Chicago, IL Duplexes for sale

$399,900

2,560 SF

Updated Two-Flat Near Parks

412 N Pine Ave, Chicago, IL 60644

Well-maintained Chicago two-flat with updated units and recent upgrades.

Two move‑in‑ready, spacious (1,280 sq ft) 2‑bedroom units, ideal for owner‑occupancy or investment.
Extensive recent upgrades including renovated bathrooms, new appliances in Unit 1, LED lighting, fresh paint, and polished wood floors (all 2024‑2025).
Excellent location: blocks from the Green Line and Austin Town Hall Park, directly across from Levin Park, with easy access to transportation and I‑290.
Secure, fully gated property with new security cameras and cedar privacy fence.
Each unit features a living room with a brick fireplace and built‑ins, a separate dining room, and a spacious kitchen with a walk‑in pantry.

Updated: Jan 22

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$249,900

Chicago Multifamily Rehab Opportunity

7521 S Ridgeland Ave, Chicago, IL 60649

Multifamily property requiring renovation in a growing Chicago neighborhood.

Potential for significant cash flow as a 2‑flat property.
After‑repair value (ARV) estimated at almost $400,000.
Located in a growing part of Chicago.
Brick construction.
Some initial rehab work already completed (boiler/radiator removal, partial demo/repair, porch/room removal).

Updated: Jan 22

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$590,000

0.08 Acres

Renovated Multi-Family in West Humboldt

Updated 2-unit building with income potential in Chicago.

4044 W Kamerling Ave, Chicago, IL 60651

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$349,999

Bridgeport Investor Special Opportunity

Two-unit property near Guaranteed Rate Field, ideal for investors.

831 W 34Th Pl, Chicago, IL 60608

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$175,000

Chicago Multifamily Investment Opportunity

Two-unit property requiring TLC, ideal for investors or first-time buyers.

7242 East End Ave, Chicago, IL 60649

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$210,000

Chicago Two-Unit Brick Building

Two-unit brick building with value-add potential in Chicago.

7531 S Wentworth Ave, Chicago, IL 60620

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Chicago Multifamily Property with Expansion Potential

$380,000

0.25 Acres

Chicago Multifamily Property with Expansion Potential

Two-unit property near Bridgeport Village with expansion possibilities.

3329 S Racine Ave, Chicago, IL 60608

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$239,900

0.07 Acres

Chicago Mixed-Use Building For Sale

Two-story mixed-use building with C-1-1 zoning in Chicago.

4217 W Division St, Chicago, IL 60651

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$129,900

Three-Unit Property Investment Opportunity

Three units for the price of two in Chicago!

5435 S Princeton Ave, Chicago, IL 60609

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Lakeview Mixed-Use Investment Opportunity

$800,000

0.07 Acres

Lakeview Mixed-Use Investment Opportunity

Mixed-use property with residential and commercial units in Lakeview.

1150 W Belmont Ave, Chicago, IL 60657

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$665,000

East Village Two-Flat Income Property

Charming two-flat in East Village with income potential.

2052 W Huron St, Chicago, IL 60612

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$349,900

Income-Producing Multi-Unit Property

Two-unit building in Chicago with non-conforming basement.

4016 W Washington Blvd, Chicago, IL 60624

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$389,000

Chicago Two-Unit Building For Sale

Well-maintained two-unit building near transportation, shopping, and amenities.

7208 S Eberhart Ave, Chicago, IL 60619

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$299,000

Chicago Multifamily Property with Basement

Legal 2-unit property with finished basement in 60630 area.

4649 N Kilbourn Ave, Chicago, IL 60630

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Contact for pricing

2,688 SF

Chicago Two-Flat with Garage

Two-unit property in Chicago with a three-car garage.

5100 W Quincy St, Chicago, IL 60644

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$180,000

0.07 Acres

Chicago Two-Unit Building Opportunity

Two-unit building with finished unit and large fenced lot.

7124 S Ellis Ave, Chicago, IL 60619

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$215,000

Englewood Multi-Family Investment Opportunity

Well-maintained 2-flat in Englewood with income potential.

6832 S Bishop St, Chicago, IL 60636

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$425,000

North Lawndale Brick 2-Unit Building

Classic brick 2-unit in North Lawndale near Douglas Park.

1350 S Fairfield Ave, Chicago, IL 60608

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$510,000

Updated Two-Flat in Tri-Taylor

Two-unit property in Chicago's Tri-Taylor area, ideal for investors.

