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 775 Longboat Club Road #804, Longboat Key, FL 34228 (MLS # A4609780)
    $1,845,000
    Photo of 775 Longboat Club Road #804, Longboat Key, FL 34228 (MLS # A4609780)
    Photo of 775 Longboat Club Road #804, Longboat Key, FL 34228 (MLS # A4609780)
    775 Longboat Club Road #804, Longboat Key, FL
    775 Longboat Club Road #804
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,602 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 510 Bowsprit Lane, Longboat Key, FL 34228 (MLS # A4609109)
    $5,600,000
    Photo of 510 Bowsprit Lane, Longboat Key, FL 34228 (MLS # A4609109)
    Photo of 510 Bowsprit Lane, Longboat Key, FL 34228 (MLS # A4609109)
    510 Bowsprit Lane, Longboat Key, FL
    510 Bowsprit Lane
    Longboat Key, FL
    • 5 Beds
    • 7 Baths
    • 4,234 Home (sqft)
    • 7 Baths
    • 10,019 Lot (sqft)
  3. Photo of 1945 Gulf Of Mexico Drive #M2-102, Longboat Key, FL 34228 (MLS # A4607120)
    $539,000
    Photo of 1945 Gulf Of Mexico Drive #M2-102, Longboat Key, FL 34228 (MLS # A4607120)
    Photo of 1945 Gulf Of Mexico Drive #M2-102, Longboat Key, FL 34228 (MLS # A4607120)
    1945 Gulf Of Mexico Drive #M2-102, Longboat Key, FL
    1945 Gulf Of Mexico Drive #M2-102
    Longboat Key, FL
    • 2 Beds
    • 1 Bath
    • 928 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  4. Photo of 216 69th Street, Holmes Beach, FL 34217 (MLS # A4608840)
    $1,995,000
    Photo of 216 69th Street, Holmes Beach, FL 34217 (MLS # A4608840)
    Photo of 216 69th Street, Holmes Beach, FL 34217 (MLS # A4608840)
    216 69th Street, Holmes Beach, FL
    216 69th Street
    Holmes Beach, FL
    • 0 Beds
    • 0 Baths
    • 2,320 Home (sqft)
    • 0 Baths
    • 9,584 Lot (sqft)
  5. Photo of 2157 Wisteria Street, Sarasota, FL 34239 (MLS # A4606954)
    $2,049,975
    Photo of 2157 Wisteria Street, Sarasota, FL 34239 (MLS # A4606954)
    Photo of 2157 Wisteria Street, Sarasota, FL 34239 (MLS # A4606954)
    2157 Wisteria Street, Sarasota, FL
    2157 Wisteria Street
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,220 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  6. Photo of 216 69th Street, Holmes Beach, FL 34217 (MLS # A4608837)
    $1,995,000
    Photo of 216 69th Street, Holmes Beach, FL 34217 (MLS # A4608837)
    Photo of 216 69th Street, Holmes Beach, FL 34217 (MLS # A4608837)
    216 69th Street, Holmes Beach, FL
    216 69th Street
    Holmes Beach, FL
    • 5 Beds
    • 5 Baths
    • 2,320 Home (sqft)
    • 5 Baths
    • 9,584 Lot (sqft)
  7. Photo of 2203 Avenue C, Bradenton Beach, FL 34217 (MLS # T3524814)
    $3,860,000
    Photo of 2203 Avenue C, Bradenton Beach, FL 34217 (MLS # T3524814)
    Photo of 2203 Avenue C, Bradenton Beach, FL 34217 (MLS # T3524814)
    2203 Avenue C, Bradenton Beach, FL
    2203 Avenue C
    Bradenton Beach, FL
    • 8 Beds
    • 6 Baths
    • 2,148 Home (sqft)
    • 6 Baths
    • 7,841 Lot (sqft)
  8. Photo of 2439 Loma Linda Street, Sarasota, FL 34239 (MLS # A4609415)
    $425,000
    Photo of 2439 Loma Linda Street, Sarasota, FL 34239 (MLS # A4609415)
    Photo of 2439 Loma Linda Street, Sarasota, FL 34239 (MLS # A4609415)
    2439 Loma Linda Street, Sarasota, FL
    2439 Loma Linda Street
    Sarasota, FL
    • 3 Beds
    • 1 Bath
    • 1,238 Home (sqft)
    • 1 Bath
    • 5,228 Lot (sqft)
  9. Photo of 1135 Florida Avenue, Sarasota, FL 34236 (MLS # A4609262)
    $1,500,000
    Photo of 1135 Florida Avenue, Sarasota, FL 34236 (MLS # A4609262)
    Photo of 1135 Florida Avenue, Sarasota, FL 34236 (MLS # A4609262)
    1135 Florida Avenue, Sarasota, FL
    1135 Florida Avenue
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,367 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  10. Photo of 4545 Gulf Of Mexico Dr #409, Longboat Key, FL 34228 (MLS # A4609663)
    $1,250,000
    Photo of 4545 Gulf Of Mexico Dr #409, Longboat Key, FL 34228 (MLS # A4609663)
    Photo of 4545 Gulf Of Mexico Dr #409, Longboat Key, FL 34228 (MLS # A4609663)
    4545 Gulf Of Mexico Dr #409, Longboat Key, FL
    4545 Gulf Of Mexico Dr #409
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,340 Home (sqft)
    • 2 Baths
    • 5.90 Lot (ac)
