Sleepy Lagoon Homes with Private Pool type

Sleepy Lagoon Homes with Private Pool type

Welcome to Sleepy Lagoon, a serene and picturesque subdivision nestled in the heart of Longboat Key, Florida. This enchanting community offers the perfect blend of coastal charm and modern luxury, making it an ideal destination for those seeking a tranquil retreat just moments away from the vibrant energy of the Gulf Coast.

Sleepy Lagoon is renowned for its stunning homes, each designed to provide a unique oasis for residents. One of the standout features of many properties in this subdivision is the private pool, allowing you to bask in the Florida sun and enjoy refreshing dips at your leisure. Imagine lounging by your own sparkling pool, surrounded by lush landscaping and the gentle sounds of nature—it's the perfect setting for relaxation and entertaining friends and family.

The subdivision is strategically located, offering easy access to pristine beaches, exquisite dining options, and boutique shopping experiences that Longboat Key is famous for. Whether you prefer a leisurely stroll along the shore, indulging in fresh seafood at a local restaurant, or exploring the vibrant arts scene, Sleepy Lagoon places you right in the heart of it all.

In addition to its prime location, the community fosters a warm and welcoming atmosphere where neighbors become friends. With well-maintained streets and beautiful homes, Sleepy Lagoon is not just a place to live; it’s a lifestyle choice that embraces the best of Florida living. Discover your dream home with a private pool in Sleepy Lagoon, where every day feels like a vacation!

Newest Sleepy Lagoon Homes with Private Pool type

$2,999,999
6 Beds ⋅ 6 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Virtually Staged. Welcome to an extraordinary waterfront estate on coveted Longboat Key, where timeless coastal elegance meets world-class boating. Perfectly situated on a deep-water saltwater canal with a private dock and direct access to the Gulf, this exceptional residence offers the rare opportunity to experience the very best of Florida luxury living just moments from the island's pristine white-sand beaches. Encompassing nearly 4,700 square feet of thoughtfully designed living space, this impressive home features six spacious bedrooms, five-and-a-half bathrooms, a private elevator, and an oversized four-car garage, providing exceptional space for family, guests, luxury vehicles, and all of your boating equipment. Whether you're searching for a full-time residence, seasonal retreat, or premier waterfront investment, this home offers the versatility to comfortably accommodate up to 20 guests. Designed to embrace its breathtaking waterfront setting, expansive balconies span the entire rear of the home, creating multiple outdoor living spaces perfect for morning coffee, sunset cocktails, or entertaining while overlooking the peaceful canal. The luxurious primary suite serves as a private sanctuary with its own waterfront balcony, where tranquil water views become part of your everyday routine. The backyard is a true resort-style oasis featuring a sparkling in-ground pool, generous lounging areas, and a private dock on a deep-water canal with quick, effortless access to the open Gulf. Spend your days boating, fishing, paddleboarding, or cruising to waterfront restaurants before returning home to your own private paradise. At the heart of the home is a stunning chef's kitchen designed for both everyday living and grand entertaining. Featuring a professional gas range, double ovens, dual wine refrigerators, two dishwashers, gorgeous granite countertops, extensive custom cabinetry, a spacious walk-in pantry, and an oversized center island with seating for six, this kitchen is equally impressive in both form and function. The open-concept floor plan flows seamlessly into elegant living and dining spaces filled with natural light, creating an inviting atmosphere ideal for entertaining on any scale. A secondary kitchenette and expansive game room offer incredible flexibility for hosting guests, creating a private guest suite, or accommodating multi-generational living with ease. For added peace of mind, all major mechanical systems and significant capital improvements have been completed within the past four years, allowing the next owner to simply move in and enjoy the home from day one. Ideally located just minutes from Longboat Key's award-winning beaches, championship golf, fine dining, marinas, boutique shopping, St. Armands Circle, and the cultural attractions of downtown Sarasota, this exceptional property represents a rare combination of luxury, location, deep-water boating, and island lifestyle. Opportunities to own a waterfront home of this caliber—with six bedrooms, deep-water dockage, Gulf access, a four-car garage, and the ability to comfortably host family and friends on one of Florida's most prestigious barrier islands—are truly few and far between. Ride your bike to Anna Maria Island for night life, restaurants and shopping. Beautiful Gulf beaches are just steps away from your new house! Please feel free to check out virtual tour https://next.frame.io/share/09e65a61-fa88-4c36-8474-69609bc826e6/view/f03db32d-b617-4f1c-85ec-54ccc2a57dae

