Cheap homes for sale & real estate in Southwest Side, IL

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ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
INVESTOR SPECIAL!! Money is to be made with this building. Building is ready to finish up, owner started making some repair. Beautiful wrought iron gate with second story balcony. Two separate units make for good rentals. Full walkout basement, possible garden apartment. Great location, close to many gas stations, retail and grocery stores, and restaurants.

$160,000

5 beds2 baths— sq ft

6454 S Winchester Ave, Chicago, IL 60636

Wrought iron gate • Second story balcony • Great location

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
Excellent Investment opportunity in the New City neighborhood, perfect for the first time homebuyer or for anyone wanting extra passive income! Two Unit with opportunity to duplex up to the unfinished attic. Recently updated, two bedroom, 1 bath units; Updated kitchen with Stainless Steel Appliances, new cabinets, newly remodeled bathrooms, Central Air, New garage. Bring your prequalified buyers! Property Sold As-Is.

$299,900

4 beds2 baths— sq ft

4845 S Throop St, Chicago, IL 60609

Two unit • New cabinets • Updated kitchen

$290,000

3 beds2 baths1,863 sq ft

Fenced yard • Finished basement • Concrete patio

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
Discover this Ranch 2-bedroom, 2-bathroom, living room and dining room gem nestled in the heart of Gage Park. Just steps away from local restaurants, shops, and more, this property offers both convenience and potential. Garage located in the front of the property with extra storage space behind the garage. Some features: Spacious layout with good bones, roof replaced in 2020, by sellers' information. Furnace and water heater updated in 2017. Plenty of room to customize and make it your own with a few personal touches and updates, Den was used as a bedroom by previous owner. This home can be transformed into a beautiful, spacious retreat. Whether you're a first-time buyer or an investor, thi

$180,000

2 beds2 baths1,000 sq ft

5635 S California Ave, Chicago, IL 60629

Extra storage space • Furnace updated • Water heater updated

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
This solid 2-unit property is being sold as-is and offers great potential for investors or owner-occupants. Each unit features 3 spacious bedrooms, providing plenty of living space and rental income potential. The property is secured with a gated front fence and offers a great-sized yard, perfect for outdoor enjoyment or additional improvements. With some updates and personal touches, this building can be transformed into a beautiful income-generating property. Don't miss the chance to add value and make it your own!

$174,900

6 beds2 baths— sq ft

5533 S Princeton Ave, Chicago, IL 60621

Great-sized yard • Gated front fence • 0.7 acre lot

Property at 7348 S Lowe Ave, Chicago, IL 60621, 5 beds, 2 baths

$160,000

5 beds2 baths— sq ft

7348 S Lowe Ave, Chicago, IL 60621

Property at 6152 S Austin Ave, Chicago, IL 60638, 3 beds, 2 baths

$349,900

3 beds2 baths1,744 sq ft

6152 S Austin Ave, Chicago, IL 60638

Property at 2415 W 32nd Pl, Chicago, IL 60608, 3 beds, 2.5 baths

$398,000

3 beds2.5 baths1,600 sq ft

2415 W 32nd Pl, Chicago, IL 60608

Property at 5517 S Justine St, Chicago, IL 60636, 8 beds, 4 baths

$275,000

8 beds4 baths— sq ft

5517 S Justine St, Chicago, IL 60636

Property at 6206 S Knox Ave, Chicago, IL 60629, 2 beds, 1.5 baths

$420,000

2 beds1.5 baths3,528 sq ft

6206 S Knox Ave, Chicago, IL 60629

Property at 4530 S Paulina St, Chicago, IL 60609, 12 beds, 18 baths

$369,000

12 beds18 baths3,040 sq ft

4530 S Paulina St, Chicago, IL 60609

Property at 7252 S Wood St, Chicago, IL 60636, 4 beds, 2 baths

$275,000

4 beds2 baths1,500 sq ft

7252 S Wood St, Chicago, IL 60636

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 7141 S Artesian Ave, Chicago, IL 60629, 6 beds, 2 baths

$325,000

6 beds2 baths1,904 sq ft

7141 S Artesian Ave, Chicago, IL 60629

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

$334,999

5 beds2 baths2,080 sq ft

3704 W 57th St, Chicago, IL 60629

Property at 5922 S Paulina St, Chicago, IL 60636, 4 beds, 2 baths

$49,900

4 beds2 baths1,700 sq ft

5922 S Paulina St, Chicago, IL 60636

Property at 6005 S Menard Ave, Chicago, IL 60638, 3 beds, 2 baths

$365,000

3 beds2 baths1,024 sq ft

6005 S Menard Ave, Chicago, IL 60638

Property at 6731 S Aberdeen St, Chicago, IL 60621, 2 beds, 1 bath

$110,000

2 beds1 bath897 sq ft

6731 S Aberdeen St, Chicago, IL 60621

Property at 7352 S Lowe Ave, Chicago, IL 60621, 6 beds, 2 baths

$199,900

6 beds2 baths— sq ft

7352 S Lowe Ave, Chicago, IL 60621

Property at 5245 S Mayfield Ave, Chicago, IL 60638, 4 beds, 4 baths

$444,000

4 beds4 baths1,868 sq ft

5245 S Mayfield Ave, Chicago, IL 60638

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 6832 S Sangamon Ave, Chicago, IL 60621, 4 beds, 2 baths

