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 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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$5,500MLS # A4572396, LONGBOAT KEY, FLMLS # A4572396
LONGBOAT KEY, FL- 2 Beds
- 2 Baths
- 1,257 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$7,495,000810 S BAY BOULEVARD #A, ANNA MARIA, FL810 S BAY BOULEVARD #A
ANNA MARIA, FL- 4 Beds
- 5 Baths
- 4,360 Home (sqft)
- 5 Baths
- 11,326 Lot (sqft)
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$925,000233 COSMOPOLITAN COURT, SARASOTA, FL233 COSMOPOLITAN COURT
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,680 Home (sqft)
- 3 Baths
- 1,307 Lot (sqft)
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$975,0001125 W PEPPERTREE DRIVE #803, SARASOTA, FL1125 W PEPPERTREE DRIVE #803
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,200 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$975,0008701 MIDNIGHT PASS ROAD #607A, SARASOTA, FL8701 MIDNIGHT PASS ROAD #607A
SARASOTA, FL- 3 Beds
- 3 Baths
- 1,922 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$1,199,0001212 BENJAMIN FRANKLIN DRIVE #308, SARASOTA, FL1212 BENJAMIN FRANKLIN DRIVE #308
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,421 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$3,985,0003017 AVENUE E, HOLMES BEACH, FL3017 AVENUE E
HOLMES BEACH, FL- 4 Beds
- 5 Baths
- 2,875 Home (sqft)
- 5 Baths
- 6,534 Lot (sqft)
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$2,6003451 SEA VIEW STREET, SARASOTA, FL3451 SEA VIEW STREET
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,565 Home (sqft)
- 2 Baths
- 8,712 Lot (sqft)
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$699,0005325 MARINA DRIVE #423, HOLMES BEACH, FL5325 MARINA DRIVE #423
HOLMES BEACH, FL- 2 Beds
- 2 Baths
- 1,023 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$3,400,000223 GOLDEN GATE POINT #5A, SARASOTA, FL223 GOLDEN GATE POINT #5A
SARASOTA, FL- 3 Beds
- 4 Baths
- 2,832 Home (sqft)
- 4 Baths
- 43,560 Lot (sqft)
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$5,800,000223 GOLDEN GATE POINT #8C, SARASOTA, FL223 GOLDEN GATE POINT #8C
SARASOTA, FL- 3 Beds
- 4 Baths
- 3,068 Home (sqft)
- 4 Baths
- 43,560 Lot (sqft)
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$699,0002737 SIESTA DRIVE, SARASOTA, FL2737 SIESTA DRIVE
SARASOTA, FL- 3 Beds
- 3 Baths
- 1,941 Home (sqft)
- 3 Baths
- 15,246 Lot (sqft)
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$1,900,000113 CEDAR AVENUE, ANNA MARIA, FL113 CEDAR AVENUE
ANNA MARIA, FL- 2 Beds
- 2 Baths
- 964 Home (sqft)
- 2 Baths
- 5,228 Lot (sqft)
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$2,275,0002208 BOUGAINVILLEA STREET, SARASOTA, FL2208 BOUGAINVILLEA STREET
SARASOTA, FL- 5 Beds
- 4 Baths
- 3,220 Home (sqft)
- 4 Baths
- 10,890 Lot (sqft)
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$2,3003240 GULF OF MEXICO DRIVE #603, LONGBOAT KEY, FL3240 GULF OF MEXICO DRIVE #603
LONGBOAT KEY, FL- 2 Beds
- 2 Baths
- 1,260 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$7,200,0004651 GULF OF MEXICO DRIVE #102, LONGBOAT KEY, FL4651 GULF OF MEXICO DRIVE #102
LONGBOAT KEY, FL- 4 Beds
- 6 Baths
- 4,007 Home (sqft)
- 6 Baths
- 3.40 Lot (ac)
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$594,500101 S GULFSTREAM AVENUE #16C, SARASOTA, FL101 S GULFSTREAM AVENUE #16C
SARASOTA, FL- 1 Bed
- 2 Baths
- 1,002 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$6,850,000538 CANAL ROAD, SARASOTA, FL538 CANAL ROAD
SARASOTA, FL- 8 Beds
- 7 Baths
- 4,094 Home (sqft)
- 7 Baths
- 6,534 Lot (sqft)
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$749,0003330 GULF OF MEXICO DRIVE #106-D, LONGBOAT KEY, FL3330 GULF OF MEXICO DRIVE #106-D
LONGBOAT KEY, FL- 2 Beds
- 2 Baths
- 1,106 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$5,9401188 N TAMIAMI TRAIL #205-B, SARASOTA, FL1188 N TAMIAMI TRAIL #205-B
SARASOTA, FL- 0 Beds
- 0 Baths
- 87 Home (sqft)
- 0 Baths
- 41,382 Lot (sqft)
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$1,8501508 DOLPHIN STREET #4, SARASOTA, FL1508 DOLPHIN STREET #4
SARASOTA, FL- 1 Bed
- 1 Bath
- 412 Home (sqft)
- 1 Bath
- 8,610.00 Lot (ac)
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$1,9503751 S SCHOOL AVENUE #26, SARASOTA, FL3751 S SCHOOL AVENUE #26
SARASOTA, FL- 2 Beds
- 2 Baths
- 964 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$1,500,0003484 HAMILTON AVENUE, SARASOTA, FL3484 HAMILTON AVENUE
SARASOTA, FL- 3 Beds
- 2 Baths
- 2,658 Home (sqft)
- 2 Baths
- 16,118 Lot (sqft)
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$675,0002107 ORCHID STREET, SARASOTA, FL2107 ORCHID STREET
SARASOTA, FL- 2 Beds
- 1 Bath
- 1,032 Home (sqft)
- 1 Bath
- 9,148 Lot (sqft)
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$1,200,000831 SIESTA DRIVE, SARASOTA, FL831 SIESTA DRIVE
SARASOTA, FL- 0 Beds
- 0 Baths
- 0 Home (sqft)
- 0 Baths
- 16,989 Lot (sqft)
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$6,0003520 MINEOLA DRIVE, SARASOTA, FL3520 MINEOLA DRIVE
SARASOTA, FL- 3 Beds
- 3 Baths
- 1,652 Home (sqft)
- 3 Baths
- 13,068 Lot (sqft)
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$2,0502055 ARLINGTON STREET #201, SARASOTA, FL2055 ARLINGTON STREET #201
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,100 Home (sqft)
- 2 Baths
- 24,830 Lot (sqft)
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$1,5753001 BEE RIDGE ROAD #210, SARASOTA, FL3001 BEE RIDGE ROAD #210
SARASOTA, FL- 1 Bed
- 1 Bath
- 560 Home (sqft)
- 1 Bath
- 1.24 Lot (ac)
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$1,6503001 BEE RIDGE ROAD #110, SARASOTA, FL3001 BEE RIDGE ROAD #110
SARASOTA, FL- 1 Bed
- 1 Bath
- 560 Home (sqft)
- 1 Bath
- 1.24 Lot (ac)
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$495,0001801 GULF DRIVE N #279, BRADENTON BEACH, FL1801 GULF DRIVE N #279
BRADENTON BEACH, FL- 1 Bed
- 1 Bath
- 691 Home (sqft)
- 1 Bath
- 0 Lot (sqft)
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