614 Norton Street, Longboat Key
$1,895,000
4 Beds ⋅ 3 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
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
$4,000,000
5 Beds ⋅ 6 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Pre-Construction. To be built. Brought to you by Noah Thomas Builders, a premier luxury builder known for crafting high-end coastal residences with exceptional attention to detail and durability, this stunning new construction home at 592 Juan Anasco Dr offers an unparalleled blend of sophistication, comfort, and waterfront living. Perfectly positioned on a canal-front lot in Longboat Key, this 5-bedroom, 5.5-bath residence is thoughtfully designed to capture the essence of refined coastal living. Expansive windows, soaring ceilings, and a light-filled interior create an inviting atmosphere, while the home’s modern coastal aesthetic is complemented by carefully curated finishes and timeless design elements that elevate every space. The spacious and well-appointed floor plan offers a seamless balance of functionality and privacy, making it ideal for both everyday living and elevated entertaining. Generous living areas provide a welcoming environment for gathering, while the primary suite serves as a true retreat—offering a peaceful escape with a spa-like feel. Each additional bedroom is designed with comfort in mind, providing flexibility for guests, family, or extended stays. Step outside to your private waterfront oasis, where a resort-style setting invites relaxation and effortless entertaining. Whether hosting friends, enjoying quiet evenings by the water, or taking advantage of Florida’s year-round sunshine, this outdoor space is designed to be experienced. With direct canal access, boating enthusiasts will appreciate the ability to enjoy the Intracoastal lifestyle right from their backyard. Built to meet current FEMA guidelines and elevation requirements, this home offers enhanced protection, improved insurance efficiency, and long-term peace of mind—an essential advantage for waterfront properties. The elevated construction is thoughtfully designed to perform in coastal conditions while maintaining both functionality and architectural appeal. Living on Longboat Key means embracing a lifestyle that is both refined and relaxed. Known for its pristine Gulf beaches, world-class golf, and exclusive residential feel, the island offers a quieter, more private alternative to neighboring destinations. Residents enjoy convenient access to the renowned shops and restaurants of St. Armands Circle, the cultural attractions of downtown Sarasota, and nearby marinas, beach clubs, and nature preserves. From morning walks along the shoreline to sunset cruises and evenings of coastal dining, every day feels like a getaway. This is more than a home—it’s a lifestyle defined by waterfront elegance, modern construction standards, and one of Florida’s most sought-after coastal communities. Pricing, availability, and final details subject to adjustment prior to completion.

592 Juan Anasco Drive, Longboat Key
$1,175,000
2 Beds ⋅ 3 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Welcome to your piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a tranquil beach lifestyle. Recently impacted by Hurricane Helene, the home has undergone professional remediation and renovation including kitchen, bathrooms and pool. The living area boasts an open floor plan with a cozy corner wood-burning fireplace that adds a warm touch, creating the perfect setting for snug evenings during the cooler winter months. The kitchen has been completely remodeled and equipped with all new cabinets, quartz countertops and appliances, offering plenty of space for culinary adventures. The master suite includes a cedar walk-in closet, an extra linen closet, and direct access to the pool area. In addition to the 2 bedrooms, there is a bonus room that could be made into a bunk room perfect for the little ones or teenagers to make their own retreat. Lyons Lane is renowned for its tranquility and privacy, with lush mangroves lining the opposite side of the street, creating a natural, peaceful ambiance. This unique setting offers the best of both worlds: a serene retreat just moments away from the pristine beaches, boutique shopping, and fine dining that Longboat Key is famous for. Don’t miss this exceptional opportunity to own a slice of paradise.

