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 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
1 – 12 of 95 Listings
Price, High to Low

6 Bed • 8 Bath • 4,420 Sf • 1 Acres

$8,100,000

5005 Gulf Of Mexico Dr #2, Longboat Key

Under Construction. Bonaire Is Exquisite In Every Detail! Gulf Front Gated Community And Custom Estate On Very Desirable Longboat Key Mirrors The B...

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4 Bed • 4 Bath • 3,490 Sf

$7,800,000

5005 Gulf Of Mexico Dr #9, Longboat Key

Under Construction. Relax Amidst Nature’s Beauty And Allow The Unparalleled Scenery Of The Bonaire Community Carry You Away To Bliss. This 4 Bedroo...

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3 Bed • 4 Bath • 3,833 Sf

$6,100,000

2251 Gulf Of Mexico #504, Longboat Key

Nothing Compares To Aria, A Coastal Contemporary Enclave Built On One Of The Last & Most Coveted Beachfront Sites On South Longboat Key. Now There ...

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Reduced 3%

4 Bed • 5 Bath • 3,595 Sf

$3,850,000

5005 Gulf Of Mexico Dr #5, Longboat Key

Extraordinary Property In The Beautiful, Exclusive Gulf Side Community Of Bonaire. Brand New British West Indies Home Is Only Steps Away From A Pri...

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Reduced 6%

4 Bed • 5 Bath • 3,895 Sf

$3,800,000

2399 Gulf Of Mexico Dr #3c3, Longboat Key

The Tropical Paradise Community Of Vizcaya Resides On The South End Of Longboat Key On 9 Acres W/31 Private Residences & 500 Ft. Of Beachfront. Upo...

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Reduced 3%

3 Bed • 4 Bath • 3,400 Sf

$3,280,000

1241 Gulf Of Mexico Dr #801, Longboat Key

Southwest Corner 3,400 Sq. Ft. 3 Bedroom/3.5 Bathroom Residence With 10 Ft. Ceilings Throughout Is Luxurious And Serene At Every Turn. Beyond The P...

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Reduced 6%

3 Bed • 5 Bath • 3,273 Sf

$3,200,000

1281 Gulf Of Mexico Dr #1007, Longboat Key

Beachfront Oasis! Driving Through The Gated Entry Of The Water Club, Up The Sun-kissed Waterfall Drive You’re Welcomed To A World Of Luxury. Reside...

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3 Bed • 2 Bath • 2,137 Sf • 2 Acres

$2,950,000

6661 Gulf Of Mexico Dr, Longboat Key

Bring Your Imagination To See This Charming Gulf & Beach Front Octagon House & Consider Renovating, Expanding Or Building A New Home There. The Pro...

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Reduced 8%

4 Bed • 5 Bath • 3,340 Sf

$2,895,000

5005 Gulf Of Mexico Dr #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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3 Bed • 3 Bath • 2,820 Sf

$2,195,000

435 L Ambiance Dr #j403, Longboat Key

Offered Furnished And Immediately Ready To Enjoy, Gulf-to-bay Living At L’ambiance Is A Sought-after Experience And This Three-bedroom, Fourth-floo...

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Reduced 7%

4 Bed • 4 Bath • 4,050 Sf

$1,950,000

1001 Longboat Club Rd, Longboat Key

Located Behind The Coveted Gates Of The Longboat Key Club, This 4 Bedroom Home Is Only 150 Yards Away From The Beach And Ideally Situated Among Lon...

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2 Bed • 3 Bath • 2,650 Sf

$1,849,000

1241 Gulf Of Mexico Dr #906, Longboat Key

Property Features: Amazing Ocean & Bay Views, Furniture & Televisions Included, 2 Parking Spaces, 1 A Private Garage W/ample Storage (was Purchase...

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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.

Listing information last updated on April 25th, 2019 at 3:45pm CDT.

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