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 78 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

$4,585,000

5005 Gulf Of Mexico Dr #9, Longboat Key

Special Limited Time Offering By Developer To Escape To Beautiful Long Boat Key. Owner Financing Available Up To 60% With 0% Financing For 6 Month...

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3 Bed • 5 Bath • 3,400 Sf

$3,195,000

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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Reduced 3%

4 Bed • 5 Bath • 3,925 Sf

$2,999,999

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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Reduced 3%

4 Bed • 5 Bath • 4,646 Sf

$2,995,000

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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Reduced 3%

3 Bed • 5 Bath • 3,273 Sf

$2,875,000

1281 Gulf Of Mexico Dr #1007, Longboat Key

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

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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 3%

4 Bed • 4 Bath • 4,210 Sf

$1,899,000

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

$1,699,000

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 • 2 Bath • 1,318 Sf

$1,599,000

590 Jessmyth Dr, Longboat Key

One Or More Photo(s) Has Been Virtually Staged. Escape To The Seclusion Of Longboat Key Estates, Where You’ll Find This Picturesque Bayfront Addres...

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2 Bed • 3 Bath • 2,665 Sf • 2 Acres

$1,495,000

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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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 May 27th, 2020 at 11:30pm CDT.

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