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

447 homes

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Recommended

$212,000

6 beds3 baths— sq ft

415 W 62nd St, Chicago, IL 60621

2 garage spots • Built 1883 • Listed 57 days

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Beautifully updated classic brick Chicago bungalow. Bright, open layout featuring new paint, doors, can lighting and hardwood flooring throughout. A spa like bathroom experience with the shower fixtures and cool toned tile. Three bedrooms on the main level with a bonus room in the basement and an unfinished attic if you need extra space in the future. A warm fireplace in the family room for those upcoming chilly nights and an eye catching kitchen which includes new stainless steel appliances, a sleek countertop and white shaker cabinets. This is a MUST SEE!

$259,000

3 beds1 bath1,188 sq ft

6424 S Washtenaw Ave, Chicago, IL 60629

Open layout • Spa like bathroom • 3,125 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
This is an opportunity for investors or savvy homeowners looking to build instant equity in Chicago's Clearing neighborhood. This charming, small-footprint brick home offers a solid foundation ready for a full-scale renovation.

$215,000

2 beds1 bath876 sq ft

6104 S Nashville Ave, Chicago, IL 60638

Solid foundation • 4,625 sq ft lot • Garage

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Exceptional Opportunity, Mixed use corner building, Spacious store front ready to start your business, 2 half bathrooms, with additional rental apartment in the second floor, 3 bedrooms, 2 baths. Sold as is.

$265,900

— beds— baths— sq ft

4629 S Ashland Ave, Chicago, IL 60609

Spacious store front • Rental apartment • 3,294 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Investment Opportunity, Well maintenance Mixed use Building located in up coming New City. A Large store front ready to stablish your own business or rent it out, nice extra room for an office in the store space, half bathroom, and full basement. Plus one apartment in the second Floor, with formal a living room and dining room, 3 bedrooms, kitchen, family room and bathroom. -Sold as is- You must to see it