  11. Photo of 1001 Benjamin Franklin Drive #207, Sarasota, FL 34236 (MLS # A4609766)
    $6,250
    Photo of 1001 Benjamin Franklin Drive #207, Sarasota, FL 34236 (MLS # A4609766)
    Photo of 1001 Benjamin Franklin Drive #207, Sarasota, FL 34236 (MLS # A4609766)
    1001 Benjamin Franklin Drive #207, Sarasota, FL
    1001 Benjamin Franklin Drive #207
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,224 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  12. Photo of 2377 Harbour Oaks Drive, Longboat Key, FL 34228 (MLS # T3524583)
    $8,000
    Photo of 2377 Harbour Oaks Drive, Longboat Key, FL 34228 (MLS # T3524583)
    Photo of 2377 Harbour Oaks Drive, Longboat Key, FL 34228 (MLS # T3524583)
    2377 Harbour Oaks Drive, Longboat Key, FL
    2377 Harbour Oaks Drive
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,487 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  13. Photo of 1255 E Peppertree Dr #403, Sarasota, FL 34242 (MLS # U8241736)
    $5,000
    Photo of 1255 E Peppertree Dr #403, Sarasota, FL 34242 (MLS # U8241736)
    Photo of 1255 E Peppertree Dr #403, Sarasota, FL 34242 (MLS # U8241736)
    1255 E Peppertree Dr #403, Sarasota, FL
    1255 E Peppertree Dr #403
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  14. Photo of 131 White Avenue, Holmes Beach, FL 34217 (MLS # A4609813)
    $1,899,000
    Photo of 131 White Avenue, Holmes Beach, FL 34217 (MLS # A4609813)
    Photo of 131 White Avenue, Holmes Beach, FL 34217 (MLS # A4609813)
    131 White Avenue, Holmes Beach, FL
    131 White Avenue
    Holmes Beach, FL
    • 5 Beds
    • 5 Baths
    • 2,039 Home (sqft)
    • 5 Baths
    • 6,534 Lot (sqft)
  15. Photo of 2240 Valencia Drive, Sarasota, FL 34239 (MLS # A4608893)
    $575,000
    Photo of 2240 Valencia Drive, Sarasota, FL 34239 (MLS # A4608893)
    Photo of 2240 Valencia Drive, Sarasota, FL 34239 (MLS # A4608893)
    2240 Valencia Drive, Sarasota, FL
    2240 Valencia Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,494 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  16. Photo of 6300 Flotilla Drive #108, Holmes Beach, FL 34217 (MLS # A4609091)
    $499,000
    Photo of 6300 Flotilla Drive #108, Holmes Beach, FL 34217 (MLS # A4609091)
    Photo of 6300 Flotilla Drive #108, Holmes Beach, FL 34217 (MLS # A4609091)
    6300 Flotilla Drive #108, Holmes Beach, FL
    6300 Flotilla Drive #108
    Holmes Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,023 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  17. Photo of 624 Dream Island Road, Longboat Key, FL 34228 (MLS # A4609458)
    $5,000,000
    Photo of 624 Dream Island Road, Longboat Key, FL 34228 (MLS # A4609458)
    Photo of 624 Dream Island Road, Longboat Key, FL 34228 (MLS # A4609458)
    624 Dream Island Road, Longboat Key, FL
    624 Dream Island Road
    Longboat Key, FL
    • 4 Beds
    • 4 Baths
    • 2,932 Home (sqft)
    • 4 Baths
    • 25,265 Lot (sqft)
  18. Photo of 750 N Tamiami Trail #PH02, Sarasota, FL 34236 (MLS # A4609644)
    $895,000
    Photo of 750 N Tamiami Trail #PH02, Sarasota, FL 34236 (MLS # A4609644)
    Photo of 750 N Tamiami Trail #PH02, Sarasota, FL 34236 (MLS # A4609644)
    50
     
    750 N Tamiami Trail #PH02, Sarasota, FL
    750 N Tamiami Trail #PH02
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 960 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  19. Photo of 750 N Tamiami Trail #912, Sarasota, FL 34236 (MLS # A4609679)
    $3,800
    Photo of 750 N Tamiami Trail #912, Sarasota, FL 34236 (MLS # A4609679)
    Photo of 750 N Tamiami Trail #912, Sarasota, FL 34236 (MLS # A4609679)
    750 N Tamiami Trail #912, Sarasota, FL
    750 N Tamiami Trail #912
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 810 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  20. Photo of 1930 Wisteria Street, Sarasota, FL 34239 (MLS # A4608180)
    $1,790,000
    Photo of 1930 Wisteria Street, Sarasota, FL 34239 (MLS # A4608180)
    Photo of 1930 Wisteria Street, Sarasota, FL 34239 (MLS # A4608180)
    1930 Wisteria Street, Sarasota, FL
    1930 Wisteria Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,060 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  21. Photo of 7811 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4609486)
