Longboat Key Homes with Intracoastal Waterway Frontage

Longboat Key Homes with Intracoastal Waterway Frontage

Welcome to Longboat Key, Florida, a hidden gem nestled along the stunning Gulf Coast. This idyllic barrier island is renowned for its pristine beaches, lush landscapes, and a vibrant community that embraces the best of coastal living. With a warm, inviting climate year-round, Longboat Key offers a serene escape for those seeking both relaxation and adventure.

One of the most alluring features of Longboat Key is its exquisite homes with Intracoastal Waterway frontage. Imagine waking up each morning to breathtaking views of the shimmering waters, where sailboats glide by and dolphins play in the surf. These waterfront properties provide not just a home, but a lifestyle filled with tranquil sunsets and the soothing sounds of nature.

Living on the Intracoastal Waterway means easy access to a myriad of water activities. Whether you enjoy boating, fishing, or simply lounging by the water, your backyard becomes an oasis of leisure. Many of these homes boast private docks, allowing you to embark on spontaneous adventures along the coast or to nearby islands.

The community of Longboat Key is equally captivating, with upscale dining, boutique shopping, and a plethora of recreational opportunities. From the stunning beaches to the lush parks, every corner of this island invites exploration and enjoyment.

If you're searching for a place where luxury meets nature, Longboat Key's Intracoastal Waterway homes offer the perfect blend of elegance and coastal charm. Discover your dream home in this paradise, where every day feels like a vacation. Come experience the magic of Longboat Key!

Newest Longboat Key Homes with Intracoastal Waterway Frontage

$499,000
2 Beds 2 Baths Longboat Harbour North SubDv. 34228 Zip Code
Experience the best of Bay-to-Gulf living in this beautifully furnished condominium located on the top-floor in Building G at Longboat Harbour. Featuring 2 bedrooms and 2 bathrooms, this move-in-ready residence offers peaceful canal views, thoughtful updates, and exclusive access to a private, gated beach club on the Longboat Key Gulf Beach, just steps away. Building G also offers a special community feature: a dedicated bump-out area designed for residents’ outdoor gatherings and entertaining. This exclusive feature is available to only two buildings within Longboat Harbour, and Building G is one of them. The bright and inviting interior features a carpet-free design with luxury vinyl plank flooring throughout with tiled bathrooms. New lighting fixtures, custom window treatments and ceiling fans add a fresh, updated touch, while the kitchen is appointed with granite countertops and a stylish backsplash. The updated primary bathroom provides additional comfort and modern appeal with custom vanity and cabinet storage. A new HVAC system installed in 2025 offers added peace of mind. Step outside to the spacious screened lanai, where beautiful canal views create a relaxing backdrop for everyday living, and on those lucky days, you may even catch a glimpse of manatees swimming peacefully through the water. Enhanced by a ceiling fan, this private outdoor space is perfect for enjoying morning coffee, reading a good book, entertaining guests, or unwinding at the end of the day. The condominium is being sold furnished with carefully selected pieces that complement the home’s coastal style and create a warm, comfortable atmosphere. Whether you are searching for a full-time residence, seasonal getaway, or coastal vacation retreat, this property is ready to enjoy from the moment you arrive. Longboat Harbour at Longboat Key offers an exceptional waterfront lifestyle with access to both Sarasota Bay and the beautiful Longboat Key Beach. The community’s private, gated beach club provides a convenient place to relax on the sand, enjoy the Gulf breeze, and take in beautiful Florida sunsets. Residents also enjoy an impressive selection of resort-style amenities, including four heated swimming pools, a fully equipped fitness center, tennis and pickleball courts, fishing piers, kayak & bicycle storage, and boat slips available on a first-come, first-served basis. The community clubhouse/banquet hall offers social events and activities, providing plenty of opportunities to meet neighbors and enjoy an active coastal lifestyle. Ideally situated on Longboat Key, this gated waterfront community offers convenient access to some of the area’s best dining, shopping, and entertainment while maintaining a peaceful and private setting. Whether used as a serene retreat, vacation property, or full-time residence, this furnished condominium provides everything needed to experience the very best of Longboat Key’s Bay-to-Gulf lifestyle.

