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Cudjoe Key, FL Houses for Sale

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  • /49

    $1,165,000

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    22737 Blackbeard Ln, Cudjoe Key, FL 33042

    Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

    Agent Photo

    Terry Garcia

    Keller Williams Key West Compass Realty

    (786) 321-8407

    22737 Blackbeard Ln, Cudjoe Key, FL 33042
  • /53

    $949,000

    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft

    22852 John Silver Ln, Summerland Key, FL 33042

    Paradise Awaits on Cudjoe KeyDiscover 22852 John Silver Lane, a rare A-frame waterfront retreat in the peaceful Cutthroat Harbor Estates. This two-bedroom, two-bath home embodies the perfect balance of Keys character and modern comfort, wrapped in lush palms and native landscaping that create a true island sanctuary.Inside, soaring vaulted ceilings and impact-rated windows and doors fill the

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    Matthew Sheehan

    Ocean Sotheby's International Realty

    (786) 981-3309

    22852 John Silver Ln, Summerland Key, FL 33042
  • /46

    $2,999,999

    • 3 Beds
    • 2 Baths
    • 1,714 Sq Ft

    653 Sawyer Dr, Summerland Key, FL 33042

    Spectacular Oceanfront Retreat in Cudjoe Gardens! Experience the ultimate in Keys living at this beautifully renovated 3 bedroom, 2 bath oceanfront oasis. This smart, solar-powered home with 6 Tesla Powerwalls, 2 EV chargers, plus an annual check for excess energy production offers eco-conscious luxury with remarkably low electric bills. Enjoy breathtaking ocean views from your private pool and

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    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 238-6782

    653 Sawyer Dr, Summerland Key, FL 33042
  • /37

    $999,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    22954 Buccaneer Ln, Summerland Key, FL 33042

    Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

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    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 230-1509

    22954 Buccaneer Ln, Summerland Key, FL 33042
  • /55

    $1,750,000

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    21865 Spain Blvd, Summerland Key, FL 33042

    Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

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    Matthew Sheehan

    Ocean Sotheby's International Realty

    (645) 215-8837

    21865 Spain Blvd, Summerland Key, FL 33042
  • /42

    $1,945,000

    • 3 Beds
    • 2 Baths
    • 2,047 Sq Ft

    20771 2nd Ave W, Summerland Key, FL 33042

    Incredible Florida Keys living! High quality concrete construction, impact windows and doors and custom metal roof- this home is ABOVE FLOOD and has no stairs! Enjoy the ease of one level living, with the storm safety of being above flood. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool and tiki! Exceptional boating- the 100' concrete dock

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 952-5792

    20771 2nd Ave W, Summerland Key, FL 33042
  • /49

    $1,599,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    22865 Redfish Ln, Summerland Key, FL 33042

    The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to the generous spacing between homes, as well as having

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    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (305) 900-5290

    22865 Redfish Ln, Summerland Key, FL 33042
  • /39

    $1,599,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    20838 5th Ave W, Summerland Key, FL 33042

    Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

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    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 952-7261

    20838 5th Ave W, Summerland Key, FL 33042
  • /60

    $2,250,000

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    743 Pattison Dr, Summerland Key, FL 33042

    Welcome to your slice of paradise in the Florida Keys! This stunning 3-bedroom, 2-bath canal-front home in desirable Cudjoe Gardens celebrates everything we love about island life -- in shades of blue. From the moment you arrive, you'll feel the calm, coastal vibe this home radiates.Beautifully remodeled in 2021 with full permits, this residence offers an open-concept living area with soaring

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 756-9163

    743 Pattison Dr, Summerland Key, FL 33042
  • /48

    $1,998,000

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation . Offering Four generous size bedrooms with Three full

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    Emily Lombard

    Ocean Sotheby's International Realty

    (786) 788-8217

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • /44

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    21855 Spain Blvd, Summerland Key, FL 33042

    Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    (786) 882-7957

    21855 Spain Blvd, Summerland Key, FL 33042
  • /28

    $896,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,195 Sq Ft

    22922 Blackbeard Ln, Cudjoe Key, FL 33042

    This 3-bedroom, 2-bathroom stilted home offers 1,200 sq ft of thoughtfully designed space on a spacious canal-front lot.Enjoy the convenience of a 40 ft seawall, 10,000 lb boat lift, outdoor shower, and an enclosed garage with plenty of room for vehicles, boats, and water toys.Inside, the open-concept kitchen, living, and dining areas are equipped with brand-new appliances, ample cabinet space,

