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 2450 Harbourside Drive #212, Longboat Key, FL 34228 (MLS # A4606987)
    $1,945,000
    Photo of 2450 Harbourside Drive #212, Longboat Key, FL 34228 (MLS # A4606987)
    Photo of 2450 Harbourside Drive #212, Longboat Key, FL 34228 (MLS # A4606987)
    51
     
    2450 Harbourside Drive #212, Longboat Key, FL
    2450 Harbourside Drive #212
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,830 Home (sqft)
    • 3 Baths
    • 7.39 Lot (ac)
  2. Photo of 850 S Tamiami Trail #225, Sarasota, FL 34236 (MLS # A4608490)
    $2,700
    Photo of 850 S Tamiami Trail #225, Sarasota, FL 34236 (MLS # A4608490)
    Photo of 850 S Tamiami Trail #225, Sarasota, FL 34236 (MLS # A4608490)
    49
     
    850 S Tamiami Trail #225, Sarasota, FL
    850 S Tamiami Trail #225
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  3. Photo of 2364 Floyd Street, Sarasota, FL 34239 (MLS # A4608332)
    $1,200,000
    Photo of 2364 Floyd Street, Sarasota, FL 34239 (MLS # A4608332)
    Photo of 2364 Floyd Street, Sarasota, FL 34239 (MLS # A4608332)
    2364 Floyd Street, Sarasota, FL
    2364 Floyd Street
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,248 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  4. Photo of 606 Buttonwood Drive, Longboat Key, FL 34228 (MLS # A4607754)
    $1,299,000
    Photo of 606 Buttonwood Drive, Longboat Key, FL 34228 (MLS # A4607754)
    Photo of 606 Buttonwood Drive, Longboat Key, FL 34228 (MLS # A4607754)
    606 Buttonwood Drive, Longboat Key, FL
    606 Buttonwood Drive
    Longboat Key, FL
    • 3 Beds
    • 2 Baths
    • 1,971 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  5. Photo of 1320 Rhodes Avenue, Sarasota, FL 34239 (MLS # A4607680)
    $390,000
    Photo of 1320 Rhodes Avenue, Sarasota, FL 34239 (MLS # A4607680)
    Photo of 1320 Rhodes Avenue, Sarasota, FL 34239 (MLS # A4607680)
    1320 Rhodes Avenue, Sarasota, FL
    1320 Rhodes Avenue
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 955 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  6. Photo of 809 N Shore Drive, Anna Maria, FL 34216 (MLS # A4608114)
    $12,999,999
    Photo of 809 N Shore Drive, Anna Maria, FL 34216 (MLS # A4608114)
    Photo of 809 N Shore Drive, Anna Maria, FL 34216 (MLS # A4608114)
    81
     
    809 N Shore Drive, Anna Maria, FL
    809 N Shore Drive
    Anna Maria, FL
    • 5 Beds
    • 6 Baths
    • 4,936 Home (sqft)
    • 6 Baths
    • 1.03 Lot (ac)
  7. Photo of 3424 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4607957)
    $4,700
    Photo of 3424 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4607957)
    Photo of 3424 Tanglewood Drive, Sarasota, FL 34239 (MLS # A4607957)
    3424 Tanglewood Drive, Sarasota, FL
    3424 Tanglewood Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,147 Home (sqft)
    • 3 Baths
    • 18,731 Lot (sqft)
  8. Photo of 524 Beach Road #B, Sarasota, FL 34242 (MLS # A4608078)
    $7,350
    Photo of 524 Beach Road #B, Sarasota, FL 34242 (MLS # A4608078)
    Photo of 524 Beach Road #B, Sarasota, FL 34242 (MLS # A4608078)
    100
     
    524 Beach Road #B, Sarasota, FL
    524 Beach Road #B
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 980 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  9. Photo of 514 56th Street, Holmes Beach, FL 34217 (MLS # A4608279)
    $1,460,000
    Photo of 514 56th Street, Holmes Beach, FL 34217 (MLS # A4608279)
    Photo of 514 56th Street, Holmes Beach, FL 34217 (MLS # A4608279)
    40
     
