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    Chicago, IL Triplexes for Sale

    131 results
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    Bronzeville Greystone Triplex Opportunity
    $799,000

    Bronzeville Greystone Triplex Opportunity

    4736 S Prairie Avenue, Chicago, IL 60615

    Classic Chicago greystone triplex near Green Line and lakefront.

    • Fully stabilized 3‑unit building generating $74,460 annual income with GRM 10.86 and Cap 6.6.
    • Classic 1890s Greystone on oversized 25x161 lot with 2‑car garage.
    • Spacious 3‑bedroom, 2‑bath units with separate GFA/CA, in‑unit washer/dryer, hardwood floors, high ceilings, fireplaces, and significant millwork.
    • Prime location: 1/4 block to Green Line, minutes to Lakefront, Kenwood/Hyde Park, and U of C Campus.
    • Large floorplans with multiple bays and expansive footprints.
    Updated: Mar 31
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    North Lawndale Greystone Investment Opportunity
    $499,999
    0.07 Acres

    North Lawndale Greystone Investment Opportunity

    1306 S Central Park Avenue, Chicago, IL 60623

    Three-unit building in historic North Lawndale near downtown Chicago.

    • Income‑generating 3‑unit building with separate utilities
    • Updated kitchens and bathrooms in all units, including stainless steel appliances and granite countertops in select units
    • Spacious units with refinished hardwood floors (1st and 2nd floor), fresh paint, double‑pane windows, and modern light fixtures
    • Ideally located near I‑290, minutes from downtown Chicago, and served by the CTA Pink Line
    • Proximity to the expansive 162‑acre Douglass Park with pools, sports fields, fitness center, and cultural amenities
    Updated: Mar 25
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    Chicago Multi-Family Investment Opportunity
    $899,999

    Chicago Multi-Family Investment Opportunity

    Well-maintained 3-flat with vacant lot for future development.

    3651 S Wood Street, Chicago, IL 60609
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    Renovated Multi-Unit Near University of Chicago
    $699,900

    Renovated Multi-Unit Near University of Chicago

    Fully renovated 3-unit property near University of Chicago.

    5419 S Wabash Avenue, Chicago, IL 60615
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    Chicago Multi-Family Investment Opportunity
    $410,000
    0.11 Acres

    Chicago Multi-Family Investment Opportunity

    All brick 3-unit building with potential for a 4th.

    7634 S Phillips Avenue, Chicago, IL 60649
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    Humboldt Park Solid Brick 3-Flat
    $559,900
    0.09 Acres

    Humboldt Park Solid Brick 3-Flat

    Well-maintained, income-producing 3-unit property in the heart of Humboldt Park.

    717 N Homan Avenue, Chicago, IL 60624
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    Chicago Brown Brick Multifamily Building
    $994,900
    0.08 Acres

    Chicago Brown Brick Multifamily Building

    Completely transformed 2-unit with finished basement in Irving Park.

    3847 N Spaulding Avenue, Chicago, IL 60618
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    New Construction Three-Unit Building
    $750,000

    New Construction Three-Unit Building

    New construction three-unit building with modern finishes and income potential.

    1309 S Avers Avenue, Chicago, IL 60623
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    Renovated Multi-Family Near University
    $715,000

    Renovated Multi-Family Near University

    8-bedroom, 6-bath multi-family property near University of Chicago.

    5419 S Wabash Avenue, Chicago, IL 60615
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    Logan Square Multi-Unit Building
    $799,000
    0.08 Acres

    Logan Square Multi-Unit Building

    Multi-unit building in Logan Square, Chicago, near transportation and amenities.

    2328 N Lawndale Avenue, Chicago, IL 60647
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    Logan Square Renovated Multi-Unit Building
    $749,000

    Logan Square Renovated Multi-Unit Building

    Three-unit building in Logan Square with modern renovations and city views.

    3719 W Palmer Street, Chicago, IL 60647
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    Woodlawn Greystone 3-Flat Investment Property
    $759,000
    0.08 Acres

    Woodlawn Greystone 3-Flat Investment Property

    Rare, fully occupied 3-flat near Obama Presidential Center.

    6402 S Greenwood Avenue, Chicago, IL 60637
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    Classic Chicago Three-Flat in Woodlawn
    $540,000

    Classic Chicago Three-Flat in Woodlawn

    Updated three-unit building near University of Chicago and Jackson Park.

    6522 S Ellis Avenue, Chicago, IL 60637
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    Income-Producing Greystone in Chicago
    $585,000

    Income-Producing Greystone in Chicago

    Fully rented 3-unit building near Garfield Park.

    3410 W Walnut Street, Chicago, IL 60624
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    Updated Income-Producing Building in Chicago
    $439,900

    Updated Income-Producing Building in Chicago

    Turnkey 3-unit building in Chatham/Park Manor neighborhood.

    7227 S Michigan Avenue, Chicago, IL 60619
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    Rare Chicago Brick 3-Flat
    $595,000

    Rare Chicago Brick 3-Flat

    Well-maintained 3-unit building in Belmont Cragin neighborhood.

    2165 N Moody Avenue, Chicago, IL 60639
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    Chicago Triplex Near Transportation
    $500,000

    Chicago Triplex Near Transportation

    Well-located Chicago triplex with easy access to public transportation.

    1940 S TRUMBULL Avenue, Chicago, IL 60623
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    Mixed-Use Building in United Yards
    $525,000
    0.11 Acres

    Mixed-Use Building in United Yards

    Three-unit building with commercial space in a developing area.

    4606 S Ashland Avenue, Chicago, IL 60609
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    Spacious Irving Park Multi-Unit Building
    $749,000

    Spacious Irving Park Multi-Unit Building

    Three-unit brick building near transit and retail in Chicago.

    4014 W Cornelia Avenue, Chicago, IL 60641
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    Bronzeville Greystone Multi-Family Opportunity
    $825,000

    Bronzeville Greystone Multi-Family Opportunity

    Turn-key multi-family building in a rapidly developing Chicago neighborhood.

    4813 S Prairie Avenue, Chicago, IL 60615
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    Remodeled Chicago Multi-Family Property
    $570,000
    0.08 Acres

    Remodeled Chicago Multi-Family Property

    Move-in ready two-unit building with non-conforming third unit.

    5955 S Whipple Street, Chicago, IL 60629
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    Rogers Park Multi-Unit Investment
    $849,000

    Rogers Park Multi-Unit Investment

    Legal 3-unit near Jarvis Red Line with modern amenities.

    7341 N Honore Street, Chicago, IL 60626
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    Englewood All-Brick 3-Flat Investment
    $410,000

    Englewood All-Brick 3-Flat Investment

    Turnkey investment opportunity in Chicago's vibrant Englewood neighborhood.

    5526 S Aberdeen Street, Chicago, IL 60621
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    East Humboldt Park Greystone Triplex
    $699,990

    East Humboldt Park Greystone Triplex

    Classic Greystone triplex in East Humboldt Park, Chicago.

    840 N California Avenue, Chicago, IL 60622
    View details

    Chicago, IL Triplexes Investment Opportunities Market Analysis

    Explore 131 triplexes for sale in Chicago, IL, showcased through 131 active listings on our real estate platform. These investment opportunities span a total of 151,385 square feet of properties for sale, with an estimated market value of $23,059,315.

    Sale prices for three-family homes in Chicago, IL start at $149,900, averaging $640,536, and reaching up to $2,490,000 — 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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    Browse Triplexes for Sale Near Chicago, IL

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