Located at the north end of Siesta Key, Sleepy Lagoon is a friendly waterfront neighborhood with an active social homeowners association. The community runs on both sides of Gulf of Mexico Dr and has 269 properties. This is the perfect spot for avid boaters and beach lovers! Many of the houses are on the water, with boat docks. The surrounding waterways are perfect for jet ski, kayak, or paddle board. In addition, deeded beach access is just a walk, bike or drive.
| Total Listings: | 32 |
| Average Price: | $4,464,699 |
| Highest Price: | $22,500,000 |
| Lowest Price: | $950,000 |
| Average Size: | 3,661 ft² |
| Average Price Per Square Foot: | $1,221 per ft² |
Condominiums
Neighborhoods
Welcome To Your Private, Gated Estate On Longboat Key, Where Coastal Luxury Meets Effortless Sophistication. Boasting Over 730 Feet Of Water Frontage, This Stunning Property Offers Panoramic Views Of Whitney Bayou And Harris Canal And Provides The...
Under Construction. You're In For Something Special With This New Beachfront Construction Set To Be Completed By May, 2026. Located On Over A Quarter Acre On Longboat Key, This Contemporary Luxury Home Is Directly On The Beach With Stunning Gulf V...
This Seaward Homes Curated Collection Residence At 6489 Gulfside Is Ready For Occupancy. Enjoy The Ultimate Longboat Key Lifestyle With Your Own Direct Gulf-front Private Access And Stunning Views Of The Gulf Of Mexico. Designed By Dsdg Architects...
This Stunning Bayfront Estate Delivers Over 480 Feet Of Pristine Bayfront Waterfront On A Prime Point Property. True Longboat Key Gold. Special Features Of This Home Include Five Bedrooms, Five Full Bathrooms, Hardwood Floors, Sky-high Ceilings P...
100' Of Direct Beach And Gulf Frontage..... Welcome To Paradise! Experience The Ultimate In Longboat Key And Gulf-front Luxury With This Spectacular Nearly 6,000 Sq. Ft. Beachfront Estate On Longboat Key. Perfectly Positioned On A Pristine Stretch...
Sign On Property. Nestled On The Pristine Shores Of Longboat Key, This Exclusive Beachfront Property Offers A Rare Opportunity To Build Your Dream Luxury Home Amidst The Breathtaking Beauty Of The Gulf Of Mexico. With Direct Access To The Sugary S...
One Or More Photo(s) Has Been Virtually Staged. Welcome To A Once-in-a-lifetime Opportunity To Own A Sleek, Modern Coastal Estate On One Of Longboat Key’s Most Coveted Stretches Of Sand. Perfectly Situated On A Rare Double Lot On The Beach Side Of...
Discover An Extraordinary Opportunity To Own Two Parcels In A Newly Developed Beachfront Enclave, Complete With Private Entry Gates When Project Is Complete Leading Directly To The Pristine Sugar Sands And Turquoise Waters Of The Gulf Of Mexico. ...
New Construction - Discover The Epitome Of Waterfront Luxury With This Newly Built Home In The Heart Of Longboat Key—competitively Priced And Move-in Ready. Nestled Along A Private Canal, This 4-bedroom Plus Den, 4,106 Sq Ft Residence Blends Conte...
Build Your Dream Beachfront Estate On Nearly Three-quarters Of An Acre On Exclusive North Longboat Key. With 100 Feet Of Private Gulf Frontage, This Rare Homesite Offers Endless Views Of Turquoise Waters Spectacular Sunsets And Direct Access To Po...
Tucked Along A Quiet Canal In Longboat Key’s Sleepy Lagoon Park, 761 Norton Street Delivers The Kind Of Waterfront Lifestyle That’s Increasingly Rare—equal Parts Boating-centric, Resort-style, And Built For Hosting At Scale. With 4 Bedrooms, 4 Ens...
Step Into A New Era Of Coastal Modern Living With This Breathtaking, Newly Constructed Waterfront Retreat, Perfectly Positioned On The Exclusive North End Of Longboat Key. Designed With Intention And Offered Fully Turnkey-furnished, This Residence...
In The Tranquil North End Of Longboat Key, Where Gulf Breezes Drift Through The Palms And The Pace Slows To A Whisper, This Extraordinary Beach Retreat Captures The Essence Of Refined Coastal Living. Positioned On Nearly Half An Acre Of Canal Fron...
Experience Exceptional Waterfront Living In This Impressive Canal-front Estate On Coveted Longboat Key, Offering Deep-water Boating, A Private Dock, And Quick, Easy Access To The Open Gulf. Perfectly Positioned On A Saltwater Canal Just Moments Fr...
Great Opportunity To Build On A Private Cu-de-sac In Sleepy Lagoon. There Is Private Sandy Beach Access Leading To The Azure Waters Of The Gulf Of Mexico. A New Home At This Location Would Have Outstanding Gulf And Stunning Sunset Views. This Cul-...
The Future Of Luxury Living On Longboat Key! Discover This Newly Constructed Coastal Retreat That Sets The Standard For Modern Waterfront Living. Located On The Private North End Of Longboat Key, This Turnkey-furnished Residence Is A Sanctuary Of ...
One Or More Photo(s) Has Been Virtually Staged. Boaters Will Love This Spacious Elevated Home In A Premier Waterfront Location On Longboat Key With Dock, Lift And By Boat It Is Just Four Homes From The Intercoastal, Open Bay Waters And A Short Boa...
One Or More Photo(s) Has Been Virtually Staged. Under Construction. Welcome To 640 Lyons Lane — A Rare Opportunity To Purchase A Brand-new, Fully Constructed Home On One Of North Longboat Key’s Most Distinctive Streets With Homes On Only One Side ...
Privacy Is Key For This Sprawling, Estate-size Lot Tucked Down A Quiet Street On The North End Of Longboat Key. While Addressed On Gulf Of Mexico Drive, The Property Is Uniquely Positioned Off The Main Roadway, Set Back Beyond Three Estate-sized P...
Come Savor Laid-back Luxury And The Island Lifestyle That Longboat Key Is Known For In This Tranquil, Seaside Retreat. And Listed More Than $100,000. Under A Current Appraisal! This Home Is A Decorators Dream! Completely Remodeled With A Brand New...
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on April 22nd, 2026 at 8:07am EDT.
