Sleepy Lagoon Homes with Boatable Water Water Frontage

Welcome to Sleepy Lagoon, a hidden gem nestled in the beautiful state of Florida. This charming subdivision is a dream come true for water enthusiasts, boasting homes with boatable water frontage, offering residents the perfect blend of luxury and tranquility.

Imagine waking up to the gentle sound of waves lapping against the shore, stepping outside to your own private dock, ready for a day of boating and water adventures. Whether you enjoy fishing, water sports, or simply cruising along the serene waters, Sleepy Lagoon provides the ideal setting for waterfront living.

Located in the Sunshine State, Sleepy Lagoon offers not just a place to call home, but a lifestyle to savor. With stunning views, lush surroundings, and a close-knit community, this subdivision provides the perfect escape from the hustle and bustle of city life.

If you're looking for a waterfront property where you can truly unwind and embrace the waterfront lifestyle, Sleepy Lagoon in Florida is the place to be. Explore the available homes with boatable water frontage and discover your own piece of paradise in this idyllic waterfront community. Live the life you've always dreamed of at Sleepy Lagoon.

Newest Sleepy Lagoon Homes with Boatable Water Water Frontage

$2,850,000

4 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4701661 MLS ⋅ Active Status

Virtually Staged. Under Construction. Pre-Construction | Custom Build | Water to Front & Rear A once-in-a-generation opportunity on one of Longboat Key's most extraordinary streets. Lyons Lane is a truly singular address — a quiet, private enclave in North Longboat Key where homes enjoy an exceptionally rare double-water setting, with sparkling canal frontage to the rear and serene, protected wetland and mangrove views to the front. This is island living at its most private and unspoiled. Design Your Dream Home The vision is still yours to shape. The buyer has the rare opportunity to work directly with the architect to customize the layout, finishes, and features of this brand-new custom home before it's complete. From floor plan adjustments to material selections, this is your chance to create a residence that is uniquely and entirely your own — without the years of planning that a true ground-up build typically demands. The Property Set on a prime lot with water on both sides, the property includes an existing pool ready to be incorporated into your design, along with a private boat dock and lift with direct access to Millar and Sarasota Bays and no fixed bridges to the Gulf of Mexico. For the boating enthusiast, it simply does not get better than this — deep water access, protected dockage, and open water within minutes. Lyons Lane — Longboat's Best-Kept Secret Unlike any other street on the island, Lyons Lane offers homes on one side only, with lush native mangroves lining the opposite side — ensuring that your views, privacy, and natural surroundings will never be compromised. It is one of the few locations on Longboat Key where you can wake up to undisturbed natural beauty in every direction while remaining just moments from the finest dining, boutique shopping, and white-sand Gulf beaches the island has to offer. Longboat Key — Florida's Premier Barrier Island Stretching 11 miles along Florida's Gulf Coast with over 25 miles of combined waterfront between the Gulf of Mexico and Sarasota Bay, Longboat Key is consistently ranked among the most desirable addresses in the country. With a median home price approaching $2.5 million in 2026, the island attracts discerning buyers who demand privacy, natural beauty, and world-class amenities — including the legendary Longboat Key Club, with 45 holes of championship golf, a full-service deep-water marina, spa, and beach club. Opportunities like this — a custom home, double waterfront, dock and lift, and the freedom to personalize — are extraordinarily rare on Longboat Key. Don't miss your chance to build exactly the island life you've always envisioned.

640 Lyons Lane, Longboat Key

$2,999,999

6 Beds ⋅ 6 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ TB8533896 MLS ⋅ Active Status

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. 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 ⋅ A4694601 MLS ⋅ Active Status

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 ⋅ A4691388 MLS ⋅ Active Status

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 ⋅ TB8490318 MLS ⋅ Active Status

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

$59,000

Sleepy Lagoon SubDv. ⋅ 34667 Zip Code ⋅ W7883961 MLS ⋅ Active Status

Waterfront living in Hudson, Florida! Ideally situated on a deep-water canal with direct access to the Gulf of Mexico within minutes & No bridges, making it a perfect retreat for boaters and water enthusiasts. 43 ft on water; enjoy the convenience of docking your boat right in your backyard and spending your days fishing, kayaking, or cruising the open water. Hudson is centrally located to many options for restaurants, shopping, minutes from Hudson Beach, hospitals & doctors. It is only 10 minutes to Sun West Park with its large man-made sandy beach & water park that everyone will enjoy. Hernando, Homosassa, Crystal River to the north & many locations south such as New Port Richey, Dunedin, Clearwater beach, there is never a shortage of things to do. Tampa & Tampa International Airport are within an hour. You own the Land. No HOA's, direct access to open water. Come and check it out!

