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 6518 MIDNIGHT PASS ROAD #510, SARASOTA, FL 34242 (MLS # A4572592)
    $1,120,000
    Photo of 6518 MIDNIGHT PASS ROAD #510, SARASOTA, FL 34242 (MLS # A4572592)
    Photo of 6518 MIDNIGHT PASS ROAD #510, SARASOTA, FL 34242 (MLS # A4572592)
    6518 MIDNIGHT PASS ROAD #510, SARASOTA, FL
    6518 MIDNIGHT PASS ROAD #510
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,215 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 1188 N TAMIAMI TRAIL #202, SARASOTA, FL 34236 (MLS # A4572551)
    $639,000
    Photo of 1188 N TAMIAMI TRAIL #202, SARASOTA, FL 34236 (MLS # A4572551)
    Photo of 1188 N TAMIAMI TRAIL #202, SARASOTA, FL 34236 (MLS # A4572551)
    1188 N TAMIAMI TRAIL #202, SARASOTA, FL
    1188 N TAMIAMI TRAIL #202
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,093 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  3. Photo of 6334 MIDNIGHT PASS ROAD #45, SARASOTA, FL 34242 (MLS # C7476411)
    $550,000
    Photo of 6334 MIDNIGHT PASS ROAD #45, SARASOTA, FL 34242 (MLS # C7476411)
    Photo of 6334 MIDNIGHT PASS ROAD #45, SARASOTA, FL 34242 (MLS # C7476411)
    17
     
    6334 MIDNIGHT PASS ROAD #45, SARASOTA, FL
    6334 MIDNIGHT PASS ROAD #45
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 612 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  4. Photo of 640 N OWL DRIVE, SARASOTA, FL 34236 (MLS # A4572272)
    $4,293,000
    Photo of 640 N OWL DRIVE, SARASOTA, FL 34236 (MLS # A4572272)
    Photo of 640 N OWL DRIVE, SARASOTA, FL 34236 (MLS # A4572272)
    640 N OWL DRIVE, SARASOTA, FL
    640 N OWL DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,344 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  5. Photo of 117 7TH STREET N #35, BRADENTON BEACH, FL 34217 (MLS # A4572494)
    $429,000
    Photo of 117 7TH STREET N #35, BRADENTON BEACH, FL 34217 (MLS # A4572494)
    Photo of 117 7TH STREET N #35, BRADENTON BEACH, FL 34217 (MLS # A4572494)
    117 7TH STREET N #35, BRADENTON BEACH, FL
    117 7TH STREET N #35
    BRADENTON BEACH, FL
    • 1 Bed
    • 1 Bath
    • 594 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  6. Photo of 1257 FRUITVILLE ROAD #A, SARASOTA, FL 34236 (MLS # A4572563)
    $3,800
    Photo of 1257 FRUITVILLE ROAD #A, SARASOTA, FL 34236 (MLS # A4572563)
    Photo of 1257 FRUITVILLE ROAD #A, SARASOTA, FL 34236 (MLS # A4572563)
    1257 FRUITVILLE ROAD #A, SARASOTA, FL
    1257 FRUITVILLE ROAD #A
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,533 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  7. Photo of 1740 ALDERMAN STREET #8, SARASOTA, FL 34236 (MLS # A4572555)
    $3,300
    Photo of 1740 ALDERMAN STREET #8, SARASOTA, FL 34236 (MLS # A4572555)
    Photo of 1740 ALDERMAN STREET #8, SARASOTA, FL 34236 (MLS # A4572555)
    1740 ALDERMAN STREET #8, SARASOTA, FL
    1740 ALDERMAN STREET #8
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,264 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  8. Photo of 5238 WINDING WAY, SARASOTA, FL 34242 (MLS # A4569996)
    $1,299,000
    Photo of 5238 WINDING WAY, SARASOTA, FL 34242 (MLS # A4569996)
