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
$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 90 Listings
Price, High to Low

5 Bed • 6 Bath • 4,808 Sf • 1 Acres

$8,900,000

5005 Gulf Of Mexico Dr #3, Longboat Key

Under Construction. Bonaire Is An Exclusive Gated Gulf Front Community Of Just 9 Homes On 3.5 Acres. Featuring New West Indies Style Homes Designed...

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6 Bed • 8 Bath • 5,763 Sf • 1 Acres

$8,100,000

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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4 Bed • 4 Bath • 3,922 Sf

$4,950,000

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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4 Bed • 5 Bath • 4,646 Sf

$3,450,000

545 Kingfisher Ln, Longboat Key

New Construction– Custom Longboat Key Waterfront Home. Live The Longboat Lifestyle To The Fullest In This Custom Built Modern Canal Front Longboa...

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New Listing

3 Bed • 5 Bath • 3,400 Sf

$3,195,000

1241 Gulf Of Mexico Dr #701, Longboat Key

Mesmerizing Gulf, Beach, City & Bay Views Far As The Eye Can See From This Sought-after 7th Floor Direct Gulf Front Location At The Coveted Water C...

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3 Bed • 4 Bath • 2,820 Sf

$3,195,000

435 L Ambiance Dr #k306, Longboat Key

This L'ambiance Home Is A Must See And Unlike Anything Else Ever Offered In The Building! Condo Living At Its Finest In L'ambiance At Longboat Key ...

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Reduced 4%

4 Bed • 5 Bath • 3,783 Sf

$3,099,000

581 Kingfisher Ln, Longboat Key

New Construction - Longboat Mid-key Deep Water Canal Home. Architected By Beacon Home Design And Built By Ross Built Construction, 581 Kingfisher L...

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3 Bed • 5 Bath • 3,273 Sf

$2,975,000

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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4 Bed • 6 Bath • 4,709 Sf

$2,950,000

604 Rountree Dr, Longboat Key

Mesmerizing In Every Sense, This Longboat Key Canal-front Home Captures The Unmistakable Warmth Of A Luxury Villa In The Spanish Mediterranean, Whi...

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New Listing

3 Bed • 3 Bath • 3,273 Sf • 2 Acres

$2,895,000

1281 Gulf Of Mexico Dr #1008, Longboat Key

Panoramic Gulf-to-bay Views Are The Highlight Throughout This Beautiful Contemporary Residence At The Exclusive Water Club Community, Located On Th...

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Reduced 6%

3 Bed • 4 Bath • 3,464 Sf • 1 Acres

$2,340,000

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 9%

3 Bed • 3 Bath • 2,820 Sf

$1,995,000

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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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 February 27th, 2020 at 2:15pm CST.

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