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 - $1,128,100
Median Home Price - $530,000
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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$7,850,0001620 GULF OF MEXICO DRIVE #502, LONGBOAT KEY, FL1620 GULF OF MEXICO DRIVE #502
LONGBOAT KEY, FL- 3 Beds
- 4 Baths
- 4,992 Home (sqft)
- 4 Baths
- 17.80 Lot (ac)
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$7,800,000612 JUAN ANASCO DRIVE, LONGBOAT KEY, FL612 JUAN ANASCO DRIVE
LONGBOAT KEY, FL- 6 Beds
- 8 Baths
- 8,976 Home (sqft)
- 8 Baths
- 1.16 Lot (ac)
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$7,600,0001620 GULF OF MEXICO DRIVE #618, LONGBOAT KEY, FL1620 GULF OF MEXICO DRIVE #618
LONGBOAT KEY, FL- 4 Beds
- 6 Baths
- 5,320 Home (sqft)
- 6 Baths
- 17.80 Lot (ac)
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$6,950,000771 OLD COMPASS ROAD, LONGBOAT KEY, FL771 OLD COMPASS ROAD
LONGBOAT KEY, FL- 4 Beds
- 6 Baths
- 5,259 Home (sqft)
- 6 Baths
- 16,898 Lot (sqft)
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$5,595,000500 HARBOR POINT ROAD, LONGBOAT KEY, FL500 HARBOR POINT ROAD
LONGBOAT KEY, FL- 4 Beds
- 8 Baths
- 6,556 Home (sqft)
- 8 Baths
- 25,407 Lot (sqft)
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$5,460,0004651 GULF OF MEXICO DRIVE #304, LONGBOAT KEY, FL4651 GULF OF MEXICO DRIVE #304
LONGBOAT KEY, FL- 4 Beds
- 5 Baths
- 4,100 Home (sqft)
- 5 Baths
- 3.40 Lot (ac)
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$5,050,0004651 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL4651 GULF OF MEXICO DRIVE #203
LONGBOAT KEY, FL- 4 Beds
- 5 Baths
- 3,900 Home (sqft)
- 5 Baths
- 3.40 Lot (ac)
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$4,895,000591 GOLF LINKS LANE, LONGBOAT KEY, FL591 GOLF LINKS LANE
LONGBOAT KEY, FL- 4 Beds
- 5 Baths
- 4,200 Home (sqft)
- 5 Baths
- 13,749 Lot (sqft)
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$4,380,0004651 GULF OF MEXICO DRIVE #402, LONGBOAT KEY, FL4651 GULF OF MEXICO DRIVE #402
LONGBOAT KEY, FL- 4 Beds
- 5 Baths
- 3,900 Home (sqft)
- 5 Baths
- 3.40 Lot (ac)
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$4,295,0005840 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL5840 GULF OF MEXICO DRIVE
LONGBOAT KEY, FL- 4 Beds
- 6 Baths
- 4,247 Home (sqft)
- 6 Baths
- 16,249 Lot (sqft)
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$3,990,000500 BUTTONWOOD DRIVE, LONGBOAT KEY, FL500 BUTTONWOOD DRIVE
LONGBOAT KEY, FL- 4 Beds
- 4 Baths
- 4,868 Home (sqft)
- 4 Baths
- 13,219 Lot (sqft)
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$3,920,0001620 GULF OF MEXICO DRIVE #411, LONGBOAT KEY, FL1620 GULF OF MEXICO DRIVE #411
LONGBOAT KEY, FL- 2 Beds
- 3 Baths
- 3,130 Home (sqft)
- 3 Baths
- 17.80 Lot (ac)
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$3,700,0005372 SANDHAMN PLACE, LONGBOAT KEY, FL5372 SANDHAMN PLACE
LONGBOAT KEY, FL- 4 Beds
- 5 Baths
- 5,484 Home (sqft)
- 5 Baths
- 15,290 Lot (sqft)
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$3,500,0005005 GULF OF MEXICO DRIVE #5, LONGBOAT KEY, FL5005 GULF OF MEXICO DRIVE #5
LONGBOAT KEY, FL- 4 Beds
- 5 Baths
- 3,595 Home (sqft)
- 5 Baths
- 10,070 Lot (sqft)
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$3,200,0006603 GULFSIDE ROAD, LONGBOAT KEY, FL6603 GULFSIDE ROAD
LONGBOAT KEY, FL- 3 Beds
- 3 Baths
