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Duplexes for Sale in Chicago, IL

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  • /19

    $399,000

    $6K PRICE DROP Pending
    • 6 Beds
    • 3 Baths

    1921 S Saint Louis Ave, Chicago, IL 60623

    Be the first to live in post rehab! First floor is a duplex with 3+ bedroom /2 bath and the top unit has 3 bed/1 bath. Central a/c, new floors, windows, kitchens/bathrooms, ROOF and more. Great for owner occupant or investor in this hot neighborhood. Close to public transportation, parks, shopping and more. Sold as-is.

    Andy Sokol The Sokol Group

    1921 S Saint Louis Ave, Chicago, IL 60623
  • /17

    $320,000

    • 4 Beds
    • 2 Baths

    321 W 47th St, Chicago, IL 60609

    Located in the heart of Chicago's Canaryville/Back of the Yards area, this solid two-flat offers a versatile opportunity for both owner-occupants and investors alike. Whether you're looking to live in one unit while generating rental income from the other, or fully lease both units for steady cash flow, this property delivers flexibility and long-term potential. Each unit offers generous living

    Tiffany Martinez North Clybourn Group, Inc.

    321 W 47th St, Chicago, IL 60609
  • /33

    $950,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,851 Sq Ft

    5748 N Hermitage Ave Unit 106, Chicago, IL 60660

    PLEASE NOTE: REACTIVATION DUE TO BUYER HOME SALE CONTINGENCY FALLING THROUGH (06/13/2026). Thoughtfully designed 4 bed / 3 bath duplex in boutique elevator building located in the heart of Andersonville. Spanning nearly 2,900 sq ft, this home offers a rare blend of scale, functionality, and modern luxury across two expansive levels and private exterior entrance. The main level is anchored by an

    Laura Meier @properties Christie's International Real Estate

    5748 N Hermitage Ave Unit 106, Chicago, IL 60660
  • /13

    $519,000

    $20K PRICE DROP
    • 7 Beds
    • 3 Baths

    6520 S Ellis Ave, Chicago, IL 60637

    Move right into this beautifully updated East Woodlawn two-unit offering the perfect blend of immediate income potential and comfortable owner-occupancy. The spacious first-floor duplex features 4 bedrooms, 2 full baths, two separate living areas, an updated kitchen with stainless steel appliances and a dishwasher, private laundry with storage, and a private entrance-ideal for related living,

    Naja Morris @properties Christie's International Real Estate

    6520 S Ellis Ave, Chicago, IL 60637
  • /61

    $1,100,000

    Pending
    • 7 Beds
    • 5 Baths

    2245 W Melrose St, Chicago, IL 60618

    Classic Roscoe Village legal two-flat with additional third-floor in-law/flex space, offering exceptional versatility for investors, owner-occupants, or those considering a single-family conversion. The owner's duplex-down residence features 4 bedrooms and 3 bathrooms and offers an open-concept kitchen and family room, a separate formal dining room, and multiple living and entertaining spaces

    Leigh Marcus @properties Christie's International Real Estate

    2245 W Melrose St, Chicago, IL 60618
  • /8

    $1,570,000

    • 4 Beds
    • 3 Baths

    2742 N Kenmore Ave, Chicago, IL 60614

    Two unit building in Lincoln Park. Sunny well designed second floor duplex with vaulted ceilings, spacious layout and working fireplace. Second floor unit has its own washer dryer install installed and is easy to rent. First floo unit is large and attractive. Both units have private decks with sliding glass doors. Both units have fireplaces. Both unit units were recently remodeled and have their

    David Grieco Westward Properties LLc

    2742 N Kenmore Ave, Chicago, IL 60614
  • /26

    $659,000

    • 5 Beds
    • 4 Baths

    1221 E Marquette Rd, Chicago, IL 60637

    Attainable, comfortable, healthy, and cool! Award-winning, Greenline Homes Two Flat in Southeast Woodlawn! Greenline Homes has made Woodlawn the destination for high-performance homes in Chicago. We're thrilled to offer a resale of a groundbreaking two-unit building that showcases cutting-edge construction and high-performance materials and design throughout. Unit 1 is a bright, modern garden