$265,900

— beds— baths— sq ft

4627 S Ashland Ave, Chicago, IL 60609

Large store front • Full basement • Dining room

Property at 1718 W 48th St, Chicago, IL 60609

$260,000

— beds— baths— sq ft

1718 W 48th St, Chicago, IL 60609

Property at 7326 S Francisco Ave, Chicago, IL 60629, 3 beds, 1 bath

$270,000

3 beds1 bath1,216 sq ft

7326 S Francisco Ave, Chicago, IL 60629

Property at 3907 W Marquette Rd, Chicago, IL 60629, 3 beds, 1.5 baths

$285,000

3 beds1.5 baths1,287 sq ft

3907 W Marquette Rd, Chicago, IL 60629

Property at 5658 S Hermitage Ave, Chicago, IL 60636, 6 beds, 2 baths

$160,000

6 beds2 baths— sq ft

5658 S Hermitage Ave, Chicago, IL 60636

Property at 5924 S Paulina St, Chicago, IL 60636, 5 beds, 2 baths

$97,200

5 beds2 baths— sq ft

5924 S Paulina St, Chicago, IL 60636

Property at 2453 W 56th St Unit 1N, Chicago, IL 60629

$200

— beds— baths— sq ft

2453 W 56th St Unit 1N, Chicago, IL 60629

Property at 2453 W 56th St Unit 1S, Chicago, IL 60629

$200

— beds— baths— sq ft

2453 W 56th St Unit 1S, Chicago, IL 60629

Property at 5749 W 64th Pl, Chicago, IL 60638, 4 beds, 3 baths

$460,000

4 beds3 baths— sq ft

5749 W 64th Pl, Chicago, IL 60638

Property at 604 W 43rd St, Chicago, IL 60609, 4 beds, 3 baths

$579,000

4 beds3 baths— sq ft

604 W 43rd St, Chicago, IL 60609

Property at 6235 S Kedvale Ave, Chicago, IL 60629, 5 beds, 4 baths

$459,900

5 beds4 baths2,080 sq ft

6235 S Kedvale Ave, Chicago, IL 60629

Property at 2103 W 52nd St, Chicago, IL 60609

$180,000

0 beds— baths— sq ft

2103 W 52nd St, Chicago, IL 60609

Property at 6124 S Sangamon St, Chicago, IL 60621, 5 beds, 2 baths

$199,900

5 beds2 baths— sq ft

6124 S Sangamon St, Chicago, IL 60621

Property at 1114 W 51st St, Chicago, IL 60609, 4 beds, 3 baths

$111,000

4 beds3 baths4,675 sq ft

1114 W 51st St, Chicago, IL 60609

Property at 6221 S Wolcott Ave, Chicago, IL 60636, 4 beds, 2 baths

$200,000

4 beds2 baths— sq ft

6221 S Wolcott Ave, Chicago, IL 60636

Property at 5237 S Long Ave, Chicago, IL 60638, 6 beds, 2.5 baths

$419,000

6 beds2.5 baths— sq ft

5237 S Long Ave, Chicago, IL 60638

Property at 6221 S Talman Ave, Chicago, IL 60629, 6 beds, 2 baths

$339,999

6 beds2 baths1,775 sq ft

6221 S Talman Ave, Chicago, IL 60629

Property at 3920 W Marquette Rd, Chicago, IL 60629, 2 beds, 2 baths

$280,000

2 beds2 baths855 sq ft

3920 W Marquette Rd, Chicago, IL 60629

Property at 6317 S Morgan St, Chicago, IL 60621, 6 beds, 2 baths

$104,000

6 beds2 baths— sq ft

6317 S Morgan St, Chicago, IL 60621

Property at 6010 S Richmond St, Chicago, IL 60629, 6 beds, 2 baths

$385,000

6 beds2 baths1,176 sq ft

6010 S Richmond St, Chicago, IL 60629

Property at 7130 S Richmond St, Chicago, IL 60629, 2 beds, 2 baths

$236,000

2 beds2 baths1,328 sq ft

7130 S Richmond St, Chicago, IL 60629

Property at 5731 S Hoyne Ave, Chicago, IL 60636, 4 beds, 3 baths

$245,000

4 beds3 baths1,556 sq ft

5731 S Hoyne Ave, Chicago, IL 60636

Property at 5820 S Washtenaw Ave, Chicago, IL 60629, 6 beds, 2 baths

$304,900

6 beds2 baths1,350 sq ft

5820 S Washtenaw Ave, Chicago, IL 60629

Property at 5614 S Kolmar Ave, Chicago, IL 60629, 3 beds, 1.5 baths

$277,654

3 beds1.5 baths1,746 sq ft

5614 S Kolmar Ave, Chicago, IL 60629

Property at 5224 S Morgan St, Chicago, IL 60609, 5 beds, 2 baths

$260,000

5 beds2 baths— sq ft

5224 S Morgan St, Chicago, IL 60609

Property at 5752 S Paulina St, Chicago, IL 60636, 4 beds, 2 baths

$99,000

4 beds2 baths1,332 sq ft

5752 S Paulina St, Chicago, IL 60636

Property at 6543 S Washtenaw Ave, Chicago, IL 60629, 6 beds, 3 baths

$399,000

6 beds3 baths— sq ft

6543 S Washtenaw Ave, Chicago, IL 60629

Property at 6155 S Whipple Ave, Chicago, IL 60629, 8 beds, 6 baths

$320,000

8 beds6 baths— sq ft

6155 S Whipple Ave, Chicago, IL 60629

Property at 4036 W 57th St, Chicago, IL 60629, 3 beds, 1 bath

$349,900

3 beds1 bath1,200 sq ft

4036 W 57th St, Chicago, IL 60629

Property at 5514 S May St, Chicago, IL 60621, 4 beds, 2 baths

$295,000

4 beds2 baths— sq ft

5514 S May St, Chicago, IL 60621

Property at 7205 S Hamlin Ave, Chicago, IL 60629, 5 beds, 2 baths

$359,900

5 beds2 baths1,080 sq ft

7205 S Hamlin Ave, Chicago, IL 60629

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

$279,000

6 beds2 baths1,900 sq ft

6627 S Marshfield Ave, Chicago, IL 60636

Property at 7017 S Hermitage Ave, