Longboat Key Homes with Awning(s) Exterior Features

Longboat Key Homes with Awning(s) Exterior Features

Welcome to Longboat Key, Florida—a picturesque paradise where sun-kissed beaches meet vibrant coastal living. Nestled along the stunning Gulf of Mexico, this charming barrier island is renowned for its breathtaking sunsets, pristine sandy shores, and a serene atmosphere that beckons both relaxation and adventure. With its lush landscapes and crystal-clear waters, Longboat Key is the perfect place to call home.

One of the unique features of the homes in this idyllic locale is the presence of awnings. These delightful exterior features not only enhance the aesthetic appeal of your property but also provide essential shade and comfort. Imagine sipping your morning coffee or enjoying a sunset cocktail under a beautifully designed awning, shielded from the sun’s rays while still soaking in the stunning views that Longboat Key has to offer. Awnings can transform outdoor spaces into inviting retreats, perfect for entertaining friends or enjoying a peaceful afternoon with a good book.

The real estate market in Longboat Key boasts a variety of stunning properties, from luxurious beachfront estates to charming bungalows. Many of these homes feature awnings that complement their architectural style, providing both functionality and elegance. Whether you’re looking for a vacation getaway or a permanent residence, Longboat Key’s homes with awnings offer the perfect blend of comfort and coastal charm.

Discover the allure of Longboat Key, where every day feels like a vacation, and your dream home awaits under the inviting shade of a beautiful awning. Embrace the best of Florida living and make Longboat Key your new home today!

Newest Longboat Key Homes with Awning(s) Exterior Features

677 Lands End Drive, Longboat Key
$2,500,000
3 Beds ⋅ 3 Baths ⋅ Lands End SubDv. ⋅ 34228 Zip Code
Nestled on the coveted north end of Longboat Key, this exceptional residence is tucked away on the secluded and private Lands End Drive, one of the island's most treasured addresses. Rich in history, Lands End is celebrated for its maritime heritage, world-class fishing, and preservation of Old Florida charm. With just twelve homes in this exclusive gated enclave, residents enjoy an unparalleled sense of privacy while embracing an effortless waterfront lifestyle. The community offers an impressive collection of amenities, including deep water boat slips on the open bay, a heated swimming pool, tennis and pickleball courts, and maintenance-free living—creating the ideal year-round residence or luxurious seasonal retreat. Surrounded by lush tropical landscaping, the home offers a series of serene outdoor living spaces, private terraces, and a waterfront dock, inviting you to enjoy peaceful mornings, spectacular sunsets, and endless days on the water. Elevated and thoughtfully designed on a single living level, the residence evokes the feeling of a sophisticated treehouse, with tranquil views through a canopy of tropical greenery. Inside, you are greeted with a dramatic great room that features soaring vaulted cedar-lined ceilings and exposed beams creating warmth and architectural character throughout the open-concept floor plan. Designed for both relaxed living and effortless entertaining, the home features three spacious bedrooms, three full baths, and a split floor plan that offers guests their own private wing, with two bedrooms opening directly onto terraces with atrium views. The separate library and a dedicated office, with custom built-in cabinetry, add distinctive character and are ideal for working remotely or pursuing creative passions. The island kitchen invites family gatherings, while the primary suite offers a full wall of windows over the bayou, dual walk-in closets, and additional custom storage. The expansive dual garages provide exceptional storage and accommodate up to four vehicles, with additional space for a golf cart, paddleboards, kayaks, bicycles, and all the essentials for embracing Longboat Key's laid-back coastal lifestyle. With pristine Gulf beaches just a short walk or golf cart ride away, this property offers the rare combination of historic island character, boating convenience, exceptional privacy, and maintenance-free ownership. This remarkable home is more than a residence—it is a sanctuary where every day feels like a vacation.

