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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 114 31st Street, Holmes Beach, FL 34217 (MLS # A4628578)
    $1,125,000
    Photo of 114 31st Street, Holmes Beach, FL 34217 (MLS # A4628578)
    Photo of 114 31st Street, Holmes Beach, FL 34217 (MLS # A4628578)
    114 31st Street, Holmes Beach, FL
    114 31st Street
    Holmes Beach, FL
    • 1 Bed
    • 1 Bath
    • 602 Home (sqft)
    • 1 Bath
    • 1,307 Lot (sqft)
  2. Photo of 3240 Gulf Of Mexico Drive #B404, Longboat Key, FL 34228 (MLS # A4627070)
    $5,000
    Photo of 3240 Gulf Of Mexico Drive #B404, Longboat Key, FL 34228 (MLS # A4627070)
    Photo of 3240 Gulf Of Mexico Drive #B404, Longboat Key, FL 34228 (MLS # A4627070)
    3240 Gulf Of Mexico Drive #B404, Longboat Key, FL
    3240 Gulf Of Mexico Drive #B404
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  3. Photo of 204 Tarpon Street #A, Anna Maria, FL 34216 (MLS # A4627231)
    $925,000
    Photo of 204 Tarpon Street #A, Anna Maria, FL 34216 (MLS # A4627231)
    Photo of 204 Tarpon Street #A, Anna Maria, FL 34216 (MLS # A4627231)
    204 Tarpon Street #A, Anna Maria, FL
    204 Tarpon Street #A
    Anna Maria, FL
    • 4 Beds
    • 2 Baths
    • 1,344 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  4. Photo of 2563 Prospect Street, Sarasota, FL 34239 (MLS # A4626010)
    $1,275,000
    Photo of 2563 Prospect Street, Sarasota, FL 34239 (MLS # A4626010)
    Photo of 2563 Prospect Street, Sarasota, FL 34239 (MLS # A4626010)
    46
     
