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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31 - 60 of 500+ | Previous Page 2 of 17 Next
  1. Photo of 415 Alamanda Road, Anna Maria, FL 34216 (MLS # A4617294)
    $1,495,000
    Photo of 415 Alamanda Road, Anna Maria, FL 34216 (MLS # A4617294)
    Photo of 415 Alamanda Road, Anna Maria, FL 34216 (MLS # A4617294)
    415 Alamanda Road, Anna Maria, FL
    415 Alamanda Road
    Anna Maria, FL
    • 2 Beds
    • 2 Baths
    • 1,304 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  2. Photo of 3430 Jaffa Drive, Sarasota, FL 34239 (MLS # A4616125)
    $435,000
    Photo of 3430 Jaffa Drive, Sarasota, FL 34239 (MLS # A4616125)
    Photo of 3430 Jaffa Drive, Sarasota, FL 34239 (MLS # A4616125)
    3430 Jaffa Drive, Sarasota, FL
    3430 Jaffa Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,624 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  3. Photo of 6005 Midnight Pass Road #S7, Sarasota, FL 34242 (MLS # A4618009)
    $6,500
    Photo of 6005 Midnight Pass Road #S7, Sarasota, FL 34242 (MLS # A4618009)
    Photo of 6005 Midnight Pass Road #S7, Sarasota, FL 34242 (MLS # A4618009)
    6005 Midnight Pass Road #S7, Sarasota, FL
    6005 Midnight Pass Road #S7
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 755 Home (sqft)
    • 1 Bath
    • 2.64 Lot (ac)
  4. Photo of Anna Maria, FL 34216 (MLS # A4617881)
    $1,395,000
    Photo of Anna Maria, FL 34216 (MLS # A4617881)
    Photo of Anna Maria, FL 34216 (MLS # A4617881)
    17
     
    MLS # A4617881, Anna Maria, FL
    MLS # A4617881
    Anna Maria, FL
    • 2 Beds
    • 2 Baths
    • 1,064 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  5. Photo of 5830 Midnight Pass Road #502, Sarasota, FL 34242 (MLS # A4617982)
    $1,450,000
    Photo of 5830 Midnight Pass Road #502, Sarasota, FL 34242 (MLS # A4617982)
    Photo of 5830 Midnight Pass Road #502, Sarasota, FL 34242 (MLS # A4617982)
    30
     
    5830 Midnight Pass Road #502, Sarasota, FL
    5830 Midnight Pass Road #502
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,285 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  6. Photo of 2525 Floyd Street, Sarasota, FL 34239 (MLS # A4617999)
    $465,000
    Photo of 2525 Floyd Street, Sarasota, FL 34239 (MLS # A4617999)
    Photo of 2525 Floyd Street, Sarasota, FL 34239 (MLS # A4617999)
    2525 Floyd Street, Sarasota, FL
    2525 Floyd Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,193 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  7. Photo of 33 S Gulfstream Avenue #704, Sarasota, FL 34236 (MLS # A4617964)
    $338,000
    Photo of 33 S Gulfstream Avenue #704, Sarasota, FL 34236 (MLS # A4617964)
    Photo of 33 S Gulfstream Avenue #704, Sarasota, FL 34236 (MLS # A4617964)
    33 S Gulfstream Avenue #704, Sarasota, FL
    33 S Gulfstream Avenue #704
    Sarasota, FL
    • 0 Beds
    • 1 Bath
    • 590 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  8. Photo of 212 83rd Street, Holmes Beach, FL 34217 (MLS # A4616664)
    $1,195,000
    Photo of 212 83rd Street, Holmes Beach, FL 34217 (MLS # A4616664)
    Photo of 212 83rd Street, Holmes Beach, FL 34217 (MLS # A4616664)
    212 83rd Street, Holmes Beach, FL
    212 83rd Street
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,702 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  9. Photo of 432 Avenida De Mayo #B, Sarasota, FL 34242 (MLS # A4617496)
    $2,250
    Photo of 432 Avenida De Mayo #B, Sarasota, FL 34242 (MLS # A4617496)
    Photo of 432 Avenida De Mayo #B, Sarasota, FL 34242 (MLS # A4617496)
    432 Avenida De Mayo #B, Sarasota, FL
    432 Avenida De Mayo #B
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 460 Home (sqft)
    • 1 Bath
    • 6,099 Lot (sqft)
  10. Photo of 6006 Midnight Pass Road #16, Sarasota, FL 34242 (MLS # A4617495)
    $3,150
    Photo of 6006 Midnight Pass Road #16, Sarasota, FL 34242 (MLS # A4617495)
    Photo of 6006 Midnight Pass Road #16, Sarasota, FL 34242 (MLS # A4617495)
    35
     
