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 2551 Temple Street, Sarasota, FL 34239 (MLS # P4931354)
    $465,000
    Photo of 2551 Temple Street, Sarasota, FL 34239 (MLS # P4931354)
    Photo of 2551 Temple Street, Sarasota, FL 34239 (MLS # P4931354)
    2551 Temple Street, Sarasota, FL
    2551 Temple Street
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,194 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  2. Photo of 628 N Orange Avenue, Sarasota, FL 34236 (MLS # A4618435)
    $3,200,000
    Photo of 628 N Orange Avenue, Sarasota, FL 34236 (MLS # A4618435)
    Photo of 628 N Orange Avenue, Sarasota, FL 34236 (MLS # A4618435)
    80
     
    628 N Orange Avenue, Sarasota, FL
    628 N Orange Avenue
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 30,057 Lot (sqft)
  3. Photo of 1928 9th Street, Sarasota, FL 34236 (MLS # A4618429)
    $919,000
    Photo of 1928 9th Street, Sarasota, FL 34236 (MLS # A4618429)
    Photo of 1928 9th Street, Sarasota, FL 34236 (MLS # A4618429)
    1928 9th Street, Sarasota, FL
    1928 9th Street
    Sarasota, FL
    • 4 Beds
    • 2 Baths
    • 2,045 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  4. Photo of 2026 Grove Street, Sarasota, FL 34239 (MLS # A4617252)
    $639,999
    Photo of 2026 Grove Street, Sarasota, FL 34239 (MLS # A4617252)
    Photo of 2026 Grove Street, Sarasota, FL 34239 (MLS # A4617252)
    2026 Grove Street, Sarasota, FL
    2026 Grove Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,263 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  5. Photo of 628 N Orange Avenue, Sarasota, FL 34236 (MLS # A4618354)
    $3,250,000
    Photo of 628 N Orange Avenue, Sarasota, FL 34236 (MLS # A4618354)
    Photo of 628 N Orange Avenue, Sarasota, FL 34236 (MLS # A4618354)
    79
     
    628 N Orange Avenue, Sarasota, FL
    628 N Orange Avenue
    Sarasota, FL
    • 7 Beds
    • 4 Baths
    • 3,396 Home (sqft)
    • 4 Baths
    • 30,057 Lot (sqft)
  6. Photo of 1928 9th Street, Sarasota, FL 34236 (MLS # A4618413)
    $919,000
    Photo of 1928 9th Street, Sarasota, FL 34236 (MLS # A4618413)
    Photo of 1928 9th Street, Sarasota, FL 34236 (MLS # A4618413)
    1928 9th Street, Sarasota, FL
    1928 9th Street
    Sarasota, FL
    • 4 Beds
    • 2 Baths
    • 2,045 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  7. Photo of 1945 Gulf Of Mexico Drive #M2-414, Longboat Key, FL 34228 (MLS # A4618406)
    $4,500
    Photo of 1945 Gulf Of Mexico Drive #M2-414, Longboat Key, FL 34228 (MLS # A4618406)
    Photo of 1945 Gulf Of Mexico Drive #M2-414, Longboat Key, FL 34228 (MLS # A4618406)
    1945 Gulf Of Mexico Drive #M2-414, Longboat Key, FL
    1945 Gulf Of Mexico Drive #M2-414
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 928 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  8. Photo of 360 Gulf Of Mexico Drive #312, Longboat Key, FL 34228 (MLS # A4618386)
    $6,000
    Photo of 360 Gulf Of Mexico Drive #312, Longboat Key, FL 34228 (MLS # A4618386)
    Photo of 360 Gulf Of Mexico Drive #312, Longboat Key, FL 34228 (MLS # A4618386)
    360 Gulf Of Mexico Drive #312, Longboat Key, FL
    360 Gulf Of Mexico Drive #312
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,298 Home (sqft)
    • 3 Baths
    • 10.93 Lot (ac)
  9. Photo of 825 S Osprey Avenue #302, Sarasota, FL 34236 (MLS # A4618148)
    $549,000
    Photo of 825 S Osprey Avenue #302, Sarasota, FL 34236 (MLS # A4618148)
    Photo of 825 S Osprey Avenue #302, Sarasota, FL 34236 (MLS # A4618148)
    825 S Osprey Avenue #302, Sarasota, FL
    825 S Osprey Avenue #302
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 6.06 Lot (ac)
  10. Photo of 2275 Temple Street, Sarasota, FL 34239 (MLS # A4616039)
    $2,900
    Photo of 2275 Temple Street, Sarasota, FL 34239 (MLS # A4616039)
    Photo of 2275 Temple Street, Sarasota, FL 34239 (MLS # A4616039)
    2275 Temple Street, Sarasota, FL
    2275 Temple Street
    Sarasota, FL
    • 4 Beds
    • 2 Baths
    • 2,057 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  11. Photo of 6157 Midnight Pass Road #C12, Sarasota, FL 34242 (MLS # A4618161)
    $600,000
    Photo of 6157 Midnight Pass Road #C12, Sarasota, FL 34242 (MLS # A4618161)
    Photo of 6157 Midnight Pass Road #C12, Sarasota, FL 34242 (MLS # A4618161)
    6157 Midnight Pass Road #C12, Sarasota, FL
    6157 Midnight Pass Road #C12
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,332 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  12. Photo of 1050 Longboat Club Road #602, Longboat Key, FL 34228 (MLS # A4618338)
    $4,440
    Photo of 1050 Longboat Club Road #602, Longboat Key, FL 34228 (MLS # A4618338)
    Photo of 1050 Longboat Club Road #602, Longboat Key, FL 34228 (MLS # A4618338)
    1050 Longboat Club Road #602, Longboat Key, FL
    1050 Longboat Club Road #602
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,290 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  13. Photo of 1271 Dockside Place #215, Sarasota, FL 34242 (MLS # A4616895)
    $1,100,000
    Photo of 1271 Dockside Place #215, Sarasota, FL 34242 (MLS # A4616895)
    Photo of 1271 Dockside Place #215, Sarasota, FL 34242 (MLS # A4616895)
    1271 Dockside Place #215, Sarasota, FL
    1271 Dockside Place #215
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,737 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  14. Photo of 505 69th Street, Holmes Beach, FL 34217 (MLS # A4617508)
    $3,495,000
    Photo of 505 69th Street, Holmes Beach, FL 34217 (MLS # A4617508)
    Photo of 505 69th Street, Holmes Beach, FL 34217 (MLS # A4617508)
    505 69th Street, Holmes Beach, FL
    505 69th Street
    Holmes Beach, FL
    • 4 Beds
    • 4 Baths
    • 2,263 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  15. Photo of 1406 Tangier Way, Sarasota, FL 34239 (MLS # A4618315)
    $8,000,000
    Photo of 1406 Tangier Way, Sarasota, FL 34239 (MLS # A4618315)
    Photo of 1406 Tangier Way, Sarasota, FL 34239 (MLS # A4618315)
    24
     
