Chicago, IL Homes for Sale under $500,000

• 

  

  

  /36

  $449,000

  • 4 Beds
  • 2 Baths

  3504 S Maplewood Ave, Chicago, IL 60632

  This charming two-unit building at 3504 S. Maplewood St. offers an excellent investment or owner-occupied opportunity, featuring two spacious units each with two bedrooms and one bathroom. Both units have been fully updated with new kitchens, fresh paint, and new appliances, providing modern comfort and move-in readiness. The property also includes a two-car garage and a large backyard, perfect

  

  Evan Peng

  Landmark Property Group Realty, LLC

  3504 S Maplewood Ave, Chicago, IL 60632
• 

  

  

  /35

  $249,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  10118 S Luella Ave, Chicago, IL 60617

  Step into worry-free living with this beautifully renovated home, complete with a home warranty. This impressive all brick home features 3 spacious bedrooms and 1 full bath on the second level, plus an additional half bath in the finished basement for added convenience. The updated kitchen shines with new appliances, modern finishes, and stylish cabinetry, making it perfect for everyday living

  

  Tamika Bishop

  Coldwell Banker Realty

  10118 S Luella Ave, Chicago, IL 60617
• 

  

  

  /29

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  201 E Chestnut St Unit 8B, Chicago, IL 60611

  This spacious 2-bedroom, 2-bathroom southeast corner residence offers approximately 1,600 square feet of thoughtfully designed living space, highlighted by an expansive 27' x 8' private terrace. A welcoming foyer leads into a generous living room with floor-to-ceiling sliding glass doors providing seamless access to the terrace--true indoor/outdoor living! The separate dining area flows into a

  

  Tyler Stallings

  Corcoran Urban Real Estate

  201 E Chestnut St Unit 8B, Chicago, IL 60611
• 

  

  

  /31

  $399,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,350 Sq Ft

  5705 W Melrose St, Chicago, IL 60634

  Don't miss this bright and spacious Portage Park brick bungalow, offering 4 bedrooms and 2 full bathrooms with plenty of space to fit your lifestyle. The main level features hardwood floors throughout the open-concept living and dining areas, along with two generously sized bedrooms and a spacious kitchen. The inviting living room showcases a decorative fireplace, built-in bookcases, and charming

  

  Mary Aloisio

  @properties Christie's International Real Estate

  5705 W Melrose St, Chicago, IL 60634
• 

  

  

  /26

  $445,000

  $30K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,733 Sq Ft

  3121 N Nottingham Ave, Chicago, IL 60634

  Nestled on a quiet tree-lined street in the desirable northwest side of Chicago, this charming English tutor blends classic character with everyday comfort. Featuring a spacious layout with sun-filled living areas, this well-maintained residence offers the perfect opportunity for homeowners seeking both functionality and charm. The inviting kitchen provides ample cabinet space and flows

  

  Darren Allen

  Real Broker LLC

  3121 N Nottingham Ave, Chicago, IL 60634
• 

  

  /24

  $349,999

  Pending

  • 3 Beds
  • 2 Baths

  10560 S Lafayette Ave, Chicago, IL 60628

  Don't miss this incredible opportunity to own a pristine, fully renovated 2-flat located in the heart of Chicago's South Side. Perfect for both investors and owner-occupants, this meticulously maintained property blends modern finishes with functional design, offering strong rental potential and long-term value. Each spacious unit boasts an open-concept living and dining area, ideal for

  

  Melanie Miller

  Keller Williams ONEChicago

  10560 S Lafayette Ave, Chicago, IL 60628
• 

  

  /13

  $215,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  3153 W 85th St, Chicago, IL 60652

  ***MULTIPLE OFFERS RECEIVED** Highest and best is due Sunday, August 2 at 6pm***Discover the potential at 3153 W. 85th Street in the desirable Ashburn neighborhood of Chicago. This solid brick estate sale features three bedrooms on the main level and a large unfinished basement with endless possibilities for additional bedrooms, a spacious family room, recreation area, home office, or extra

  

  Omar Sanchez

  Habloft LLC

  3153 W 85th St, Chicago, IL 60652
• 

  