    2563 Prospect Street, Sarasota, FL
    2563 Prospect Street
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,046 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)
  5. Photo of 580 Neptune Avenue, Longboat Key, FL 34228 (MLS # A4626912)
    $1,875,000
    Photo of 580 Neptune Avenue, Longboat Key, FL 34228 (MLS # A4626912)
    Photo of 580 Neptune Avenue, Longboat Key, FL 34228 (MLS # A4626912)
    580 Neptune Avenue, Longboat Key, FL
    580 Neptune Avenue
    Longboat Key, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 18,731 Lot (sqft)
  6. Photo of 2215 River Ridge Drive, Sarasota, FL 34239 (MLS # A4626315)
    $1,397,000
    Photo of 2215 River Ridge Drive, Sarasota, FL 34239 (MLS # A4626315)
    Photo of 2215 River Ridge Drive, Sarasota, FL 34239 (MLS # A4626315)
    2215 River Ridge Drive, Sarasota, FL
    2215 River Ridge Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,386 Home (sqft)
    • 3 Baths
    • 16,118 Lot (sqft)
  7. Photo of 750 N Tamiami Trail #1604, Sarasota, FL 34236 (MLS # A4626839)
    $599,000
    Photo of 750 N Tamiami Trail #1604, Sarasota, FL 34236 (MLS # A4626839)
    Photo of 750 N Tamiami Trail #1604, Sarasota, FL 34236 (MLS # A4626839)
    750 N Tamiami Trail #1604, Sarasota, FL
    750 N Tamiami Trail #1604
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,180 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  8. Photo of 3060 Grand Bay Boulevard #112, Longboat Key, FL 34228 (MLS # A4624619)
    $1,695,000
    Photo of 3060 Grand Bay Boulevard #112, Longboat Key, FL 34228 (MLS # A4624619)
    Photo of 3060 Grand Bay Boulevard #112, Longboat Key, FL 34228 (MLS # A4624619)
    3060 Grand Bay Boulevard #112, Longboat Key, FL
    3060 Grand Bay Boulevard #112
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,250 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  9. Photo of 577 Venice Lane, Sarasota, FL 34242 (MLS # A4626411)
    $2,499,000
    Photo of 577 Venice Lane, Sarasota, FL 34242 (MLS # A4626411)
    Photo of 577 Venice Lane, Sarasota, FL 34242 (MLS # A4626411)
    577 Venice Lane, Sarasota, FL
    577 Venice Lane
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,641 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  10. Photo of 1348 Harbor Drive, Sarasota, FL 34239 (MLS # A4628522)
    $4,999,000
    Photo of 1348 Harbor Drive, Sarasota, FL 34239 (MLS # A4628522)
    Photo of 1348 Harbor Drive, Sarasota, FL 34239 (MLS # A4628522)
    1348 Harbor Drive, Sarasota, FL
    1348 Harbor Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 16,553 Lot (sqft)
  11. Photo of 1348 Harbor Drive, Sarasota, FL 34239 (MLS # A4628424)
    $4,999,000
    Photo of 1348 Harbor Drive, Sarasota, FL 34239 (MLS # A4628424)
    Photo of 1348 Harbor Drive, Sarasota, FL 34239 (MLS # A4628424)
    1348 Harbor Drive, Sarasota, FL
    1348 Harbor Drive
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 6,946 Home (sqft)
    • 5 Baths
    • 16,553 Lot (sqft)
  12. Photo of 5941 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4626774)
    $9,500,000
    Photo of 5941 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4626774)
    Photo of 5941 Gulf Of Mexico Drive, Longboat Key, FL 34228 (MLS # A4626774)
    5941 Gulf Of Mexico Drive, Longboat Key, FL
    5941 Gulf Of Mexico Drive
    Longboat Key, FL
    • 3 Beds
    • 4 Baths
    • 2,417 Home (sqft)
    • 4 Baths
    • 1.07 Lot (ac)
  13. Photo of 606 Owl Way, Sarasota, FL 34236 (MLS # A4626798)
    $2,299,000
    Photo of 606 Owl Way, Sarasota, FL 34236 (MLS # A4626798)
    Photo of 606 Owl Way, Sarasota, FL 34236 (MLS # A4626798)
    606 Owl Way, Sarasota, FL
    606 Owl Way
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,475 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  14. Photo of 3851 Tangier Terrace, Sarasota, FL 34239 (MLS # A4626720)
    $4,200,000
    Photo of 3851 Tangier Terrace, Sarasota, FL 34239 (MLS # A4626720)
    Photo of 3851 Tangier Terrace, Sarasota, FL 34239 (MLS # A4626720)
    3851 Tangier Terrace, Sarasota, FL
    3851 Tangier Terrace
    Sarasota, FL
    • 5 Beds
    • 6 Baths
    • 3,223 Home (sqft)
    • 6 Baths
    • 13,940 Lot (sqft)
  15. Photo of 174 Golden Gate Point #43, Sarasota, FL 34236 (MLS # A4623567)
    $799,000
    Photo of 174 Golden Gate Point #43, Sarasota, FL 34236 (MLS # A4623567)
    Photo of 174 Golden Gate Point #43, Sarasota, FL 34236 (MLS # A4623567)
    174 Golden Gate Point #43, Sarasota, FL
    174 Golden Gate Point #43
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,367 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 8630 Midnight Pass Road #308A, Sarasota, FL 34242 (MLS # A4626749)
    $7,500
    Photo of 8630 Midnight Pass Road #308A, Sarasota, FL 34242 (MLS # A4626749)
    Photo of 8630 Midnight Pass Road #308A, Sarasota, FL 34242 (MLS # A4626749)
    25
     
    8630 Midnight Pass Road #308A, Sarasota, FL
    8630 Midnight Pass Road #308A
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,267 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  17. Photo of 1321 Dockside Place, Siesta Key, FL 34242 (MLS # A4626616)
    $5,900
    Photo of 1321 Dockside Place, Siesta Key, FL 34242 (MLS # A4626616)
    Photo of 1321 Dockside Place, Siesta Key, FL 34242 (MLS # A4626616)
    21
     
    1321 Dockside Place, Siesta Key, FL
    1321 Dockside Place
    Siesta Key, FL
    • 2 Beds
    • 2 Baths
    • 1,307 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  18. Photo of 6480 Midnight Pass Road #506, Sarasota, FL 34242 (MLS # A4626559)
    $6,300
    Photo of 6480 Midnight Pass Road #506, Sarasota, FL 34242 (MLS # A4626559)
    Photo of 6480 Midnight Pass Road #506, Sarasota, FL 34242 (MLS # A4626559)
    6480 Midnight Pass Road #506, Sarasota, FL
    6480 Midnight Pass Road #506
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 5.66 Lot (ac)
  19. Photo of 6480 Midnight Pass Road #311, Sarasota, FL 34242 (MLS # A4626558)
    $5,250
    Photo of 6480 Midnight Pass Road #311, Sarasota, FL 34242 (MLS # A4626558)
    Photo of 6480 Midnight Pass Road #311, Sarasota, FL 34242 (MLS # A4626558)
    36
     