    Photo of 5238 WINDING WAY, SARASOTA, FL 34242 (MLS # A4569996)
    5238 WINDING WAY, SARASOTA, FL
    5238 WINDING WAY
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,620 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  9. Photo of 3806 GULF OF MEXICO DRIVE #C311, LONGBOAT KEY, FL 34228 (MLS # A4572554)
    $3,000
    Photo of 3806 GULF OF MEXICO DRIVE #C311, LONGBOAT KEY, FL 34228 (MLS # A4572554)
    Photo of 3806 GULF OF MEXICO DRIVE #C311, LONGBOAT KEY, FL 34228 (MLS # A4572554)
    3806 GULF OF MEXICO DRIVE #C311, LONGBOAT KEY, FL
    3806 GULF OF MEXICO DRIVE #C311
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,062 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  10. Photo of 2180 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4572536)
    $2,995,000
    Photo of 2180 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4572536)
    Photo of 2180 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4572536)
    2180 HILLVIEW STREET, SARASOTA, FL
    2180 HILLVIEW STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,322 Home (sqft)
    • 5 Baths
    • 9,148 Lot (sqft)
  11. Photo of 301 N BAY BOULEVARD, ANNA MARIA, FL 34216 (MLS # A4572525)
    $1,795,000
    Photo of 301 N BAY BOULEVARD, ANNA MARIA, FL 34216 (MLS # A4572525)
    Photo of 301 N BAY BOULEVARD, ANNA MARIA, FL 34216 (MLS # A4572525)
    301 N BAY BOULEVARD, ANNA MARIA, FL
    301 N BAY BOULEVARD
    ANNA MARIA, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  12. Photo of 501 GULF DRIVE N #108, BRADENTON BEACH, FL 34217 (MLS # A4572342)
    $549,000
    Photo of 501 GULF DRIVE N #108, BRADENTON BEACH, FL 34217 (MLS # A4572342)
    Photo of 501 GULF DRIVE N #108, BRADENTON BEACH, FL 34217 (MLS # A4572342)
    501 GULF DRIVE N #108, BRADENTON BEACH, FL
    501 GULF DRIVE N #108
    BRADENTON BEACH, FL
    • 2 Beds
    • 2 Baths
    • 1,128 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  13. Photo of 2132 HYDE PARK CIRCLE, SARASOTA, FL 34239 (MLS # A4570518)
    $850,430
    Photo of 2132 HYDE PARK CIRCLE, SARASOTA, FL 34239 (MLS # A4570518)
    Photo of 2132 HYDE PARK CIRCLE, SARASOTA, FL 34239 (MLS # A4570518)
    2132 HYDE PARK CIRCLE, SARASOTA, FL
    2132 HYDE PARK CIRCLE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,888 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  14. Photo of 111 S PINEAPPLE AVENUE #1007, SARASOTA, FL 34236 (MLS # A4571605)
    $1,890,000
    Photo of 111 S PINEAPPLE AVENUE #1007, SARASOTA, FL 34236 (MLS # A4571605)
    Photo of 111 S PINEAPPLE AVENUE #1007, SARASOTA, FL 34236 (MLS # A4571605)
    111 S PINEAPPLE AVENUE #1007, SARASOTA, FL
    111 S PINEAPPLE AVENUE #1007
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,786 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  15. Photo of 903 N SHORE DRIVE #A, ANNA MARIA, FL 34216 (MLS # A4572367)
    $7,900,000
    Photo of 903 N SHORE DRIVE #A, ANNA MARIA, FL 34216 (MLS # A4572367)
    Photo of 903 N SHORE DRIVE #A, ANNA MARIA, FL 34216 (MLS # A4572367)
    903 N SHORE DRIVE #A, ANNA MARIA, FL
    903 N SHORE DRIVE #A
    ANNA MARIA, FL
    • 4 Beds