2436 W Fillmore St, Chicago, IL 60612

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Chicago Two-Unit Building with Potential

Pending

$214,900

Chicago Two-Unit Building with Potential

Two-unit building in Chicago, ideal for investment or owner-occupancy.

8022 S Peoria Ave, Chicago, IL 60620

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$530,000

Chicago Brick 2-Flat with Garage

Solid brick 2-flat with finished basement and 2-car garage.

5221 W Montrose Ave, Chicago, IL 60641

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$499,000

0.22 Acres

Spacious West Rogers Park Duplex

Two-flat duplex on oversized corner lot in West Rogers Park.

2175 W Touhy Ave, Chicago, IL 60645

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$499,900

Rebuilt Two-Unit Property with Vacant Lot

Completely rebuilt two-unit property with modern finishes and adjacent vacant lot.

818 S Karlov Ave, Chicago, IL 60624

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$115,000

0.07 Acres

Calumet Park Duplex Opportunity

Duplex in Calumet Park, convertible to single-family home.

12538 S Honore St, Calumet Park, IL 60827

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Chicago, IL Duplexes Investment Opportunities Market Analysis

Explore 423 duplexes for sale in Chicago, IL, showcased through 423 active listings on our real estate platform. These investment opportunities span a total of 168,834,295 square feet of properties for sale, with an estimated market value of $48,430,587.

Prices for duplexes in Chicago, IL start at $54,900, averaging $361,422, and reaching up to $1,100,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

Chicago, IL Duplexes for Sale

Updated Two-Flat Near Parks

Well-maintained Chicago two-flat with updated units and recent upgrades.

Chicago Multifamily Rehab Opportunity

Multifamily property requiring renovation in a growing Chicago neighborhood.

Renovated Multi-Family in West Humboldt

Bridgeport Investor Special Opportunity

Chicago Multifamily Investment Opportunity

Chicago Two-Unit Brick Building

Chicago Multifamily Property with Expansion Potential

Chicago Mixed-Use Building For Sale

Three-Unit Property Investment Opportunity

Lakeview Mixed-Use Investment Opportunity

East Village Two-Flat Income Property

Income-Producing Multi-Unit Property

Chicago Two-Unit Building For Sale

Chicago Multifamily Property with Basement

Chicago Two-Flat with Garage

Chicago Two-Unit Building Opportunity

Englewood Multi-Family Investment Opportunity

North Lawndale Brick 2-Unit Building

Updated Two-Flat in Tri-Taylor

Chicago Two-Unit Building with Potential

Chicago Brick 2-Flat with Garage

Spacious West Rogers Park Duplex

Rebuilt Two-Unit Property with Vacant Lot

Calumet Park Duplex Opportunity

Chicago, IL Duplexes Investment Opportunities Market Analysis

Browse Duplexes for Sale Near Chicago, IL

Popular Searches in Chicago, IL

Popular Categories

Most Searched ZIP Codes in Chicago, IL

Chicago, IL Duplexes for Sale

Updated Two-Flat Near Parks

Well-maintained Chicago two-flat with updated units and recent upgrades.

Chicago Multifamily Rehab Opportunity

Multifamily property requiring renovation in a growing Chicago neighborhood.

Renovated Multi-Family in West Humboldt

Bridgeport Investor Special Opportunity

Chicago Multifamily Investment Opportunity

Chicago Two-Unit Brick Building

Chicago Multifamily Property with Expansion Potential

Chicago Mixed-Use Building For Sale

Three-Unit Property Investment Opportunity

Lakeview Mixed-Use Investment Opportunity

East Village Two-Flat Income Property

Income-Producing Multi-Unit Property

Chicago Two-Unit Building For Sale

Chicago Multifamily Property with Basement

Chicago Two-Flat with Garage

Chicago Two-Unit Building Opportunity

Englewood Multi-Family Investment Opportunity

North Lawndale Brick 2-Unit Building

Updated Two-Flat in Tri-Taylor

Chicago Two-Unit Building with Potential

Chicago Brick 2-Flat with Garage

Spacious West Rogers Park Duplex

Rebuilt Two-Unit Property with Vacant Lot

Calumet Park Duplex Opportunity

Chicago, IL Duplexes Investment Opportunities Market Analysis

Browse Duplexes for Sale Near Chicago, IL

Popular Searches in Chicago, IL

Popular Categories

Most Searched ZIP Codes in Chicago, IL

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