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    Chicago, IL Duplexes for Sale

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    Springfield, IL Hoffman Estates, IL Belleville, IL
    364 results
    Two-Flat Investment Opportunity in Chicago
    $689,999

    Two-Flat Investment Opportunity in Chicago

    4512 N Kasson Avenue, Chicago, IL 60630

    Updated two-flat near Wrigley Field with investment potential.

    • Four separate updated apartments offer significant investment or multi‑generational living potential.
    • Updated kitchens in all units (2023), with quartz countertops and stainless steel appliances in first and second floor units.
    • Newer major systems: Roof (2020), windows (2022), boiler and central AC, and updated electrical.
    • Finished basement with two additional 1‑bedroom apartments, each with full kitchens and living spaces.
    • Spacious 2‑car garage with potential for additional parking via driveway extension.
    Updated: Apr 30
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    Renovated Jefferson Park Two-Flat
    $499,000

    Renovated Jefferson Park Two-Flat

    5042 W Winnemac Avenue, Chicago, IL 60630

    Meticulously renovated 1929 two-flat in Jefferson Park neighborhood.

    • Prime Jefferson Park location: Walkable to the Jefferson Park Transit Center and close to I‑90/I‑94.
    • Meticulously renovated 1929 all‑brick 2‑flat: Combines historic charm with modern luxury.
    • First‑floor duplex‑down unit: Features 2 bedrooms, 2 baths, a gourmet kitchen with granite countertops and stainless steel appliances, and a private yard.
    • Attic penthouse unit: Includes 1 bedroom, 1 bath, an eat‑in kitchen with butcher block countertops and a stainless steel stove, and in‑unit washer/dryer combo.
    • Oversized 2‑car garage: Tall ceilings can accommodate a work van or truck.
    Updated: Apr 29
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    Renovated Two-Unit Building in Chicago
    $565,000

    Renovated Two-Unit Building in Chicago

    Updated 2-unit building in Jefferson Park/Mayfair neighborhood, perfect for investors.

    5028 W Lawrence Avenue, Chicago, IL 60630
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    Bridgeport Multifamily Property in Chicago
    $545,000

    Bridgeport Multifamily Property in Chicago

    Multifamily property in prime Bridgeport location with many updates.

    3841 S Lowe Avenue, Chicago, IL 60609
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    Contemporary Chicago Two-Flat For Sale
    $799,000

    Contemporary Chicago Two-Flat For Sale

    Move-in ready two-flat in West Loop, perfect for investors.

    2832 W WILCOX Street, Chicago, IL 60612
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    East Garfield Park Multifamily Opportunity
    $620,000
    0.07 Acres

    East Garfield Park Multifamily Opportunity

    Two-unit building with buildable lot near downtown Chicago.

    3248 W Maypole Avenue, Chicago, IL 60624
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    Well-Maintained Chicago Multi-Family Property
    $398,500
    0.12 Acres

    Well-Maintained Chicago Multi-Family Property

    Two-unit building near transportation, schools, and parks.

    224 N Lockwood Avenue, Chicago, IL 60644
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    Mixed-Use Building with Residential Space
    $549,900
    0.07 Acres

    Mixed-Use Building with Residential Space

    Mixed-use brick building with retail/office and residential rental unit.

    5110 W Fullerton Avenue, Chicago, IL 60639
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    Rehabbed 2-Flat in Austin
    $500,000

    Rehabbed 2-Flat in Austin

    Gut rehabbed 2-flat with modern amenities and excellent accessibility.

    853 N Laramie Avenue, Chicago, IL 60651
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    Mixed-Use Building in High-Traffic Area
    $499,900
    0.07 Acres

    Mixed-Use Building in High-Traffic Area

    Mixed-use property with commercial space and residential units in Chicago.

    5039 W Diversey Avenue, Chicago, IL 60639
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    Chicago Two-Flat Investment Opportunity
    $325,000

    Chicago Two-Flat Investment Opportunity

    Well-maintained two-flat near schools, expressway, and public transportation.

    2620 S Sawyer Avenue, Chicago, IL 60623
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    Modern-Industrial Chicago Two-Unit Property
    $650,000

    Modern-Industrial Chicago Two-Unit Property

    Unique two-unit property with modern-industrial design and income potential.

    1011 N MOZART Street, Chicago, IL 60622
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    Reimagined Oversized Chicago Multi-Unit Property
    $425,000
    0.08 Acres

    Reimagined Oversized Chicago Multi-Unit Property

    Fully renovated 2-unit property with income potential near I-90/94.

    1847 W Garfield Boulevard, Chicago, IL 60636
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    Bronzeville Two-Flat Investment Opportunity
    $500,000
    0.06 Acres

    Bronzeville Two-Flat Investment Opportunity

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

    4829 S CHAMPLAIN Avenue, Chicago, IL 60615
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    Chicago Two-Flat in Mount Greenwood
    $425,000
    0.08 Acres

    Chicago Two-Flat in Mount Greenwood

    Two-unit building in Mount Greenwood, ideal for owners or investors.

    11143 S Christiana Avenue, Chicago, IL 60655
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    Renovated Pullman Historical Park Rowhouse
    $304,900

    Renovated Pullman Historical Park Rowhouse

    Rare, renovated 2-flat in Pullman National Historical Park.

    11412 S Saint Lawrence Avenue, Chicago, IL 60628
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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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    Two-Unit Property with Pool
    $589,000

    Two-Unit Property with Pool

    Well-maintained two-unit property with garage, basement, and pool.

    4131 N Richmond Street, Chicago, IL 60618
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    Well-Maintained Brick 2-Flat in Chicago
    $345,000

    Well-Maintained Brick 2-Flat in Chicago

    Spacious 2-flat in Auburn Gresham, perfect for owner-occupant or investor.

    8004 S May Street, Chicago, IL 60620
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    Two-Unit Brick Building in Chicago
    $324,500
    0.09 Acres

    Two-Unit Brick Building in Chicago

    Well-maintained two-unit building with income potential in Chicago.

    5632 S Wabash Avenue, Chicago, IL 60637
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    Logan Square Two-Unit Property
    $975,000

    Logan Square Two-Unit Property

    Rehabbed two-unit property in Logan Square near The 606 trail.

    3806 W Armitage Avenue, Chicago, IL 60647
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    All-Brick Two-Flat Near Smith Park
    $749,900
    0.07 Acres

    All-Brick Two-Flat Near Smith Park

    Well-maintained two-flat with modern amenities and convenient location.

    2642 W Superior Street, Chicago, IL 60612
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    Versatile Two-Flat in Chicago
    $400,000
    0.12 Acres

    Versatile Two-Flat in Chicago

    Two-unit property ideal for owner-occupants or investors.

    4709 W Washington Boulevard, Chicago, IL 60644
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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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    Chicago, IL Duplexes Investment Opportunities Market Analysis

    Explore 367 duplexes for sale in Chicago, IL, showcased through 364 active listings on our real estate platform. These investment opportunities span a total of 47,462 square feet of properties for sale, with an estimated market value of $10,699,000.

    Sale prices for duplexes in Chicago, IL start at $325,000, averaging $1,188,777, and reaching up to $3,500,000 — 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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