616 Lyons Lane, Longboat Key
$2,500,000
5 Beds ⋅ 4 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Boaters will love this spacious elevated home in a premier waterfront location on Longboat Key with dock, lift and by boat it is just four homes from the intercoastal, open bay waters and a short boat ride to the Gulf. Built for large gatherings, this home is beautifully designed with loads of gathering and entertaining spaces. The open plan home was thoughtfully designed with five bedrooms, four with en-suite baths. The kitchen features custom wood cabinets and granite countertops. Entertaining will be a breeze with two large gathering spaces, including a great room with dining area and adjacent bonus room that would be a wonderful media or game room. Ground level highlights include two bonus areas and a huge four-car garage. The composite dock has a 10,000-pound boat lift, water and electric. Recent updates include hurricane windows and doors (2025), metal roof (2025), pool equipment and pool heater (2025) and interior freshly painted. This location on Longboat Key can't be beat with community beach access just across the street, and a heated pool and boating in your own backyard. This is the ideal home to create wonderful island memories.

771 Marbury Lane, Longboat Key
$13,995,000
4 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

6489 Gulfside Road, Longboat Key
$1,700,000
3 Beds ⋅ 4 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
$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 ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
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
$15,000,000
5 Beds ⋅ 6 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Under Construction. Just steps from the sand along Longboat Key’s prized coastline, the construction of a modern architectural showpiece is now complete and ready for living the ultimate lifestyle. Majestically poised on over a third of an acre, this modern residence’s visual presentation was intentionally and expertly planned with no detail overlooked. Expansive walls of glass take full advantage of the dramatic Gulf views that stretch across the horizon and set the stage for viewing memorable sunsets in brilliant hues of yellows, oranges and reds. The sophisticated coastal aesthetic has been cohesively designed to evoke a peaceful ambiance, captivate the senses, and create harmonious spaces that inspire and uplift. This exceptional beachfront estate offers a light-filled floor plan of 4,925 sq. ft. and provides five bedrooms, six baths, an executive office and a den. Encompassing nearly 1,000 sq. ft., the living, dining and kitchen area is simply breathtaking with walls of glass on two sides and cerulean blue water panoramas stretch as far as the eye can see. Style and comfort easily flow throughout the residence with its crisp clean lines and spacious open areas filled with natural light, balanced by organic materials and earthy neutral tones to create an open, airy ambiance. From sleek Walker Zanger porcelain tile to custom cabinetry and polished nickel fixtures, the finishes are top-tier. The kitchen façade is artistically impressive and features everything you’d expect in a home of this caliber with a large waterfall-edge island and premium Sub-Zero and Wolf appliance package including double ovens, induction cooktop, and full-size temperature-controlled wine storage. The owner’s retreat is a true showstopper with floor-to-ceiling glass sliders that open wide to a sweeping terrace perched high above the water. Inside, the suite offers a fully customized wardrobe room and a resort-inspired bath featuring tiled walls, a walk-in shower with multiple heads, a freestanding designer tub, dual floating vanities, and a private water closet. Upstairs, an executive office and three generous bedroom suites—each with its own walk-in closet—gives plenty of space for family or guests. A fourth bedroom shares a cozy den, perfect for lounging or movie nights. This incredible residence is well suited for entertaining, whether enjoying small intimate gatherings or hosting elaborate sunset soirees. The enormous ground-level outdoor space is highlighted by a 36-foot lap pool, sun shelf, heated spa, and a fully equipped summer kitchen with a grilling station. Additionally on this level are a three-car garage, an outdoor shower, and an elevator to all 3 levels plus a staircase in a glass enclosed entry. Living along the water’s edge introduces magical nuances with the dawning of every new day. The sights and sounds in one of nature’s most beautiful settings will lull you into peaceful bliss. Life on the water is truly a dream come true—a place to be cherished and appreciated for years to come.

6603 Gulfside Road, Longboat Key
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