    $10,500,000
    Photo of 7811 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4609486)
    Photo of 7811 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4609486)
    7811 Midnight Pass Road, Sarasota, FL
    7811 Midnight Pass Road
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 2,244 Home (sqft)
    • 3 Baths
    • 3.65 Lot (ac)
  22. Photo of 519 Rountree Drive, Longboat Key, FL 34228 (MLS # A4609202)
    $5,950,000
    Photo of 519 Rountree Drive, Longboat Key, FL 34228 (MLS # A4609202)
    Photo of 519 Rountree Drive, Longboat Key, FL 34228 (MLS # A4609202)
    519 Rountree Drive, Longboat Key, FL
    519 Rountree Drive
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 3,554 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  23. Photo of 5830 Midnight Pass Road #51, Sarasota, FL 34242 (MLS # A4609623)
    $584,900
    Photo of 5830 Midnight Pass Road #51, Sarasota, FL 34242 (MLS # A4609623)
    Photo of 5830 Midnight Pass Road #51, Sarasota, FL 34242 (MLS # A4609623)
    5830 Midnight Pass Road #51, Sarasota, FL
    5830 Midnight Pass Road #51
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 728 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  24. Photo of 314 Hardin Avenue, Anna Maria, FL 34216 (MLS # OM677344)
    $1,500,000
    Photo of 314 Hardin Avenue, Anna Maria, FL 34216 (MLS # OM677344)
    Photo of 314 Hardin Avenue, Anna Maria, FL 34216 (MLS # OM677344)
    20
     
    314 Hardin Avenue, Anna Maria, FL
    314 Hardin Avenue
    Anna Maria, FL
    • 4 Beds
    • 2 Baths
    • 1,504 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  25. Photo of 225 Bird Key Drive, Sarasota, FL 34236 (MLS # A4609213)
    $1,995,000
    Photo of 225 Bird Key Drive, Sarasota, FL 34236 (MLS # A4609213)
    Photo of 225 Bird Key Drive, Sarasota, FL 34236 (MLS # A4609213)
    225 Bird Key Drive, Sarasota, FL
    225 Bird Key Drive
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 3,140 Home (sqft)
    • 4 Baths
    • 14,375 Lot (sqft)
  26. Photo of 4390 Exeter Drive #204, Longboat Key, FL 34228 (MLS # A4608354)
    $398,500
    Photo of 4390 Exeter Drive #204, Longboat Key, FL 34228 (MLS # A4608354)
    Photo of 4390 Exeter Drive #204, Longboat Key, FL 34228 (MLS # A4608354)
    4390 Exeter Drive #204, Longboat Key, FL
    4390 Exeter Drive #204
    Longboat Key, FL
    • 1 Bed
    • 1 Bath
    • 837 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  27. Photo of 518 74th Street, Holmes Beach, FL 34217 (MLS # T3524178)
    $8,500
    Photo of 518 74th Street, Holmes Beach, FL 34217 (MLS # T3524178)
    Photo of 518 74th Street, Holmes Beach, FL 34217 (MLS # T3524178)
    518 74th Street, Holmes Beach, FL
    518 74th Street
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 2,343 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  28. Photo of 2903 Avenue B #A & B, Holmes Beach, FL 34217 (MLS # A4609567)
    $1,250,000
    Photo of 2903 Avenue B #A & B, Holmes Beach, FL 34217 (MLS # A4609567)
    Photo of 2903 Avenue B #A & B, Holmes Beach, FL 34217 (MLS # A4609567)
    2903 Avenue B #A & B, Holmes Beach, FL
    2903 Avenue B #A & B
    Holmes Beach, FL
    • 0 Beds
    • 0 Baths
    • 1,464 Home (sqft)
    • 0 Baths
    • 4,792 Lot (sqft)
  29. Photo of 3651 Bayou Circle, Longboat Key, FL 34228 (MLS # A4609562)
    $1,200,000
    Photo of 3651 Bayou Circle, Longboat Key, FL 34228 (MLS # A4609562)
    Photo of 3651 Bayou Circle, Longboat Key, FL 34228 (MLS # A4609562)
    26
     
    3651 Bayou Circle, Longboat Key, FL
    3651 Bayou Circle
    Longboat Key, FL
    • 4 Beds
    • 4 Baths
    • 3,202 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  30. Photo of 2700 Gulf Drive N #203, Bradenton Beach, FL 34217 (MLS # A4609265)
    $899,000
    Photo of 2700 Gulf Drive N #203, Bradenton Beach, FL 34217 (MLS # A4609265)
    Photo of 2700 Gulf Drive N #203, Bradenton Beach, FL 34217 (MLS # A4609265)
    2700 Gulf Drive N #203, Bradenton Beach, FL
    2700 Gulf Drive N #203
    Bradenton Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,092 Home (sqft)
    • 2 Baths
    • 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 5/8/24 10:07 AM PDT.

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