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: | 21 |
| Average Price: | $5,447,156 |
| Highest Price: | $24,500,000 |
| Lowest Price: | $999,900 |
| Average Size: | 3,749 ft² |
| Average Price Per Square Foot: | $1,461 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 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...
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...
Gulf Front Masterpiece With Bayside Boathouse And 12klb Lift Experience The Pinnacle Of Coastal Living At This Unparalleled Gulf-to-bay Estate On Longboat Key, Where 100 Feet Of Private, Sugar-white Beachfront Meets The Rare Luxury Of A Deede...
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...
Discover A Truly Rare Opportunity To Own Two Parcels In A New, Beachfront Enclave Being Developed With Private Entry Gates Directly On The Pristine Sugar Sand And Turquoise Waters Of The Gulf Of Mexico. The Offering Includes: Parcel One - Property...
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...
Experience The Pinnacle Of Coastal Luxury In This Exceptional Custom Estate, Completed In 2021 By Renowned Mason Martin Builders. Designed And Sparingly Used By The Original Owners Who Crafted It With Precision And Care, This Like-new Residence Ha...
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-...
Experience Refined Coastal Living In This Stunning Custom Canal-front Home, Where Timeless Architectural Elegance Blends Seamlessly With Effortless Luxury On The Exclusive North End Of Longboat Key. The Attention To Detail In This Exquisitely Reno...
No Busy Street To Cross!! Situated On The West Side Of Gulf Of Mexico Dr, 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. This Lot Has The Added Bonus Of Backing ...
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 Relaxed Sleepy Lagoon Neighborho...
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...
Welcome To Your Waterfront Paradise! Discover This Coastal Retreat In The Highly Desirable Sleepy Lagoon Community, Perfectly Positioned On A Deep-water, Saltwater Canal Just Seconds From The Intracoastal And The Gulf. This Beautifully Renovated...
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 ...
Some Homes Whisper. Others Make A Statement. 501 De Narvaez Drive Commands Attention—with Bold Architecture, Elegant Updates, And A Prime Waterfront Location That Elevates The Florida Lifestyle Into Something Exceptional. Nestled On A Quiet Corner...
616 Lyons Lane, Longboat Key – A Unique Opportunity To Create Your Coastal Dream Home Nestled On The Serene And Picturesque Lyons Lane, On A Stunning Saltwater Canal. This Property Offers A Rare Chance To Embrace The Coveted Longboat Key Lifesty...
Discover A Rare Opportunity To Build Your Dream Home On North Longboat Key. This 100’ X 100’ Lot Offers 100 Feet Of Frontage On A Serene 37-foot-wide Canal With No Fixed Bridges—perfect For Boating, Paddle Boarding, And Kayaking. Enjoy Quick Acces...
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on December 14th, 2025 at 8:43am EST.