    6480 Midnight Pass Road #311, Sarasota, FL
    6480 Midnight Pass Road #311
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 5.66 Lot (ac)
  20. Photo of 5830 Midnight Pass Road #54, Sarasota, FL 34242 (MLS # A4626557)
    $3,150
    Photo of 5830 Midnight Pass Road #54, Sarasota, FL 34242 (MLS # A4626557)
    Photo of 5830 Midnight Pass Road #54, Sarasota, FL 34242 (MLS # A4626557)
    5830 Midnight Pass Road #54, Sarasota, FL
    5830 Midnight Pass Road #54
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 728 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  21. Photo of 750 N Tamiami Trail #PH2, Sarasota, FL 34236 (MLS # A4626698)
    $799,000
    Photo of 750 N Tamiami Trail #PH2, Sarasota, FL 34236 (MLS # A4626698)
    Photo of 750 N Tamiami Trail #PH2, Sarasota, FL 34236 (MLS # A4626698)
    750 N Tamiami Trail #PH2, Sarasota, FL
    750 N Tamiami Trail #PH2
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 960 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  22. Photo of 1900 Benjamin Franklin Drive #V12, Sarasota, FL 34236 (MLS # A4626755)
    $825,000
    Photo of 1900 Benjamin Franklin Drive #V12, Sarasota, FL 34236 (MLS # A4626755)
    Photo of 1900 Benjamin Franklin Drive #V12, Sarasota, FL 34236 (MLS # A4626755)
    1900 Benjamin Franklin Drive #V12, Sarasota, FL
    1900 Benjamin Franklin Drive #V12
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,242 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 1129 Seaside Drive #7, Sarasota, FL 34242 (MLS # O6251637)
    $749,000
    Photo of 1129 Seaside Drive #7, Sarasota, FL 34242 (MLS # O6251637)
    Photo of 1129 Seaside Drive #7, Sarasota, FL 34242 (MLS # O6251637)
    16
     
    1129 Seaside Drive #7, Sarasota, FL
    1129 Seaside Drive #7
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 567 Home (sqft)
    • 1 Bath
    • 1.80 Lot (ac)
  24. Photo of 2174 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4626614)
    $27,000
    Photo of 2174 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4626614)
    Photo of 2174 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4626614)
    2174 Mcclellan Parkway, Sarasota, FL
    2174 Mcclellan Parkway
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 3,512 Home (sqft)
    • 5 Baths
    • 13,068 Lot (sqft)
  25. Photo of 2425 Clematis Street, Sarasota, FL 34239 (MLS # A4626676)
    $795,000
    Photo of 2425 Clematis Street, Sarasota, FL 34239 (MLS # A4626676)
    Photo of 2425 Clematis Street, Sarasota, FL 34239 (MLS # A4626676)
    2425 Clematis Street, Sarasota, FL
    2425 Clematis Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,868 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  26. Photo of 8213 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4626623)
    $3,500,000
    Photo of 8213 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4626623)
    Photo of 8213 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4626623)
    8213 Midnight Pass Road, Sarasota, FL
    8213 Midnight Pass Road
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 3,328 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  27. Photo of 1111 N Gulfstream Avenue #2A, Sarasota, FL 34236 (MLS # A4626622)
    $4,350
    Photo of 1111 N Gulfstream Avenue #2A, Sarasota, FL 34236 (MLS # A4626622)
    Photo of 1111 N Gulfstream Avenue #2A, Sarasota, FL 34236 (MLS # A4626622)
    1111 N Gulfstream Avenue #2A, Sarasota, FL
    1111 N Gulfstream Avenue #2A
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,577 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  28. Photo of 1801 Gulf Drive N #192, Bradenton Beach, FL 34217 (MLS # A4626619)
    $535,000
    Photo of 1801 Gulf Drive N #192, Bradenton Beach, FL 34217 (MLS # A4626619)
    Photo of 1801 Gulf Drive N #192, Bradenton Beach, FL 34217 (MLS # A4626619)
    1801 Gulf Drive N #192, Bradenton Beach, FL
    1801 Gulf Drive N #192
    Bradenton Beach, FL
    • 2 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 10.79 Lot (ac)
  29. Photo of 4866 Commonwealth Drive, Sarasota, FL 34242 (MLS # A4626507)
    $2,875,000
    Photo of 4866 Commonwealth Drive, Sarasota, FL 34242 (MLS # A4626507)
    Photo of 4866 Commonwealth Drive, Sarasota, FL 34242 (MLS # A4626507)
    4866 Commonwealth Drive, Sarasota, FL
    4866 Commonwealth Drive
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,973 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  30. Photo of 2212 Bahia Vista Street #I1, Sarasota, FL 34239 (MLS # A4626576)
    $274,528
    Photo of 2212 Bahia Vista Street #I1, Sarasota, FL 34239 (MLS # A4626576)
    Photo of 2212 Bahia Vista Street #I1, Sarasota, FL 34239 (MLS # A4626576)
    2212 Bahia Vista Street #I1, Sarasota, FL
    2212 Bahia Vista Street #I1
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,146 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
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