$55,000

4 beds2 baths— sq ft

6832 S Sangamon Ave, Chicago, IL 60621

Property at 1453 W Garfield Blvd #1, Chicago, IL 60636, 3 beds, 2 baths

$79,999

3 beds2 baths1,200 sq ft

1453 W Garfield Blvd #1, Chicago, IL 60636

Property at 2115 W 68th Pl, Chicago, IL 60636, 3 beds, 1 bath

$99,900

3 beds1 bath1,040 sq ft

2115 W 68th Pl, Chicago, IL 60636

Property at 3555 W 65th Pl, Chicago, IL 60629, 3 beds, 1 bath

$299,000

3 beds1 bath8,000 sq ft

3555 W 65th Pl, Chicago, IL 60629

Property at 3328 S Damen Ave, Chicago, IL 60608, 4 beds, 2 baths

$429,900

4 beds2 baths2,000 sq ft

3328 S Damen Ave, Chicago, IL 60608

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 5607 S Laflin Ave, Chicago, IL 60636, 3 beds, 1 bath

$199,000

3 beds1 bath900 sq ft

5607 S Laflin Ave, Chicago, IL 60636

Property at 6827 S Green St, Chicago, IL 60621, 5 beds, 2 baths

$270,000

5 beds2 baths861 sq ft

6827 S Green St, Chicago, IL 60621

Property at 6111 S Wolcott Ave, Chicago, IL 60636, 4 beds, 2 baths

$259,000

4 beds2 baths— sq ft

6111 S Wolcott Ave, Chicago, IL 60636

Property at 6634 S Winchester Ave, Chicago, IL 60636, 4 beds, 3 baths

$339,000

4 beds3 baths1,496 sq ft

6634 S Winchester Ave, Chicago, IL 60636

Property at 4629 S Laflin St, Chicago, IL 60609, 5 beds, 2 baths

$349,000

5 beds2 baths1,200 sq ft

4629 S Laflin St, Chicago, IL 60609

Property at 6925 S Stewart Ave, Chicago, IL 60621, 4 beds, 2 baths

$59,900

4 beds2 baths2,106 sq ft

6925 S Stewart Ave, Chicago, IL 60621

Property at 5817 W 64th St, Chicago, IL 60638, 4 beds, 2 baths

$349,900

4 beds2 baths1,200 sq ft

5817 W 64th St, Chicago, IL 60638

Property at 5137 S Rutherford Ave, Chicago, IL 60638, 3 beds, 1 bath

$350,000

3 beds1 bath1,022 sq ft

5137 S Rutherford Ave, Chicago, IL 60638

Property at 7255 S Washtenaw Ave, Chicago, IL 60629, 4 beds, 5 baths

$400,000

4 beds5 baths— sq ft

7255 S Washtenaw Ave, Chicago, IL 60629

Property at 6927 S Hermitage Ave, Chicago, IL 60636, 8 beds, 3 baths

$359,900

8 beds3 baths— sq ft

6927 S Hermitage Ave, Chicago, IL 60636

Property at 6850 W 64th St, Chicago, IL 60638, 5 beds, 2.5 baths

$380,000

5 beds2.5 baths1,152 sq ft

6850 W 64th St, Chicago, IL 60638

Property at 5545 S Throop St, Chicago, IL 60636, 7 beds, 2 baths

$209,000

7 beds2 baths— sq ft

5545 S Throop St, Chicago, IL 60636

Property at 5718 S Green St, Chicago, IL 60621, 12 beds, 6 baths

$450,000

12 beds6 baths— sq ft

5718 S Green St, Chicago, IL 60621

Property at Sign in for address, Chicago, IL 60621, 4 beds, 2 baths

$280,000

4 beds2 baths— sq ft

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Based on information submitted to the MLS GRID as of Sat Nov 29 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.

Cheap Homes for Sale in Southwest Side

There are currently 563 cheap homes for sale in Southwest Side at a median listing price of $285K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Southwest Side stay on the market for 58 days and receive 3 offers. Popular neighborhoods include Beverly, Bronzeville, South Loop, Bridgeport, and Hyde Park. This map is refreshed with the newest listings in Southwest Side every 15 minutes.

In the past month, 195 homes have been sold in Southwest Side. In addition to houses in Southwest Side, there were also 55 condos, 13 townhouses, and 268 multi-family units for sale in Southwest Side last month. Find your dream home in Southwest Side using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Southwest Side are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Southwest Side. If you're looking to sell your home in the Southwest Side area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Southwest Side with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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