4370 Chatham Drive Unit 304, Longboat Key

$689,000
2 Beds 2 Baths Portobello SubDv. 34228 Zip Code
Welcome to Portobello, a Gulf to Bay community on mid Longboat Key where residents enjoy their own private beach access just across the street and a bayside dock right outside the door. This beautifully remodeled, turnkey furnished fifth floor condo overlooks the quiet waters of Cranes Bayou, positioned to catch soft morning light while the terrace stays comfortably shaded through the afternoon. Inside, the open floor plan is filled with natural light and finished with new laminate wood flooring, crown molding, plantation shutters, and new light fixtures throughout. The updated kitchen offers stainless steel appliances, custom white cabinetry with crown molding, under cabinet lighting, and a breakfast bar that opens to the dining area. The split bedroom layout is ideal for hosting guests. The oversized primary suite features its own water views, space for a king sized bed, an oversized walk in closet, and an en suite bath with a smart split sink and shower design, while the equally spacious second bedroom sits beside a fully updated second bath. A sleeper sofa in the living room allows the condo to comfortably sleep six, and an in unit washer and dryer adds everyday convenience. The full length screened terrace spans the entire width of the unit and is accessible through new impact sliding doors from the living room and both bedrooms, so the water view follows you from room to room. Portobello's amenities complete the picture. A BRAND NEW AC unit was installed in September 2026, ensuring peace of mind for years to come. Residents enjoy a heated pool with tennis courts, a fully renovated recreation room, kayak and canoe storage with a launch area, and a dock and walkway for fishing or docking your boat for up to two days. A bayside picnic area with a gas grill and umbrella tables sits near the kayak launch, perfect for sunset cookouts by the water. Just across the street, Portobello's private beach access puts the Gulf and its sugar sand shoreline a short stroll from your door, complete with a beach shower for rinsing off after a day in the sand. Each unit has its own extra ground floor storage locker, and the freshly painted, recently inspected building is centered on a lush tropical courtyard with a fountain, surrounded by beautifully landscaped grounds with paver parking. Condominium fees include water, sewer, trash, and basic cable. You are also just moments from everyday shopping and convenience at the Shoppes of Bay Isles, home to a Publix, CVS, and more, all without ever leaving the island, while St. Armands Circle and downtown Sarasota are an easy drive down the Key. With upgraded windows and doors, furnishings, appliances, and modern baths already in place, this is a Longboat Key retreat ready to enjoy from the very first day. Come experience it for yourself. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

3240 Gulf Of Mexico Drive Unit B504, Longboat Key

$200,000
Longboat Key Moorings SubDv. 34228 Zip Code
Nestled in a beautifully protected marina on the exclusive Longboat Key, this premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation lifestyle with full-time live-aboard privileges. Boating enthusiasts will enjoy seamless, unrestricted deep-water access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico with zero fixed bridges. The slip is fully equipped with robust dual 50-amp and dual 30-amp electrical hookups, while the marina provides comprehensive dockside services including both diesel and gasoline at the fuel dock and complimentary vessel pump-outs by professional dock hands. Owners also enjoy the flexibility to lease the slip to marina-approved vessels, offering excellent investment versatility without requiring a Longboat Key Club membership. Life at the marina combines everyday convenience with resort-style perks, featuring stunning, unobstructed sunrise and sunset views daily. The property includes water, sewer, cable TV, and Wi-Fi, alongside access to a well-maintained bathhouse, coin laundry facilities, a secure package delivery center, and free bicycle rentals. Parking is highly accessible with multiple spaces located directly next to the dock. Ownership integrates you into the Bay Isles HOA, which ensures peace of mind through 24-hour guarded gates, active security, and immaculate common area maintenance. For just $600 a year, owners can also join the walkable Bay Isles Beach Club to enjoy newly renovated beachfront facilities, volleyball nets, and picnic areas with grills. To complete the luxury experience, a complimentary community shuttle is available to transport you directly to the premier shopping and dining at St. Armand's Circle or the Longboat Key Club Resort properties.