    Krystal Thomas eXp Realty LLC

    22922 Blackbeard Ln, Cudjoe Key, FL 33042
  • /43

    $1,799,999 Open Sat 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    Jolly Roger Drive on Cudjoe Key, where custom design meets open water views. This 4-bedroom, 2-bathroom residence showcases a designer kitchen with Viking appliances and high-end finishes, perfect for entertaining. The first floor offers two guest bedrooms, an office, and a full bath, while the second floor features a spacious guest room and the primary suite with a private balcony, ensuite bath,

    Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
  • /29

    $1,377,000

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    141 Arica Ln, Cudjoe Key, FL 33042

    Experience the best of Florida Keys living in this beautifully maintained & extensively updated waterfront home on a desirable corner lot. Featuring a new 60 ft. concrete dock & 14,000 lb. elevator-style boat lift, you'll enjoy quick access to the Atlantic Ocean & Gulf for world-class fishing, diving, & sandbar adventures- making this property a true boater's dream! Inside, the split floor plan

    Madeleine Lowe Expert Realty LLC (HQ)

    141 Arica Ln, Cudjoe Key, FL 33042
  • /29

    $1,549,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    20841 8th Ave W, Cudjoe Key, FL 33042

    Meticulously maintained and located in the desirable boating community of Cudjoe Gardens, this nearly 1,900 sq ft home includes 90 feet of dockage, a 10,000 lb boat lift, hurricane impact windows, doors, and garage door, as well as a gorgeous pool creating your own private oasis. A boater's paradise with easy access to both ocean side and gulf side! The inside boasts 3 spacious bedrooms and an

    Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

    20841 8th Ave W, Cudjoe Key, FL 33042
  • /42

    $2,300,000

    • 5 Beds
    • 3 Baths
    • 1,978 Sq Ft

    94 Sacarma Dr, Cudjoe Key, FL 33042

    Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

    Michelle Blades Realty Executives Florida Keys Old Town

    94 Sacarma Dr, Cudjoe Key, FL 33042
  • /45

    $1,950,000

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft

    489 Sawyer Dr, Summerland Key, FL 33042

    OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    489 Sawyer Dr, Summerland Key, FL 33042
  • /41

    $2,500,000

    • 2 Beds
    • 2 Baths
    • 1,577 Sq Ft

    1176 Thatch Ln, Summerland Key, FL 33042

    Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

    Jonathan Minerick Homecoin.com

    1176 Thatch Ln, Summerland Key, FL 33042
  • /38

    $1,599,000

    • 2 Beds
    • 2 Baths
    • 1,127 Sq Ft

    1113 de Lussan Ln, Summerland Key, FL 33042

    Breathtaking Open Water Home in Cudjoe Key - Comes FULLY FURNISHED!Welcome to paradise! This stunning 2-bedroom, 2-bath home captures magnificent open water views and embodies the ultimate Florida Keys lifestyle.Main Living Area:Step inside to an open-concept kitchen, living room, and dining area bathed in natural light. Every detail is designed to highlight the beauty of the surrounding water

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    1113 de Lussan Ln, Summerland Key, FL 33042
  • /59

    $1,599,999 New Construction

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

    Alejandro Perez Amerifirst Realty

    142 Peg Leg Ln, Cudjoe Key, FL 33042
  • /28

    $699,000 Open Tue 11AM - 12:30PM

    • 1 Bed
    • 1 Bath
    • 576 Sq Ft

    22970 Sharp Ln, Summerland Key, FL 33042

    Step into island living at its most authentic. This charming 1 bedroom, 1 bath 576 square foot fishing camp-style home blends coastal simplicity with lush tropical artistry. Tucked among mature palms, plumeria, croton, and native foliage, the bohemian-inspired garden feels like a private oasis--perfect for morning coffee or winding down after a day on the water.The home itself offers a cozy, open

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    22970 Sharp Ln, Summerland Key, FL 33042
  • /58

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    164 Tortuga Ln, Summerland Key, FL 33042

    Experience the best of island living at this beautifully updated Cudjoe Key retreat with quick ocean access. Built in 1990 and extensively renovated in 2020 this stilted coastal home blends modern comfort with timeless Keys style.The 1,400 sq ft interior features a bright open layout, custom kitchen, and spa-inspired bathrooms.Outside enjoy a resort-style saltwater pool with both heater and

    Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    164 Tortuga Ln, Summerland Key, FL 33042
  • /55

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft

    20844 4th Ave W, Summerland Key, FL 33042

    Welcome to 20844 4th Ave W, a remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up one of the two brick paver driveways on this over sized lot you will find two entrances, beautiful landscaping and tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning concrete residence blends timeless elegance with coastal