    Wayne Beals Exit Strategy Realty / EMA Management

    1221 E Marquette Rd, Chicago, IL 60637
  • /21

    $658,000

    New Construction $8K PRICE INCREASE Pending
    • 6 Beds
    • 5 Baths

    732 N Pine Ave, Chicago, IL 60644

    OWNER-OCCUPIED BUYERS ONLY! QUALIFIES FOR 20,000 GRANT FROM THE COUNTY. ANOTHER PROJECT BY AN AWARD WINNING DEVELOPER - GT ALTERNATIVES LLC. This gorgeous 2 unit new construction is expected to be completed in June, 2026 and will feature 4 bedrooms and 3 bathrooms in the duplex down first floor unit with white shaker designer kitchen cabinets, a large peninsula, quartz counters, stainless steel

    Marika Kakhiani Pedestal Realty LLC

    732 N Pine Ave, Chicago, IL 60644
  • /21

    $474,900

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

    732 S Financial Place Unit 810, Chicago, IL 60605

    For those drawn to authentic loft living, this remarkable home offers a creative, connected layout unlike anything else on the market. A beautiful architectural spiral staircase located within the primary bedroom leads to the second bedroom and its private full bath, creating a distinctive arrangement ideal for a guest suite, home office, creative space or private upper-level retreat. Rare

    Maria DelBoccio @properties Christie's International Real Estate

    732 S Financial Place Unit 810, Chicago, IL 60605
  • /21

    $299,000

    $31K PRICE DROP Pending
    • 4 Beds
    • 2 Baths

    1440 E 76th St, Chicago, IL 60619

    Brick 2-flat located at on a quiet, tree lined block in Chicago's Greater Grand Crossing/Avalon Park area. This solid property offers classic Chicago charm with spacious, light-filled units, functional layouts, and generously sized rooms throughout. The full basement provides a strong value-add opportunity ideal for additional living space, duplex-down expansion, or the potential to increase

    Sachet White Century 21 IMPACT

    1440 E 76th St, Chicago, IL 60619
  • /21

    $2,100,000

    Pending
    • 6 Beds
    • 5 Baths

    1726 N Cleveland Ave, Chicago, IL 60614

    Located in the heart of Chicago's sought-after Old Town neighborhood, this classic multi-unit redstone offers incredible space, versatility and investment potential. The top-floor owner's duplex features 3 spacious bedrooms and 3 full baths, providing the perfect blend of comfort and functionality for owner-occupants. The first floor includes 3 bedrooms and 1 bathroom.ideal for rental income or

    Annie Caltabiano @properties Christie's International Real Estate

    1726 N Cleveland Ave, Chicago, IL 60614
  • /35

    $929,900

    • 4 Beds
    • 3 Baths
    • 2,650 Sq Ft

    1536 W Walton St Unit 1, Chicago, IL 60642

    Noble Square, beautifully maintained duplex down condo on a treelined street with 3 private outdoor spaces! This spacious, facing South residence floods with light all day long. The main level features a sun-filled living with fireplace ,dining area, large, modern eat-in kitchen with custom huge island with quartz countertops, marble backsplash, custom cabinetry and high-end stainless steel

    Beata Gaska @properties Christie's International Real Estate

    1536 W Walton St Unit 1, Chicago, IL 60642
  • /22

    $930,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,907 Sq Ft

    2743 N Ashland Ave Unit 1N, Chicago, IL 60614

    Located in the heart of Lincoln Park within an intimate 6-unit building and steps from the Blue Ribbon award-winning Prescott Elementary, this beautifully designed 3-bedroom, 2.5-bath duplex offers exceptional living space, luxury finishes, and incredible outdoor living rarely found in the city. Built in 2019 with brick and steel construction, the home offers a surprisingly quiet, peaceful

