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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 543 Key Royale Drive, Holmes Beach, FL 34217 (MLS # A4627140)
    $3,450,000
    Photo of 543 Key Royale Drive, Holmes Beach, FL 34217 (MLS # A4627140)
    Photo of 543 Key Royale Drive, Holmes Beach, FL 34217 (MLS # A4627140)
    543 Key Royale Drive, Holmes Beach, FL
    543 Key Royale Drive
    Holmes Beach, FL
    • 4 Beds
    • 2 Baths
    • 2,768 Home (sqft)
    • 2 Baths
    • 23,523 Lot (sqft)
  2. Photo of 4440 Exeter Drive #301, Longboat Key, FL 34228 (MLS # A4625829)
    $669,000
    Photo of 4440 Exeter Drive #301, Longboat Key, FL 34228 (MLS # A4625829)
    Photo of 4440 Exeter Drive #301, Longboat Key, FL 34228 (MLS # A4625829)
    4440 Exeter Drive #301, Longboat Key, FL
    4440 Exeter Drive #301
    Longboat Key, FL
    • 2 Beds
    • 2 Baths
    • 1,168 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  3. Photo of 230 Sands Point Road #3505, Longboat Key, FL 34228 (MLS # A4627411)
    $1,118,000
    Photo of 230 Sands Point Road #3505, Longboat Key, FL 34228 (MLS # A4627411)
    Photo of 230 Sands Point Road #3505, Longboat Key, FL 34228 (MLS # A4627411)
    44
     
    230 Sands Point Road #3505, Longboat Key, FL
    230 Sands Point Road #3505
    Longboat Key, FL
    • 1 Bed
    • 1 Bath
    • 634 Home (sqft)
    • 1 Bath
    • 14.16 Lot (ac)
  4. Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4627985)
    $3,775,000
    Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4627985)
    Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4627985)
    1671 Arlington Street, Sarasota, FL
    1671 Arlington Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,250 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  5. Photo of 2534 Grove Street, Sarasota, FL 34239 (MLS # A4627589)
    $3,240,000
    Photo of 2534 Grove Street, Sarasota, FL 34239 (MLS # A4627589)
    Photo of 2534 Grove Street, Sarasota, FL 34239 (MLS # A4627589)
    22
     
    2534 Grove Street, Sarasota, FL
    2534 Grove Street
    Sarasota, FL
    • 6 Beds
    • 7 Baths
    • 4,615 Home (sqft)
    • 7 Baths
    • 10,890 Lot (sqft)
  6. Photo of 2124 Clematis Place, Sarasota, FL 34239 (MLS # A4627462)
    $2,960,000
    Photo of 2124 Clematis Place, Sarasota, FL 34239 (MLS # A4627462)
    Photo of 2124 Clematis Place, Sarasota, FL 34239 (MLS # A4627462)
    22
     
    2124 Clematis Place, Sarasota, FL
    2124 Clematis Place
    Sarasota, FL
    • 6 Beds
    • 7 Baths
    • 3,574 Home (sqft)
    • 7 Baths
    • 10,019 Lot (sqft)
  7. Photo of 3400 S Tamiami Trail #300, Sarasota, FL 34239 (MLS # A4627427)
    $34,000
    Photo of 3400 S Tamiami Trail #300, Sarasota, FL 34239 (MLS # A4627427)
    Photo of 3400 S Tamiami Trail #300, Sarasota, FL 34239 (MLS # A4627427)
    3400 S Tamiami Trail #300, Sarasota, FL
    3400 S Tamiami Trail #300
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 25,047 Home (sqft)
    • 0 Baths
    • 1.33 Lot (ac)
  8. Photo of 3400 S Tamiami Trail #304, Sarasota, FL 34239 (MLS # A4627429)
    $24,000
    Photo of 3400 S Tamiami Trail #304, Sarasota, FL 34239 (MLS # A4627429)
    Photo of 3400 S Tamiami Trail #304, Sarasota, FL 34239 (MLS # A4627429)
    3400 S Tamiami Trail #304, Sarasota, FL
    3400 S Tamiami Trail #304
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 25,047 Home (sqft)
    • 0 Baths
    • 1.33 Lot (ac)
  9. Photo of 2442 Hibiscus Street, Sarasota, FL 34239 (MLS # A4627419)
    $2,195
    Photo of 2442 Hibiscus Street, Sarasota, FL 34239 (MLS # A4627419)
    Photo of 2442 Hibiscus Street, Sarasota, FL 34239 (MLS # A4627419)
    2442 Hibiscus Street, Sarasota, FL
    2442 Hibiscus Street
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,454 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  10. Photo of 2100 Benjamin Franklin Drive #205, Sarasota, FL 34236 (MLS # A4627311)
    $699,000
    Photo of 2100 Benjamin Franklin Drive #205, Sarasota, FL 34236 (MLS # A4627311)
    Photo of 2100 Benjamin Franklin Drive #205, Sarasota, FL 34236 (MLS # A4627311)
    2100 Benjamin Franklin Drive #205, Sarasota, FL
    2100 Benjamin Franklin Drive #205
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,172 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  11. Photo of 2532 Fruit Tree, Sarasota, FL 34239 (MLS # A4627289)
    $2,750,000
    Photo of 2532 Fruit Tree, Sarasota, FL 34239 (MLS # A4627289)
    Photo of 2532 Fruit Tree, Sarasota, FL 34239 (MLS # A4627289)
    23
     