    • 5 Baths
    • 2,971 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  16. Photo of 1526 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4572399)
    $975,000
    Photo of 1526 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4572399)
    Photo of 1526 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4572399)
    1526 S OSPREY AVENUE, SARASOTA, FL
    1526 S OSPREY AVENUE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,825 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  17. Photo of 1915 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4571582)
    $3,150,000
    Photo of 1915 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4571582)
    Photo of 1915 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4571582)
    1915 CLEMATIS STREET, SARASOTA, FL
    1915 CLEMATIS STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,161 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  18. Photo of 3740 GULF OF MEXICO DRIVE #116, LONGBOAT KEY, FL 34228 (MLS # A4572169)
    $479,900
    Photo of 3740 GULF OF MEXICO DRIVE #116, LONGBOAT KEY, FL 34228 (MLS # A4572169)
    Photo of 3740 GULF OF MEXICO DRIVE #116, LONGBOAT KEY, FL 34228 (MLS # A4572169)
    3740 GULF OF MEXICO DRIVE #116, LONGBOAT KEY, FL
    3740 GULF OF MEXICO DRIVE #116
    LONGBOAT KEY, FL
    • 1 Bed
    • 1 Bath
    • 861 Home (sqft)
    • 1 Bath
    • 1,307 Lot (sqft)
  19. Photo of 2919 MARSHALL DRIVE, SARASOTA, FL 34239 (MLS # A4572178)
    $1,425,000
    Photo of 2919 MARSHALL DRIVE, SARASOTA, FL 34239 (MLS # A4572178)
    Photo of 2919 MARSHALL DRIVE, SARASOTA, FL 34239 (MLS # A4572178)
    2919 MARSHALL DRIVE, SARASOTA, FL
    2919 MARSHALL DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,520 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  20. Photo of 401 QUAY #1101, SARASOTA, FL 34236 (MLS # A4572356)
    $7,695,000
    Photo of 401 QUAY #1101, SARASOTA, FL 34236 (MLS # A4572356)
    Photo of 401 QUAY #1101, SARASOTA, FL 34236 (MLS # A4572356)
    401 QUAY #1101, SARASOTA, FL
    401 QUAY #1101
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,647 Home (sqft)
    • 4 Baths
    • 1.87 Lot (ac)
  21. Photo of 3314 JAFFA DR, SARASOTA, FL 34239 (MLS # A4572454)
    $585,000
    Photo of 3314 JAFFA DR, SARASOTA, FL 34239 (MLS # A4572454)
    Photo of 3314 JAFFA DR, SARASOTA, FL 34239 (MLS # A4572454)
    3314 JAFFA DR, SARASOTA, FL
    3314 JAFFA DR
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,699 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  22. Photo of 1111 RITZ CARLTON DRIVE #1704, SARASOTA, FL 34236 (MLS # A4572456)
    $25,000
    Photo of 1111 RITZ CARLTON DRIVE #1704, SARASOTA, FL 34236 (MLS # A4572456)
    Photo of 1111 RITZ CARLTON DRIVE #1704, SARASOTA, FL 34236 (MLS # A4572456)
    100
     
    1111 RITZ CARLTON DRIVE #1704, SARASOTA, FL
    1111 RITZ CARLTON DRIVE #1704
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 4,943 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  23. Photo of 800 BENJAMIN FRANKLIN DRIVE #108, SARASOTA, FL 34236 (MLS # A4572441)
    $5,800
    Photo of 800 BENJAMIN FRANKLIN DRIVE #108, SARASOTA, FL 34236 (MLS # A4572441)