    Tim Sacks @properties Christie's International Real Estate

    2743 N Ashland Ave Unit 1N, Chicago, IL 60614
  • /27

    $1,275,000

    Pending
    • 8 Beds
    • 4 Baths

    1609 N Wood St, Chicago, IL 60622

    Proud to present this sensational center entrance 4 flat opportunity. Extra Wide structure rests on a 48 x 47 lot just north of North Ave. The property is centered around Wicker Park's many restaurants, boutique shops, bars, cafe's and so much more. The classic victorian structure features the original masonry facade with its ornate bay windows, red brick exterior, stone lintels and architectural

    Wilfredo Aguilar Compass

    1609 N Wood St, Chicago, IL 60622
  • /37

    $799,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,786 Sq Ft

    1330 W Monroe St Unit 410, Chicago, IL 60607

    Duplex penthouse loft in Chicago's West Loop - one of the neighborhood's most distinctive and sought-after residences. Corner unit in the iconic Block Y complex. Two-story top floor corner unit, 2BD+Den/2BA timber loft with soaring 15-ft ceilings, exposed brick throughout, and a private ~220 SF wrap around top floor deck that gets all day sunshine and has unobstructed skyline views of the Willis

    Stephanie Turner Jameson Sotheby's Intl Realty

    1330 W Monroe St Unit 410, Chicago, IL 60607
  • /20

    $299,800

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

    6651 S Drexel Ave Unit 1E, Chicago, IL 60637

    Beautifully Renovated 3-Bedroom, 3-Bath Duplex Condo with Private Entrance Experience the comfort of townhome-style living in this beautifully renovated duplex condominium featuring a private entrance and an inviting multi-level layout. The main level offers an open living and dining area with beautifully sanded and stained hardwood floors, creating a warm and welcoming atmosphere. The updated

    Lynn Reidl Forza Advantage Realty

    6651 S Drexel Ave Unit 1E, Chicago, IL 60637
  • /21

    $445,000

    Pending
    • 6 Beds
    • 3 Baths

    1218 N Mason Ave, Chicago, IL 60651

    Exceptional investment opportunity in the heart of Austin! This impressive all-BRICK 2-flat with an in-law suite offers strong income potential, currently generating over $55,300+ annually. Ideal for investors or owner-occupants seeking additional rental income. The main level features TWO spacious bedrooms, and one full bath. All units have separate living and dining rooms, beautiful original

    Melissa Dondalski @properties Christie's International Real Estate

    1218 N Mason Ave, Chicago, IL 60651
  • /19

    $487,000

    Pending
    • 5 Beds
    • 2 Baths

    1510 N Harding Ave, Chicago, IL 60651

    Classic Chicago greystone 2-flat offering the perfect blend of character, functionality, and investment potential. First unit features 3 bedrooms and 1 bath, while the second unit offers 2 bedrooms and 1 bath, with separate heat and electric-ideal for both owner-occupants and investors seeking strong rental flexibility. The first-floor unit showcases beautiful hardwood floors, original trim, and

    Jack Michalkiewicz Coldwell Banker Realty

    1510 N Harding Ave, Chicago, IL 60651
  • /21

    $744,900

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    2438 N Western Ave Unit 1, Chicago, IL 60647

    Stunning newer construction (2022) duplex-down offering an exceptional blend of luxury and functionality that is sure to check all of your boxes. This sun-drenched home features a thoughtfully designed open-concept layout including a formal living room, incredible kitchen, spacious family room with a gas log fireplace, and a stylish wet bar complete with a beverage fridge-perfect for

    Sarah Rothman Robins Rothman Real Estate

    2438 N Western Ave Unit 1, Chicago, IL 60647
  • /35

    $699,000

    • 6 Beds
    • 3 Baths

    4239 N Albany Ave, Chicago, IL 60618

    Completely renovated two-unit building in a great Chicago neighborhood! This property has been rebuilt with quality and offers peace of mind with everything new, including the roof, electrical, plumbing, HVAC systems, ductwork, windows, walls, kitchens, and appliances. Both kitchens feature quality cabinets, quartz countertops, and brand-new appliances. The second-floor unit is a duplex with a

    Martha Lozano RE/MAX City

    4239 N Albany Ave, Chicago, IL 60618
  • /13

    $130,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,240 Sq Ft

    8127 S Coles Ave, Chicago, IL 60617

    Incredible Cash flow, currently rented at $2,100/mo HCV Just a few steps from the lake. Minor renovation completed spring 2025. Bathroom basement already in place. Part of a 6 property portfolio(5 sgl fam, 1 duplex)

    Kuchambi Myhand Manage Chicago, Inc.