677 Lands End Drive, Longboat Key

1916 Harbourside Drive Unit 804, Longboat Key
$1,599,000
4 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
FAIRWAY BAY’S FINEST — WATERFRONT LUXURY " END UNIT " WITH UNPARALLELED VIEWS Experience the ultimate Longboat Key lifestyle in this exceptional, move-in-ready waterfront residence in the prestigious gated Bay Isles community of Fairway Bay. Recently renovated and thoughtfully designed, this stunning 4-bedroom, 3-bath home offers more than 2,750 square feet of beautifully appointed living space, framed by expansive windows and soaring ceilings that invite an abundance of natural light. From nearly every room, enjoy breathtaking panoramic views across Sarasota Bay to the iconic Ringling Bridge and downtown Sarasota. The seamless open-concept design creates an effortless flow between the sophisticated great room with a fireplace, dining room & beautifully appointed kitchen, featuring high-end appliances and exquisite quartz and marble finishes throughout the home. The light-colored wide planked wood floors add great warmth & grounding while the whole family gathers around the kitchen island or wrap-around sectional to enjoy a movie together! Designed for both elegant entertaining and relaxed coastal living, the residence offers two luxurious primary suite options one on the main floor or the panoramic terraced 2nd floor, including a private second-floor retreat that serves as an office or the 4th bedroom enjoying a sunrise terrace with a colorful flowerbox to enhance your relaxation. A versatile lower-level bonus room offers ample space for hosting family and friends or creating a private fitness studio, media room, or game room. The previous owner combined recreation and guest accommodations, furnishing the space with two king beds, an oversized couch, a ping-pong table, and a shuffleboard table. Step onto your private screened terrace and enjoy sweeping views across Sarasota Bay to downtown Sarasota, framed by spectacular sunrises and sunsets. Just steps away, your private dock accommodates a boat up to 40 feet, inviting spontaneous excursions along the Intracoastal Waterway and into the Gulf of Mexico. When it’s time to unwind, Fairway Bay offers an array of resort-style amenities, including access to the private Bay Isles Beach Club, a pool, spa, clubhouse, and tennis and pickleball courts. Scenic walking and biking paths invite outdoor exploration, while convenient kayaking access offers opportunities to discover the area’s abundant coastal wildlife. Enjoy convenient access to your private Bay Isles Beach Club via a pedestrian and bicycle tunnel, allowing you to reach the beach without crossing Gulf of Mexico Drive—just one of the many features this fabulous community offers. You’re also minutes from The Resort at Longboat Key Club, with its golf, restaurants, and marina, and a short drive from St. Armands Circle for exceptional dining, shopping, and art experiences. This is more than a beautiful home—it is a private waterfront retreat offering the very best of Longboat Key living. Simply arrive, unpack and begin enjoying the waterfront luxury lifestyle you deserve.

1916 Harbourside Drive Unit 804, Longboat Key

6529 Gulfside Road, Longboat Key
$15,000,000
5 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Be renewed and inspired by this striking Gulf-front residence in an exclusive island community, featuring an impressive 100 feet of direct beachfront. Renovated and redesigned in 2025 to offer seamless indoor-outdoor integration and wide, unobstructed Gulf views, the setting is simply spectacular. This sophisticated contemporary masterpiece captures the relaxed spirit of beachfront living through clean lines, organic textures, and a crisp, minimalist aesthetic, creating a space that feels airy, bright, and deeply connected to nature. Interior layouts embrace high ceilings and expansive open-plan living zones that share light across the entire footprint through vast expanses of glass. The distinctive 6,660-square-foot beach house blends rigorous structural engineering with minimalist design to celebrate the coastal environment. Luxury finishes and fixtures include Louis XIV champagne White Oak floors, Dennis & Leen custom chandeliers and sconces, and a custom Murano glass chandelier. The living room, dining room, and kitchen span nearly 1,200 square feet of open living, enhanced by a dramatic two-story ceiling and seamless access to the oversized lanai. Multiple sets of triple-glazed sliders open wide, dissolving the boundaries between indoors and out and creating a dramatic setting for effortless entertaining, relaxed gatherings, and unforgettable open-air living. In addition to mesmerizing tropical views and a light-drenched workspace, the extraordinary kitchen and butler’s pantry feature marble counters and high-end appliances, including a Wolf double-range oven, a Wolf steam oven, an integrated Sub-Zero refrigerator and freezer, and two Sub-Zero beverage refrigerators. Elevated to showcase the 180-degree unobstructed horizon views, a glamorous primary suite offers an exquisite bath surrounded by plush comfort amenities, with gorgeous vistas dominating the space. Two additional en-suite bedrooms, a third bedroom currently used as an office with a bath, and a loft library with a long wall of built-in bookcases offer plenty of room for everyone to unwind and rejuvenate at day’s end. The ground-floor space has 2 garage doors for vehicle and water-toy access, an elevator to the second and third levels, a huge lounge with abundant seating, a large-screen TV, an adjoining exercise room, and 2 mini-split air conditioners dedicated to this enormous ground-level space. Notable features throughout the house include 5 full bathrooms, a laundry room with marble counters and flooring, a water filtration system and softener, a Generac generator, a security system with ten cameras, and a Sonos audio system. Outdoor living is integral to this exceptional beachside residence, with multiple levels designed to capture breathtaking water panoramas and embrace the surrounding beauty. Spanning the entire Gulf-facing façade, a covered ground-level patio, a second-level lanai, and a third-level balcony create an effortless progression of spaces for relaxing, entertaining, and enjoying spectacular sunsets. A truly exceptional beachside retreat, 6529 Gulfside Road delivers a refined coastal experience that embraces everything that makes Florida living so extraordinary. From its spectacular setting to its thoughtfully designed spaces, every element celebrates the beauty, ease, and allure of Gulfside living. *Variance in place and plans drawn for 1,000 sq. ft. guest house and pool, making the square footage over 7,500 under air.

6529 Gulfside Road, Longboat Key

1920 Harbourside Drive Unit 1003, Longboat Key
$624,900
2 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
Virtually Staged. Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. Access to Bay Isles EXCLUSIVE Beach Club right across the street! The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities. Optional membership in the Longboat Key Club offers access, depending on membership category, to 45 holes of championship golf, more than 20 Har-Tru tennis courts, pickleball, multiple dining venues, private beach and pool facilities, a full-service spa, fitness and wellness facilities, member events, Marina Village and the Club’s deep-water marina.

