South Side, IL homes for sale & real estate

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ABOUT THIS HOME
South Side, IL Homes for Sale
Rehab Opportunity! This solid brick 2-flat offers incredible potential with much of the renovation already underway. Framing, new electrical service, plumbing rough-ins, and brand new back porches are already in place, saving time and upfront costs for the next owner. Each unit offers a spacious layout with classic Chicago architecture and great natural light. Full basement provides additional options for in-law/ family unit. Perfect for investors or owner-occupants looking to build equity. Conveniently located near public transportation, expressways, and local amenities. Sold as-is - finish the rehab and bring this property to full market value.

$199,900

6 beds4.5 baths— sq ft

4752 S Princeton Ave, Chicago, IL 60609

Solid brick • New back porches • Spacious layout

$310,000

5 beds2 baths— sq ft

6959 S Calumet Ave, Chicago, IL 60637

6,250 sq ft lot • Built 1893 • Listed 27 days

$189,999

3 beds2 baths1,149 sq ft

7846 S Maryland Ave, Chicago, IL 60619

Parking • Built 1920 • Listed 19 days

ABOUT THIS HOME
South Side, IL Homes for Sale
This corner condo with exposed, original timber beams, high ceilings and hardwood floors is a rarely available opportunity to own a blend of historic charm with modern comfort and style in the heart of Armor Square! Private and cozy, this spacious, open floor plan connects the living room with private balcony access, an attractive dining area and an inviting kitchen. Beyond the 1 bedroom and 1 bath, a versatile den offers endless possibilities, ideal for a home office, hobby room, possible bedroom, storage or family room. Spend your evenings on the private balcony or enjoying the bustling atmosphere of the nearby dining and shopping in Chinatown, Pilsen, University Village, and the South L

$249,900

1 bed1 bath— sq ft

2310 S Canal St #212, Chicago, IL 60616

Open floor plan • Versatile den • High ceilings

ABOUT THIS HOME
South Side, IL Homes for Sale
Bigger Than Most Townhomes - Welcome Home to Armour Square Living!!! Looking for more space without the maintenance of a single-family home? This 2,200 sq. ft. , 4-bedroom, 2.5-bath duplex-down in coveted Armour Square checks every box-and then some. From the moment you walk in, you'll feel the openness. Soaring 10+ ft ceilings, rich hardwood floors, and natural light throughout the main level set the tone for comfort and connection. The heart of the home is the spacious kitchen-complete with 42" cabinets, granite countertops, stainless steel appliances, a brand-new backsplash, and a large island perfect for gatherings or quiet mornings. The primary suite is a true retreat with a walk

