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: | 31 |
| Average Price: | $4,485,907 |
| Highest Price: | $25,950,000 |
| Lowest Price: | $859,000 |
| Average Size: | 2,133 ft² |
| Average Price Per Square Foot: | $1,350 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. Enjoy The Ultimate Longboat Key Lifestyle In Your Very Own Direct Gulf Front Private Access With Stunning Gulf Of Mexico Views! The Progress At This Seaward Homes Curated Collection At 6489 Gulfside Is Moving Right Along, With ...
Pre-construction. To Be Built. Introducing A Rare Gem Of Contemporary Luxury On Longboat Key: A Brand-new, Direct Gulf-front Masterpiece Crafted By Vertical Design Build To The Most Exacting Standards. Still In The Beginning Stages, There Is Plent...
Rare Opportunity: Beach And Boating Lifestyle On Longboat Key. Experience The Best Of Both Worlds With Breathtaking Gulf Of Mexico Views And Deeded Bay Access, Including A Renovated Boathouse With A Lift Just Across Gulf Of Mexico Drive. This Thre...
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...
This Stunning Gulf Front Gated Estate Property Boasts A Beautifully Almost One Acre Landscaped Setting With A Long, Elegant Paver Driveway Leading To A Spacious Six-bedroom, Six-bathroom Home. Designed With A Bright And Airy Interior, The Home Fea...
An Ideal Opportunity To Own A Direct Gulf-front Estate-sized Lot On The Coveted Shores Of Longboat Key. Spanning Nearly 3/4 Of An Acre, This Expansive Parcel Offers The Perfect Canvas To Create A Custom Coastal Retreat. Cleared And Primed For Deve...
Nestled In The North Longboat Key Area, This Stunning Five-bedroom Home Rebuilt In 2014 With New Pool And Many Other Features Offers Unparalleled Luxury And Breathtaking Views. As You Step Through The Sliding Glass Doors From The Main Living Area ...
Experience Coastal Luxury Living In This Stunning Custom Estate, Built In 2021 By Mason Martin Builders And Located Near The North End Of Longboat Key. Perfectly Blending Modern Gulf Coast Architecture With Superior Craftsmanship, This Home Is Nes...
Here Is Your Opportunity For An Elevated Pool Home With Beautiful Views Of The Sparkling Gulf Of Mexico On The Fabulous North End Of Longboat Key. 3 Bedrooms And 2 And A Half Baths Located On An Oversized 19,400sf Lot That Sits On The Beach Side O...
Luxurious Longboat Key Canal Front Home – A Coastal Entertainer’s Dream! Welcome To This Stunning 6-bedroom, 5.5-bathroom Canal-front Estate On Longboat Key, Designed For Those Who Love Space, Views, And Waterfront Living. This Three-level, Ful...
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-...
Gulf Views From This Spacious And Bright Home On An Oversized 17,000-plus-square-foot Lot With Beach Access Just A Short Distance Away. This Smartly Designed Home Features All Living Areas On One Level And Offers Four Bedrooms, Two With En-suite B...
Pre-construction. To Be Built. Elevated To The Latest Codes To Alleviate Concerns About Flooding And Storm Surges, This Modern Milano Home Is Designed For The Elements. Welcome To This Stunning 5 Bedroom, 5 Bath Modern Residence, A True Masterpiec...
Privacy Is Key For This Sprawling, Estate-size Lot Down A Quiet Street Not On Gulf Of Mexico Drive As Address Suggests, On North End Of Longboat Key. Tranquil, Quiet And Peaceful, This Canal-front Location Offers One Of The Largest Single-family H...
Discover The Ultimate Florida Waterfront Lifestyle At 569 Juan Anasco Dr—an Elegant Retreat Where Sophistication, Comfort, And Coastal Beauty Blend Seamlessly. Nestled Along A Tranquil Canal, This Exceptional Property Offers Deeded Private Beach A...
6501 Gulf Of Mexico Drive – A Dream Home Opportunity This Is Your Chance To Create The Ultimate Beachfront Retreat On A Quiet, Private Street In North Longboat Key. Enjoy Stunning, Picturesque Sunsets And The Serenity Of A Private Beach Just St...
Build Your Dream Home Just Steps From The Sugar Sand Beach On Beautiful Longboat Key On The Gulf Of Mexico. Large Lot (16,000 Sq Ft) Under Contract To Be Cleared In March. This Lot Has The Added Bonus Of Backing Up To Gulfside Road And Walk To Bea...
*no Flood/storm Damage*move-in-ready*fully-furnished*waterfront* Welcome To 550 De Narvaez Drive, A Meticulously Maintained Waterfront Residence Nestled On A Spacious 10,000 Square Foot Elevated Lot In The Coveted North End Of Longboat Key. This ...
This Waterfront Retreat Is Nestled In The Sought-after Community Of Sleepy Lagoon, Offering Direct Access To A Deep-water Saltwater Canal. While The Home Has Recently Experienced Flood Damage, It Presents A Fantastic Opportunity For Those With A V...
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on March 15th, 2025 at 10:50pm EDT.