  /46

  $435,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft

  5525 S Cornell Ave Unit 4, Chicago, IL 60637

  Elegant and beautifully finished, this vintage condo sits on the quietest block in East Hyde Park. The one-way street north of 56th is just minutes from Lake Michigan, the University of Chicago, the Museum of Science and Industry, the Obama Presidential Center, the Metra station, and the Hyde Park Shopping Center (with Trader Joe's, Walgreens, and lovely restaurants and shops). With the

  

  Margie Smigel

  The Margie Smigel Group, LLC

  5525 S Cornell Ave Unit 4, Chicago, IL 60637
• 

  

  /21

  $280,000

  Pending

  • 5 Beds
  • 2 Baths

  307 E 136th Place, Chicago, IL 60827

  A charming, recently refreshed 2-flat frame property offering versatility for both homeowners and investors. With 5 total bedrooms and 2 full bathrooms, each unit delivers a comfortable, functional layout ideal for long-term living or steady rental income. The first-floor unit features 3 well-proportioned bedrooms and 1 bath, providing ample space for families or reliable tenants. The

  

  Ericka Taylor

  Coldwell Banker Realty

  307 E 136th Place, Chicago, IL 60827
• 

  

  /46

  $279,900

  Pending

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

  9232 S Essex Ave, Chicago, IL 60617

  Beautifully Updated Single-Family Home! This move-in ready home offers the perfect combination of space, style, and comfort. The main level features a stunning dining room, a bright and inviting living room, two generously sized bedrooms, an elegant eat-in kitchen, and a beautifully updated full bathroom. The second floor offers three additional spacious bedrooms and a breathtaking full bathroom,

  

  Jorge Mariscal

  RE/MAX Partners

  9232 S Essex Ave, Chicago, IL 60617
• 

  

  /39

  $389,000

  • 9 Beds
  • 3 Baths

  Unlisted Address

  Fantastic opportunity to own a 3-unit building in a growing Chicago area with strong rental income potential. Whether you're an investor looking to expand your portfolio or an owner-occupant looking to live in one unit while generating rental income from the others, this property offers flexibility and upside. The building could use some refreshing and updating, giving the next owner an

  

  Brandice Hampton

  Baird & Warner

  Unlisted Address
• 

  

  /26

  $230,000

  • 1 Bed
  • 1.5 Baths
  • 1,055 Sq Ft

  2323 W Pershing Rd Unit 132, Chicago, IL 60609

  Welcome to this spacious 1-bedroom plus den, 1.5 bath condo featuring an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The versatile den offers the perfect space for a home office, guest room, or flex space, while the primary suite includes a private full bath. Enjoy abundant closet space, additional storage, and your own private terrace for relaxing or

  

  Victor Senteno

  Senteno Real Estate LLC

  2323 W Pershing Rd Unit 132, Chicago, IL 60609
• 

  

  /31

  $310,000

  Pending

  • 1 Bed
  • 1 Bath
  • 925 Sq Ft

  1111 W 14th Place Unit 216, Chicago, IL 60608

  Come escape the noise and hustle & bustle of the city in this serene, calming, airy and spacious Condo with 1-Bedroom and a fully-enclosed Den! Price INCLUDES a designated, extra-wide, heated parking space in a secured access garage. No more searching for parking after a long day or scraping snow in the morning. This home features one of the largest 1-Bedroom + Den floor plans in the community.

  

  Rafay Qamar

  Real Broker LLC

  1111 W 14th Place Unit 216, Chicago, IL 60608
• 

  

  /33

  $429,000

  • 2 Beds
  • 1.5 Baths
  • 1,823 Sq Ft

  701 S Carpenter St Unit C, Chicago, IL 60607

  ** Multiple offers received, highest and best by Sunday 08/30/2026 at 12PM** Welcome to 701 S. Carpenter Street, Unit C, located in the sought-after Vernon Park Place Townhomes in the heart of Little Italy/University Village! This beautifully updated, wide and spacious 2-bedroom, 1.1-bath home offers comfortable single-level living with a private entrance and inviting foyer. The open living and