$524,500

4 beds2.5 baths2,600 sq ft

3106 S Wells St #1, Chicago, IL 60616

Spa-like bath • Walk-in closet • Spacious kitchen

Property at 654 E 65th St, Chicago, IL 60637, 6 beds, 3 baths

$78,000

6 beds3 baths— sq ft

654 E 65th St, Chicago, IL 60637

Property at 307 E 50th St Unit 307A, Chicago, IL 60615, 2 beds, 1 bath

$167,500

2 beds1 bath850 sq ft

307 E 50th St Unit 307A, Chicago, IL 60615

Property at 4827 S Saint Lawrence Ave, Chicago, IL 60615, 9 beds, 6.5 baths

$1,395,000

9 beds6.5 baths— sq ft

4827 S Saint Lawrence Ave, Chicago, IL 60615

Property at 5114 S Kenwood Ave Unit PHA, Chicago, IL 60615, 3 beds, 2.5 baths

$1,000,000

3 beds2.5 baths1,898 sq ft

5114 S Kenwood Ave Unit PHA, Chicago, IL 60615

Property at 512 E Oakwood Blvd #2, Chicago, IL 60653, 3 beds, 3 baths

$359,999

3 beds3 baths2,200 sq ft

512 E Oakwood Blvd #2, Chicago, IL 60653

Property at 1502 E Marquette Rd, Chicago, IL 60637, 5 beds, 3.5 baths

$599,000

5 beds3.5 baths3,700 sq ft

1502 E Marquette Rd, Chicago, IL 60637

Property at 7825 S Ingleside Ave, Chicago, IL 60619, 3 beds, 3 baths

$259,000

3 beds3 baths1,800 sq ft

7825 S Ingleside Ave, Chicago, IL 60619

Property at 6700 S South Shore Dr Unit 24E, Chicago, IL 60649, 1 bed, 1 bath

$110,000

1 bed1 bath— sq ft

6700 S South Shore Dr Unit 24E, Chicago, IL 60649

Property at 7725 S Champlain Ave, Chicago, IL 60619, 4 beds, 2 baths

$169,900

4 beds2 baths1,200 sq ft

7725 S Champlain Ave, Chicago, IL 60619

Property at 706 E 72nd St, Chicago, IL 60619, 5 beds, 1.5 baths

$109,900

5 beds1.5 baths1,718 sq ft

706 E 72nd St, Chicago, IL 60619

Property at 1755 E 55th St #1201, Chicago, IL 60615, 3 beds, 3 baths

$289,500

3 beds3 baths1,800 sq ft

1755 E 55th St #1201, Chicago, IL 60615

Property at 5050 S East End Ave Unit 7A, Chicago, IL 60615, 2 beds, 1 bath

$165,000

2 beds1 bath1,190 sq ft

5050 S East End Ave Unit 7A, Chicago, IL 60615

Property at 5942 S Calumet Ave, Chicago, IL 60637, 12 beds, 4 baths

$585,000

12 beds4 baths— sq ft

5942 S Calumet Ave, Chicago, IL 60637

Property at 5032 S Michigan Ave, Chicago, IL 60615, 5 beds, 3.5 baths

$659,000

5 beds3.5 baths3,400 sq ft

5032 S Michigan Ave, Chicago, IL 60615

Property at 1404 E 56th St #1, Chicago, IL 60637, 2 beds, 1 bath

$309,000

2 beds1 bath950 sq ft

1404 E 56th St #1, Chicago, IL 60637

Property at 5000 S East End Ave Unit 2D, Chicago, IL 60615, 2 beds, 2 baths

$235,000

2 beds2 baths1,600 sq ft

5000 S East End Ave Unit 2D, Chicago, IL 60615

Property at 7345 S Bennett Ave, Chicago, IL 60649, 6 beds, 2 baths

$372,900

6 beds2 baths3,463 sq ft

7345 S Bennett Ave, Chicago, IL 60649

Property at 5637 S Prairie Ave, Chicago, IL 60637, 9 beds, 6 baths

$1,049,000

9 beds6 baths— sq ft

5637 S Prairie Ave, Chicago, IL 60637

Property at 5133 S Greenwood Ave #2, Chicago, IL 60615, 3 beds, 2 baths

$329,000

3 beds2 baths1,700 sq ft

5133 S Greenwood Ave #2, Chicago, IL 60615

Property at 2734 S Wentworth Ave Unit PS-38, Chicago, IL 60616

$19,500

— beds— baths— sq ft

2734 S Wentworth Ave Unit PS-38, Chicago, IL 60616

Property at 4922-B S Cornell Ave, Chicago, IL 60615, 3 beds, 2.5 baths

$735,000

3 beds2.5 baths2,700 sq ft

4922-B S Cornell Ave, Chicago, IL 60615

Property at 2605 S Indiana Ave #409, Chicago, IL 60616, 1 bed, 1 bath

$149,900

1 bed1 bath727 sq ft

2605 S Indiana Ave #409, Chicago, IL 60616

Property at 6640 S Maryland Ave #3, Chicago, IL 60637, 2 beds, 2 baths

$349,000

2 beds2 baths— sq ft

6640 S Maryland Ave #3, Chicago, IL 60637

Property at 4744 S Prairie Ave Unit 1A, Chicago, IL 60615, 2 beds, 2 baths

$170,000

2 beds2 baths1,560 sq ft

4744 S Prairie Ave Unit 1A, Chicago, IL 60615

Property at 6736 S Merrill Ave Unit 1N, Chicago, IL 60649, 4 beds, 3 baths

$250,000

4 beds3 baths3,000 sq ft

6736 S Merrill Ave Unit 1N, Chicago, IL 60649

