Sleepy Lagoon Homes with Two Story Style

Sleepy Lagoon Homes with Two Story Style

Welcome to Sleepy Lagoon, a charming subdivision located in the heart of Longboat Key, Manatee County, Florida. Known for its tranquil surroundings and close-knit community, Sleepy Lagoon offers a peaceful retreat for those seeking a relaxed coastal lifestyle.

One of the unique features of Sleepy Lagoon is its collection of homes with a two-story style. These homes are designed to maximize living space while maintaining a sense of privacy and comfort. With spacious layouts and modern amenities, the two-story homes in Sleepy Lagoon are perfect for families or individuals looking for a bit of extra space.

Living in Sleepy Lagoon means being just a stone's throw away from the beautiful beaches of Longboat Key, where you can enjoy sun-kissed days and breathtaking sunsets. The subdivision is also conveniently located near shopping, dining, and recreational activities, making it easy to experience everything this vibrant area has to offer.

Whether you're looking for a permanent residence or a vacation home, Sleepy Lagoon has something for everyone. Come and experience the laid-back luxury of Sleepy Lagoon and discover why it's one of the most sought-after subdivisions in Longboat Key.

Newest Sleepy Lagoon Homes with Two Story Style

$1,895,000
4 Beds ⋅ 3 Baths ⋅ A4694601 MLS
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 and doors ensure safety, and two brand-new air conditioning units—still under warranty—keep you cool. A tankless water heater, just three years old, provides endless hot water. In the garage, there’s a Mitsubishi AC dehumidifier, and the roof was replaced in 2026, giving you peace of mind. The kitchen is fully outfitted with Wolf and Sub-Zero appliances, and every bathroom has been completely remodeled. You’ll find extra storage in the garage, and deeded beach access means the sand is just moments away. Beyond the home, the location is unbeatable. You’re right across from the island’s pristine white sand beaches and close to golf, tennis, and the Longboat Key Club. You’re also a short drive from Anna Maria’s restaurants and bars. And if you love the outdoors, you can paddleboard, boat, kayak, and enjoy the island’s abundant wildlife—all right at your doorstep. This home offers both elegance and adventure, all in one stunning package.

523 Juan Anasco Drive, Longboat Key
$1,499,000
2 Beds ⋅ 3 Baths ⋅ A4684674 MLS
Welcome to Your Beach House Sanctuary on Longboat Key! Experience the ultimate coastal lifestyle in this beautifully renovated island retreat, ideally situated just four homes from Tarawitt Point on a deep-water canal. Set on an expansive 125x90 ft lot, this waterfront property offers 125 feet of seawall with dockage for a boat up to 30 feet, a jet ski lift, and additional space for all your water toys. With the Intracoastal Waterway just 50 yards from the canal’s end, you’ll enjoy direct, no-bridge access to Sarasota Bay—perfect for fishing, cruising, or sunset boating. Catch bait and be fishing in under 30 minutes! Inside, this meticulously maintained home features: 3 spacious bedrooms, 2 full baths + 1 half bath, 1-car garage, Open-concept floor plan with stunning bay views! The oversized primary suite offers a comfortable seating area, TV space, a generous walk-in closet, and a beautifully updated bath with dual vanities and a large walk-in shower. The kitchen and living area flow seamlessly onto a porch overlooking the bay—ideal for morning coffee or evening cocktails. Renovated in 2022, the home boasts a new roof, new windows and doors, granite countertops, new appliances, updated bathrooms, new flooring, fresh interior and exterior paint, and even a relaxing hot tub. Deeded beach access sits directly across Tarawitt Drive, offering effortless enjoyment of the Gulf’s turquoise waters and sugar-sand beaches. Enjoy walkable access to some of the island’s favorite dining destinations, including: Harry's Restaurant, Euphemia Haye, The Lazy Lobster, A short bike ride takes you to: The Shore Restaurant, Mar Vista Dockside Restaurant And you’re just an easy drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. This is more than a home—it’s a waterfront lifestyle defined by boating, beach days, and breathtaking bay views.

825 Tarawitt Drive, Longboat Key
$1,700,000
3 Beds ⋅ 4 Baths ⋅ A4669634 MLS
$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 relaxed Sleepy Lagoon neighborhood with deeded beach access just around the corner, leading you to never crowded stretches of sand. The home is located on a boating canal just three houses in from the bay offering direct access to Sarasota Bay and the Intercoastal Waterway. This large ( 5328 SF total) very well maintained and upgraded elevated home offers 2800 SF on the main living level plus 2500 SF of bonus space on the first floor with an elevator. This elevated, well-built custom home sustained no damage nor have any flood claims ever been filed. This home spans two level of living and has an open floor plan, blending indoor and outdoor living. The main living area is upstairs with large flowing open rooms, vaulted ceilings, a fireplace and features French Doors leading to a screened Lanai overlooking the natural canal with foliage for privacy. The bedrooms are arranged in a split plan with each having en-suite bathrooms with lots of closets and built-ins. The large eat-in kitchen has custom cabinetry with crown molding, pull-outs, granite countertops and stainless appliances plus a large separate dining room perfect for all your family or friends. Just off the kitchen on the main living level is a very large laundry room along with all the closets in this home you will have all the storage you need. On the first level is the open foyer leading up to the living area with the elevator access and oversized split garages. There is an additional 2500 SF of AC/heated of interior space that is finished with polished concrete floors and walls of sliding doors leading to the pool area, porch, deck, yard and dock area. Also just outside your bonus space is private 60’ long screened, heated lap pool with a full bath. The property would provide great renal income also for a part time owner as it has in the past. Walk the beach, swim in the pool or ocean, ride your bike on the Longboat Key Bike path, fish, boat, kayak, paddle board, jet ski and enjoy your spacious home that is just a short drive to Sarasota, St. Armand’s circle and Anna Maria Island. Please see the videos. What are you waiting for? Start living the dream.

569 Juan Anasco Drive, Longboat Key
$8,925,000
5 Beds ⋅ 6 Baths ⋅ A4653251 MLS
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 plus walls of glass. The home opens to multiple covered terraces built for soaking in endless Bay views and the best of Florida living at its finest. The open-concept layout blends indoor comfort with outdoor style, perfect for hosting or unwinding in total privacy. The kitchen is sleek and spacious with high end Wolf package and Sub Zero ready for gourmet meals or casual bites with a view. The adjoining family room also features a large stone fireplace. The primary suite is a retreat all its own with private terrace access, spa-style bath and water views that never quit. Outside, the lifestyle really takes off. A large Bayfront resort-style pool with a hot tub anchors the backyard, surrounded by multiple fire pits perfect for evening gatherings under the stars. Need space for guests? A separate guest house is available to design to your personal touch, offers total privacy and comfort, ideal for hosting family or friends without sacrificing your own space. This estate isn’t just a home it’s a waterfront playground built for bold living. There's kayak storage and room for multiple docks and all your water toys. The new seawall built in 2010 adds peace of mind. There is a four car garage. This North Longboat property is a must see for anyone seeking a luxurious lifestyle combined with natural beauty. With its modern amenities, prime location, and stunning views, it stands out as a dream home. Don’t miss the opportunity to make this exquisite residence your own. This north Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.

630 De Narvaez Drive, Longboat Key
Start Your Search