1920 Harbourside Drive Unit 1003, Longboat Key

843 Bayport Way Unit 843, Longboat Key
$645,000
2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code
EXPERIENCE THE BEST OF LONGBOAT KEY—FROM THE GULF TO THE BAY! Welcome to Bayport Beach & Tennis Club, an exceptional Gulf-to-Bay community where pristine beaches, breathtaking sunsets, lush tropical surroundings, and resort-style amenities create the ultimate Florida lifestyle! Nestled among beautifully landscaped grounds, this desirable 2-bedroom, 2-bath SECOND-FLOOR END UNIT offers an inviting combination of privacy, natural light, and coastal charm—with the added benefit of NO NEIGHBORS ABOVE YOU! Step inside to discover a bright, welcoming residence featuring an open living and dining area, ideal for relaxing or entertaining. The thoughtfully designed split-bedroom floor plan provides privacy for owners and guests alike. The kitchen and bathrooms have been tastefully updated, newer windows enhance comfort and efficiency, and a full-size washer and dryer inside the residence add everyday convenience. The spacious primary suite features a walk-in closet and a versatile bonus area, perfect for a home office, cozy reading retreat, or additional storage. OUTDOOR LIVING IS JUST AS INVITING! Enjoy your morning coffee on the open-air deck, surrounded by tropical beauty, or unwind on the screened lanai while enjoying the peaceful setting. Covered parking, convenient guest parking, multiple storage areas, and a private owner's closet provide the practical features that make island living effortless. WHAT TRULY MAKES BAYPORT SPECIAL IS ITS EXTRAORDINARY GULF-TO-BAY LIFESTYLE! Situated on approximately 27 beautifully landscaped acres stretching from the Gulf of Mexico to Sarasota Bay, this distinctive community offers approximately 1,200 FEET OF PRIVATE GULF BEACH ACCESS, where soft sands, turquoise waters, and spectacular sunsets are part of everyday life. Enjoy an impressive collection of resort-style amenities, including a heated Junior Olympic-size swimming pool, four Har-Tru tennis courts, a fitness center, kayak launch, fishing pier, and beach chairs and umbrellas for residents. Meandering pathways wind through mature tropical landscaping, creating a serene, park-like atmosphere that makes Bayport one of Longboat Key's truly special communities. And the location? SIMPLY FABULOUS! You're just minutes from Longboat Key's wonderful restaurants, boutique shopping, St. Armands Circle, and the cultural attractions of downtown Sarasota. Imagine starting your morning with a peaceful walk along the Gulf, spending the afternoon kayaking on Sarasota Bay, and ending your day watching another unforgettable Florida sunset. Whether you're searching for a full-time residence, seasonal retreat, or your own coastal escape, this is an incredible opportunity to enjoy the best of Longboat Key living. BEACH. BAY. BEAUTIFUL ISLAND LIVING. YOUR LITTLE PIECE OF PARADISE AWAITS AT BAYPORT BEACH & TENNIS CLUB!

843 Bayport Way Unit 843, Longboat Key

732 Bayport Way, Longboat Key
$1,050,000
2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code
Welcome to 732 Bayport Way, a completely remodeled and beautifully furnished coastal retreat offering a rare Gulf view within Bayport Beach & Tennis Club, one of Longboat Key’s distinctive Gulf to Bay communities. Thoughtfully redesigned and renovated in 2023, this 2 bedroom, 2 bath residence offers approximately 1,456 square feet of sophisticated, move in ready living with virtually every detail updated. The renovation includes new flooring, countertops and windows, along with a dedicated home office that creates the perfect space for working remotely or enjoying a quiet study. The sleek, redesigned kitchen features premium JennAir appliances, crisp contemporary cabinetry, beautiful countertops, a water purification system and thoughtful finishes throughout. Designed with entertaining in mind, the residence also features a custom bar complete with a wine cooler, dedicated whisky display and built in cigar humidor, creating a distinctive space for cocktails, wine and evenings with friends. New furnishings throughout, including select pieces from Restoration Hardware, complete the refined yet relaxed coastal feel. Bayport offers an exceptional Longboat Key lifestyle, stretching from the Gulf of Mexico to Sarasota Bay and giving residents the opportunity to enjoy both beach and bay. Community amenities include private Gulf beach access, a heated swimming pool, tennis courts, fitness facilities, clubhouse, walking and nature paths, kayak facilities and access to Sarasota Bay. Start the morning with a walk along the Gulf, work from your private home office, spend the afternoon by the pool or on the water, and finish the evening entertaining at home or taking in a Longboat Key sunset. Completely remodeled, beautifully furnished and ready to enjoy from day one, 732 Bayport Way offers the opportunity to step directly into the Longboat Key lifestyle without the time, expense or inconvenience of undertaking a major renovation.

732 Bayport Way, Longboat Key

614 Norton Street, Longboat Key
$2,794,900
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

2350 Harbour Oaks Drive, Longboat Key
$950,000
3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code
Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

2350 Harbour Oaks Drive, Longboat Key

948 Spanish Drive S, 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

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