Southwest Side, IL homes for sale & real estate

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ABOUT THIS HOME
Southwest Side, IL Homes for Sale
This multi-parcel commercial site at 5937-5943 S Ashland Ave offers outstanding visibility, easy access to public transportation, and flexible C2-2 zoning suitable for retail, service, or mixed-use development. Spanning an expansive 100x125 ft, the property provides ample space for strategic use and planning. Located just south of 59th Street and minutes from the Ashland/63rd Green Line station, the site's location and development potential make it an ideal choice for owner-users or investors looking to establish a presence on the South Side.

$170,000

— beds— baths— sq ft

5937 S Ashland Ave, Chicago, IL 60636

Flexible c2-2 zoning • 0.28 acre lot • Built 1956

ABOUT THIS HOME
Southwest Side, IL Homes for Sale
"Double the Dwellings, Double the Treats-Tour This Spooktacular Home!" open this Friday! Welcome to this beautifully updated 3-bedroom residence offering exceptional curb appeal on a well-maintained block. This unique property blends charm, functionality, and versatility-ideal for multi-generational living, guest accommodations, or creative use. The main home features 3 bedrooms and 1 bathroom, a spacious a kitchen that shines with new white shaker cabinetry, Quartz countertops, stainless steel appliances, and ample lighting-perfect for everyday cooking and entertaining. The fully upgraded bathroom includes new ceramic tile on both the shower and floor, modern vanity, and updated

$349,900

4 beds2 baths1,200 sq ft

5817 W 64th St, Chicago, IL 60638

Large family room • Attached workshop • Full basement

$159,900

7 beds3 baths— sq ft

5935 S Elizabeth St, Chicago, IL 60636

2 parking spots • Built 1903 • Listed 42 days

ABOUT THIS HOME
Southwest Side, IL Homes for Sale
GORGEOUS RENOVATION IN THE HEART OF MCKINLEY PARK! STEP INTO THIS BEAUTIFULLY UPDATED 4-BEDROOM, 2-BATH GEM FEATURING A FULL FINISHED BASEMENT AND A 2-CAR GARAGE-PERFECTLY DESIGNED FOR COMFORT, STYLE, AND VERSATILITY. REMODELED IN 2024 WITH A SLEEK KITCHEN BOASTING QUARTZ COUNTERTOPS, EXTENDED GRAY CABINETRY, AND NEW APPLIANCES. BATHROOMS SHOWCASE STATE-OF-THE-ART CERAMIC TILE DESIGNS FOR A SPA-LIKE FEEL. NEW WATERPROOF VINYL LAMINATE FLOORING FLOWS SEAMLESSLY THROUGHOUT THE HOME, COMPLEMENTED BY FRESHLY PAINTED INTERIORS. EXPANSIVE BASEMENT WITH DUAL ENTRANCES, A SUMMER KITCHEN, AND A FULL BATH-IDEAL FOR RELATED LIVING OR ENTERTAINING. ROOF REPLACED JUST 3 YEARS AGO ON BOTH HOUSE AND GARAG

$429,900

4 beds2 baths2,000 sq ft

3328 S Damen Ave, Chicago, IL 60608

Quartz countertops • New appliances • Sleek kitchen

ABOUT THIS HOME
Southwest Side, IL Homes for Sale
* * * AGENT OWNED * * * Welcome to this move-in ready, beautifully updated loft condo in the heart of McKinley Park. This spacious unit boasts an open-concept layout with 1 bedroom, 1 den (easily convertible to a 2nd bedroom), and 1.5 bathrooms. The entire home features new waterproof laminate flooring and fresh paint. The kitchen is a highlight with new maple cabinets, granite countertops, a large island with breakfast bar, pantry, and new stainless steel appliances. The master suite offers a large walk-in closet and a renovated bathroom with high-end amenities, including a bidet toilet with seat warmer and a smart LED mirror. The den provides excellent flexibility for an office or gu