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • /47

    $895,000

    • 2 Beds
    • 1.5 Baths
    • 1,256 Sq Ft

    22880 Blackbeard Ln, Summerland Key, FL 33042

    This gorgeous and unique waterfront 2 bedroom, 1.5 bathroom home with a 3rd guest room/office that has panoramic views of Cudjoe Key and Cudjoe Bay offers everything you need to start enjoying the Florida Keys Lifestyle. Pride of ownership with every detail for comfortable and convenient waterfront living and it comes turn-key! Fully furnished inside and out, all indoor/outdoor furniture, grill,

    Pamela Stangler Expert Realty LLC

    22880 Blackbeard Ln, Summerland Key, FL 33042
  • /65

    $1,099,000

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, Summerland Key, FL 33042
  • /23

    $3,750,000

    • 4 Beds
    • 4.5 Baths
    • 3,228 Sq Ft

    22815 Port Royal Ln, Summerland Key, FL 33042

    DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

    Rhonda Gailey Gailey Enterprises Real Estate

    22815 Port Royal Ln, Summerland Key, FL 33042
  • /35

    $865,000

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft

    22878 Privateer Dr, Summerland Key, FL 33042

    Adorable 2 bed, 2 bath home with many new improvements! New impact windows and doors, new hardie-board siding installed on exterior of house, newer 60 foot concrete dock with cut-ins for a boat lift, roof replaced in October 2017 and newer hot water heater. All the heavy lifting has been done on this house located in sought after Cudjoe Key. Quick boating access to the Gulf and Atlantic, property

    Pamela Stangler Expert Realty LLC

    22878 Privateer Dr, Summerland Key, FL 33042
  • /16

    $989,999

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

    Rayden Vega CASA MIAMI REAL ESTATE

    22961 John Avery Ln, Summerland Key, FL 33042
  • /46

    $999,965

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    701 Spanish Main 369 370 Dr Unit 369, Cudjoe Key, FL 33042

    Boater's Paradise with Expansive Waterfront Views!Rare opportunity to own one of only three double lots in Venture Out on Cudjoe Key! This 2-bedroom, 2-bath home offers unbeatable waterfront living with a newer 70-ft concrete seawall equipped with davits, bumpers, swim ladder, fish cleaning station, and upgraded dock posts and cleats--perfect for accommodating your large boats. Enjoy sweeping

    Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

    701 Spanish Main 369 370 Dr Unit 369, Cudjoe Key, FL 33042
  • /2

    $350,000

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

    This sale is for one 6000 square foot lot with a home in need of repairs or replacement.

    Joseph Ordini Keller Williams Key West Compass Realty

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
  • /9

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

    Robin Nilsson Keller Williams Key West Compass Realty

    22920 Privateer Dr, Summerland Key, FL 33042
  • /39

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft

    21073 7th Ave, Summerland Key, FL 33042

    Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    21073 7th Ave, Summerland Key, FL 33042
  • /43

    $1,135,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    22837 Calico Jack Cir, Summerland Key, FL 33042

    Seller says Bring Offers ! Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

    Beata Sharpe Coldwell Banker Vanguard Realty

    22837 Calico Jack Cir, Summerland Key, FL 33042

Why Live in Cudjoe Key

Cudjoe Key, FL, is a small community known for its waterfront properties and unique attractions. The island, which began as a U.S. Air Force base in the late 1950s, features a mix of single-family homes and resort rentals, with much of the land remaining undeveloped. The National Key Deer Refuge, a 9,000-acre preserve, protects the endangered Key deer on the island. A notable feature is the aerostat site at the northern tip, where a large white blimp, nicknamed “Fat Albert,” hovers. Residential areas like Cutthroat Harbor Estates and Cudjoe Gardens offer stilt homes and canal-front properties, with prices ranging from $600,000 to over $3 million. The island lacks traditional parks, but residents enjoy water activities such as deep-sea diving, boating, and fishing. Bahia Honda State Park, located 15 miles away, provides additional outdoor recreation with its beach, hiking trails, and snorkeling sites. Dining options include Broil, a gourmet steakhouse, and The Bent Prop, known for its happy hour specials. For groceries, Murray’s Market is 2 miles away on Summerland Key, and a Winn-Dixie is 9 miles away on Big Pine Key. Students attend highly rated schools like Key West High School and Big Pine Academy. The Overseas Highway connects Cudjoe Key to Key West, 20 miles south, and Marathon, 30 miles north. Residents face high home and flood insurance premiums due to the island's susceptibility to hurricanes.

Home Trends in Cudjoe Key, FL

Housing Trends

Median Sale Price
$998,000
Median Single Family Sale Price
$1,165,000
Average Price Per Sq Ft
$864
Number of Homes for Sale
9
Last 12 months Home Sales
13
Months of Supply
8.30
Median List Price
$1,249,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-25%
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