    8127 S Coles Ave, Chicago, IL 60617
  • /24

    $560,000

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

    6445 N Greenview Ave Unit 1, Chicago, IL 60626

    A rare find in this incredibly spacious Rogers Park duplex - it feels like you are living in a single-family home! The inviting living room features a cozy gas fireplace and it flows seamlessly into a charming sunroom lined with west facing windows-an ideal space for a reading nook, home office or indoor garden. A separate, generously sized dining room easily accommodates a large dining table,

    Christina Carmody Fulton Grace Realty

    6445 N Greenview Ave Unit 1, Chicago, IL 60626
  • /38

    $294,900

    • 5 Beds
    • 2 Baths

    6123 S Troy St, Chicago, IL 60629

    With inventory remaining limited, this spacious multi-unit property in the desirable West Lawn area presents an exceptional opportunity for both investors and owner-occupants. Blending classic Chicago character with generous living space, the building features beautiful natural woodwork, hardwood floors, and a timeless brick exterior. The finished basement offers front and rear egress, providing

    Ryan Smith RE/MAX Premier

    6123 S Troy St, Chicago, IL 60629
  • /19

    $2,350,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    2679 N Orchard St Unit PHN, Chicago, IL 60614

    We are pleased to introduce 2679 N Orchard, East Lincoln Park's newest boutique luxury development. Ideally situated on an oversized lot within the highly sought-after Alcott Elementary and Lincoln Park School Districts these oversized duplex homes are a must see. This exclusive offering features four expansive duplex residences, each thoughtfully designed with four bedrooms and three-and-a-half

    Andrew Thurston Meridian Real Estate Chicago LLC

    2679 N Orchard St Unit PHN, Chicago, IL 60614
  • /32

    $650,000

    • 6 Beds
    • 4 Baths

    2923 N Marmora Ave, Chicago, IL 60634

    Amazing Investment Opportunity for New Home Buyers to Have Their Mortgage Paid by Their Renters and live Rent/ Mortgage Free!! This Zoned 3 Unit In Building Belmont Cragin offers One 2 Bed One Bath Vacant Unit That is Move In Ready Along With a 2 Bed 2 Bath Duplex Coachhouse in the Rear and a 2.5 Bed 1 Bath On the 1st Floor. Each Unit Comes Equipped with High End Stainless Steel Appliances;

    Adam Antonucci Fulton Grace Realty

    2923 N Marmora Ave, Chicago, IL 60634
  • /26

    $1,095,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    1101 W Armitage Ave Unit 205, Chicago, IL 60614

    MULTIPLE OFFERS RECEIVED. All offers due Sunday 7/12 at 5PM. Exquisite 3 bedroom/2.1 bathroom duplex up in prime Lincoln Park Location! Step into this bright corner unit featuring high ceilings and sizable windows flooding the space with natural light. The kitchen was renovated in 2025 with new cabinetry, quartz counters, stainless steel appliances, a large island with white oak & custom bar

    Heather Seidelman @properties Christie's International Real Estate

    1101 W Armitage Ave Unit 205, Chicago, IL 60614
  • /28

    $579,000

    New Construction Pending
    • 3 Beds
    • 3 Baths

    5217 S Bishop St, Chicago, IL 60609

    NEW CITY! Award winning developer Greenline Homes is rebuilding Chicago into a sustainable city with a vision of homes that work harder for their owners. Discover your dream home with this sun-fueled sanctuary, perfect for first-time buyers and those seeking ADA-accessible, affordable, and multigenerational living solutions. Built by award-winning Greenline Homes, this brand new all-electric