$219,900

1 bed1.5 baths1,050 sq ft

2323 W Pershing Rd #104, Chicago, IL 60609

Large island • Updated loft condo • Granite countertops

Property at 2913 W 63rd St, Chicago, IL 60629

$369,900

— beds— baths— sq ft

2913 W 63rd St, Chicago, IL 60629

Property at 6243 S Wood St, Chicago, IL 60636, 8 beds, 4 baths

$515,000

8 beds4 baths— sq ft

6243 S Wood St, Chicago, IL 60636

Property at 4317 S Sawyer Ave, Chicago, IL 60632, 6 beds, 3 baths

$424,000

6 beds3 baths— sq ft

4317 S Sawyer Ave, Chicago, IL 60632

Property at 4411 S Wallace St, Chicago, IL 60609, 5 beds, 3.5 baths

$750,000

5 beds3.5 baths3,300 sq ft

4411 S Wallace St, Chicago, IL 60609

Property at 7318 S Aberdeen St, Chicago, IL 60621, 5 beds, 2.5 baths

$255,000

5 beds2.5 baths1,250 sq ft

7318 S Aberdeen St, Chicago, IL 60621

Property at 5326 S Nagle Ave, Chicago, IL 60638, 4 beds, 2 baths

$549,900

4 beds2 baths2,036 sq ft

5326 S Nagle Ave, Chicago, IL 60638

Property at 420 W 65th Pl, Chicago, IL 60621, 4 beds, 2 baths

$199,999

4 beds2 baths— sq ft

420 W 65th Pl, Chicago, IL 60621

Property at 6016 S Mayfield Ave, Chicago, IL 60638, 5 beds, 3.5 baths

$699,000

5 beds3.5 baths3,300 sq ft

6016 S Mayfield Ave, Chicago, IL 60638

Property at 5042 S Laflin St, Chicago, IL 60609, 4 beds, 2 baths

$165,000

4 beds2 baths— sq ft

5042 S Laflin St, Chicago, IL 60609

Property at 7130 S Seeley Ave, Chicago, IL 60636, 4 beds, 2 baths

$279,999

4 beds2 baths1,100 sq ft

7130 S Seeley Ave, Chicago, IL 60636

Property at 6528 S Sangamon St, Chicago, IL 60621, 4 beds, 2 baths

$269,999

4 beds2 baths1,634 sq ft

6528 S Sangamon St, Chicago, IL 60621

Property at 5009 S Kostner Ave, Chicago, IL 60632, 4 beds, 2 baths

$435,000

4 beds2 baths1,317 sq ft

5009 S Kostner Ave, Chicago, IL 60632

Property at 3604 W 65th Pl, Chicago, IL 60629, 6 beds, 2 baths

$324,900

6 beds2 baths1,315 sq ft

3604 W 65th Pl, Chicago, IL 60629

Property at 6700 S Stewart Ave, Chicago, IL 60621, 6 beds, 3 baths

$99,900

6 beds3 baths2,428 sq ft

6700 S Stewart Ave, Chicago, IL 60621

Property at 3704 W 57th St, Chicago, IL 60629, 5 beds, 2 baths

$339,999

5 beds2 baths2,080 sq ft

3704 W 57th St, Chicago, IL 60629

Property at 5549 S Shields Ave, Chicago, IL 60621, 4 beds, 2 baths

$245,000

4 beds2 baths— sq ft

5549 S Shields Ave, Chicago, IL 60621

Property at 7228 S Hermitage Ave, Chicago, IL 60636, 4 beds, 2 baths

$40,000

4 beds2 baths1,638 sq ft

7228 S Hermitage Ave, Chicago, IL 60636

Property at 6454 S Winchester Ave, Chicago, IL 60636, 5 beds, 2 baths

$160,000

5 beds2 baths— sq ft

6454 S Winchester Ave, Chicago, IL 60636

Property at 5243 S Maplewood Ave, Chicago, IL 60632, 6 beds, 3 baths

$260,000

6 beds3 baths— sq ft

5243 S Maplewood Ave, Chicago, IL 60632

Property at 6738 S Normal Blvd, Chicago, IL 60621, 4 beds, 2.5 baths

$115,000

4 beds2.5 baths2,464 sq ft

6738 S Normal Blvd, Chicago, IL 60621

Property at 2951 W 43rd St, Chicago, IL 60632

$160,000

— beds— baths2,277 sq ft

2951 W 43rd St, Chicago, IL 60632

Property at 5152 S Lawler St, Chicago, IL 60638, 4 beds, 2 baths

$399,000

4 beds2 baths1,300 sq ft

5152 S Lawler St, Chicago, IL 60638

Property at 6333 S Racine Ave, Chicago, IL 60636, 8 beds, 5 baths

$375,000

8 beds5 baths— sq ft

6333 S Racine Ave, Chicago, IL 60636

Property at 6608 S Bell Ave, Chicago, IL 60636, 5 beds, 2 baths

$195,000

5 beds2 baths1,008 sq ft

6608 S Bell Ave, Chicago, IL 60636

Property at 6843 S Racine Ave, Chicago, IL 60636, 3 beds, 3.5 baths

$330,000

3 beds3.5 baths— sq ft

6843 S Racine Ave, Chicago, IL 60636

Property at 3502 W 58th Pl, Chicago, IL 60629, 5 beds, 2 baths

