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Florida Keys LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Total Listings 1,108
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$2,300,000
Key West
Old Town Unlisted   - MM: 1.00
8 Bed, 8 Baths, 3,383 SqFt Days Listed: 247
-8.00% ($200,000) 1 Price Change : Last Change 30 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

BIG TIME INVESTMENT OPPORTUNITY in the heart of the Historic District of Key West. Originally built as a former church, this 4 unit active rental property offers 3,383 square feet of living space, featuring 8 bedrooms and 4 bathrooms, and currently generates $10,908.50 in monthly rental income. (See below for a breakdown of beds and baths per unit) With versatile possibilities, it has the potential for improvement and the possibility of condominium conversion. Each unit is large and spacious by Key West standards and includes high ceilings. The building is of concrete block construction and currently had all concrete spalling issues resolved and painted. Off street parking for three cars, a rarity for Old Town, Key West. This property is located in one of the most desirable neighborhoods and is just a short walk to World famous Duval street, the islands best restaurants, shopping and more! Unit breakdown: (A) 3BD/1BA leased for $3,039.50 per month (B) STUDIO/1BA leased for $2,369 per month (C) 2BD/1BA leased for $2,700 per month (D) 2BD/1BA leased for $2,800 per month

$2,300,000
Key West
Sunset Key   - MM: 0.00
2 Bed, 2 Baths, 1,681 SqFt Days Listed: 328
-4.17% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Tranquil well maintained home professionally decorated on a private island five minutes off of Key West. Sunset Key. Tropical island living at its finest. The island has beautiful sand beaches , community resort style pool, tennis courts , fitness center, full service spa and a ocean front five star restaurant and bar. This exclusive community is dreamy and very secure. the ferry service to and from Key West runs 24 hours. Experience the serenity of truly being away from it all while just a short ferry ride to all Key West has to offer. Great investment opportunity for vacation rental.,history can be provided.

$2,300,000
Lower Matecumbe
Fantasy Harbor   - MM: 77.00
3 Bed, 3 Baths, 2,000 SqFt Days Listed: 245
-4.17% ($100,000) 1 Price Change : Last Change 70 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin99ft.

Make all of your Florida Keys fantasies come true at Fantasy Harbor! Were willing to bet you never even knew this gated community on Islamoradas Lower Matecumbe existed. This concrete harborfront home is being offered for the very first time. Upstairs 2 bedroom 2 bathrooms suites with open and spacious harborview living areas plus downstairs bedroom and bathroom with a bonus party hut reminiscent of relaxing Bahamian nights after a day on the water. Quiet & private living situated just off the Florida Bay in a protected harbor with 99 concrete seawall on cap rock plus boat lift. This one is a winner!

$2,300,000
Big Pine Key
Doctors Arm   - MM: 30.50
4 Bed, 4 Baths, 2,400 SqFt Days Listed: 61
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges

FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent bridge that is rarely used due to the fact that only a few homes are on the other side of the bridge.

$2,300,000
Lower Matecumbe
Port Antigua   - MM: 74.50
2 Bed, 2 Baths, 1,178 SqFt Days Listed: 170
-8.00% ($200,000) 1 Price Change : Last Change 94 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

This solid concrete home is located in one of Lower Matecumbes most sought-after subdivisions, offering 75 feet of prime waterfrontage on a peaceful canal with serene nature views--no neighboring homes across canal. The ground level features a permitted bath, a spacious workshop, and a carport with soaring high ceilings, providing ample storage.Enjoy your private slice of paradise with a dock complete with a Tiki hut for shade, and a 16,000 lb. 4-post boat lift, ideal for boating enthusiasts. The expansive backyard offers plenty of space to build your dream pool.With a little polish, this gem has endless potential to become your perfect waterfront oasis! Dont miss out on this unique opportunity!

$2,300,000
Summerland Key
Summerland Cove Isle   - MM: 25.00
3 Bed, 3 Baths, 2,256 SqFt Days Listed: 166
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

Elevated concrete home with enclosed aircraft and hangar below. Largest parcel of land on Summerland Key airport, surrounded by concrete privacy wall and lush landscaping. A true piece of paradise with a private runway in your front yard and a Dock with boat lift in the back - minutes from world-class diving and fishing.