    1406 Tangier Way, Sarasota, FL
    1406 Tangier Way
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,069 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
  16. Photo of 2171 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4618309)
    $2,500,000
    Photo of 2171 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4618309)
    Photo of 2171 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4618309)
    34
     
    2171 Mcclellan Parkway, Sarasota, FL
    2171 Mcclellan Parkway
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  17. Photo of 1345 2nd Street #C, Sarasota, FL 34236 (MLS # A4618267)
    $5,500
    Photo of 1345 2nd Street #C, Sarasota, FL 34236 (MLS # A4618267)
    Photo of 1345 2nd Street #C, Sarasota, FL 34236 (MLS # A4618267)
    1345 2nd Street #C, Sarasota, FL
    1345 2nd Street #C
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,130 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  18. Photo of 1915 Harbour Links Circle #6, Longboat Key, FL 34228 (MLS # A4617230)
    $1,950,000
    Photo of 1915 Harbour Links Circle #6, Longboat Key, FL 34228 (MLS # A4617230)
    Photo of 1915 Harbour Links Circle #6, Longboat Key, FL 34228 (MLS # A4617230)
    1915 Harbour Links Circle #6, Longboat Key, FL
    1915 Harbour Links Circle #6
    Longboat Key, FL
    • 3 Beds
    • 4 Baths
    • 2,476 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  19. Photo of 601 Tremont Street, Sarasota, FL 34242 (MLS # A4618260)
    $4,500,000
    Photo of 601 Tremont Street, Sarasota, FL 34242 (MLS # A4618260)
    Photo of 601 Tremont Street, Sarasota, FL 34242 (MLS # A4618260)
    601 Tremont Street, Sarasota, FL
    601 Tremont Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,996 Home (sqft)
    • 5 Baths
    • 15,246 Lot (sqft)
  20. Photo of 500 S Washington Drive #10B, Sarasota, FL 34236 (MLS # A4616788)
    $665,000
    Photo of 500 S Washington Drive #10B, Sarasota, FL 34236 (MLS # A4616788)
    Photo of 500 S Washington Drive #10B, Sarasota, FL 34236 (MLS # A4616788)
    500 S Washington Drive #10B, Sarasota, FL
    500 S Washington Drive #10B
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,034 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 662 Cedars Court, Longboat Key, FL 34228 (MLS # C7495408)
    $648,000
    Photo of 662 Cedars Court, Longboat Key, FL 34228 (MLS # C7495408)
    Photo of 662 Cedars Court, Longboat Key, FL 34228 (MLS # C7495408)
    662 Cedars Court, Longboat Key, FL
    662 Cedars Court
    Longboat Key, FL
    • 2 Beds
    • 3 Baths
    • 1,440 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  22. Photo of 1650 Pine Tree Lane #103, Sarasota, FL 34236 (MLS # A4618186)
    $350,000
    Photo of 1650 Pine Tree Lane #103, Sarasota, FL 34236 (MLS # A4618186)
    Photo of 1650 Pine Tree Lane #103, Sarasota, FL 34236 (MLS # A4618186)
    1650 Pine Tree Lane #103, Sarasota, FL
    1650 Pine Tree Lane #103
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 940 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 301 Quay Commons #1003, Sarasota, FL 34236 (MLS # A4618022)
    $8,000
    Photo of 301 Quay Commons #1003, Sarasota, FL 34236 (MLS # A4618022)
    Photo of 301 Quay Commons #1003, Sarasota, FL 34236 (MLS # A4618022)
    301 Quay Commons #1003, Sarasota, FL
    301 Quay Commons #1003
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,828 Home (sqft)
    • 3 Baths
    • 42,689 Lot (sqft)
  24. Photo of 1601 S Shade Avenue, Sarasota, FL 34239 (MLS # A4617932)
    $3,500
    Photo of 1601 S Shade Avenue, Sarasota, FL 34239 (MLS # A4617932)
    Photo of 1601 S Shade Avenue, Sarasota, FL 34239 (MLS # A4617932)
    1601 S Shade Avenue, Sarasota, FL
    1601 S Shade Avenue
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,018 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
  25. Photo of 6005 Midnight Pass Road #N3, Sarasota, FL 34242 (MLS # A4618021)
    $10,125
    Photo of 6005 Midnight Pass Road #N3, Sarasota, FL 34242 (MLS # A4618021)
    Photo of 6005 Midnight Pass Road #N3, Sarasota, FL 34242 (MLS # A4618021)
    33
     