2600 Harbourside Drive Unit P-05, Longboat Key

$4,300,000
4 Beds 5 Baths Country Club Shores SubDv. 34228 Zip Code
Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant millwork, walls of glass, and exquisite finishes create a light-filled home that perfectly frames the surrounding water views while offering nearly 4,400 square feet of beautifully designed living space. Ideally situated just one home from Sarasota Bay, this rare waterfront property captures sweeping bay views while providing the privacy, protection, and peace of mind that come with its prime location and newer construction. Beautifully updated in 2025 by Brista Homes, the residence features four bedrooms, five full baths, a spacious game room, and a generous loft office with breathtaking bay views—an inspiring space for working remotely or simply relaxing while enjoying spectacular sunsets. Multiple indoor and outdoor living areas are thoughtfully designed for effortless entertaining and everyday coastal living. Light-filled interiors blend refined custom details with relaxed elegance. The gourmet kitchen, appointed with newer appliances (2022), opens seamlessly to the living and dining areas, creating an inviting setting for intimate family gatherings or grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring direct pool access, an elegant tray ceiling, and dual custom walk-in closets. Upstairs, guest suites offer en-suite baths and generous closets, providing exceptional privacy and comfort for family and visitors alike. Extensive recent improvements include a new roof (2025), updated windows, new balusters, and thoughtfully selected designer finishes throughout, creating a residence that perfectly balances timeless elegance with today's modern conveniences. Outdoor living is equally extraordinary. Expansive terraces, a sparkling pool, and tranquil waterfront views create the perfect backdrop for the coveted Florida lifestyle. For boating enthusiasts, the deep-water canal frontage features a composite dock, a 12,000-pound boat lift, and a newer seawall, providing immediate access to Sarasota Bay and just minutes to the Gulf of Mexico. Country Club Shores is one of Longboat Key's most prestigious waterfront communities, encompassing 19 picturesque streets with distinctive nautical and golf-inspired names. The homeowners association maintains the beautifully landscaped common areas and hosts a variety of neighborhood social events, fostering an exceptional sense of community. Residents enjoy convenient beach access and an unbeatable location just minutes from the world-class shopping and dining of St. Armands Circle, as well as the acclaimed restaurants, theaters, galleries, and cultural attractions of downtown Sarasota. Offering panoramic water views, exceptional boating, beach access,and an outstanding south Longboat Key location, this is a rare opportunity to own an extraordinary waterfront residence where timeless architecture, modern luxury, and the very best of Florida coastal living come together.

657 Halyard Lane, Longboat Key

$5,995,000
4 Beds 4 Baths La Lenaire Isle SubDv. 34228 Zip Code
Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two decades. The home is a custom built, over 2,700 square feet of living space designed to embrace panoramic water views and effortless indoor-outdoor living, four bedrooms and four baths, finished in 2011 on a 1.24-acre titled lot with roughly 300 feet of water frontage. From the island you are minutes by water to Longboat Key, St Armands Circle, and Anna Maria Island. Every room captures breathtaking western-facing vistas, creating a constant backdrop of sparkling water, coastal breezes, and unforgettable sunsets. The main living areas open onto covered outdoor space and frame the sunset over the intercoastal waters, and the evening light fills the rooms. It was built to handle a quiet weekend or a full house of guests. The private deep-water dock provides immediate boating access to Sarasota Bay, the Intracoastal Waterway, Longboat Key Pass, and the Gulf of Mexico, making this a true boater’s paradise. Jewfish Key is a hidden gem spanning approximately 38 acres, offering a level of privacy and tranquility rarely found along Florida’s Gulf Coast. Surrounded by pristine shoreline, sandbars, native wildlife, and crystal-clear waters, the island delivers an unmatched blend of exclusivity and natural beauty while still being conveniently located near Longboat Key, Anna Maria Island, and Sarasota’s world-class dining, shopping, and entertainment. Whether used as a private family compound, luxury waterfront getaway, or one-of-a-kind investment opportunity, 7143 La Lenaire Drive represents a truly irreplaceable island lifestyle. Turn Key - Furnished.