  

  Amy Sunshine

  @properties Christie's International Real Estate

  701 S Carpenter St Unit C, Chicago, IL 60607
• 

  

  /27

  $275,000

  Pending

  • 6 Beds
  • 2 Baths

  7948 S Drexel Ave, Chicago, IL 60619

  Well-maintained brick 2-flat located in the desirable East Chatham. Each unit features 3 spacious bedrooms and 1 full bath, offering comfortable living space for owners or tenants alike. The finished basement is duplexed, providing additional living space - perfect for extended family, recreation, or added rental potential. Enjoy rear parking with space for 2 cars and convenient access to

  

  Rafay Qamar

  Real Broker LLC

  7948 S Drexel Ave, Chicago, IL 60619
• 

  

  /32

  $450,000

  Pending Pre-Foreclosure

  • 8 Beds
  • 3 Baths

  8841 S Muskegon Ave, Chicago, IL 60617

  Step into a standout investment opportunity with this 3-unit building perfect for investors or owner occupants! Completely rehabbed in 2023, this property offers the perfect mix of modern upgrades and strong income potential including all-new electrical and plumbing systems, stylish kitchens and bathrooms, stainless steel appliances, and classic hardwood flooring throughout. The building includes

  

  Stephen Taylor

  HomeSmart Realty Group

  8841 S Muskegon Ave, Chicago, IL 60617
• 

  

  /6

  $375,000

  $25K PRICE DROP

  • 7 Beds
  • 3 Baths

  8039 S Marquette Ave, Chicago, IL 60617

  Great investment opportunity at 8039 S Marquette! This solid 3-unit building offers strong income potential with each unit featuring its own separate heating system-an attractive benefit for both owners and tenants. The property includes three spacious units with functional layouts and ample natural light. While some updating is needed, this presents the perfect opportunity to add value and

  

  Tammy Jackson

  KM Realty Group, LLC

  8039 S Marquette Ave, Chicago, IL 60617
• 

  

  /42

  $419,900

  • 3 Beds
  • 2 Baths
  • 2,700 Sq Ft

  4991 N Kolmar Ave, Chicago, IL 60630

  Multiple offers received. Highest and best Sunday 8/30 at 7:30 PM. Welcome to your private oasis in North Mayfair. An entertainers paradise! This sunny, happy home has been well maintained by it's long term owners. It offers 3 bedrooms, 2 full bathrooms across 3 finished levels. Upon entry, you'll find the living and dining combo with hardwoof floors throughout most of the home. Behind the

  

  Pedro Castaneda

  Compass

  4991 N Kolmar Ave, Chicago, IL 60630
• 

  

  /14

  $249,900

  Pending

  • 1 Bed
  • 1 Bath

  1733 W Balmoral Ave Unit 3A, Chicago, IL 60640

  Bright and spacious top-floor 1-bedroom condo in a beautiful courtyard building in Andersonville! The unit features an open floor plan with hardwood floors throughout. The kitchen is equipped with 42-inch wood cabinets, granite counters, a breakfast bar, and stainless-steel appliances. In addition to a good-sized bedroom and a neutral white bathroom, the condo includes in-unit laundry, central

  

  Patty Cerny

  Compass

  1733 W Balmoral Ave Unit 3A, Chicago, IL 60640
• 

  

  /32

  $499,000

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  1223 Edmer Ave, Oak Park, IL 60302

  This classic three plus-bedroom, three-bathroom brick bungalow offers three levels of finished living space. The main floor features a living room, formal dining room, and an eat-in kitchen updated with granite countertops and stainless steel appliances, family room, plus a main-level bedroom and full bath. The second floor is dedicated to a private primary suite complete with a full bath and

  

  Andrew Gagliardo

  Compass

  1223 Edmer Ave, Oak Park, IL 60302
• 

  

