A Neighborhood Defined by Waterfront Living
Sleepy Lagoon is split by Gulf of Mexico Drive, offering two distinct experiences:
On the Bay side, homes reflect a relaxed Old Florida vibe—narrower streets, mature trees, and classic canal-front homes with private boat docks.
This side is a haven for boaters, kayakers, and paddleboarders, thanks to nine navigable canals that flow into Sarasota Bay.
On the Gulf side, the vibe shifts to elevated coastal luxury. Homes here are often steps from the sand, with some featuring direct beachfront access and unobstructed Gulf views.
Properties along Gulfside Road and Gulf of Mexico Drive come at a premium, offering the ultimate in location and lifestyle.
Diverse Architecture & Home Options
Whether you're looking for a 1960s ranch-style home to renovate or a newly constructed modern beach estate, Sleepy Lagoon has it all. Homes range from just over 1,400 square feet to more than 6,000 square feet, giving buyers options at every stage of life and investment level.
Current listings range from around $699,000 for a tear-down or renovation project and up to $16M+ for custom Gulf-front estates on premium lots.
There’s no cookie-cutter layout here—each home is unique, reflecting the character and creativity of its owner.
Community Features & Resident Perks
Pet-Friendly: Dogs and cats are welcome, making Sleepy Lagoon a favorite among families and retirees with pets.
Rental-Friendly: The neighborhood allows monthly rentals up to 12 times per year, following the Town of Longboat Key’s zoning ordinance—great for part-time residents or investors looking for rental flexibility.
Voluntary HOA: With an optional $25/year HOA, the community stays connected through local events and gatherings without high fees.
Private Pools & Custom Yards: There’s no shared pool or clubhouse—but many homeowners have built their own resort-style backyards, complete with pools, fencing, and lush landscaping.
