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: | 22 |
| Average Price: | $3,989,273 |
| Highest Price: | $15,000,000 |
| Lowest Price: | $950,000 |
| Average Size: | 3,704 ft² |
| Average Price Per Square Foot: | $1,218 per ft² |
Condominiums
Neighborhoods
Under Construction. Just Steps From The Sand Along Longboat Key’s Prized Coastline, The Construction Of A Modern Architectural Showpiece Is Now Complete And Ready For Living The Ultimate Lifestyle. Majestically Poised On Over A Third Of An Acre, T...
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...
Rarely Does An Estate-sized Gulf-front Lot Of This Stature Become Available On The Northern End Of Longboat Key. 6351 Gulf Of Mexico Drive Presents A Truly Exceptional 100-foot By 388-foot Direct Beachfront Parcel — Nearly 39,000 Square Feet Of Pr...
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. ...
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...
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 5-bedroom Plus Den, 4,106 Sq Ft Residence Blends Conte...
Pre-construction. To Be Built. Brought To You By Noah Thomas Builders, A Premier Luxury Builder Known For Crafting High-end Coastal Residences With Exceptional Attention To Detail And Durability, This Stunning New Construction Home At 592 Juan Ana...
Virtually Staged. Welcome To An Extraordinary Waterfront Estate On Coveted Longboat Key, Where Timeless Coastal Elegance Meets World-class Boating. Perfectly Situated On A Deep-water Saltwater Canal With A Private Dock And Direct Access To The Gul...
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-...
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 Boat Ride To The Gulf. Built For Large Gatherings, ...
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...
Flanked By Multi-million-dollar Homes, Uniquely Situated On The West Side Of Gulf Of Mexico Dr With No Busy Street Between You And The Beach! Lot Is Cleared And Ready With Utilities At The Lot. Build Your Dream Home On This Large Lot (16,000 Sq Ft...
This Beautifully Reimagined John Cannon Home, In The Tranquil North End Of Longboat Key, Blends Luxury With Island Living. The Custom, Spanish-style Design Offers Four Bedrooms And A Complete Top-to-bottom Renovation. New Hurricane-rated Windows A...
$100,000 Price Reduction!!! Live The Ultimate Florida Waterfront Lifestyle In This Private, Calm, Secure, Spacious And Elegant Large Elevated Coastal Home. Located On The North End Of Longboat Key Less Than A Mile To Anna Maria Island In The Rela...
6500 Gulfside Road In Longboat Key...a Rare Opportunity To Build Steps From The Beach. Welcome To An Exceptional Chance To Create Your Own Coastal Sanctuary On One Of Longboat Key’s Most Treasured Streets. Situated Just Steps From The Powder-soft ...
One Or More Photo(s) Has Been Virtually Staged. Welcome To 550 De Narvaez Drive, A Meticulously Maintained Waterfront Residence Set On An Elevated 10,000 Sq. Ft. Lot In The Highly Desirable Sleepy Lagoon Neighborhood On The North End Of Longboat K...
Welcome To Your Piece Of Paradise! This Beautiful Canal Front Home Is Located In The Idyllic And Picturesque Longboat Key. A Charming Mid-century Style Cottage Nestled In One Of Longboat Key's Most Private And Serene Settings. This Spacious 2 Bedr...
Discover The Exceptional Potential Of 640 Lyons Lane, A Perfectly Situated Vacant Lot On A Unique Street In North Longboat Key, With Homes Only On One Side And Protected Wetlands On The Other. This Property Offers An Outstanding Opportunity To Bui...
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...
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on August 11th, 2026 at 8:07am EDT.