    6006 Midnight Pass Road #16, Sarasota, FL
    6006 Midnight Pass Road #16
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 600 Home (sqft)
    • 1 Bath
    • 6.39 Lot (ac)
  11. Photo of 432 Avenida De Mayo #A, Sarasota, FL 34242 (MLS # A4617497)
    $3,000
    Photo of 432 Avenida De Mayo #A, Sarasota, FL 34242 (MLS # A4617497)
    Photo of 432 Avenida De Mayo #A, Sarasota, FL 34242 (MLS # A4617497)
    432 Avenida De Mayo #A, Sarasota, FL
    432 Avenida De Mayo #A
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 772 Home (sqft)
    • 1 Bath
    • 6,099 Lot (sqft)
  12. Photo of 5963 Midnight Pass Road #332, Sarasota, FL 34242 (MLS # A4617494)
    $10,500
    Photo of 5963 Midnight Pass Road #332, Sarasota, FL 34242 (MLS # A4617494)
    Photo of 5963 Midnight Pass Road #332, Sarasota, FL 34242 (MLS # A4617494)
    5963 Midnight Pass Road #332, Sarasota, FL
    5963 Midnight Pass Road #332
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,270 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  13. Photo of 4390 Exeter Drive #305, Longboat Key, FL 34228 (MLS # A4615872)
    $430,000
    Photo of 4390 Exeter Drive #305, Longboat Key, FL 34228 (MLS # A4615872)
    Photo of 4390 Exeter Drive #305, Longboat Key, FL 34228 (MLS # A4615872)
    4390 Exeter Drive #305, Longboat Key, FL
    4390 Exeter Drive #305
    Longboat Key, FL
    • 1 Bed
    • 1 Bath
    • 756 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  14. Photo of 850 S Tamiami Trail #203, Sarasota, FL 34236 (MLS # A4617820)
    $2,000
    Photo of 850 S Tamiami Trail #203, Sarasota, FL 34236 (MLS # A4617820)
    Photo of 850 S Tamiami Trail #203, Sarasota, FL 34236 (MLS # A4617820)
    850 S Tamiami Trail #203, Sarasota, FL
    850 S Tamiami Trail #203
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  15. Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4617809)
    $2,298,000
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4617809)
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4617809)
    65356537 Peacock Road, Sarasota, FL
    65356537 Peacock Road
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 3,000 Home (sqft)
    • 6 Baths
    • 6,099 Lot (sqft)
  16. Photo of 722 Siesta Key Circle, Sarasota, FL 34242 (MLS # A4617797)
    $3,650,000
    Photo of 722 Siesta Key Circle, Sarasota, FL 34242 (MLS # A4617797)
    Photo of 722 Siesta Key Circle, Sarasota, FL 34242 (MLS # A4617797)
    722 Siesta Key Circle, Sarasota, FL
    722 Siesta Key Circle
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,488 Home (sqft)
    • 5 Baths
    • 12,197 Lot (sqft)
  17. Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4618001)
    $2,500,000
    Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4618001)
    Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4618001)
    303 Beach Road, Sarasota, FL
    303 Beach Road
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  18. Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4616649)
    $2,500,000
    Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4616649)
    Photo of 303 Beach Road, Sarasota, FL 34242 (MLS # A4616649)
    303 Beach Road, Sarasota, FL
    303 Beach Road
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 1,380 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  19. Photo of 1701 Hillview Street, Sarasota, FL 34239 (MLS # A4617068)
    $2,199,000
    Photo of 1701 Hillview Street, Sarasota, FL 34239 (MLS # A4617068)
    Photo of 1701 Hillview Street, Sarasota, FL 34239 (MLS # A4617068)
    1701 Hillview Street, Sarasota, FL
    1701 Hillview Street
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,545 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  20. Photo of 508 65th Street, Holmes Beach, FL 34217 (MLS # A4617789)
    $1,500,000
    Photo of 508 65th Street, Holmes Beach, FL 34217 (MLS # A4617789)
    Photo of 508 65th Street, Holmes Beach, FL 34217 (MLS # A4617789)
    508 65th Street, Holmes Beach, FL
    508 65th Street
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,985 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  21. Photo of 830 Tarawitt Drive, Longboat Key, FL 34228 (MLS # A4617446)
    $17,000
    Photo of 830 Tarawitt Drive, Longboat Key, FL 34228 (MLS # A4617446)
    Photo of 830 Tarawitt Drive, Longboat Key, FL 34228 (MLS # A4617446)
    830 Tarawitt Drive, Longboat Key, FL
    830 Tarawitt Drive
    Longboat Key, FL
    • 4 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  22. Photo of 6250 Holmes Boulevard #34, Holmes Beach, FL 34217 (MLS # A4616846)
    $849,000
    Photo of 6250 Holmes Boulevard #34, Holmes Beach, FL 34217 (MLS # A4616846)
    Photo of 6250 Holmes Boulevard #34, Holmes Beach, FL 34217 (MLS # A4616846)
    6250 Holmes Boulevard #34, Holmes Beach, FL
    6250 Holmes Boulevard #34
    Holmes Beach, FL
    • 3 Beds
    • 3 Baths
    • 1,512 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  23. Photo of 630 Companion Way, Longboat Key, FL 34228 (MLS # A4617730)
    $11,000
    Photo of 630 Companion Way, Longboat Key, FL 34228 (MLS # A4617730)
    Photo of 630 Companion Way, Longboat Key, FL 34228 (MLS # A4617730)
    630 Companion Way, Longboat Key, FL
    630 Companion Way
    Longboat Key, FL
    • 4 Beds
    • 5 Baths
    • 2,900 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  24. Photo of 1125 Lake House Circle #C112, Sarasota, FL 34242 (MLS # A4617715)
    $725,000
    Photo of 1125 Lake House Circle #C112, Sarasota, FL 34242 (MLS # A4617715)
    Photo of 1125 Lake House Circle #C112, Sarasota, FL 34242 (MLS # A4617715)
    1125 Lake House Circle #C112, Sarasota, FL
    1125 Lake House Circle #C112
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,352 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 4822 Ocean Boulevard #4D, Sarasota, FL 34242 (MLS # A4617651)
    $850,000
    Photo of 4822 Ocean Boulevard #4D, Sarasota, FL 34242 (MLS # A4617651)
    Photo of 4822 Ocean Boulevard #4D, Sarasota, FL 34242 (MLS # A4617651)
    4822 Ocean Boulevard #4D, Sarasota, FL
    4822 Ocean Boulevard #4D
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,440 Home (sqft)
    • 2 Baths
    • 40,076 Lot (sqft)
  26. Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617702)
    $11,000
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617702)
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617702)
    53
     