$2,299,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
3 Bed, 3 Baths, 1,938 SqFt Days Listed: 26
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Tucked behind a new privacy fence, 1706 Seminary Street is a fully renovated home where thoughtful design meets laid-back Key West living. Set on a generous 7,480 square foot lot, this 3-bedroom, 3-bathroom (two en suite) home offers nearly 2,000 square feet of indoor space that has been completely reimagined to deliver easy, breezy island living with all the modern updates already done for you. Inside, youll find a gorgeous new kitchen with quartz waterfall-edge countertops, custom cabinetry, KitchenAide stainless steel appliances, and new flooring throughout. The spacious family room is surrounded by glass, filling the space with natural light, while a working fireplace adds warmth and charm. Sliding doors open directly to the pool deck, creating a seamless indoor-outdoor flow. A standout feature is the third bedroom, which has its own private entrance and the option to be used as a lock-out suite--ideal for guests, extended stays, or rental potential.Outdoors, meandering pathways guide you through lush landscaping to a resort-style L-shaped lap pool, two covered lounging areas, a Bahama-style outdoor dining space, a private outdoor shower, and a secure shed for additional storage. Whether youre looking for your full-time home or a part-time escape, this move-in ready residence has all the essentials for relaxed island living--just minutes from the best of Key West.

$2,299,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
3 Bed, 3 Baths, 1,250 SqFt Days Listed: 75
+2.68% ($60,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift175ft.Concr

Welcome to CASA DEL BOTE an Oasis at Tarpon Basin, Your Dream Waterfront Retreat!Step into a world of tranquility with this exceptional bay-front property, where breathtaking sunsets and the soothing sounds of the water are a daily delight. Nestled behind a custom gate, this stunning home is a hidden gem that promises privacy and serenity, all while offering over 175 feet of pristine waterfront, complete with your very own sandy beach. As you approach, the pavered driveway guides you to this beautifully remodeled 3-bedroom, 2-bath haven, designed for both comfort and style. The thoughtfully crafted split floor plan allows for seamless living, with ample space for both relaxation and entertaining. Beautiful water views frame your experience from almost every room, inviting the outside in and creating a serene ambiance throughout the home. The spacious master suite is a true sanctuary, featuring expansive windows that showcase the shimmering waters of the basin. Imagine waking up to the gentle lapping of waves and stepping onto your private balcony with your morning coffee in hand. The second bedroom also boasts enchanting water views, making it a perfect guest room or a cozy retreat for family. The heart of this home lies in its open living and dining areas, where the natural light pours in, and the inviting atmosphere beckons. The modern kitchen is equipped with stainless appliances and ample counter space, perfect for both intimate gatherings and grand celebrations. Step outside into your own private paradise, where outdoor living takes center stage. The recently resurfaced pool sparkles under the sun, inviting you to take a refreshing dip or lounge poolside with a good book. The property features a convenient boat lift and PWC lift, making it easy to embrace the coastal lifestyle and explore the crystal-clear waters at your leisure. Safety and efficiency are paramount, with impact windows/doors throughout the home and a newer metal roof. Its a lifestyle.

$2,299,000
Key Largo
Ocean Isle Estates   - MM: 106.00
4 Bed, 4 Baths, 2,699 SqFt Days Listed: 105
-4.01% ($96,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift70ft

Your Dream Waterfront Oasis Awaits!Welcome to this extraordinary custom-built waterfront home located on Exuma Rd in the serene Ocean Isle Estates. This stunning residence harmoniously combines luxury and comfort, perfectly poised to embrace the refreshing ocean breezes and breathtaking water views all year round.As you step through the grand entrance, youll be greeted by a spacious garage and an inviting first-floor guest suite, complete with its own private screened-in porch--ideal for morning coffee or evening relaxation. Take a leisurely stroll through the elegant pass-through to the poolside area and spa, where you can unwind and soak up the sun.Ascend the exquisite interior marble staircase, adorned with a unique rock-lined wall that leads you to the heart of the home--the magnificent great room. Here, youll be captivated by the meticulous attention to detail, featuring tray ceilings, crown molding, and stunning travertine marble that elevate every corner of this residence.The gourmet kitchen is a chefs delight, boasting custom hardwood cabinets, stylish lighting, a wine chiller, luxurious granite countertops, and top-of-the-line stainless steel appliances. Its a perfect setting for preparing culinary masterpieces or entertaining friends and family.With direct and easy access to the ocean, your aquatic adventures are just steps away! Enjoy the tranquility of the neighborhood, with a fantastic local restaurant and marina just a stones throw from your doorstep. This home is conveniently located near Miami, making it an ideal retreat while remaining close to the vibrant keys life. Dont miss this incredible opportunity to own a slice of paradise at an unbeatable price! Schedule your private tour today and feel the magic of waterfront living!

