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

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NEW 14 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
Welcome to 5716 S May Street, a beautifully renovated, greystone 2-flat, perfect for an investor or owner-occupant. This property offers peace of mind with new mechanicals, appliances, roof, modern finishes, and thoughtful layouts throughout. Offering over 1,300 Sq. feet of living space per unit, both units feature spacious 3-bedroom, 1-bath floor plans with LVP flooring and a contemporary kitchen with stainless steel appliances. Clean unfinished basement with shared washer and dryer & separate utility panels. Outside, you'll find a tidy, low-maintenance yard and 2-car garage, rounding out the appeal for both renters and owners. Whether you're looking to house hack your first property

$399,900

6 beds2 baths— sq ft

5716 S May St, Chicago, IL 60621

Contemporary kitchen • Renovated greystone • Thoughtful layouts

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
* * * * * CASH OR HARD-MONEY LOANS ONLY * * * * * Rarely available fully Remodeled Legal 3 unit!! Building consists of a total of 5 bedrooms and 3 bathrooms. On the first floor unit you will find an open concept kitchen/living room area along with 2 bedrooms, huge pantry, and 1 full bath. On the second level unit, you find another 2 bedrooms, 1 bath, with a full kitchen and living room. Downstairs in the ground unit you will find 1 huge bedroom, 1 full bath annd open layout kitchen/ living room Combined. Each unit has its own high efficiency furnace along with their own individual entrance and exits. There is an ample front yard, private balconies, and gated throughout! Located i

$189,999

5 beds3 baths— sq ft

4329 S Wood St, Chicago, IL 60609

Huge pantry • Private balconies • Fully remodeled

LISTED BY REDFIN

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
Great opportunity to own this home on a double lot, with a detached garage in West Englewood. This property is being sold as-is, and is ideal for investors, rehabbers, or buyers seeking a large property. The interior of the property is livable but needs work. Total lot size is 6,273 square feet.

$85,000

2 beds1 bath774 sq ft

6450 S Marshfield Ave, Chicago, IL 60636

3,075 sq ft lot • Garage • Built 1898

NEW 10 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
STUNNING WEST ENGLEWOOD GEM! Don't miss out on this incredible opportunity to own a beautifully updated home in a prime Chicago neighborhood! This charming property has been thoughtfully updated to perfection, boasting modern updates, beautiful flooring, brand new Stainless Steel Refrigerator and Stove and a brand-new roof (just 2 years young!). Nestled near the vibrant Murray Park, this home offers the perfect blend of community charm and urban convenience. With its recently updated bathroom and kitchen, you'll be ready to move in and start enjoying the best of Chicago living. Key Features: - Modern bathroom and kitchen - Brand-new roof (2 years young!) - Prime location near Murray Park -

$215,000

4 beds1.5 baths1,020 sq ft

7246 S Wood St, Chicago, IL 60636

Brand-new roof • Updated home • Modern bathroom

NEW 14 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Southwest Side, IL:
Calling all Investors. Complete gut and rehab needed!! AS IS. Cash Only. back taxes will be paid by the seller. Seller MOTIVATED!!!