  /23

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,179 Sq Ft

  8728 S Rockwell Ave, Evergreen Park, IL 60805

  Welcome to this charming 3-bedroom, 2-bathroom two-story home nestled on a quiet residential street in the heart of Evergreen Park. Well maintained and thoughtfully laid out, this home offers spacious living areas, abundant natural light, and a versatile floor plan suited for a variety of lifestyles. The main level features a bright and inviting living room with large front windows, a functional

  

  Israel Valadez

  Realty of America, LLC

  8728 S Rockwell Ave, Evergreen Park, IL 60805
• 

  

  /24

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  4024 W 106th St, Oak Lawn, IL 60453

  Move-In Ready. Beautifully updated split-level with 3 beds and 2 baths; featuring soaring vaulted ceilings, refinished hardwood floors, a stunning fireplace, an updated kitchen with granite countertops, renovated bathrooms, and a spacious lower-level family room. Enjoy a large fenced backyard, oversized brick garage, and plenty of space to relax or entertain. Conveniently located near top-rated

  

  Israel Valadez

  Realty of America, LLC

  4024 W 106th St, Oak Lawn, IL 60453
• 

  

  /15

  $425,000

  Pending

  • 6 Beds
  • 3 Baths

  1428 N Austin Blvd, Oak Park, IL 60302

  Exceptional investment opportunity in the heart of Oak Park! This beautiful yellow brick 2-flat at 1428 N Austin Blvd, Oak Park, IL 60302 offers tremendous value-add potential for investors, owner-occupants, and house hackers alike. Each unit features a spacious and functional 3-bedroom, 1-bathroom layout, providing strong rental appeal and comfortable living space. The property's standout

  

  Victoria Waliczek

  Coldwell Banker Realty

  1428 N Austin Blvd, Oak Park, IL 60302
• 

  

  /13

  $424,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft

  1244 N Kedzie Ave Unit 1, Chicago, IL 60651

  Only 2 units LEFT!! Welcome to this stunning ground-level residence on Chicago's vibrant west side of Humboldt Park-a brand-new construction condo that perfectly blends modern comfort with a timeless sense of style. Boasting soaring 10-foot ceilings and an open-concept layout, this spacious home feels anything but below grade. The thoughtfully designed kitchen features sleek cabinetry, a large

  

  Omar Sanchez

  Habloft LLC

  1244 N Kedzie Ave Unit 1, Chicago, IL 60651
• 

  

  /29

  $299,999

  • 1 Bed
  • 1 Bath
  • 1,087 Sq Ft

  10 E Ontario St Unit 4207, Chicago, IL 60611

  Location, Location, Location! Enjoy elevated city living in this beautifully updated, oversized one-bedroom residence in the heart of River North. Spanning approximately 1,087 square feet, this high-floor home offers expansive city views, abundant natural light through floor-to-ceiling windows, and a private balcony to take it all in. The thoughtfully designed open layout features a spacious

  Matt Laricy Americorp, Ltd

  10 E Ontario St Unit 4207, Chicago, IL 60611
• 

  

  /15

  $245,000

  • 1 Bed
  • 1 Bath

  526 W Roscoe St Unit 2A, Chicago, IL 60657

  Top-floor penthouse in the heart of East Lakeview! Completely refreshed in 2026, this move-in-ready home features a newly opened kitchen with brand-new appliances, an updated bathroom, refinished hardwood floors, and fresh paint throughout. The spacious living room flows seamlessly into the charming open kitchen, creating a bright and inviting living space. The generously sized bedroom offers

  Matt Laricy Americorp, Ltd

  526 W Roscoe St Unit 2A, Chicago, IL 60657
• 

  

  /60

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  6334 N Sheridan Rd Unit 3E, Chicago, IL 60660

  Rare opportunity to own an exceptional, completely renovated three-bedroom, two-bathroom vintage residence in Edgewater's historic Devonshire building designed by the renowned firm of McNally/Quinn in 1924. Old-World glamour and sophistication embrace modern luxury and state-of-the art convenience in this exquisitely appointed home which draws inspiration from the Art Deco and Art Nouveau

  Bridgett McKenzie Engel & Voelkers Chicago North Shore

  6334 N Sheridan Rd Unit 3E, Chicago, IL 60660
• 

  

