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 Over $1,000,000
1 – 12 of 38 Listings
Price, High to Low

3 Bed • 5 Bath • 4,967 Sf • 18 Acres

$8,000,000

1620 Gulf Of Mexico Drive 304, LONGBOAT KEY

Pre-construction. To Be Built. Undoubtedly One Of The Most Breathtaking Views And Locations At The Residences At The St. Regis In The Coveted Arman...

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5 Bed • 5 Bath • 5,126 Sf • 1 Acres

$7,990,000

5030 Gulf Of Mexico Drive, LONGBOAT KEY

Check Out The New Video "virtual Tour Link 1" This Is One Of The Most Prominent Longboat Key Bayfront Estates "bayside Villa". Rich With History ...

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4 Bed • 5 Bath • 4,017 Sf • 18 Acres

$6,670,000

1620 Gulf Of Mexico Drive 405, LONGBOAT KEY

Pre-construction. To Be Built. This 4-bedroom Corner Residence Offers A Wonderful Opportunity To Be Above It All At The New St. Regis Resort And Sp...

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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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New Listing

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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4 Bed • 5 Bath • 4,641 Sf

$2,400,000

431 North Shore Road, LONGBOAT KEY

This Amazing Home Was Built To The Highest Standards And You Realize It From The Moment You Step Inside! Located On The Beachside Of Gulf Of Mexico...

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1 Bed • 2 Bath • 1,721 Sf • 18 Acres

$2,195,000

1620 Gulf Of Mexico Drive 307, LONGBOAT KEY

Pre-construction. To Be Built. Elegant And Gracious One Bedroom Residence With Spacious Rooms, Floor To Ceiling Glass And Soaring Ceilings. Well-ap...

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1 Bed • 2 Bath • 1,721 Sf • 18 Acres

$2,095,000

1620 Gulf Of Mexico Drive 407, LONGBOAT KEY

Pre-construction. To Be Built. Elegant And Gracious One Bedroom Residence With Spacious Rooms, Floor To Ceiling Glass And 10’ Ceilings. Well Appoin...

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New Listing

3 Bed • 2 Bath • 1,621 Sf

$1,675,000

545 Rountree Drive, LONGBOAT KEY

Beautiful Remodeled Home On A Canal With Direct Access To The Intracoastal Waterway Of Sarasota Bay And The Gulf Of Mexico. Located In The Exclusiv...

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4 Bed • 3 Bath • 3,320 Sf

$1,599,000

651 Broadway Street, LONGBOAT KEY

This Is Truly One Of The Finest Homes Located In The Famous And Friendly Long Beach Village Where All The Joys Of Island Living Abound. The Neighbo...

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3 Bed • 4 Bath • 2,583 Sf

$1,395,000

6320 Gulf Of Mexico Drive, LONGBOAT KEY

Opportunity To Own A Wonderful Three Bedroom Home Across From The Beach And Gorgeous Gulf Water With A Deeded Dock With A Lift. The Bay Water Is D...

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New Listing

2 Bed • 2 Bath • 1,578 Sf

$1,195,000

775 Longboat Club Road 1007, LONGBOAT KEY

Beachfront Penthouse With The Most Beautiful Views Of The Gulf, Sarasota Skyline, Golf Course And Sarasota Bay! Water Views From Every Room From Th...

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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 7th, 2021 at 8:48pm CDT.

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