$25,000

4 beds1 bath1,035 sq ft

7357 S Green St, Chicago, IL 60621

4,125 sq ft lot

Property at 1275 W 71st St, Chicago, IL 60636, 5 beds, 1.5 baths

$239,900

5 beds1.5 baths969 sq ft

1275 W 71st St, Chicago, IL 60636

Property at 2107 W 70th Pl, Chicago, IL 60636, 4 beds, 2 baths

$187,900

4 beds2 baths936 sq ft

2107 W 70th Pl, Chicago, IL 60636

Property at 6031 S Normandy Ave, Chicago, IL 60638, 5 beds, 2 baths

$399,000

5 beds2 baths1,117 sq ft

6031 S Normandy Ave, Chicago, IL 60638

Property at 4314 S Hermitage Ave, Chicago, IL 60609, 12 beds, 6 baths

$340,000

12 beds6 baths3,632 sq ft

4314 S Hermitage Ave, Chicago, IL 60609

Property at 3826 S Honore St, Chicago, IL 60609, 4 beds, 3 baths

$389,900

4 beds3 baths— sq ft

3826 S Honore St, Chicago, IL 60609

Property at 5531 S May St, Chicago, IL 60621, 6 beds, 2 baths

$425,000

6 beds2 baths— sq ft

5531 S May St, Chicago, IL 60621

Property at 7332 S Honore St, Chicago, IL 60636, 3 beds, 2 baths

$290,000

3 beds2 baths1,863 sq ft

7332 S Honore St, Chicago, IL 60636

Property at 5245 S Racine Ave, Chicago, IL 60609, 2 beds, 1.5 baths

$74,900

2 beds1.5 baths903 sq ft

5245 S Racine Ave, Chicago, IL 60609

Property at 5106 S Carpenter St, Chicago, IL 60609, 4 beds, 2 baths

$175,000

4 beds2 baths— sq ft

5106 S Carpenter St, Chicago, IL 60609

Property at 4932 S Winchester Ave, Chicago, IL 60609, 6 beds, 3 baths

$149,000

6 beds3 baths— sq ft

4932 S Winchester Ave, Chicago, IL 60609

Property at 5918 S Albany Ave, Chicago, IL 60629, 3 beds, 2 baths

$175,000

3 beds2 baths832 sq ft

5918 S Albany Ave, Chicago, IL 60629

Property at 4931 S Knox Ave, Chicago, IL 60632, 5 beds, 2 baths

$419,900

5 beds2 baths1,032 sq ft

4931 S Knox Ave, Chicago, IL 60632

Property at 5605 S Justine St, Chicago, IL 60636, 2 beds, 1 bath

$84,000

2 beds1 bath1,118 sq ft

5605 S Justine St, Chicago, IL 60636

Property at 6441 S Campbell Ave, Chicago, IL 60629, 5 beds, 2 baths

$384,900

5 beds2 baths1,415 sq ft

6441 S Campbell Ave, Chicago, IL 60629

Property at 5631 W 64th Pl, Chicago, IL 60638, 4 beds, 2 baths

$379,900

4 beds2 baths1,020 sq ft

5631 W 64th Pl, Chicago, IL 60638

Property at 6004 S Carpenter St, Chicago, IL 60621, 7 beds, 2.5 baths

$395,000

7 beds2.5 baths— sq ft

6004 S Carpenter St, Chicago, IL 60621

Property at 1508 W 72nd St, Chicago, IL 60636, 3 beds, 2 baths

$135,000

3 beds2 baths1,079 sq ft

1508 W 72nd St, Chicago, IL 60636

Property at 1444 W 72nd Pl, Chicago, IL 60636, 4 beds, 2 baths

$299,900

4 beds2 baths1,034 sq ft

1444 W 72nd Pl, Chicago, IL 60636

Property at 7041 S Throop St, Chicago, IL 60636, 3 beds, 1 bath

$195,000

3 beds1 bath987 sq ft

7041 S Throop St, Chicago, IL 60636

Property at 6049 S Morgan St, Chicago, IL 60621, 6 beds, 2 baths

$250,000

6 beds2 baths— sq ft

6049 S Morgan St, Chicago, IL 60621

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

$309,900

6 beds2 baths1,904 sq ft

7141 S Artesian Ave, Chicago, IL 60629

Property at 6953 S Loomis Blvd, Chicago, IL 60636, 4 beds, 1 bath

$129,900

4 beds1 bath1,300 sq ft

6953 S Loomis Blvd, Chicago, IL 60636

Property at 6627 S Marshfield Ave, Chicago, IL 60636, 6 beds, 2 baths

$277,000

6 beds2 baths1,900 sq ft

6627 S Marshfield Ave, Chicago, IL 60636

Property at 4837 S Union Ave, Chicago, IL 60609, 6 beds, 3 baths

$201,450

6 beds3 baths— sq ft

4837 S Union Ave, Chicago, IL 60609

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

$189,000

3 beds1 bath900 sq ft

5607 S Laflin Ave, Chicago, IL 60636

Property at 1813 W 63rd St, Chicago, IL 60636

$439,900

— beds— baths2,424 sq ft

1813 W 63rd St, Chicago, IL 60636

Property at 7034 S Normal Blvd, Chicago, IL 60621, 11 beds, 3 baths

$423,500

11 beds3 baths3,540 sq ft

7034 S Normal Blvd, Chicago, IL 60621

Property at 7326 S Francisco Ave, Chicago, IL 60629, 3 beds, 2 baths

$255,000

3 beds2 baths1,216 sq ft

7326 S Francisco Ave, Chicago, IL 60629

Property at 4305 S Wood St, Chicago, IL 60609, 4 beds, 1.5 baths

$290,000

4 beds1.5 baths1,100 sq ft

4305 S Wood St, Chicago, IL 60609

Property at 5006 S La Crosse Ave, Chicago, IL 60638, 4 beds, 2 baths

$359,900

4 beds2 baths1,075 sq ft

5006 S La Crosse Ave, Chicago, IL 60638

Property at 6210 S Keeler Ave, Chicago, IL 60629, 4 beds, 2 baths

$369,900

4 beds2 baths2,400 sq ft

6210 S Keeler Ave, Chicago, IL 60629

Property at 531 W 61st Pl, Chicago, IL 60621, 5 beds, 2 baths

$179,000

5 beds2 baths— sq ft

531 W 61st Pl, Chicago, IL 60621

Property at 5700 S Neenah Ave, Chicago, IL 60638, 3 beds, 2 baths

$375,000

3 beds2 baths950 sq ft

5700 S Neenah Ave, Chicago, IL 60638

Property at 6932 S Eggleston Ave, Chicago, IL 60621, 5 beds, 2 baths

$100,000

5 beds2 baths— sq ft

6932 S Eggleston Ave, Chicago, IL 60621

Property at 6123 S Laflin St, Chicago, IL 60636, 5 beds, 2 baths

$125,000

5 beds2 baths— sq ft

6123 S Laflin St, Chicago, IL 60636

Property at 5938 S Richmond St, Chicago, IL 60629, 5 beds, 2 baths

$319,900

5 beds2 baths2,309 sq ft

5938 S Richmond St, Chicago, IL 60629

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Based on information submitted to the MLS GRID as of Mon Jan 05 2026. 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 515 cheap homes for sale in Southwest Side at a median listing price of $282K. 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 72 days and receive 8 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, 155 homes have been sold in Southwest Side. In addition to houses in Southwest Side, there were also 36 condos, 11 townhouses, and 215 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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