    2532 Fruit Tree, Sarasota, FL
    2532 Fruit Tree
    Sarasota, FL
    • 5 Beds
    • 6 Baths
    • 3,931 Home (sqft)
    • 6 Baths
    • 10,019 Lot (sqft)
  12. Photo of 7247 Turnstone Road, Sarasota, FL 34242 (MLS # A4627192)
    $1,950,000
    Photo of 7247 Turnstone Road, Sarasota, FL 34242 (MLS # A4627192)
    Photo of 7247 Turnstone Road, Sarasota, FL 34242 (MLS # A4627192)
    7247 Turnstone Road, Sarasota, FL
    7247 Turnstone Road
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 36,155 Lot (sqft)
  13. Photo of 9397 Midnight Pass Road #603, Sarasota, FL 34242 (MLS # A4627224)
    $4,500
    Photo of 9397 Midnight Pass Road #603, Sarasota, FL 34242 (MLS # A4627224)
    Photo of 9397 Midnight Pass Road #603, Sarasota, FL 34242 (MLS # A4627224)
    9397 Midnight Pass Road #603, Sarasota, FL
    9397 Midnight Pass Road #603
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 778 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  14. Photo of 5329 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4627052)
    $850,000
    Photo of 5329 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4627052)
    Photo of 5329 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4627052)
    5329 Avenida Del Mare, Sarasota, FL
    5329 Avenida Del Mare
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 7,406 Lot (sqft)
  15. Photo of 100 Central Avenue #F-812, Sarasota, FL 34236 (MLS # A4627222)
    $1,150,000
    Photo of 100 Central Avenue #F-812, Sarasota, FL 34236 (MLS # A4627222)
    Photo of 100 Central Avenue #F-812, Sarasota, FL 34236 (MLS # A4627222)
    100 Central Avenue #F-812, Sarasota, FL
    100 Central Avenue #F-812
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,532 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  16. Photo of 908 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4627214)
    $1,700,000
    Photo of 908 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4627214)
    Photo of 908 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4627214)
    908 Pomelo Avenue, Sarasota, FL
    908 Pomelo Avenue
    Sarasota, FL
    • 5 Beds
    • 3 Baths
    • 2,358 Home (sqft)
    • 3 Baths
    • 20,909 Lot (sqft)
  17. Photo of 835 S Osprey Avenue #211, Sarasota, FL 34236 (MLS # A4627710)
    $375,000
    Photo of 835 S Osprey Avenue #211, Sarasota, FL 34236 (MLS # A4627710)
    Photo of 835 S Osprey Avenue #211, Sarasota, FL 34236 (MLS # A4627710)
    835 S Osprey Avenue #211, Sarasota, FL
    835 S Osprey Avenue #211
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 721 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  18. Photo of 2415 Floyd Street, Sarasota, FL 34239 (MLS # A4627912)
    $1,699,000
    Photo of 2415 Floyd Street, Sarasota, FL 34239 (MLS # A4627912)
    Photo of 2415 Floyd Street, Sarasota, FL 34239 (MLS # A4627912)
    51
     
    2415 Floyd Street, Sarasota, FL
    2415 Floyd Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,665 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
  19. Photo of 50 Central Avenue #17PHC, Sarasota, FL 34236 (MLS # A4627561)
    $5,450,000
    Photo of 50 Central Avenue #17PHC, Sarasota, FL 34236 (MLS # A4627561)
    Photo of 50 Central Avenue #17PHC, Sarasota, FL 34236 (MLS # A4627561)
    50 Central Avenue #17PHC, Sarasota, FL
    50 Central Avenue #17PHC
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 4,174 Home (sqft)
    • 4 Baths
    • 20,474 Lot (sqft)
  20. Photo of 6415 Midnight Pass Road #708, Sarasota, FL 34242 (MLS # A4627297)
    $570,000
    Photo of 6415 Midnight Pass Road #708, Sarasota, FL 34242 (MLS # A4627297)
    Photo of 6415 Midnight Pass Road #708, Sarasota, FL 34242 (MLS # A4627297)
    6415 Midnight Pass Road #708, Sarasota, FL
    6415 Midnight Pass Road #708
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,287 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  21. Photo of 1322 N Tamiami Trail, Sarasota, FL 34236 (MLS # A4627132)
    $2,740,000
    Photo of 1322 N Tamiami Trail, Sarasota, FL 34236 (MLS # A4627132)
    Photo of 1322 N Tamiami Trail, Sarasota, FL 34236 (MLS # A4627132)
    37
     