    1255 N Gulfstream Avenue #402, Sarasota, FL
    1255 N Gulfstream Avenue #402
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,269 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617698)
    $1,975,000
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617698)
    Photo of 1255 N Gulfstream Avenue #402, Sarasota, FL 34236 (MLS # A4617698)
    41
     
    1255 N Gulfstream Avenue #402, Sarasota, FL
    1255 N Gulfstream Avenue #402
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,269 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  28. Photo of 300 Bay Dr S, Bradenton Beach, FL 34217 (MLS # A4617625)
    $595,000
    Photo of 300 Bay Dr S, Bradenton Beach, FL 34217 (MLS # A4617625)
    Photo of 300 Bay Dr S, Bradenton Beach, FL 34217 (MLS # A4617625)
    300 Bay Dr S, Bradenton Beach, FL
    300 Bay Dr S
    Bradenton Beach, FL
    • 0 Beds
    • 0 Baths
    • 1,226 Home (sqft)
    • 0 Baths
    • 0 Lot (sqft)
  29. Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4616843)
    $2,298,000
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4616843)
    Photo of 65356537 Peacock Road, Sarasota, FL 34242 (MLS # A4616843)
    65356537 Peacock Road, Sarasota, FL
    65356537 Peacock Road
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,000 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  30. Photo of 5858 Midnight Pass Road #27, Sarasota, FL 34242 (MLS # A4616738)
    $659,900
    Photo of 5858 Midnight Pass Road #27, Sarasota, FL 34242 (MLS # A4616738)
    Photo of 5858 Midnight Pass Road #27, Sarasota, FL 34242 (MLS # A4616738)
    5858 Midnight Pass Road #27, Sarasota, FL
    5858 Midnight Pass Road #27
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 531 Home (sqft)
    • 1 Bath
    • 5.02 Lot (ac)
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