Lot 34 Indigo Lane, Hudson

$2,500,000

5 Beds ⋅ 4 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4686401 MLS ⋅ Active Status

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

$1,499,000

2 Beds ⋅ 3 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4684674 MLS ⋅ Active Status

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

$2,995,000

5 Beds ⋅ 3 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4683196 MLS ⋅ Active Status

PRICE IMPROVEMENT! In the tranquil north end of Longboat Key, where Gulf breezes drift through the palms and the pace slows to a whisper, this extraordinary beach retreat captures the essence of refined coastal living. Positioned on nearly half an acre of canal front property and encompassing over 3,000 square feet of interior living space (more than 6,000 square feet total), the residence sits just across from the ultra convenient public beach access. This unique residence offers the rare luxury of both boating and beachside lifestyles in one remarkable setting. Recently transformed through a stunning renovation and offered turnkey furnished, the five bedroom, three bath waterfront home showcases long, picturesque canal views and an effortless indoor outdoor flow. A NEW ROOF in 2023 and new impact windows were installed in 2022 provide peace of mind. Vaulted ceilings and light-filled spaces that feel both expansive and inviting. At the heart of the home, the chef’s kitchen blends timeless style with modern performance, featuring classic shaker cabinetry, gleaming white quartz countertops, high-end white Café appliances, and generous island seating ideal for gathering. The primary suite is a private sanctuary of nearly 700 square feet, complete with dual walk-in closets and a spa-inspired bath designed for indulgence, including a dramatic double soaking tub with jets, fireplace and TV, a Moen technology-enhanced shower, and electronic Woodbridge toilets that elevate daily living with comfort and innovation. Each of the guest bedrooms offer sizeable walk in closets. Step from the screened lanai off the living room down to a resort-caliber outdoor environment that rivals the finest destinations, where a heated pool and spa anchor the space alongside a putting green, waterfront fire pit, game area, and a beautifully pavered outdoor kitchen designed for effortless entertaining. For boating enthusiasts, the property is exceptionally equipped with a 10,000-pound boat lift and a second dock for added enjoyment. Substantial non-conforming enhanced storage beneath the home and a spacious three-car garage provide versatility without compromising luxury, making this a rare waterfront compound where mornings begin at the beach, afternoons unfold on the water, and evenings are spent poolside under the stars. Located a short distance to the Bridge Street Pier which offers ample dining, shopping and entertainment options, this residence truly is the ultimate beach getaway.

501 Norton Street, Longboat Key

$1,295,000

3 Beds ⋅ 2 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4683082 MLS ⋅ Active Status

One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.

550 De Narvaez Drive, Longboat Key

$65,000

Sleepy Lagoon SubDv. ⋅ 34667 Zip Code ⋅ W7882806 MLS ⋅ Active Status

Waterfront living in Hudson, Florida! Ideally situated on a deep-water canal with direct access to the Gulf of Mexico within minutes & No bridges, making it a perfect retreat for boaters and water enthusiasts. 63.38 ft on water; 1.5 lots combined. Enjoy the convenience of docking your boat right in your backyard and spending your days fishing, kayaking, or cruising the open water. Hudson is centrally located to many options for restaurants, shopping, minutes from Hudson Beach, hospitals & doctors. It is only 10 minutes to Sun West Park with its large man-made sandy beach & water park that everyone will enjoy. Hernando, Homosassa, Crystal River to the north & many locations south such as New Port Richey, Dunedin, Clearwater beach, there is never a shortage of things to do. Tampa & Tampa International Airport are within an hour. You own the Land. No HOA's, direct access to open water. Come and check it out!

Lot 23 and S1/2 of 24 Indigo Lane, Hudson

$2,000,000

Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ A4679439 MLS ⋅ Active Status

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home, nearly one acre of land, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 280 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and the sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

6604-6608 Gulf Of Mexico Drive, Longboat Key

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