$2,295,000
Plantation Key
Plantation Key Colony   - MM: 90.00
5 Bed, 5 Baths, 2,450 SqFt Days Listed: 152
-8.20% ($204,999) 1 Price Change : Last Change 79 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 40ft.

$2,294,700
Key West
Sunshine Subdivision Plat 1   - MM: 3.00
5 Bed, 5 Baths, 2,560 SqFt Days Listed: 152
-18.05% ($505,300) 2 Price Changes : Last Change 62 Days Ago
Duplex - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This Key West resort-style home sounds like an absolute dream! It combines the perfect blend of luxury, functionality, and tropical charm. With almost 2,800 sq ft of living space, 5 bedrooms, and 3 baths, its designed for both comfort and elegance. The fact that its just steps from White Street Pier and the beach makes it an ideal location for those who love coastal living. Some standout features includes an expansive lot at 7,775 sq ft, theres plenty of space for the lush tropical landscaping and custom amenities like the grilling area, electric gate, and the stunning 20x40 pool with a spillover spa (one of the largest pools in Key West). The heated and chilled pool makes it suitable for year-round enjoyment. Enjoy your own tropical Oasis with the daybed swing under the lanai next to a custom water feature is the perfect spot for relaxation. The tiki bar also sounds like a great place to unwind after a swim or a day out exploring Key West. The 12ft elevation and oversized windows let in tons of natural light, making the home feel airy and bright. The 20-foot cathedral ceilings add grandeur to the living areas, and the built-in bookshelves give the space a cozy, welcoming vibe. The High-end Kitchen with sleek countertops, stainless steel appliances, and top-notch finishes, the gourmet kitchen is both stylish and functional--perfect for entertaining guests or cooking up a family feast. This home seems to be a perfect blend of relaxation and luxury with a variety of features to enjoy both inside and out. It truly is a must-see for anyone looking to live in or invest in Key West!Separate Apartment: The one-bedroom, one-bath apartment is an added bonus--whether for a caretaker or potential extra income, it adds flexibility to the property.

$2,294,700
Key West
Sunshine Subdivision Plat 1   - MM: 3.00
5 Bed, 5 Baths, 2,560 SqFt Days Listed: 152
-18.05% ($505,300) 2 Price Changes : Last Change 62 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This Key West resort-style home sounds like an absolute dream! It combines the perfect blend of luxury, functionality, and tropical charm. With almost 2,800 sq ft of living space, 5 bedrooms, and 3 baths, its designed for both comfort and elegance. The fact that its just steps from White Street Pier and the beach makes it an ideal location for those who love coastal living. Some standout features includes an expansive lot at 7,775 sq ft, theres plenty of space for the lush tropical landscaping and custom amenities like the grilling area, electric gate, and the stunning 20x40 pool with a spillover spa (one of the largest pools in Key West). The heated and chilled pool makes it suitable for year-round enjoyment. Enjoy your own tropical Oasis with the daybed swing under the lanai next to a custom water feature is the perfect spot for relaxation. The tiki bar also sounds like a great place to unwind after a swim or a day out exploring Key West. The 12ft elevation and oversized windows let in tons of natural light, making the home feel airy and bright. The 20-foot cathedral ceilings add grandeur to the living areas, and the built-in bookshelves give the space a cozy, welcoming vibe. The High-end Kitchen with sleek countertops, stainless steel appliances, and top-notch finishes, the gourmet kitchen is both stylish and functional--perfect for entertaining guests or cooking up a family feast. This home seems to be a perfect blend of relaxation and luxury with a variety of features to enjoy both inside and out. It truly is a must-see for anyone looking to live in or invest in Key West!Separate Apartment: The one-bedroom, one-bath apartment is an added bonus--whether for a caretaker or potential extra income, it adds flexibility to the property.

