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: | 26 |
| Average Price: | $4,969,812 |
| Highest Price: | $23,950,000 |
| Lowest Price: | $699,000 |
| Average Size: | 2,059 ft² |
| Average Price Per Square Foot: | $1,495 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 ...
Under Construction. You're In For Something Special With This New Beachfront Construction Set To Be Completed By December, 2025. Located On Over A Quarter Acre On Longboat Key, This Contemporary Luxury Home Is Directly On The Beach With Stunning G...
This Stunning Bayfront Estate Delivers Over 680 Feet Of Pristine Bayfront Waterfront On Nearly An Acre And A Half Of Prime Point Property. True Longboat Key Gold. Special Features Of This Home Include Five Bedrooms, Five Full Bathrooms, Hardwood F...
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...
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...
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...
Refined Coastal Living Is Waiting For You At 795 Marbury Lane In Longboat Key. Perfectly Positioned Between The Gulf Of Mexico And Sarasota's Intercoastal Waterway - This Stunning Waterfront Estate Combines High-end Finishes And Effortless Access...
Discover The Perfect Blend Of Luxury, Creativity, And Coastal Living In This Expansive Longboat Key Residence. Situated On A Deep Water Canal With A Private Dock, This Solid Block Construction Home Offers Direct Access To The Gulf And Is Ideal For...
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 ...
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...
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 On This Large Lot (16,000 Sq Ft) Just Steps From The Sugar Sand Beach On Beautiful Longboat Key On The Gulf Of Mexico. This Lot Has The Added Bonus Of Backing Up To Gulfside Road With A Very Short Walk To Beach Access At Th...
Welcome To Bougain Villa, Your Tropical Island Oasis On A Deep Water Canal Leading To Secluded Sandbars, The Turquoise Waters Of The Gulf Of Mexico, And Several Nearby Waterfront Restaurants. From The Moment You Arrive At This Magical Property, Z...
*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 ...
Build Your Dream Waterfront Oasis On Longboat Key! Discover The Ultimate In Florida Coastal Living With This Cleared And Build-ready Vacant Lot On Coveted Longboat Key. Featuring A 80ft Wide Seawall, Private Boat Dock, And 10,000lb Lift, This Prim...
Short Stories:...prime Canalfront Property On Longboat Key---endless Potential!!! The Choice Is Yours With This Unique 3 Bedroom 2 Bath Home L
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 Includes Permitted Plans For A Stunning ...
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 July 13th, 2025 at 10:04am EDT.
