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    Chicago, IL Triplexes for Sale

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    Springfield, IL Hoffman Estates, IL Belleville, IL
    150 results
    Roscoe Village Three-Flat Investment Opportunity
    $1,000,000
    0.10 Acres

    Roscoe Village Three-Flat Investment Opportunity

    2317 W Barry Avenue, Chicago, IL 60618

    Well-maintained three-flat in Roscoe Village with upside potential.

    • Prime Roscoe Village/West Lake View location on an oversized lot with convenient access to amenities and public transit.
    • Significant recent improvements, including a gut renovation and dormer expansion of the top floor, creating a spacious 4‑bedroom + den duplex.
    • High‑performing three‑flat with immediate upside potential through increased rents, particularly in the garden unit.
    • Detached three‑car garage provides additional income potential.
    • Second‑floor unit recently renovated with 3 bedrooms and 1 bathroom, currently rented at $2,750/month.
    Updated: Apr 22
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    Old Irving Park Multi-Family Property
    $599,999
    0.07 Acres

    Old Irving Park Multi-Family Property

    3311 N Kostner Avenue, Chicago, IL 60641

    Updated three-unit property near Kilbourne Park, Chicago.

    • Three separate units (lives like a 3‑unit, legal 2‑flat) with separate utilities, offering income potential.
    • Updated with hardwood floors, laminate floors, stainless steel appliances, and updated kitchens.
    • Opportunity to live in the vacant first‑floor unit while collecting rent from the other two units.
    • Convenient location near Kilbourne Park, shopping, restaurants, public transportation, and highway access.
    • Privacy fence surrounding the entire yard.
    Updated: Apr 15
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    Bronzeville Greystone Triplex Opportunity
    $799,000

    Bronzeville Greystone Triplex Opportunity

    Classic Chicago greystone triplex near Green Line and lakefront.

    4736 S Prairie Avenue, Chicago, IL 60615
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    North Lawndale Greystone Investment Opportunity
    $499,999
    0.07 Acres

    North Lawndale Greystone Investment Opportunity

    Three-unit building in historic North Lawndale, Chicago.

    1306 S Central Park Avenue, Chicago, IL 60623
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    Chicago Triplex: Investment Opportunity
    $589,900

    Chicago Triplex: Investment Opportunity

    Legal 3-unit building with strong income potential in Chicago.

    3704 W Lexington Street, Chicago, IL 60624
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    Updated Chicago Multi-Family Property
    $780,000

    Updated Chicago Multi-Family Property

    Well-maintained, updated 9-bed, 3-bath brick 2-flat with upside potential.

    5723 N TALMAN Avenue, Chicago, IL 60659
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    Spacious Chicago Multi-Family Investment
    $600,000

    Spacious Chicago Multi-Family Investment

    Turnkey, low-maintenance investment property with endless potential in Chicago.

    4520 W Jackson Boulevard, Chicago, IL 60624
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    Renovated Chicago Multi-Unit Building
    $875,000
    0.07 Acres

    Renovated Chicago Multi-Unit Building

    Three-unit building with 10 bedrooms and modern renovations.

    3646 W Wabansia Avenue, Chicago, IL 60647
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    Remodeled Chicago Triplex with Expansion Potential
    $549,000

    Remodeled Chicago Triplex with Expansion Potential

    Remodeled triplex with expansion potential near Ogden Ave and I-290.

    1431 S Tripp Avenue, Chicago, IL 60623
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    Chicago Brick 3-Flat Investment
    $720,000

    Chicago Brick 3-Flat Investment

    Well-maintained Chicago 3-flat with updated units and separate utilities.

    3651 S Wood Street, Chicago, IL 60609
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    Multi-Unit Building Investment Opportunity
    $375,000
    0.08 Acres

    Multi-Unit Building Investment Opportunity

    Multi-unit building with spacious units, ideal for rental income.

    7927 S LANGLEY Avenue, Chicago, IL 60619
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    Updated Logan Square 3-Flat
    $970,000

    Updated Logan Square 3-Flat

    Updated 3-flat in Logan Square, ideal for investors.

    3041 W Fullerton Avenue, Chicago, IL 60647
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    Rogers Park Multi-Unit Investment
    $824,900

    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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    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 Two-Flat with Garden Apartment
    $499,900
    0.08 Acres

    Chicago Two-Flat with Garden Apartment

    Two-flat with garden apartment near transportation, schools, and shopping.

    6113 S Sacramento Avenue, Chicago, IL 60629
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    Chicago All-Brick 3-Flat Income Property
    $825,000

    Chicago All-Brick 3-Flat Income Property

    Rare, fully-rented, all-brick 3-flat in Chicago with updated mechanicals.

    2442 W Fillmore Street, Chicago, IL 60612
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    Bridgeport Multifamily Value-Add Opportunity
    $499,900
    0.06 Acres

    Bridgeport Multifamily Value-Add Opportunity

    Three-unit building with non-conforming fourth unit in Chicago.

    2921 S Bonfield Street, Chicago, IL 60608
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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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    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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    Updated Multi-Unit Building in Chicago
    $400,000

    Updated Multi-Unit Building in Chicago

    Turnkey investment opportunity: fully updated 3-unit building in Chatham/Park Manor.

    7227 S Michigan Avenue, Chicago, IL 60619
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    Logan Square Renovated Multi-Unit Building
    $699,000

    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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    Well-Kept Chicago 2-Flat
    $549,022

    Well-Kept Chicago 2-Flat

    Tenant-occupied 2-flat with finished basement, immediate income potential.

    4735 N Keating Avenue, Chicago, IL 60630
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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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    Three-Unit Property on Oversized Lot
    $975,000

    Three-Unit Property on Oversized Lot

    Meticulously maintained three-unit property with modern finishes and large lot.

    1914 W Farwell Avenue, Chicago, IL 60626
    View details

    Chicago, IL Triplexes Investment Opportunities Market Analysis

    Explore 152 triplexes for sale in Chicago, IL, showcased through 150 active listings on our real estate platform. These investment opportunities span a total of 42,590 square feet of properties for sale, with an estimated market value of $9,939,800.

    Sale prices for three-family homes in Chicago, IL start at $435,000, averaging $828,316, and reaching up to $1,275,000 — 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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