$389,900

5 beds2 baths1,400 sq ft

3502 W 58th Pl, Chicago, IL 60629

Property at 5584 S Archer Ave Unit 3C, Chicago, IL 60638, 2 beds, 1 bath

$130,000

2 beds1 bath1,000 sq ft

5584 S Archer Ave Unit 3C, Chicago, IL 60638

Property at 3641 W 57th St, Chicago, IL 60629, 6 beds, 3 baths

$409,900

6 beds3 baths— sq ft

3641 W 57th St, Chicago, IL 60629

Property at 3416 W 64th Pl, Chicago, IL 60629, 4 beds, 2 baths

$349,900

4 beds2 baths1,391 sq ft

3416 W 64th Pl, Chicago, IL 60629

Property at 5621 S Sawyer Ave, Chicago, IL 60629, 3 beds, 3 baths

$315,000

3 beds3 baths1,680 sq ft

5621 S Sawyer Ave, Chicago, IL 60629

Property at 5635 S California Ave, Chicago, IL 60629, 2 beds, 2 baths

$180,000

2 beds2 baths1,000 sq ft

5635 S California Ave, Chicago, IL 60629

Property at 415 W 62nd St, Chicago, IL 60621, 6 beds, 3 baths

$212,000

6 beds3 baths— sq ft

415 W 62nd St, Chicago, IL 60621

Property at 2323 W Pershing Rd #140, Chicago, IL 60609, 2 beds, 2 baths

$235,000

2 beds2 baths1,085 sq ft

2323 W Pershing Rd #140, Chicago, IL 60609

Property at 6424 S Washtenaw Ave, Chicago, IL 60629, 3 beds, 1 bath

$259,000

3 beds1 bath1,188 sq ft

6424 S Washtenaw Ave, Chicago, IL 60629

Property at 6104 S Nashville Ave, Chicago, IL 60638, 2 beds, 1 bath

$215,000

2 beds1 bath876 sq ft

6104 S Nashville Ave, Chicago, IL 60638

Property at 4629 S Ashland Ave, Chicago, IL 60609

$265,900

— beds— baths— sq ft

4629 S Ashland Ave, Chicago, IL 60609

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Based on information submitted to the MLS GRID as of Thu Nov 20 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 Southwest Side, IL

Cities

Glen Ellyn homes for sale
$540,000
Schaumburg homes for sale
$299,900
Wheaton homes for sale
$459,450
Des Plaines homes for sale
$398,500
Downers Grove homes for sale
$510,000
Glenview homes for sale
$759,000
Arlington Heights homes for sale
$432,500
Mount Prospect homes for sale
$406,000
Lombard homes for sale
$382,000
Evanston homes for sale
$429,900
Oak Park homes for sale
$400,000
Naperville homes for sale
$627,000
Skokie homes for sale
$449,000
Chicago homes for sale
$350,000
Orland Park homes for sale
$379,450

Neighborhoods

Beverly homes for sale
$459,900
Bronzeville homes for sale
$331,950
South Loop homes for sale
$389,500
Kenwood homes for sale
$280,000
Humboldt Park homes for sale
$499,999
Garfield Ridge homes for sale
$359,900
Pilsen Historic District homes for sale
$587,450
Bridgeport homes for sale
$536,900
McKinley Park homes for sale
$419,900
Hyde Park homes for sale
$304,500

Southwest Side, IL real estate trends

All Home Types trends in Southwest Side, IL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$294,275

+5.1% 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

Southwest Side, IL

$294,275

+5.1%

See more Southwest Side, IL market insights

More to explore in Southwest Side, IL

How to buy a house in Southwest Side, IL

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How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Illinois

Chicago homes for sale
$350,000
Naperville homes for sale
$625,000
Schaumburg homes for sale
$299,900
Arlington Heights homes for sale
$427,500
Glenview homes for sale
$737,500
Oak Park homes for sale
$400,000
Evanston homes for sale
$435,000
Des Plaines homes for sale
$398,000
Orland Park homes for sale
$377,000
Downers Grove homes for sale
$518,000
Mount Prospect homes for sale
$406,000
St. Charles homes for sale
$449,995
Skokie homes for sale
$447,000
Glen Ellyn homes for sale
$545,000
Northbrook homes for sale
$565,000

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