$2,290,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
4 Bed, 4 Baths, 2,376 SqFt Days Listed: 179
-16.73% ($460,000) 5 Price Changes : Last Change 27 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Exceptional newly built (2023) 4-bedroom, 4 1/2-bath home situated on a corner lot in Key West, featuring a large saltwater, heated pool and hot tub. This home offers a blend of luxury and practicality with highlights including: a corner lot location, soaring ceilings on both levels, crown molding, and a full ensuite bath in every bedroom. The open-concept first floor is perfect for entertaining, with a spacious kitchen boasting a large island, white 42 cabinetry, and high-end appliances. The living area flows seamlessly into the kitchen and beautifully landscaped backyard with a pool and hot tub. A covered deck with fans provides a relaxing spot to enjoy the outdoors, while the fenced yard offers privacy. The second-floor laundry room includes ample cabinet storage, and the home is raised on piers above flood zone, with several private parking spaces. The first-floor primary suite features a walk-in closet and an ensuite with a 5 shower, double sinks, and a separate whirlpool tub. Built to the highest wind load and flood standards, this home is both a sanctuary and a fortress. Enjoy the perfect balance of privacy and convenience, just moments from all that Key West has to offer. Dont miss this rare opportunity to own your dream retreat! One of the owners is a licensed Florida real estate agent. Home appraised for $2.8 M in December, so you would have instant equity! Owner financing considered.

$2,290,000
Key West
Key Estates   - MM: 3.00
5 Bed, 5 Baths, 2,366 SqFt Days Listed: 137
-4.18% ($100,000) 1 Price Change : Last Change 64 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover the perfect blend of modern elegance and island charm in this updated 5-bedroom, 4-bathroom Key West retreat. Just blocks from the beach and moments from the vibrant energy of Duval Street, this fully furnished home is ideal for full-time residency or a high-performing investment property.Step inside to an inviting open floor plan featuring gorgeous gray-blue tile flooring and a stylish kitchen with premium finishes. The main level boasts spacious living and dining areas, while the upper level offers two additional rooms--perfect for guests, a home office, or a cozy den. With accommodations for up to 14 guests, this home is designed for both comfort and convenience.Outside, escape to your private oasis featuring a large deck, lush landscaping, and an expansive pool--perfect for relaxing or entertaining. A detached pool house adds incredible value, offering a 1-bedroom, 1-bathroom studio with a kitchenette.With new exterior paint and thoughtful updates throughout, this home is a rare opportunity to own a slice of paradise in Key West. Dont miss your chance to experience the best of island living!

$2,285,000
Plantation Key
Fontaine Lake   - MM: 90.00
3 Bed, 3 Baths, 2,669 SqFt Days Listed: 56
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Custom Waterfront Pool Home! Offering teak wood floors and doors, 16 vaulted ceilings, custom crown and baseboard molding, chefs kitchen with 6 burner Viking gas range and stainless steel appliances.The home is situated on 2 mature landscaped lots with new irrigation system, free form pool with spill-over spa and resurfaced with Diamond Brite coating, new pool heater, chiller and pump including system control for wifi app, expansive patio with stone decking, fire pit and outdoor shower.The home has been well maintained with new tankless water heater, extensive water sealer and barrier to the crawl space under the house, 22 kw Generac generator enables the entire house to function. Concrete dock with permit in place for extended dockage (please see documents for current permit) The harbor provides immediate ocean access.Truly a beautiful traditional family home!

$2,275,000
Key Colony
Key Colony Beach   - MM: 53.50
5 Bed, 5 Baths, 3,234 SqFt Days Listed: 110
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.Concre

Expansive and elegant waterfront residence situated on the canal, offering an eastern exposure overlooking the in-ground pool and 100-foot wide canal. The property features a covered patio on the lower level and a spacious wooden deck on the upper level, complete with spiral stairs leading from the living room to a tropical keys-inspired kitchen. Ideal for hosting gatherings and unwinding in comfort. This 5-bedroom, 3-bathroom home includes two bedrooms and two baths upstairs, as well as three bedrooms and one bath downstairs. The circular paver driveway provides ample parking space. A large family home or corporate retreat boasting a Corian kitchen, fireplace, and separate living and dining areas on both floors. Equipped with a boatlift and convenient access to the Atlantic, whether you are looking for a vacation rental or a permanent residence, this property has it all.

$2,250,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
3 Bed, 3 Baths, 2,110 SqFt Days Listed: 106
-2.17% ($50,000) 1 Price Change : Last Change 27 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina district with unique design 1104 South St will appeal to those who demand the best in quality design, finishes, and lifestyle. The indoor-outdoor spaces are seamlessly connected by stack-away sliding-glass doors, promoting a flawless integration of outdoor/indoor living with architectural detailing that adds a romantic touch. The property is surrounded by landscaped gardens and a tranquil pool with a water feature that provides the soothing sound of the water throughout the home. The new kitchen has ample counter space, is equipped with stainless appliances, and adjoins the dining room for easy communication between hosts and guests. The lower level contains office space, a full bedroom, and 1.5 baths. On the second floor, youll find an airy, light-filled master suite with a walk-in closet, ensuite bathroom with an oversized soaking tub and two adjoining balconies. A second guest suite is accessible from the circular exterior staircase, complete with a private balcony and bathroom. Garage and off-street parking, private entry, and courtyard designed for comfort and practicality while maintaining aesthetic excellence. This property presents an outstanding lifestyle or vacation rental investment opportunity. Schedule your private tour now.

