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    Chicago, IL Duplexes for Sale

    378 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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    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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    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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    Bronzeville Two-Flat Investment Opportunity
    $500,000
    0.06 Acres

    Bronzeville Two-Flat Investment Opportunity

    Two-unit building in historic Bronzeville near amenities and transportation.

    4829 S CHAMPLAIN Avenue, Chicago, IL 60615
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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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    Albany Park Two-Unit Building
    $574,900

    Albany Park Two-Unit Building

    Two-unit building in Albany Park with recent updates.

    4612 N Avers Avenue, Chicago, IL 60625
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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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    Bridgeport Two-Unit Building For Sale
    $575,000
    0.07 Acres

    Bridgeport Two-Unit Building For Sale

    Two-unit building in Bridgeport with steady rental income.

    3749 S Union Avenue, Chicago, IL 60609
    View details

    Chicago, IL Duplexes Investment Opportunities Market Analysis

    Explore 378 duplexes for sale in Chicago, IL, showcased through 378 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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