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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
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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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