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    Chicago, IL Duplexes for Sale

    431 results
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    Bridgeport Two-Unit Property with Expansion Potential
    $360,000
    0.25 Acres

    Bridgeport Two-Unit Property with Expansion Potential

    3329 S Racine Ave, Chicago, IL 60608

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

    • Prime location across from Bridgeport Village and the Riverwalk
    • Significant expansion potential with favorable setback for rear addition
    • Oversized brick garage with overhead doors to both alley and yard
    • Zoned for 2 units, offering investment or owner‑occupancy options
    • Minutes to the expressway and located in the path of upcoming development along Pershing
    Updated: Mar 4
    View details
    East Village Two-Flat Income Property
    $665,000

    East Village Two-Flat Income Property

    2052 W Huron St, Chicago, IL 60612

    Charming two-flat in East Village with income potential.

    • Prime East Village location, steps from boutiques, cafes, dining, and conveniences.
    • Income‑generating two‑flat property with both units currently leased through 2026.
    • Secured parking with carport.
    • Expansive rear deck, ideal for entertaining.
    • Unit 1 features in‑unit washer and dryer and a new stove.
    Updated: Mar 4
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    Brighton Park 2-Flat with Character
    $465,000

    Brighton Park 2-Flat with Character

    Spacious 9-bedroom, 3-bathroom Chicago 2-flat with original details.

    4217 S Mozart Ave, Chicago, IL 60632
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    Chicago Brick 2-Flat with Garage
    $307,000
    0.07 Acres

    Chicago Brick 2-Flat with Garage

    Solid brick 2-flat with garage, investor or owner-occupant opportunity.

    1512 S Sawyer Ave, Chicago, IL 60623
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    Chicago Brick Two-Flat on Corner
    $469,900
    0.09 Acres

    Chicago Brick Two-Flat on Corner

    Two-unit brick building on a corner lot in Chicago.

    3653 W 71St St, Chicago, IL 60629
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    Two-Flat Bungalow on Oversized Lot
    $699,000

    Two-Flat Bungalow on Oversized Lot

    Unique multi-family property with income potential in Chicago, IL.

    6212 W Norwood St, Chicago, IL 60646
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    Two-Unit Brick Building in Chicago
    $339,000
    0.09 Acres

    Two-Unit Brick Building in Chicago

    Well-maintained two-unit building with short-term rental potential.

    5632 S Wabash Ave, Chicago, IL 60637
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    Renovated Multi-Family Building
    $925,000
    0.08 Acres

    Renovated Multi-Family Building

    Impeccably maintained building near Lincoln Square, Ravenswood + Andersonville.

    5426 N Western Ave, Chicago, IL 60625
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    Bridgeport Two-Unit Building For Sale
    $575,000
    0.07 Acres

    Bridgeport Two-Unit Building For Sale

    Well-maintained two-unit building in vibrant Bridgeport neighborhood.

    3749 S Union Ave, Chicago, IL 60609
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    Chicago Multifamily Property For Sale
    $425,000
    0.11 Acres

    Chicago Multifamily Property For Sale

    Gut rehabbed duplex in 2013 with updated amenities.

    7249 S Calumet Ave, Chicago, IL 60619
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    Lincoln Square Mixed-Use Investment
    $550,000
    0.06 Acres

    Lincoln Square Mixed-Use Investment

    Well-maintained mixed-use building in a desirable Chicago neighborhood.

    5015 N Western Ave, Chicago, IL 60625
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    Two-Unit Brick Building in Chicago
    $459,900
    2,300 SF

    Two-Unit Brick Building in Chicago

    Spacious, income-producing two-unit building in South Lawndale, Chicago.

    2841 W 25Th St, Chicago, IL 60623
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    Edgebrook/Sauganash Two-Flat Income Property
    $668,000
    0.09 Acres

    Edgebrook/Sauganash Two-Flat Income Property

    Solid brick two-flat in desirable Edgebrook/Sauganash area.

    6138 N Meade Ave, Chicago, IL 60646
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    Chicago Bungalow with Income Potential
    $549,900

    Chicago Bungalow with Income Potential

    Versatile Chicago bungalow in Portage Park with income potential.

    4042 N Monitor Ave, Chicago, IL 60634
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    Renovated Two-Unit Building in Chicago
    $570,000

    Renovated Two-Unit Building in Chicago

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

    5028 W Lawrence Ave, Chicago, IL 60630
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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 St, Chicago, IL 60624
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    Renovated 2-Unit Brick Residence
    $539,000

    Renovated 2-Unit Brick Residence

    7-bedroom, 4-bathroom renovated 2-unit building in Chicago.

    4447 W Van Buren St, Chicago, IL 60624
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    Bridgeport Two-Flat with Updates
    $560,000
    0.08 Acres

    Bridgeport Two-Flat with Updates

    Meticulously maintained two-flat near Guaranteed Rate Field.

    928 W 35Th St, Chicago, IL 60609
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    Rehabbed Two-Unit Building in Chicago
    $425,000
    0.08 Acres

    Rehabbed Two-Unit Building in Chicago

    Completely renovated two-unit building in North Lawndale, Chicago.

    4107 W Cermak Rd, Chicago, IL 60623
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    Pilsen Two-Unit Cottage with Charm
    $545,000

    Pilsen Two-Unit Cottage with Charm

    Two-unit property in Pilsen with income potential and classic charm.

    2314 S Hoyne Ave, Chicago, IL 60608
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    Reimagined West Town Two-Flat
    $985,000

    Reimagined West Town Two-Flat

    Stunning, renovated 2-flat near Humboldt Park with modern luxury.

    877 N Mozart St, Chicago, IL 60622
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    Chicago Brick Two-Flat For Sale
    $310,000

    Chicago Brick Two-Flat For Sale

    Two-unit building with separate utilities in established Chicago neighborhood.

    4219 W Cullerton St, Chicago, IL 60623
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    Two-Unit Brick Building in Chicago
    $465,000

    Two-Unit Brick Building in Chicago

    Two-unit brick building with parking in Chicago's Medical District.

    718 S Claremont Ave, Chicago, IL 60612
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    Avondale Two-Unit Building Opportunity
    Pending
    $399,900

    Avondale Two-Unit Building Opportunity

    Two-unit building in Avondale with investment potential.

    3348 N Albany Ave, Chicago, IL 60618
    View details

    Chicago, IL Duplexes Investment Opportunities Market Analysis

    Explore 434 duplexes for sale in Chicago, IL, showcased through 431 active listings on our real estate platform. These investment opportunities span a total of 164,431,024 square feet of properties for sale, with an estimated market value of $43,930,830.

    Sale prices for duplexes in Chicago, IL start at $40,000, averaging $410,568, and reaching up to $2,000,000 — 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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