    Wayne Beals Exit Strategy Realty / EMA Management

    5217 S Bishop St, Chicago, IL 60609
  • /40

    $450,000

    Pending
    • 4 Beds
    • 3 Baths

    5617 W Lawrence Ave Unit 1, Chicago, IL 60630

    *** Under Contract but showings/offers welcomed. The current buyer is awaiting FHA approval of the building *** Set within an all-brick building in the heart of Jefferson Park, this meticulously maintained extra-wide 4 bedroom, 3 bath duplex-down offers the perfect combination of generous living space, thoughtful upgrades, and an unbeatable location. Completely move-in ready, this home is filled

    Hayley Westhoff Compass

    5617 W Lawrence Ave Unit 1, Chicago, IL 60630
  • /36

    $925,000

    • 6 Beds
    • 5 Baths

    4836 S Dorchester Ave, Chicago, IL 60615

    Looking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Single Family Home in the Hyde Park/Kenwood Community, where historical elegance is seamlessly integrated with contemporary living. This rare gem has been updated on the 1st level only to offer both classic charm and modern amenities perfect for short-term rentals generating great annual income. Bring your own

    Carlas Gilbert Prince Realty Group LLC

    4836 S Dorchester Ave, Chicago, IL 60615
  • /33

    $689,900

    $35K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    2133 N Southport Ave Unit 3, Chicago, IL 60614

    Discover this meticulously updated, oversized two-bedroom, two-bathroom duplex up in Lincoln Park. The main level makes a grand impression with dramatic 20-foot ceilings and a flood of natural light from soaring skylights. At the heart of the home is a modern white kitchen featuring premium stainless steel appliances, stone countertops, a tiled backsplash, and a dedicated bar for seamless

    Brooke Daitchman Baird & Warner

    2133 N Southport Ave Unit 3, Chicago, IL 60614
  • /28

    $629,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,048 Sq Ft

    4035 N Keystone Ave Unit G, Chicago, IL 60641

    Location, location, and location. Just across from Irving Park Blueline and Metra stations. Great investment opportunity. Rare model duplex townhouse in Old Irving Park near expressway I-90/94. This townhouse consists of two legal units with separate utilities(except water service), HVAC system, washer and dryer. You live in one unit and rent out the other unit. It is very easy to rent out the

    Luyang Sue Yang Kale Realty

    4035 N Keystone Ave Unit G, Chicago, IL 60641
  • /14

    $215,000

    • 1 Bed
    • 1 Bath

    633 S Plymouth Ct Unit 301, Chicago, IL 60605

    Welcome to Printers Row! Dramatic 2-story duplex loft with floor-to-ceiling windows, newly refinished hardwood floors, NEW BATHROOM REMODEL, white cabinetry, NEW air conditioner, NEW furnace, and fresh paint. Oversized primary bedroom on upper level with second entrance. This pet-friendly building features a basement laundry room and unit includes a storage locker. Parking garage is located next

    Sera Sousley Keller Williams ONEChicago

    633 S Plymouth Ct Unit 301, Chicago, IL 60605
  • /25

    $249,000

    • 6 Beds
    • 3 Baths

    6045 S Peoria St, Chicago, IL 60621

    Don't Miss Out!!! This is an excellent opportunity to own this Classic 2-flat Greystone on a quiet cul-de-sac block in Englewood. Each unit offers 3 bedrooms, 1 full bath, formal dining rooms, spacious living areas, and kitchens with pantries. The first-floor unit is a duplex-down with 1 bathroom 2 rooms providing additional living space-perfect for owner-occupants or multi-generational living.