Property at 4537 S Evans Ave, Chicago, IL 60653, 10 beds, 8 baths

$1,189,000

10 beds8 baths— sq ft

4537 S Evans Ave, Chicago, IL 60653

Property at 7121 S Yale Ave, Chicago, IL 60621, 6 beds, 2 baths

$375,000

6 beds2 baths2,655 sq ft

7121 S Yale Ave, Chicago, IL 60621

Property at 442 E 48th St Unit B1, Chicago, IL 60615, 3 beds, 3 baths

$360,000

3 beds3 baths1,400 sq ft

442 E 48th St Unit B1, Chicago, IL 60615

Property at 442-444 E 48th St, Chicago, IL 60615, 29 beds, 23 baths

$4,000,000

29 beds23 baths— sq ft

442-444 E 48th St, Chicago, IL 60615

Property at 6121 S Woodlawn Ave #2, Chicago, IL 60637, 4 beds, 2 baths

$399,000

4 beds2 baths— sq ft

6121 S Woodlawn Ave #2, Chicago, IL 60637

Property at 4014 S Drexel Blvd Unit 4R, Chicago, IL 60653, 3 beds, 2 baths

$310,000

3 beds2 baths1,900 sq ft

4014 S Drexel Blvd Unit 4R, Chicago, IL 60653

Property at 7718 S Jeffery Blvd Unit GN, Chicago, IL 60649, 2 beds, 2 baths

$144,900

2 beds2 baths950 sq ft

7718 S Jeffery Blvd Unit GN, Chicago, IL 60649

Property at 7363 S South Shore Dr #209, Chicago, IL 60649, 1 bed, 1 bath

$69,999

1 bed1 bath800 sq ft

7363 S South Shore Dr #209, Chicago, IL 60649

Property at 4706 S Saint Lawrence Ave Unit 2E, Chicago, IL 60615, 3 beds, 2 baths

$440,000

3 beds2 baths1,500 sq ft

4706 S Saint Lawrence Ave Unit 2E, Chicago, IL 60615

Property at 2310 S Canal St #210, Chicago, IL 60616, 1 bed, 1 bath

$225,000

1 bed1 bath900 sq ft

2310 S Canal St #210, Chicago, IL 60616

Property at 7246 S East End Ave, Chicago, IL 60649, 7 beds, 3 baths

$175,000

7 beds3 baths— sq ft

7246 S East End Ave, Chicago, IL 60649

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Based on information submitted to the MLS GRID as of Mon Nov 24 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near South Side, IL

Cities

Elmhurst homes for sale
$735,000
Des Plaines homes for sale
$385,000
Downers Grove homes for sale
$520,000
Glenview homes for sale
$759,000
Wilmette homes for sale
$875,000
Arlington Heights homes for sale
$430,000
Mount Prospect homes for sale
$425,000
Northbrook homes for sale
$565,000
Lombard homes for sale
$382,000
Evanston homes for sale
$435,000
Oak Park homes for sale
$372,450
Skokie homes for sale
$442,000
Park Ridge homes for sale
$599,000
Chicago homes for sale
$350,000
Orland Park homes for sale
$379,450

Neighborhoods

Bronzeville homes for sale
$343,000
South Shore homes for sale
$179,900
South Loop homes for sale
$389,000
Kenwood homes for sale
$280,000
Pilsen Historic District homes for sale
$575,000
West Loop homes for sale
$495,000
Bridgeport homes for sale
$538,800
McKinley Park homes for sale
$419,450
Hyde Park homes for sale
$300,000
Woodlawn homes for sale
$342,500

South Side, IL real estate trends

All Home Types trends in South Side, IL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$274,950

+2.7% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

South Side, IL

$274,950

+2.7%

See more South Side, IL market insights

More to explore in South Side, IL

How to buy a house in South Side, IL

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First-time homebuyer's guide

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Popular Markets in Illinois

Chicago homes for sale
$349,900
Naperville homes for sale
$635,000
Schaumburg homes for sale
$299,900
Arlington Heights homes for sale
$432,500
Glenview homes for sale
$754,500
Oak Park homes for sale
$375,000
Evanston homes for sale
$429,900
Des Plaines homes for sale
$385,000
Orland Park homes for sale
$375,000
Downers Grove homes for sale
$519,000
Mount Prospect homes for sale
$425,000
St. Charles homes for sale
$460,000
Skokie homes for sale
$439,000
Glen Ellyn homes for sale
$550,000
Northbrook homes for sale
$554,900

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