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Longboat Key

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As much an international destination as it is a beloved favorite among visitors and residents from all over the U.S., Longboat Key’s span crosses through both Sarasota and Manatee Counties. This magnificent length of shoreline got its first road courtesy of circus magnate John Ringling in 1925. Originally, it extended only from New Pass at the southernmost tip to the Manatee County line, but Ringling envisioned a beautifully landscaped boulevard that would run the full length of the barrier island.

Today’s Gulf of Mexico Drive is the magnificently landscaped thoroughfare that Ringling had imagined to run the full length of Longboat Key. It winds past splendid homes and condominiums, lush greenways and parks, hidden driveways and side streets, yacht basins and captivating stretches of the Gulf of Mexico. Along both sides are discreet shopping plazas—filled with upscale shopping and fine dining—and the emerald-shaded fairways that comprise the two championship courses of Longboat Key Club

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Single Family Home for Sale in Longboat Key - MLS # 334894

Sarasota MLS # 334894

$9,900,000
  • Beds : 5
  • |
  • Baths : 5 F 3 H
  • |
  • Sq Ft : 9,000
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Single Family Home for Sale in Longboat Key - MLS # 356725

Sarasota MLS # 356725

$9,900,000
  • Beds : 5
  • |
  • Baths : 6 F 2 H
  • |
  • Sq Ft : 10,797
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Single Family Home for Sale in Longboat Key - MLS # 559011

Manatee MLS # 559011

$9,900,000
  • Beds : 5
  • |
  • Baths : 8 F
  • |
  • Sq Ft : 10,797
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Single Family Home for Sale at 558 Harbor Point Rd, Longboat Key, Florida 34228 - MLS # 380705

558 HARBOR POINT RD, LONGBOAT KEY 34228

$6,950,000
  • Beds : 5
  • |
  • Baths : 5 F 2 H
  • |
  • Sq Ft : 6,644
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Michael Saunders & Company
Single Family Home for Sale in Longboat Key - MLS # 551023

Manatee MLS # 551023

$6,900,000
  • Beds : 7
  • |
  • Baths : 9 F
  • |
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Single Family Home for Sale in Longboat Key - MLS # 378745

Sarasota MLS # 378745

$6,499,000
  • Beds : 3
  • |
  • Baths : 5 F 1 H
  • |
  • Sq Ft : 6,400
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Single Family Home for Sale in Longboat Key - MLS # 333194

Sarasota MLS # 333194

$6,200,000
  • Beds : 5
  • |
  • Baths : 5 F 1 H
  • |
  • Sq Ft : 5,000
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Single Family Home for Sale in Longboat Key - MLS # 374190

Sarasota MLS # 374190

$6,095,000
  • Beds : 4
  • |
  • Baths : 3 F 1 H
  • |
  • Sq Ft : 4,500
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Single Family Home for Sale in Longboat Key - MLS # 370528

Sarasota MLS # 370528

$5,995,000
  • Beds : 6
  • |
  • Baths : 6 F
  • |
  • Sq Ft : 6,190
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Single Family Home for Sale in Longboat Key - MLS # 371394

Sarasota MLS # 371394

$5,900,000
  • Beds : 6
  • |
  • Baths : 4 F 1 H
  • |
  • Sq Ft : 3,148
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260 LISTINGS FOUND
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