- 3,051 Home (sqft)
- 3 Baths
- 20,430 Lot (sqft)
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$3,075,0001511 GULF OF MEXICO DRIVE #202, LONGBOAT KEY, FL1511 GULF OF MEXICO DRIVE #202
LONGBOAT KEY, FL- 3 Beds
- 4 Baths
- 2,940 Home (sqft)
- 4 Baths
- 3.40 Lot (ac)
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$2,495,000550 BUTTONWOOD DRIVE, LONGBOAT KEY, FL550 BUTTONWOOD DRIVE
LONGBOAT KEY, FL- 4 Beds
- 3 Baths
- 4,390 Home (sqft)
- 3 Baths
- 11,525 Lot (sqft)
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$2,491,000595 BOWSPRIT LANE, LONGBOAT KEY, FL595 BOWSPRIT LANE
LONGBOAT KEY, FL- 3 Beds
- 3 Baths
- 2,582 Home (sqft)
- 3 Baths
- 11,015 Lot (sqft)
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$2,445,000545 SANCTUARY DRIVE #B706, LONGBOAT KEY, FL545 SANCTUARY DRIVE #B706
LONGBOAT KEY, FL- 3 Beds
- 3 Baths
- 2,375 Home (sqft)
- 3 Baths
- 24,656 Lot (sqft)
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$1,999,0001055 GULF OF MEXICO DRIVE #106, LONGBOAT KEY, FL1055 GULF OF MEXICO DRIVE #106
LONGBOAT KEY, FL- 3 Beds
- 2 Baths
- 1,819 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$1,995,0001620 GULF OF MEXICO DRIVE #307, LONGBOAT KEY, FL1620 GULF OF MEXICO DRIVE #307
LONGBOAT KEY, FL- 1 Bed
- 2 Baths
- 1,721 Home (sqft)
- 2 Baths
- 17.80 Lot (ac)
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$1,899,000798 JUNGLE QUEEN WAY, LONGBOAT KEY, FL798 JUNGLE QUEEN WAY
LONGBOAT KEY, FL- 4 Beds
- 4 Baths
- 4,210 Home (sqft)
- 4 Baths
- 11,250 Lot (sqft)
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$1,895,0002224 HARBOUR COURT DRIVE, LONGBOAT KEY, FL2224 HARBOUR COURT DRIVE
LONGBOAT KEY, FL- 3 Beds
- 4 Baths
- 2,959 Home (sqft)
- 4 Baths
- 7,498 Lot (sqft)
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$1,875,0007147 LA LENAIRE DRIVE, LONGBOAT KEY, FL7147 LA LENAIRE DRIVE
LONGBOAT KEY, FL- 6 Beds
- 6 Baths
- 3,503 Home (sqft)
- 6 Baths
- 1.35 Lot (ac)
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$1,795,000415 L AMBIANCE DRIVE #E507, LONGBOAT KEY, FL415 L AMBIANCE DRIVE #E507
LONGBOAT KEY, FL- 2 Beds
- 3 Baths
- 2,385 Home (sqft)
- 3 Baths
- 10.16 Lot (ac)
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$1,699,0005870 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL5870 GULF OF MEXICO DRIVE
LONGBOAT KEY, FL- 4 Beds
- 4 Baths
- 2,316 Home (sqft)
- 4 Baths
- 25,976 Lot (sqft)
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$1,195,0006320 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL6320 GULF OF MEXICO DRIVE
LONGBOAT KEY, FL- 3 Beds
- 4 Baths
- 2,583 Home (sqft)
- 4 Baths
- 14,941 Lot (sqft)
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$1,195,0004239 GULF OF MEXICO DRIVE #MH4, LONGBOAT KEY, FL4239 GULF OF MEXICO DRIVE #MH4
LONGBOAT KEY, FL- 3 Beds
- 2 Baths
- 1,549 Home (sqft)
- 2 Baths
- 0 Lot (sqft)
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$1,100,0005055 GULF OF MEXICO DRIVE #334 & 324, LONGBOAT KEY, FL5055 GULF OF MEXICO DRIVE #334 & 324
LONGBOAT KEY, FL- 3 Beds
- 3 Baths
- 2,968 Home (sqft)
- 3 Baths
- 8.77 Lot (ac)
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$1,079,000370 GULF OF MEXICO DRIVE #422, LONGBOAT KEY, FL370 GULF OF MEXICO DRIVE #422
LONGBOAT KEY, FL- 2 Beds
- 3 Baths
- 2,255 Home (sqft)
- 3 Baths
- 10.93 Lot (ac)
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