7143 La Lenaire Drive, Longboat Key

$350,000
1 Beds 1 Baths Whitney Beach SubDv. 34228 Zip Code
Bring your boat!!! Excellent water views in this north end desirable Whitney Beach waterfront community. If you’ve been waiting for the perfect second-floor residence in the highly sought-after Whitney Beach community on Longboat Key, this is the one. Offering some of the finest views in the complex, this turn-key condominium has been thoughtfully upgraded and is move-in ready. What truly sets Whitney Beach apart is its rare combination of resort-style living and relaxed island charm: Pet-friendly paradise — One of the few communities on Longboat Key that welcomes up to two large dogs, making it a dream for dog lovers. Private boat docks on the protected bayou, providing easy access to the water. One of the widest and most beautiful private beaches on the island, with direct deeded access. Resort-style heated and cooled pools for year-round enjoyment. Prime second-floor positioning that delivers the community’s best panoramic views. Unforgettable wildlife moments right from your home — watch mama manatees nurturing their calves in the canal and dolphins feeding just offshore. Convenient kayak storage and launch area. Exceptionally walkable location — just steps from upscale restaurants, shops, and a fitness center. One of the most pedestrian-friendly communities on all of Longboat Key. A thoughtfully designed floor plan with a low-density, intimate feel — no high-rise hotel atmosphere here. Spacious, peaceful surroundings where residents enjoy privacy and breathing room. Serene walking path to the iconic Beer Can Island (Greer Island), with its pristine beach and natural beauty. Just over the bridge lies Coquina Beach, home to vibrant weekly craft fairs and farmers markets. Nestled at the tranquil northern end of Longboat Key, this location offers the best of both worlds — easy proximity to the charming village atmosphere and world-class amenities of Anna Maria Island, one of America’s most treasured coastal gems. Don’t miss your opportunity to own a piece of this turquoise paradise at an exceptional value. Wake up every morning in one of Florida’s most exclusive island retreats — where luxury, nature, and relaxed coastal living come together perfectly.

6750 Gulf Of Mexico Drive Unit 152, Longboat Key

$1,199,000
2 Beds 2 Baths Spanish Main Yacht Club SubDv. 34228 Zip Code
A few photos virtually staged. Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. Brand new roof completed by 8/31/2026. . There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.

948 Spanish Drive S, Longboat Key

$22,000,000
4 Beds 7 Baths Longboat Key SubDv. 34228 Zip Code
Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this palatial Bayfront estate stands as a singular expression of architectural distinction and craftsmanship. Encompassing close to five acres on the north end of Longboat Key spanning Sarasota Bay, the combined offering of 6610 and 6630 Gulf of Mexico Drive represents one of the most significant residential holdings available in the area, a legacy estate where endless views of sea and sky create an unforgettable backdrop for living. The property unfolds like a private peninsula, offering exceptional width, depth and privacy. On the eastern shoreline, calm bay waters reflect the morning light with open water, protected shoreline and bridgeless access to the Gulf of Mexico. The primary residence is gracefully positioned on the bayfront, designed to capture eastern exposure and long, tranquil water views across Sarasota Bay. Clean architectural lines, soaring interior volumes, and walls of glass create a continuous dialogue between interior and exterior. Ceilings soar up to 21 feet, allowing light to move freely throughout the home while maintaining warmth and livability. The elevator provides access across levels, while Lutron lighting and automated shades on every window and door allow the home to respond intuitively to the changing light of day. The residence has been impeccably maintained by its original owner, reflecting a level of care and stewardship rarely found. Infrastructure has been thoughtfully addressed, including a whole-home generator that ensures continuity and peace of mind. The owner’s garage sits under a cantilever with access to the interior elevator and an additional air-conditioned four-car garage with large workspace offers a total space for 6 cars and exceptional flexibility for collectors, hobbies or future customization. A lagoon-style pool sits within the landscape, offering a resort-like atmosphere while preserving privacy and water views. A private dock with two boat lifts provides immediate access to Sarasota Bay and the Intracoastal Waterway, creating a seamless boating lifestyle that complements the estate’s waterfrontage. The inclusion of 6630 Gulf of Mexico Drive allows owners to construct a guest house or secondary structure, offering flexibility for multigenerational living, guests, or staff accommodations, offering extraordinary future optionality and ensures the next owner retains control over one of Longboat Key’s irreplaceable resources, land. What ultimately distinguishes this offering is its irreplaceability. Estates of this size, with this combination of architectural pedigree, boating infrastructure, development flexibility and maintained condition are no longer being created. Despite its scale and seclusion, you are moments from the refined lifestyle Longboat Key is known for, private clubs, championship golf, fine dining, IMG Academy and the cultural offerings of Anna Maria Island, St. Armands Circle and downtown Sarasota just beyond the bridge. This is not merely a waterfront home, it is a generational legacy, unmatched in design, scale, privacy and location.

6610 Gulf Of Mexico Drive, Longboat Key

$769,000
2 Beds 2 Baths Windward Bay SubDv. 34228 Zip Code
This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

4500 Gulf Of Mexico Drive Unit 206, Longboat Key

$6,295,000
4 Beds 5 Baths Hideaway Bay Subdivision SubDv. 34228 Zip Code
Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze. With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms. Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance. Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.

757 Hideaway Bay Drive, Longboat Key

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