$2,250,000
Key Largo
Twin Lakes   - MM: 103.00
3 Bed, 3 Baths, 1,605 SqFt Days Listed: 65
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,BasinConcr

WELCOME TO THIS FULLY REMODELED OVER SIZED WATER FRONT PROPERTY. ABSOLUTELY EVERYTHING YOU SEE HAS BEEN NEWLY REMODELED. THIS OVER SIZED LOT REQUIRES VERY LITTLE MAINTENANCE. AS YOU WALK THROUGH THE 6 FOOT METAL GATE YOU FIND PAVED PARKING FOR OVER 10 CARS. THE REST OF THE YARD FEATURES HIGH GRADE ASTRO TURF, NEW POOL & WATER HEATER. THE DOCK WAS COMPLETED IN 2024 WITH SOLID CONCRETE AND NEW 20,000LB LIFT. THIS HOME IS SOLID CONCRETE INCLUDING THE ROOF. BRAND NEW IMPACT WINDOWS AND DOORS. BRAND NEW PLUMBING AND ELECTRICAL. EVERYTHING IN THIS PROPERTY IS STILL UNDER WARRANTY. BUILT INS IN ALL CLOSETS. OUT DOOR KITCHEN WILL BE COMPLETE BEFORE CLOSING. NO EXPENSE WAS SPARED IN THE CONSTRUCTION OF THIS HOME.

$2,250,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 1,738 SqFt Days Listed: 164
-9.96% ($249,000) 2 Price Changes : Last Change 65 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Situated in the coveted Historic Seaport neighborhood, 1015 Eaton Street offers charm and convenience, creating the ultimate Key West lifestyle. This meticulously reimagined Historic Eyebrow home offers 4 bedrooms and 3 bathrooms thoughtfully designed for quintessential island life. As you enter through the white picket fence, the home welcomes you with an inviting front porch, ideal for soaking in the sights and energy of this sought-after neighborhood. Upon opening the front door adorned with a stained glass transom, you are greeted by Dade County pine floors and walls lined with elegant wallpaper. The airy open-concept kitchen and living space are highlighted by soaring ceilings and a waterfall island. Stainless steel appliances and a marble counter top complete this ideal chefs kitchen. Natural light cascades through expansive wall-to-wall sliding glass doors, seamlessly connecting the indoor and outdoor living areas.The main-level primary ensuite bedroom features a luxurious bath with a basalt accent wall, sleek natural finishes, and direct access to the pool area. A first-floor ensuite guest bedroom and two additional upstairs bedrooms ensure plenty of space for family and friends. Each bathroom features custom anti-fog mirrors, porcelain tiles, and exquisite accents, blending functionality with sophisticated design. IPE decking along with a dazzling saltwater pool and adjoining hot tub with a glass mosaic-tiled waterfall sets the stage for relaxation and entertaining. This fully fenced backyard oasis offers the ideal space for tanning and unwinding after a long day on the island.With its unbeatable location and close proximity to all Key West has to offer, from eclectic boutiques, waterfront dining, or the islands renowned attraction, 1015 Eaton Street offers a rare opportunity to embrace the vibrancy of island life. Schedule your private showing today and make this Historic Seaport home yours!

$2,250,000
Key Largo
Cross Key Waterways   - MM: 103.00
4 Bed, 4 Baths, 3,198 SqFt Days Listed: 55
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Coastal elegance meets boaters paradise in this modern tri-level home with an elevator, set on a wide canal with direct Bay and ocean access. A gated entry leads to covered parking and expansive balconies capturing serene water views. Inside, a chefs kitchen showcases rich wood cabinetry, stainless steel appliances, and sleek tile finishes. Sunlit living areas flow seamlessly, while a private office doubles as a secure safe room. The primary suite offers a tranquil retreat with a sitting area and private balcony. Outside, enjoy a waterfront tiki hut, lounge area, fish station, and private dock with boat lift.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-17-2025.
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