # A4629105)
    Photo of 800 N Tamiami Trail #321, Sarasota, FL 34236 (MLS # A4629105)
    800 N Tamiami Trail #321, Sarasota, FL
    800 N Tamiami Trail #321
    Sarasota, FL
    • 1 Bed
    • 2 Baths
    • 1,734 Home (sqft)
    • 2 Baths
    • 2.18 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 11/21/24 6:12 AM PST.

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