    6005 Midnight Pass Road #N3, Sarasota, FL
    6005 Midnight Pass Road #N3
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,148 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  26. Photo of 6144 Midnight Pass Road #2N, Sarasota, FL 34242 (MLS # A4616371)
    $1,950,000
    Photo of 6144 Midnight Pass Road #2N, Sarasota, FL 34242 (MLS # A4616371)
    Photo of 6144 Midnight Pass Road #2N, Sarasota, FL 34242 (MLS # A4616371)
    6144 Midnight Pass Road #2N, Sarasota, FL
    6144 Midnight Pass Road #2N
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,204 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  27. Photo of 2020 Harbourside Drive #424, Longboat Key, FL 34228 (MLS # N6133799)
    $1,550,000
    Photo of 2020 Harbourside Drive #424, Longboat Key, FL 34228 (MLS # N6133799)
    Photo of 2020 Harbourside Drive #424, Longboat Key, FL 34228 (MLS # N6133799)
    2020 Harbourside Drive #424, Longboat Key, FL
    2020 Harbourside Drive #424
    Longboat Key, FL
    • 3 Beds
    • 3 Baths
    • 2,462 Home (sqft)
    • 3 Baths
    • 3.90 Lot (ac)
  28. Photo of 3702 5th Avenue, Bradenton Beach, FL 34217 (MLS # A4618112)
    $4,490,000
    Photo of 3702 5th Avenue, Bradenton Beach, FL 34217 (MLS # A4618112)
    Photo of 3702 5th Avenue, Bradenton Beach, FL 34217 (MLS # A4618112)
    3702 5th Avenue, Bradenton Beach, FL
    3702 5th Avenue
    Bradenton Beach, FL
    • 5 Beds
    • 5 Baths
    • 2,784 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  29. Photo of 835 S Osprey Avenue #204, Sarasota, FL 34236 (MLS # A4617985)
    $494,000
    Photo of 835 S Osprey Avenue #204, Sarasota, FL 34236 (MLS # A4617985)
    Photo of 835 S Osprey Avenue #204, Sarasota, FL 34236 (MLS # A4617985)
    835 S Osprey Avenue #204, Sarasota, FL
    835 S Osprey Avenue #204
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 940 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  30. Photo of Sarasota, FL 34236 (MLS # O6223615)
    $320,000
    Photo of Sarasota, FL 34236 (MLS # O6223615)
    Photo of Sarasota, FL 34236 (MLS # O6223615)
    MLS # O6223615, Sarasota, FL
    MLS # O6223615
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 750 Home (sqft)
    • 0 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 7/26/24 11:34 PM PDT.

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