    514 56th Street, Holmes Beach, FL
    514 56th Street
    Holmes Beach, FL
    • 3 Beds
    • 2 Baths
    • 1,966 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  10. Photo of 4234 Gulf Of Mexico Drive #D1, Longboat Key, FL 34228 (MLS # A4608256)
    $4,500
    Photo of 4234 Gulf Of Mexico Drive #D1, Longboat Key, FL 34228 (MLS # A4608256)
    Photo of 4234 Gulf Of Mexico Drive #D1, Longboat Key, FL 34228 (MLS # A4608256)
    4234 Gulf Of Mexico Drive #D1, Longboat Key, FL
    4234 Gulf Of Mexico Drive #D1
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,248 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  11. Photo of 210 Haverkos Court, Holmes Beach, FL 34217 (MLS # T3519172)
    $1,375,000
    Photo of 210 Haverkos Court, Holmes Beach, FL 34217 (MLS # T3519172)
    Photo of 210 Haverkos Court, Holmes Beach, FL 34217 (MLS # T3519172)
    210 Haverkos Court, Holmes Beach, FL
    210 Haverkos Court
    Holmes Beach, FL
    • 0 Beds
    • 0 Baths
    • 1,368 Home (sqft)
    • 0 Baths
    • 6,534 Lot (sqft)
  12. Photo of 511 Bayport Way #511, Longboat Key, FL 34228 (MLS # A4608285)
    $5,000
    Photo of 511 Bayport Way #511, Longboat Key, FL 34228 (MLS # A4608285)
    Photo of 511 Bayport Way #511, Longboat Key, FL 34228 (MLS # A4608285)
    511 Bayport Way #511, Longboat Key, FL
    511 Bayport Way #511
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,601 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  13. Photo of 2165 Orchid Street, Sarasota, FL 34239 (MLS # A4607235)
    $3,500
    Photo of 2165 Orchid Street, Sarasota, FL 34239 (MLS # A4607235)
    Photo of 2165 Orchid Street, Sarasota, FL 34239 (MLS # A4607235)
    17
     