  /17

  $245,000

  Pending

  • 1 Bed
  • 1 Bath
  • 770 Sq Ft

  20 N State St Unit 611, Chicago, IL 60602

  Stylish loft living in the heart of downtown at 20 N State St #611! This inviting unit features beautiful hardwood floors, exposed brick walls, and an open-concept layout perfect for modern living and entertaining. The updated kitchen seamlessly flows into the living space, offering both functionality and contemporary appeal. Enjoy the convenience of in-unit laundry and unwind in the enclosed

  Kellye Jackson Redfin Corporation

  20 N State St Unit 611, Chicago, IL 60602
• 

  

  /13

  $299,000

  Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  1636 N Wells St Unit 2907, Chicago, IL 60614

  Beautifully updated high-floor 1-bedroom condo in sought-after Americana Towers in the heart of Old Town. This spacious east-facing home features floor-to-ceiling windows, an open-concept layout with lake views. Enjoy your brand new stainless steel appliances (2026), wooden cabinets, and granite counter tops that flow seamlessly into expansive living and dining spaces perfect for entertaining.

  David Betancourt Redfin Corporation

  1636 N Wells St Unit 2907, Chicago, IL 60614
• 

  

  /23

  $325,000

  Open Sun 12PM - 1:30PM

  • 2 Beds
  • 1 Bath
  • 683 Sq Ft

  1800 W Superior St Unit 1N, Chicago, IL 60622

  Charming 2 bed 1 bath in the heart of West Town/East Village with stunning common rooftop deck, tucked inside "The Nicholas," a historic all brick building converted to condos in 1999. This raised first floor unit offers 700 sqft of functional living space with tall 9'5" ceilings, tons of natural light, and hardwood floors throughout. Fresh paint touchups and move-in ready. The living room offers

  Jason Wagner Greystone Realty

  1800 W Superior St Unit 1N, Chicago, IL 60622
• 

  

  /14

  $300,000

  Pending

  • 1 Bed
  • 1 Bath

  550 W Surf St Unit 302, Chicago, IL 60657

  Vintage charm meets thoughtful modern updates in this exceptional East Lake View end unit at the iconic Commodore, one of Chicago's most iconic pre-war buildings. Filled with natural light, this turnkey home offers a spacious and inviting floor plan with beautiful original character throughout. The stylishly renovated kitchen features stainless steel appliances, a touchless Kohler faucet, and

  Elizabeth Caya Redfin Corporation

  550 W Surf St Unit 302, Chicago, IL 60657
• 

  

  /24

  $300,000

  Pending

  • 2 Beds
  • 2 Baths

  211 E Ohio St Unit 2118, Chicago, IL 60611

  Enjoy abundant natural light in this highly sought-after south-facing 2-bedroom, 2-bathroom condo at The Grand Ohio, ideally located in the heart of Streeterville. The unit features a well-appointed kitchen with 42-inch maple cabinetry, granite countertops, stainless steel that flows seamlessly into the spacious living and dining area-perfect for both everyday living and entertaining. Both

  Stacey Dombar Redfin Corporation

  211 E Ohio St Unit 2118, Chicago, IL 60611
• 

  

  /45

  $349,900

  Pending

  • 4 Beds
  • 3 Baths

  9350 S Manistee Ave, Chicago, IL 60617

  Welcome to this beautiful renovated contemporary house that offers 4 spacious bedrooms and 3 full baths, in the desirable Calumet Heights neighborhood. This charming home boasts style, elegance, and modern amenities. Step into the bright and roomy main level, which features a great-sized living room with a fireplace, 1 bedroom, 1 full bathroom, and new hardwood flooring throughout. Modern kitchen

  Mihaela Pintilie Century 21 S.G.R., Inc.

