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    Chicago, IL Duplexes for Sale

    377 results
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    Contemporary Multifamily Property in Chicago
    $850,000

    Contemporary Multifamily Property in Chicago

    2832 W WILCOX Street, Chicago, IL 60612

    Move-in ready duplex in West Loop, ideal for investors.

    • Flexible 2‑flat design allows for varied living arrangements or rental income.
    • Move‑in ready, new construction with contemporary design and high‑end finishes.
    • Spacious duplex‑up owner's unit featuring 3 beds, 2.5 baths, 2100 sq ft, open concept layout, fireplace, professional grade kitchen, and luxurious primary suite.
    • English garden level rental unit (2 bed, 2 bath, 1050 sq ft) with private side entry and full kitchen.
    • Dual primary suites, HVAC systems, laundry centers, and kitchens offer maximum flexibility.
    Updated: Mar 24
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    Bridgeport Multi-Family Opportunity
    $545,000

    Bridgeport Multi-Family Opportunity

    3841 S Lowe Avenue, Chicago, IL 60609

    Two buildings with updates in prime Chicago location.

    • Two separate buildings offer flexible living arrangements: a 2‑bedroom, 2‑bathroom front house and a 3‑bedroom, 2 full and 2 half‑bathroom rear house.
    • Extensive recent updates, including tuckpointing, roof work (2020), concrete work (2019), fencing (2022), and new exterior steel stairs (2025) ensure structural integrity and modern appeal.
    • Both houses feature finished basements, providing additional living space with family rooms and laundry areas.
    • The rear house boasts a maple wood kitchen with granite countertops and an ample master bedroom with a private bathroom and plenty of closet space.
    • Updated bathrooms in both houses, with features like white subway tile in the front house and remodels completed in recent years.
    Updated: Mar 18
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    Gladstone Park Two-Unit Building
    $830,000

    Gladstone Park Two-Unit Building

    Well-maintained two-unit building in Chicago's desirable Gladstone Park neighborhood.

    5728 N McVicker Avenue, Chicago, IL 60646
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    North Center Two-Unit Property
    $775,000

    North Center Two-Unit Property

    Updated two-unit property in desirable North Center neighborhood.

    4159 N Maplewood Avenue, Chicago, IL 60618
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    Turnkey Chicago Two-Unit Building
    $675,000
    0.05 Acres

    Turnkey Chicago Two-Unit Building

    Well-maintained, fully rented 2-unit building in Chicago.

    1927 W Ohio Street, Chicago, IL 60622
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    Hermosa Two-Flat with Garage
    $549,900

    Hermosa Two-Flat with Garage

    Zoned two-flat in Chicago's Hermosa neighborhood with garage.

    2045 N Tripp Avenue, Chicago, IL 60639
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    Renovated Two-Unit Building in Chicago
    $570,000

    Renovated Two-Unit Building in Chicago

    Updated 2-unit property in Jefferson Park/Mayfair neighborhood.

    5028 W Lawrence Avenue, Chicago, IL 60630
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    Chicago Two-Unit Flat Opportunity
    $344,900

    Chicago Two-Unit Flat Opportunity

    Solid brick 2-unit flat in Grand Crossing neighborhood.

    7140 S Eberhart Avenue, Chicago, IL 60619
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    Remodeled Chicago Multi-Family Property
    $679,500

    Remodeled Chicago Multi-Family Property

    Remodeled brick 2-flat in Belmont Cragin neighborhood.

    5029 W ALTGELD Street, Chicago, IL 60639
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    South Austin Well-Maintained Duplex
    $499,900

    South Austin Well-Maintained Duplex

    Move-in ready duplex near Columbus Park and public transportation.

    128 S Parkside Avenue, Chicago, IL 60644
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    Jefferson Park Two-Flat Investment Opportunity
    $599,990

    Jefferson Park Two-Flat Investment Opportunity

    Well-maintained two-flat near O'Hare, updated unit, rental income.

    5552 N Major Avenue, Chicago, IL 60630
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    Chicago Brick Two-Unit Building
    $829,000

    Chicago Brick Two-Unit Building

    Immaculate two-unit building with spacious apartments and ample storage.

    5805 N Merrimac Avenue, Chicago, IL 60646
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    Chicago Two-Flat Investment Opportunity
    $320,000

    Chicago Two-Flat Investment Opportunity

    All-brick two-flat near transit, ideal for investors or homeowners.

    8548 S Manistee Avenue, Chicago, IL 60617
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    Chicago Brick 2-Flat Investment
    $365,000

    Chicago Brick 2-Flat Investment

    Turnkey 2-unit property with updated systems and income potential.

    3833 W Arthington Street, Chicago, IL 60624
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    Mixed-Use Property in Chicago
    $799,000
    0.27 Acres

    Mixed-Use Property in Chicago

    Mixed-use property with warehouse, office, and residential spaces.

    3612 W Roosevelt Road, Chicago, IL 60624
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    Rehabbed Humboldt Park Two-Flat
    $485,000

    Rehabbed Humboldt Park Two-Flat

    Updated 2-flat near Humboldt Park with income potential.

    1033 N Lawndale Avenue, Chicago, IL 60651
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    East Garfield Park Two-Unit Building
    $649,000

    East Garfield Park Two-Unit Building

    Two-unit building near United Center redevelopment project.

    2852 W Polk Street, Chicago, IL 60612
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    Updated West Ridge Income Property
    $729,000

    Updated West Ridge Income Property

    Fully updated 2-flat in West Ridge near Warren Park.

    6609 N Artesian Avenue, Chicago, IL 60645
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    Bridgeport Two-Unit Property with Expansion Potential
    $360,000
    0.25 Acres

    Bridgeport Two-Unit Property with Expansion Potential

    Two-unit property near Bridgeport Village with expansion and development potential.

    3329 S Racine Avenue, Chicago, IL 60608
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    Updated Two-Flat in Portage Park
    $619,900

    Updated Two-Flat in Portage Park

    Move-in ready two-flat near Six Corners shopping and dining.

    4314 N Menard Avenue, Chicago, IL 60634
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    Chicago Two-Unit Flat Opportunity
    $344,900

    Chicago Two-Unit Flat Opportunity

    Solid brick 2-unit flat in Grand Crossing, Chicago.

    7140 S Eberhart Avenue, Chicago, IL 60619
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    Renovated Chicago Multi-Unit Property
    $824,999
    0.07 Acres

    Renovated Chicago Multi-Unit Property

    Legal 2-unit property with modern updates and flexible living spaces.

    7508 W Devon Avenue, Chicago, IL 60631
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    West Ridge Two-Unit Building
    $799,000

    West Ridge Two-Unit Building

    Well-maintained two-unit building in Chicago's West Ridge neighborhood.

    6540 N Sacramento Avenue, Chicago, IL 60659
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    Updated Duplex Near 606 Trail
    $790,000

    Updated Duplex Near 606 Trail

    Updated two-unit building in Logan Square near the 606 Trail.

    1814 N Sawyer Avenue, Chicago, IL 60647
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    Chicago, IL Duplexes Investment Opportunities Market Analysis

    Explore 377 duplexes for sale in Chicago, IL, showcased through 377 active listings on our real estate platform. These investment opportunities span a total of 164,195,538 square feet of properties for sale, with an estimated market value of $44,155,038.

    Sale prices for duplexes in Chicago, IL start at $40,000, averaging $428,689, and reaching up to $1,550,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Most Searched ZIP Codes in Chicago, IL

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