    Photo of 800 BENJAMIN FRANKLIN DRIVE #108, SARASOTA, FL 34236 (MLS # A4572441)
    800 BENJAMIN FRANKLIN DRIVE #108, SARASOTA, FL
    800 BENJAMIN FRANKLIN DRIVE #108
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,350 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  24. Photo of 4307 GULF DR #206, HOLMES BEACH, FL 34217 (MLS # A4572418)
    $599,000
    Photo of 4307 GULF DR #206, HOLMES BEACH, FL 34217 (MLS # A4572418)
    Photo of 4307 GULF DR #206, HOLMES BEACH, FL 34217 (MLS # A4572418)
    4307 GULF DR #206, HOLMES BEACH, FL
    4307 GULF DR #206
    HOLMES BEACH, FL
    • 2 Beds
    • 2 Baths
    • 1,027 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 85 AVENIDA MESSINA, SARASOTA, FL 34242 (MLS # A4571948)
    $8,950,000
    Photo of 85 AVENIDA MESSINA, SARASOTA, FL 34242 (MLS # A4571948)
    Photo of 85 AVENIDA MESSINA, SARASOTA, FL 34242 (MLS # A4571948)
    85 AVENIDA MESSINA, SARASOTA, FL
    85 AVENIDA MESSINA
    SARASOTA, FL
    • 6 Beds
    • 8 Baths
    • 3,504 Home (sqft)
    • 8 Baths
    • 6,099 Lot (sqft)
  26. Photo of 316 BEACH ROAD, SARASOTA, FL 34242 (MLS # A4571947)
    $8,450,000
    Photo of 316 BEACH ROAD, SARASOTA, FL 34242 (MLS # A4571947)
    Photo of 316 BEACH ROAD, SARASOTA, FL 34242 (MLS # A4571947)
    316 BEACH ROAD, SARASOTA, FL
    316 BEACH ROAD
    SARASOTA, FL
    • 8 Beds
    • 10 Baths
    • 4,681 Home (sqft)
    • 10 Baths
    • 5,663 Lot (sqft)
  27. Photo of 332 AVENIDA DE MAYO, SARASOTA, FL 34242 (MLS # A4571946)
    $6,750,000
    Photo of 332 AVENIDA DE MAYO, SARASOTA, FL 34242 (MLS # A4571946)
    Photo of 332 AVENIDA DE MAYO, SARASOTA, FL 34242 (MLS # A4571946)
    332 AVENIDA DE MAYO, SARASOTA, FL
    332 AVENIDA DE MAYO
    SARASOTA, FL
    • 8 Beds
    • 9 Baths
    • 4,055 Home (sqft)
    • 9 Baths
    • 5,663 Lot (sqft)
  28. Photo of 522 PINE AVENUE #2D, ANNA MARIA, FL 34216 (MLS # A4572382)
    $659,000
    Photo of 522 PINE AVENUE #2D, ANNA MARIA, FL 34216 (MLS # A4572382)
    Photo of 522 PINE AVENUE #2D, ANNA MARIA, FL 34216 (MLS # A4572382)
    522 PINE AVENUE #2D, ANNA MARIA, FL
    522 PINE AVENUE #2D
    ANNA MARIA, FL
    • 2 Beds
    • 2 Baths
    • 822 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  29. Photo of 632 MOURNING DOVE DRIVE, SARASOTA, FL 34236 (MLS # A4571982)
    $3,250,000
    Photo of 632 MOURNING DOVE DRIVE, SARASOTA, FL 34236 (MLS # A4571982)
    Photo of 632 MOURNING DOVE DRIVE, SARASOTA, FL 34236 (MLS # A4571982)
    632 MOURNING DOVE DRIVE, SARASOTA, FL
    632 MOURNING DOVE DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 2,743 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
  30. Photo of LONGBOAT KEY, FL 34228 (MLS # A4572396)
    $5,500
    Photo of LONGBOAT KEY, FL 34228 (MLS # A4572396)
    Photo of LONGBOAT KEY, FL 34228 (MLS # A4572396)
    MLS # A4572396, LONGBOAT KEY, FL
    MLS # A4572396
    LONGBOAT KEY, FL
    • 2 Beds
    • 2 Baths
    • 1,257 Home (sqft)
    • 2 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 6/3/23 10:32 AM PDT.

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