This 11-mile stretch of beach-to-bay resort living boasts a variety of great homes: sprawling beach front mansions, chic million-dollar condominiums, wooden bungalows, cozy canal homes, vacation rentals, and casual low-rise condos. Gulf of Mexico Drive, which runs the length of the island, is lined with colorful flowers and banyan trees and bordered by a popular bike and jogging trail. Many people call Longboat Key home year-round, while others visit seasonally.

While some beaches on the island are private, there are many public access points.  Many take advantage of the clear blue waters for boating, swimming, fishing, parasailing, and jet skiing or some enjoy land activities like golfing and tennis.

Longboat Key

All Listings $100,000 - $200,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $800,000 - $900,000
Over $1,000,000
1 – 12 of 21 Listings
Price, High to Low

5 Bed • 9 Bath • 9,947 Sf • 1 Acres

$12,900,000

3105 Gulf Of Mexico Drive, LONGBOAT KEY

Live Your Best Life Now In This Amazing, Rarely Available Beachfront Residence On Longboat Key. Enjoy Endless Water Views, Early Morning Walks, Gen...

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4 Bed • 6 Bath • 4,247 Sf

$4,295,000

5840 Gulf Of Mexico Drive, LONGBOAT KEY

Under Construction. Welcome To Your Well-deserved Paradise! Here On Longboat Key, Retreat To A Gorgeous, Newly Constructed, Canal Front Getaway On ...

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4 Bed • 5 Bath • 3,340 Sf

$3,695,000

5005 Gulf Of Mexico Drive 6, LONGBOAT KEY

Masterfully Combining Quality, Class And Elegance, This Luxurious Newly Constructed West Indies Style Home, Is Situated Just Steps From The Beach, ...

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New Listing

2 Bed • 4 Bath • 3,045 Sf

$2,500,000

1241 Gulf Of Mexico Drive 304, LONGBOAT KEY

Featuring Stunning Views Of The Gulf Of Mexico, This Exceptionally Furnished Brighton Residence Has Over 3,000 Square Feet, Including An Open Floor...

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2 Bed • 3 Bath • 1,905 Sf

$2,500,000

629 Kingfisher Lane, LONGBOAT KEY

Your New Home Awaits, A Rare Opportunity To Call This Your Own. Enjoy Stunning Sunrises Over Still Bay Waters With Abundant Wildlife And Canopied F...

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3 Bed • 4 Bath • 2,928 Sf • 2 Acres

$2,295,000

595 Dream Island Road 31, LONGBOAT KEY

Rarely Available Opportunity To Own This Exquisite Bayfront Residence Located In The Waterfront Grand Mariner Complex On Longboat Key. This Condo C...

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Reduced 3%

3 Bed • 3 Bath • 1,350 Sf

$875,000

600 Fox Street, LONGBOAT KEY

Your Little Piece Of Southwest Florida Paradise Awaits In This Island Gem! Completely Hardscaped Around This Home, You Will Love Your Outdoor Life ...

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1 Acres

$475,000

2600 Harbourside Drive B-4, LONGBOAT KEY

85' X 24' Boat Dock ~ Longboat Key Moorings Is Strategically Located Just A Few Miles From Downtown Sarasota, Fl. This Location Provides Direct Acc...

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1 Acres

$325,000

2600 Harbourside Drive C-17, LONGBOAT KEY

72' X 21' Boat Dock ~ Longboat Key Moorings Is Strategically Located Just A Few Miles From Downtown Sarasota, Fl. This Location Provides Direct Acc...

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1 Acres

$325,000

2600 Harbourside Drive C-13, LONGBOAT KEY

72' X 21' Boat Dock ~ Longboat Key Moorings Is Strategically Located Just A Few Miles From Downtown Sarasota, Fl. This Location Provides Direct Acc...

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1 Acres

$325,000

2600 Harbourside Drive C-15, LONGBOAT KEY

72' X 21' Boat Dock ~ Longboat Key Moorings Is Strategically Located Just A Few Miles From Downtown Sarasota, Fl. This Location Provides Direct Acc...

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1 Acres

$298,000

2600 Harbourside Drive G-17, LONGBOAT KEY

57 X 23 Ft. Boat Slip With Exceptional Views Of Sarasota Bay, At Longboat Key Moorings Marina. Direct Access To Sarasota Bay And The Icw With Excep...

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on September 28th, 2021 at 8:50am CDT.

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