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 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
1 – 12 of 69 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...

View Listing

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...

View Listing
Reduced 5%

4 Bed • 5 Bath • 3,921 Sf

$6,100,000

2251 Gulf Of Mexico Dr #ph 501, Longboat Key

This Is A Rare Opportunity To Own A Luxury Waterfront Penthouse In The Newest Building On Longboat Key. Aria Is An Exclusive, Boutique Property, Li...

View Listing
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...

View Listing

3 Bed • 2 Bath • 2,137 Sf • 2 Acres

$2,950,000

6661 Gulf Of Mexico Dr, Longboat Key

A Beach Setting Beyond Compare, This 1.5 Acre Property Extends Along 96 Feet Of Sandy Shoreline. Listen To The Sound Of The Waves & Experience Eac...

View Listing

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...

View Listing

4 Bed • 4 Bath • 4,210 Sf

$1,999,000

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...

View Listing
Reduced 11%

3 Bed • 3 Bath • 3,414 Sf

$1,950,000

811 Jungle Queen Way, Longboat Key

Immaculate 2 Story Canal Front Home With In Ground Pool Located In N. Longboat Key On A 200 Ft. Seawall. This Beautiful Turnkey Furnished Home Offe...

View Listing
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...

View Listing

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...

View Listing

3 Bed • 4 Bath • 3,054 Sf

$1,800,000

1281 Gulf Of Mexico Dr #803, Longboat Key

Live The Lavish Lifestyle Only Found At The Water Club On Longboat Key. This Exceptional Furnished Brighton Residence Features Stunning Views Of Th...

View Listing

2 Bed • 2 Bath • 1,318 Sf

$1,599,000

590 Jessmyth Dr, Longboat Key

One Or More Photo(s) Has Been Virtually Staged. A Rare Opportunity To Build Your Dream Waterfront Home Overlooking The Panorama Of Sarasota Bay. ...

View Listing

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 August 25th, 2019 at 10:45pm CDT.

Have a Question?

Contact Us

Follow Us