  9350 S Manistee Ave, Chicago, IL 60617
• 

  

  /24

  $384,500

  Pending

  • 1 Bed
  • 1.5 Baths

  2100 N Lincoln Park W Unit 3FN, Chicago, IL 60614

  Experience elevated city living in this beautifully updated two-level duplex residence in the heart of highly sought-after Lincoln Park. Offering over 1,000 square feet of thoughtfully designed living space, this spacious 1-bedroom, 1.5-bath home seamlessly blends modern comfort with sophisticated style. The open-concept main level is filled with natural light from expansive windows and features

  John Floros Fulton Grace Realty

  2100 N Lincoln Park W Unit 3FN, Chicago, IL 60614
• 

  

  /20

  $299,950

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1550 N Lake Shore Dr Unit 23E, Chicago, IL 60610

  NEWLY RENOVATED! Experience elevated city living in this beautifully renovated 1-bedroom, 1-bath residence with rare northeast views in one of Chicago's most coveted Gold Coast locations. Perched on the 23rd floor directly across from Lincoln Park, this home showcases sweeping, unobstructed views of Lake Michigan, North Avenue Beach, Lake Shore Drive, Lincoln Park, and the downtown skyline.

  Matt Laricy Americorp, Ltd

  1550 N Lake Shore Dr Unit 23E, Chicago, IL 60610
• 

  

  /33

  $220,000

  Pending

  • 1 Bed
  • 1 Bath

  1601 S Michigan Ave Unit 405, Chicago, IL 60616

  Experience urban living in this newly painted 4th-floor loft condo at 1601 S Michigan Ave #405. This 1-bedroom, 1-bathroom home features impressive 11-foot ceilings and charming exposed brick in the living room, which opens onto an attached, refinished balcony with a northern exposure. The living area is centered around a cozy, gas ventless fireplace. The kitchen is updated with modern appliances

  Miguel Lopez Redfin Corporation

  1601 S Michigan Ave Unit 405, Chicago, IL 60616
• 

  

  /25

  $449,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  800 W George St Unit 2, Chicago, IL 60657

  Fabulous Lakeview location! This bright and spacious 2-bedroom, 2-bath corner condo offers an ideal combination of vintage Chicago charm and everyday convenience. Flooded with natural light, the inviting open living and dining space features soaring ceilings, exposed brick, hardwood floors, and a cozy wood-burning fireplace-creating the perfect setting for relaxing or entertaining. The updated

  Kathryn Schrage Redfin Corporation

  800 W George St Unit 2, Chicago, IL 60657
• 

  

  /26

  $374,999

  • 2 Beds
  • 1 Bath
  • 947 Sq Ft

  303 W Ohio St Unit 2902, Chicago, IL 60654

  Bright and beautifully maintained CORNER residence at the highly sought-after Silver Tower, featuring sweeping east and north exposures in the heart of River North. This spacious 1-bedroom plus den home features an open-concept layout filled with natural light from dramatic floor-to-ceiling windows and seamless access to a private 17-foot balcony overlooking the city. The kitchen is designed for

  Matt Laricy Americorp, Ltd

  303 W Ohio St Unit 2902, Chicago, IL 60654
• 

  

  /19

  $350,000

  • 2 Beds
  • 1 Bath

  2609 W Gunnison St Unit 3, Chicago, IL 60625

  Welcome to this stylish top-floor soft loft in the heart of highly sought-after Lincoln Square. This beautifully updated 2-bedroom, 1-bath vintage home blends timeless character with modern finishes, featuring hardwood floors, exposed brick, abundant natural light, and postcard-worthy neighborhood views. The thoughtfully designed floor plan offers split bedrooms for added privacy. The spacious

  William Vezo Redfin Corporation

  2609 W Gunnison St Unit 3, Chicago, IL 60625
• 

  

  /32

  $449,499

  New Construction

  • 5 Beds
  • 3 Baths

  555 N Springfield Ave, Chicago, IL 60624

  Welcome to this stunning NEW CONSTRUCTION 5-bedroom, 3-bathroom home where luxury, comfort, and thoughtful design come together. From the moment you enter, you'll appreciate the soaring cathedral ceilings, open-concept layout, and premium finishes throughout. The spectacular chef's kitchen is the heart of the home, featuring quartz countertops, a designer tile backsplash, beautiful wood-grain

  Joe Betancourt Betancourt Realty

  555 N Springfield Ave, Chicago, IL 60624

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