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 Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$600,000 - $700,000 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
1 – 12 of 68 Listings
Price, High to Low

6 Bed • 8 Bath • 5,763 Sf • 1 Acres


5005 Gulf Of Mexico Dr #2, Longboat Key

Under Construction. Ultimate Beachfront Luxury- Newly Constructed Property With Six Bedrooms, Six Bathrooms And Expansive Living Areas Which Showc...

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11 Bed • 14 Bath • 14,005 Sf • 1 Acres


5541 Gulf Of Mexico Dr, Longboat Key

Enjoy The Easy Lifestyle Of This Home With Awe-inspiring Views Overlooking The Wide Waters Of Gulf Of Mexico. A Rare Find And A Must See Beachfront...

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Reduced 7%

4 Bed • 4 Bath • 3,922 Sf


5005 Gulf Of Mexico Dr #9, Longboat Key

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

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5 Bed • 6 Bath • 4,115 Sf


5005 Gulf Of Mexico Dr #8, Longboat Key

Bonaire, An Exclusive Gulf Side Community, Which Has 9 Custom Homes And A Private Community Beach Access. This Extraordinary Home Is Designed In T...

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3 Bed • 5 Bath • 3,400 Sf


1241 Gulf Of Mexico Dr #701, Longboat Key

“shelter-in-paradise” From This Sought-after Direct Gulf Front Location On The 7th Floor At The Coveted Water Club On Longboat Key. Be “wowed” By M...

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New Listing

3 Bed • 5 Bath • 3,273 Sf


1281 Gulf Of Mexico Dr #ph1108, Longboat Key

Discover The Pinnacle Of Beachfront Living Set Atop The Northeast Corner Of The Water Club In This Spectacular 3br Gulf-to-bay Penthouse Residence,...

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Reduced 3%

3 Bed • 5 Bath • 3,273 Sf


1281 Gulf Of Mexico Dr #1007, Longboat Key

Instant Enjoyment - No Need To Remodel...beachfront Oasis! Driving Through The Gated Entry Of The Water Club, Up The Sun-kissed Waterfall Drive You...

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Reduced 6%

3 Bed • 4 Bath • 3,464 Sf • 1 Acres


5950 Gulf Of Mexico Dr, Longboat Key

Pre-construction. To Be Built. Build This Beautiful John Cannon Home Or Pick Out One Of Their Other Custom Home Designs. Or Bring Your Own Custom H...

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Reduced 3%

4 Bed • 4 Bath • 4,210 Sf


798 Jungle Queen Way, Longboat Key

Brand New Custom Built Canal Front Home With Pool On Longboat Key. Enjoy The Island Life To The Fullest At This Beautiful New Home Located Just 4 H...

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4 Bed • 4 Bath • 2,316 Sf • 1 Acres


5870 Gulf Of Mexico Dr, Longboat Key

Waterfront Charm Nestled On Nearly .60 Acres On Gulf Of Mexico Drive. This Is A Unique Home Built At A Time When Longboat Key Was Just Incorporate...

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2 Bed • 3 Bath • 2,665 Sf • 2 Acres


1281 Gulf Of Mexico Dr #906, Longboat Key

Move Right Into This Light And Open Beach Residence At The Water Club, Offering A Flourish Of Direct Views That Stretch From Turquoise Gulf Waters ...

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2 Bed • 3 Bath • 2,650 Sf


1241 Gulf Of Mexico Dr #505, Longboat Key

Direct Vistas Of White-capped Gulf Waves, Powdery Shores And Sunny Southern Panoramas Welcome You To This Fifth-floor Cambridge Residence At The So...

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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 21st, 2020 at 1:15am CDT.

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