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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$947,0001661 7TH STREET, SARASOTA, FL1661 7TH STREET
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,222 Home (sqft)
- 2 Baths
- 6,534 Lot (sqft)
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$110,000915 SEASIDE DRIVE #511, Weeks 16-17, SARASOTA, FL915 SEASIDE DRIVE #511, Weeks 16-17
SARASOTA, FL- 4 Beds
- 4 Baths
- 2,625 Home (sqft)
- 4 Baths
- 0 Lot (sqft)
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$1,799,000365 AVENIDA DE PARADISIO, SARASOTA, FL365 AVENIDA DE PARADISIO
SARASOTA, FL- 4 Beds
- 4 Baths
- 2,542 Home (sqft)
- 4 Baths
- 10,019 Lot (sqft)
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$1,200,000104 29TH STREET #1, HOLMES BEACH, FL104 29TH STREET #1
HOLMES BEACH, FL- 3 Beds
- 2 Baths
- 1,616 Home (sqft)
- 2 Baths
- 5,228 Lot (sqft)
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$1,600,0001127 S OSPREY AVENUE, SARASOTA, FL1127 S OSPREY AVENUE
SARASOTA, FL- 4 Beds
- 4 Baths
- 2,200 Home (sqft)
- 4 Baths
- 10,019 Lot (sqft)
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$8,000111 PINEAPPLE AVENUE S #1002, SARASOTA, FL111 PINEAPPLE AVENUE S #1002
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,535 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$1,995,0001912 HIGH POINT DRIVE, SARASOTA, FL1912 HIGH POINT DRIVE
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,941 Home (sqft)
- 2 Baths
- 9,148 Lot (sqft)
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$675,0001801 GULF DRIVE N #187, BRADENTON BEACH, FL1801 GULF DRIVE N #187
BRADENTON BEACH, FL- 2 Beds
- 2 Baths
- 1,080 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$2,095,0002185 GULF OF MEXICO DRIVE #211, LONGBOAT KEY, FL2185 GULF OF MEXICO DRIVE #211
LONGBOAT KEY, FL- 3 Beds
- 3 Baths
- 2,485 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$3,350,000136 GOLDEN GATE POINT #401, SARASOTA, FL136 GOLDEN GATE POINT #401
SARASOTA, FL- 3 Beds
- 4 Baths
- 3,785 Home (sqft)
- 4 Baths
- 0 Lot (sqft)
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$1,300,0002369 BAHIA VISTA STREET, SARASOTA, FL2369 BAHIA VISTA STREET
SARASOTA, FL- 4 Beds
- 3 Baths
- 2,048 Home (sqft)
- 3 Baths
- 5,663 Lot (sqft)
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$6,5004380 EXETER DRIVE #103, LONGBOAT KEY, FL4380 EXETER DRIVE #103
LONGBOAT KEY, FL- 2 Beds
- 1 Bath
- 992 Home (sqft)
- 1 Bath
- 0 Lot (sqft)
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$1,300,0002365 BAHIA VISTA STREET, SARASOTA, FL2365 BAHIA VISTA STREET
SARASOTA, FL- 4 Beds
- 3 Baths
- 2,048 Home (sqft)
- 3 Baths
- 5,663 Lot (sqft)
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$1,300,0002355 BAHIA VISTA STREET, SARASOTA, FL2355 BAHIA VISTA STREET
SARASOTA, FL- 4 Beds
- 3 Baths
- 2,048 Home (sqft)
- 3 Baths
- 5,663 Lot (sqft)
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$1,350,0001750 BENJAMIN FRANKLIN DRIVE #3C, SARASOTA, FL1750 BENJAMIN FRANKLIN DRIVE #3C
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,364 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$979,0003311 GULF DRIVE #3, HOLMES BEACH, FL3311 GULF DRIVE #3
HOLMES BEACH, FL- 2 Beds
- 2 Baths
- 1,331 Home (sqft)
- 2 Baths
- 9,584 Lot (sqft)
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$7,4005164 WINDWARD AVENUE, SARASOTA, FL5164 WINDWARD AVENUE
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,972 Home (sqft)
- 2 Baths
- 17,424 Lot (sqft)
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$1,350420 ADELIA AVENUE, SARASOTA, FL420 ADELIA AVENUE
SARASOTA, FL- 1 Bed
- 1 Bath
- 500 Home (sqft)
- 1 Bath
- 4,792 Lot (sqft)
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$6,875,000804 N SHORE DRIVE, ANNA MARIA, FL804 N SHORE DRIVE
ANNA MARIA, FL- 7 Beds
- 3 Baths
- 5,462 Home (sqft)
- 3 Baths
- 10,019 Lot (sqft)
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$1,457,3633636 MINEOLA DRIVE, SARASOTA, FL3636 MINEOLA DRIVE
SARASOTA, FL- 2 Beds
- 2 Baths
- 2,000 Home (sqft)
- 2 Baths
- 11,762 Lot (sqft)
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$975,0005400 GULF DRIVE #32, HOLMES BEACH, FL5400 GULF DRIVE #32
HOLMES BEACH, FL- 2 Beds
- 2 Baths
- 1,188 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$649,000101 S GULFSTREAM AVENUE #15E, SARASOTA, FL101 S GULFSTREAM AVENUE #15E
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,200 Home (sqft)
- 2 Baths
- 1.01 Lot (ac)
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$12,50011 SUNSET DRIVE #805, SARASOTA, FL11 SUNSET DRIVE #805
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,433 Home (sqft)
- 2 Baths
- 1.89 Lot (ac)
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$1,500,000101 BENJAMIN FRANKLIN DRIVE #26, SARASOTA, FL101 BENJAMIN FRANKLIN DRIVE #26
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,275 Home (sqft)
- 2 Baths
- 1.42 Lot (ac)
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$1,999,5003060 GRAND BAY BOULEVARD #153, LONGBOAT KEY, FL3060 GRAND BAY BOULEVARD #153
LONGBOAT KEY, FL- 2 Beds
- 3 Baths
- 2,550 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$14,000847 HUDSON AVENUE, SARASOTA, FL847 HUDSON AVENUE
SARASOTA, FL- 3 Beds
- 3 Baths
- 2,142 Home (sqft)
- 3 Baths
- 17,424 Lot (sqft)
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$8,3001155 N GULFSTREAM AVENUE #508, SARASOTA, FL1155 N GULFSTREAM AVENUE #508
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,710 Home (sqft)
- 3 Baths
- 436 Lot (sqft)
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$675,000413 63RD STREET, HOLMES BEACH, FL413 63RD STREET
HOLMES BEACH, FL- 2 Beds
- 2 Baths
- 900 Home (sqft)
- 2 Baths
- 2,614 Lot (sqft)
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$650,000411 63RD STREET, HOLMES BEACH, FL411 63RD STREET
HOLMES BEACH, FL- 2 Beds
- 2 Baths
- 972 Home (sqft)
- 2 Baths
- 3,485 Lot (sqft)
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$1,6003001 BEE RIDGE ROAD #213, SARASOTA, FL3001 BEE RIDGE ROAD #213
SARASOTA, FL- 1 Bed
- 1 Bath
- 560 Home (sqft)
- 1 Bath
- 1.24 Lot (ac)
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