    1322 N Tamiami Trail, Sarasota, FL
    1322 N Tamiami Trail
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 4,280 Home (sqft)
    • 0 Baths
    • 11,326 Lot (sqft)
  22. Photo of 8037 Midnight Pass Road, Sarasota, FL 34242 (MLS # D6138672)
    $2,500,000
    Photo of 8037 Midnight Pass Road, Sarasota, FL 34242 (MLS # D6138672)
    Photo of 8037 Midnight Pass Road, Sarasota, FL 34242 (MLS # D6138672)
    20
     
    8037 Midnight Pass Road, Sarasota, FL
    8037 Midnight Pass Road
    Sarasota, FL
    • 5 Beds
    • 4 Baths
    • 4,201 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  23. Photo of 8037 Midnight Pass Road, Sarasota, FL 34242 (MLS # D6138673)
    $2,500,000
    Photo of 8037 Midnight Pass Road, Sarasota, FL 34242 (MLS # D6138673)
    Photo of 8037 Midnight Pass Road, Sarasota, FL 34242 (MLS # D6138673)
    20
     
    8037 Midnight Pass Road, Sarasota, FL
    8037 Midnight Pass Road
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 11,326 Lot (sqft)
  24. Photo of 5329 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4627057)
    $850,000
    Photo of 5329 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4627057)
    Photo of 5329 Avenida Del Mare, Sarasota, FL 34242 (MLS # A4627057)
    5329 Avenida Del Mare, Sarasota, FL
    5329 Avenida Del Mare
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,011 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  25. Photo of 8213 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4626945)
    $12,000
    Photo of 8213 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4626945)
    Photo of 8213 Midnight Pass Road, Sarasota, FL 34242 (MLS # A4626945)
    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)
  26. Photo of 850 S Tamiami Trail #833, Sarasota, FL 34236 (MLS # A4625073)
    $400,000
    Photo of 850 S Tamiami Trail #833, Sarasota, FL 34236 (MLS # A4625073)
    Photo of 850 S Tamiami Trail #833, Sarasota, FL 34236 (MLS # A4625073)
    56
     
    850 S Tamiami Trail #833, Sarasota, FL
    850 S Tamiami Trail #833
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  27. Photo of 1257 S Portofino Drive #406, Sarasota, FL 34242 (MLS # A4627089)
    $649,900
    Photo of 1257 S Portofino Drive #406, Sarasota, FL 34242 (MLS # A4627089)
    Photo of 1257 S Portofino Drive #406, Sarasota, FL 34242 (MLS # A4627089)
    1257 S Portofino Drive #406, Sarasota, FL
    1257 S Portofino Drive #406
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 929 Home (sqft)
    • 2 Baths
    • 2.68 Lot (ac)
  28. Photo of 361 Avenida Madera, Sarasota, FL 34242 (MLS # A4625795)
    $1,090,000
    Photo of 361 Avenida Madera, Sarasota, FL 34242 (MLS # A4625795)
    Photo of 361 Avenida Madera, Sarasota, FL 34242 (MLS # A4625795)
    361 Avenida Madera, Sarasota, FL
    361 Avenida Madera
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 8,277 Lot (sqft)
  29. Photo of 361 Avenida Madera, Sarasota, FL 34242 (MLS # A4625794)
    $1,090,000
    Photo of 361 Avenida Madera, Sarasota, FL 34242 (MLS # A4625794)
    Photo of 361 Avenida Madera, Sarasota, FL 34242 (MLS # A4625794)
    361 Avenida Madera, Sarasota, FL
    361 Avenida Madera
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,692 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  30. Photo of 301 Quay Commons #1011, Sarasota, FL 34236 (MLS # A4626988)
    $11,000
    Photo of 301 Quay Commons #1011, Sarasota, FL 34236 (MLS # A4626988)
    Photo of 301 Quay Commons #1011, Sarasota, FL 34236 (MLS # A4626988)
    74
     
    301 Quay Commons #1011, Sarasota, FL
    301 Quay Commons #1011
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 2,079 Home (sqft)
    • 3 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 11/22/24 8:13 PM PST.

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