    Tanika Fulgham Keller Williams Preferred Rlty

    6045 S Peoria St, Chicago, IL 60621
  • /68

    $456,500

    • 6 Beds
    • 3 Baths

    7644 S Cornell Ave, Chicago, IL 60649

    This is an updated multi-unit property on South Cornell Ave in Chicago. The remodel was done two years ago. The property has new mechanicals (Electric-Plumbing-Furnaces-bathrooms-floors-kitchens) The units are two-bedroom and one bath each with in unit laundry. There are hardwood floors throughout (even the garden unit). Porcelain and ceramic tile cover the bathrooms and kitchen floors. Lots of

    Jeffrey Sklar Beycome Brokerage Realty LLC

    7644 S Cornell Ave, Chicago, IL 60649
  • /19

    $825,000

    Pending
    • 4 Beds
    • 3 Baths

    2130 W Le Moyne St Unit 1, Chicago, IL 60622

    MULTIPLE OFFERS RECEIVED. DEADLINE MONDAY 6/29 AT 12PM. Massive 4 bed, 3 bath duplex situated on a quaint tree-lined street in the heart of Wicker Park! This lovely condo truly lives like a SFH. The 162' deep lot gives the main level a light & airy feel and the open floorplan is complimented by hardwood floors & an abundance of natural light. Pristine kitchen w/ ample cabinet space, beverage

    Charlie Cohen Compass

    2130 W Le Moyne St Unit 1, Chicago, IL 60622
  • /19

    $399,900

    • 2 Beds
    • 2 Baths

    1009 W Wolfram St Unit 1E, Chicago, IL 60657

    Welcome home to this beautifully updated 2-bedroom, 2-bath duplex-down condo in the highly sought-after Lakeview East neighborhood. Featuring hardwood floors throughout and an open-concept layout, this inviting home offers a spacious living area, granite countertops, and a convenient eat-in breakfast bar-perfect for everyday living and entertaining. Enjoy outdoor living with your own private

    Chikuan Wu Baird & Warner

    1009 W Wolfram St Unit 1E, Chicago, IL 60657
  • /27

    $615,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    2623 W Belmont Ave Unit 1, Chicago, IL 60618

    JUST RENOVATED & MOVE-IN READY! This spacious 2,000+ sq. ft. duplex down condo has been freshly painted and features a stunning brand-new, fully renovated kitchen with modern finishes. The first floor includes an open-concept living space, private balcony, and an oversized primary suite with a luxurious ensuite bath featuring double sinks, a separate shower, and soaking tub. The lower level

    Cristina Villegas MPower Residential Brokerage LLC

    2623 W Belmont Ave Unit 1, Chicago, IL 60618
  • /19

    $530,000

    Open Sun 12PM - 2PM $45K PRICE DROP
    • 2 Beds
    • 2.5 Baths

    2013 W Crystal St Unit 1F, Chicago, IL 60622

    Welcome home to this beautifully updated 2 bed / 2.1 bath duplex-down nestled on a quiet, tree-lined street in the heart of WICKER PARK. Thoughtfully designed for both comfort and entertaining, this exceptional home combines modern finishes with an unbeatable location. The main level features hardwood floors throughout, oversized front-facing windows that flood the space with natural light, and a

    Diana Bryl Lori Bonarek Realty

    2013 W Crystal St Unit 1F, Chicago, IL 60622
  • /43

    $1,600,000

    • 10 Beds
    • 4 Baths

    3423 N Seminary Ave, Chicago, IL 60657

    Located in the vibrant heart of Lakeview, 3423 N. Seminary is a well-maintained legal 3unit building featuring two spacious three-bedroom apartments and a four-bedroom duplex up. This property includes a two-car brick garage and offers excellent rental income, with all units leased through May and July 2027, generating a net operating income of $75,806.47 after expenses and property taxes. Pride

    Michael Saladino Keller Williams ONEChicago

    3423 N Seminary Ave, Chicago, IL 60657
  • /40

    $815,000

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,323 Sq Ft

    839 S Miller St Unit 1, Chicago, IL 60607

    Welcome to this complete remodel of a duplex-down home, which includes a surprise floor plan, in which all 3 bedrooms are located on the 1st floor, along with the living area, NOT below it. Enter the home to the newly remodeled kitchen,which includes quartz countertops, added backsplash, wine-fridge, refinished cabinets, updated plumbing, new lighting, new counter depth french-door fridge and new

    Terri Buseman RE/MAX Premier

    839 S Miller St Unit 1, Chicago, IL 60607

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