    2165 Orchid Street, Sarasota, FL
    2165 Orchid Street
    Sarasota, FL
    • 4 Beds
    • 2 Baths
    • 1,570 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  14. Photo of 1900 Benjamin Franklin Drive #305B, Sarasota, FL 34236 (MLS # A4607783)
    $1,150,000
    Photo of 1900 Benjamin Franklin Drive #305B, Sarasota, FL 34236 (MLS # A4607783)
    Photo of 1900 Benjamin Franklin Drive #305B, Sarasota, FL 34236 (MLS # A4607783)
    1900 Benjamin Franklin Drive #305B, Sarasota, FL
    1900 Benjamin Franklin Drive #305B
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,131 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  15. Photo of 800 N Tamiami Trail #1011, Sarasota, FL 34236 (MLS # R4907841)
    $3,500
    Photo of 800 N Tamiami Trail #1011, Sarasota, FL 34236 (MLS # R4907841)
    Photo of 800 N Tamiami Trail #1011, Sarasota, FL 34236 (MLS # R4907841)
    800 N Tamiami Trail #1011, Sarasota, FL
    800 N Tamiami Trail #1011
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 290 Cocoanut Avenue #9 D, Sarasota, FL 34236 (MLS # A4608007)
    $3,785,000
    Photo of 290 Cocoanut Avenue #9 D, Sarasota, FL 34236 (MLS # A4608007)
    Photo of 290 Cocoanut Avenue #9 D, Sarasota, FL 34236 (MLS # A4608007)
    290 Cocoanut Avenue #9 D, Sarasota, FL
    290 Cocoanut Avenue #9 D
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 3,154 Home (sqft)
    • 3 Baths
    • 23,958 Lot (sqft)
  17. Photo of 301 Quay Common #1203, Sarasota, FL 34236 (MLS # A4606462)
    $1,799,000
    Photo of 301 Quay Common #1203, Sarasota, FL 34236 (MLS # A4606462)
    Photo of 301 Quay Common #1203, Sarasota, FL 34236 (MLS # A4606462)
    301 Quay Common #1203, Sarasota, FL
    301 Quay Common #1203
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,811 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  18. Photo of 750 N Tamiami Trail #910, Sarasota, FL 34236 (MLS # A4607513)
    $599,900
    Photo of 750 N Tamiami Trail #910, Sarasota, FL 34236 (MLS # A4607513)
    Photo of 750 N Tamiami Trail #910, Sarasota, FL 34236 (MLS # A4607513)
    750 N Tamiami Trail #910, Sarasota, FL
    750 N Tamiami Trail #910
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,355 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 405 Beach Road #B, Sarasota, FL 34242 (MLS # A4608051)
    $3,950,000
    Photo of 405 Beach Road #B, Sarasota, FL 34242 (MLS # A4608051)
    Photo of 405 Beach Road #B, Sarasota, FL 34242 (MLS # A4608051)
    405 Beach Road #B, Sarasota, FL
    405 Beach Road #B
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 4,646 Home (sqft)
    • 5 Baths
    • 16,118 Lot (sqft)
  20. Photo of 3504 Estrada Street, Sarasota, FL 34239 (MLS # C7490893)
    $949,000
    Photo of 3504 Estrada Street, Sarasota, FL 34239 (MLS # C7490893)
    Photo of 3504 Estrada Street, Sarasota, FL 34239 (MLS # C7490893)
    3504 Estrada Street, Sarasota, FL
    3504 Estrada Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 2,643 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  21. Photo of 2307 Valencia Drive, Sarasota, FL 34239 (MLS # A4608137)
    $3,600
    Photo of 2307 Valencia Drive, Sarasota, FL 34239 (MLS # A4608137)
    Photo of 2307 Valencia Drive, Sarasota, FL 34239 (MLS # A4608137)
    2307 Valencia Drive, Sarasota, FL
    2307 Valencia Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,099 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  22. Photo of 2135 Hyde Park Street, Sarasota, FL 34239 (MLS # A4608124)
    $1,595,000
    Photo of 2135 Hyde Park Street, Sarasota, FL 34239 (MLS # A4608124)
    Photo of 2135 Hyde Park Street, Sarasota, FL 34239 (MLS # A4608124)
    2135 Hyde Park Street, Sarasota, FL
    2135 Hyde Park Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 2,053 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  23. Photo of 1064 N Tamiami Trail #1122, Sarasota, FL 34236 (MLS # A4606697)
    $2,950
    Photo of 1064 N Tamiami Trail #1122, Sarasota, FL 34236 (MLS # A4606697)
    Photo of 1064 N Tamiami Trail #1122, Sarasota, FL 34236 (MLS # A4606697)
    1064 N Tamiami Trail #1122, Sarasota, FL
    1064 N Tamiami Trail #1122
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,084 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  24. Photo of 5143 Oxford Drive, Sarasota, FL 34242 (MLS # A4605608)
    $2,299,000
    Photo of 5143 Oxford Drive, Sarasota, FL 34242 (MLS # A4605608)
    Photo of 5143 Oxford Drive, Sarasota, FL 34242 (MLS # A4605608)
    5143 Oxford Drive, Sarasota, FL
    5143 Oxford Drive
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 2,830 Home (sqft)
    • 5 Baths
    • 6,534 Lot (sqft)
  25. Photo of 817 Bayport Way #817, Longboat Key, FL 34228 (MLS # T3520822)
    $5,000
    Photo of 817 Bayport Way #817, Longboat Key, FL 34228 (MLS # T3520822)
    Photo of 817 Bayport Way #817, Longboat Key, FL 34228 (MLS # T3520822)
    817 Bayport Way #817, Longboat Key, FL
    817 Bayport Way #817
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,601 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  26. Photo of 509 S Bay Boulevard, Anna Maria, FL 34216 (MLS # A4607924)
    $2,350,000
    Photo of 509 S Bay Boulevard, Anna Maria, FL 34216 (MLS # A4607924)
    Photo of 509 S Bay Boulevard, Anna Maria, FL 34216 (MLS # A4607924)
    509 S Bay Boulevard, Anna Maria, FL
    509 S Bay Boulevard
    Anna Maria, FL
    • 5 Beds
    • 3 Baths
    • 2,898 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  27. Photo of 1350 Main Street #1702, Sarasota, FL 34236 (MLS # A4608148)
    $14,000
    Photo of 1350 Main Street #1702, Sarasota, FL 34236 (MLS # A4608148)
    Photo of 1350 Main Street #1702, Sarasota, FL 34236 (MLS # A4608148)
    1350 Main Street #1702, Sarasota, FL
    1350 Main Street #1702
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,725 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  28. Photo of 525 56th Street, Holmes Beach, FL 34217 (MLS # A4606953)
    $2,850,000
    Photo of 525 56th Street, Holmes Beach, FL 34217 (MLS # A4606953)
    Photo of 525 56th Street, Holmes Beach, FL 34217 (MLS # A4606953)
    18
     
    525 56th Street, Holmes Beach, FL
    525 56th Street
    Holmes Beach, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 10,890 Lot (sqft)
  29. Photo of 2601 Valencia Drive, Sarasota, FL 34239 (MLS # A4608130)
    $4,000
    Photo of 2601 Valencia Drive, Sarasota, FL 34239 (MLS # A4608130)
    Photo of 2601 Valencia Drive, Sarasota, FL 34239 (MLS # A4608130)
    2601 Valencia Drive, Sarasota, FL
    2601 Valencia Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  30. Photo of 603 Crestwood Lane, Holmes Beach, FL 34217 (MLS # A4606866)
    $6,800,000
    Photo of 603 Crestwood Lane, Holmes Beach, FL 34217 (MLS # A4606866)
    Photo of 603 Crestwood Lane, Holmes Beach, FL 34217 (MLS # A4606866)
    100
     
    603 Crestwood Lane, Holmes Beach, FL
    603 Crestwood Lane
    Holmes Beach, FL
    • 3 Beds
    • 4 Baths
    • 2,980 Home (sqft)
    • 4 Baths
    • 12,197 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 4/24/24 10:04 PM PDT.

This Custom IDX is (c) Diverse Solutions 2024.

 
 

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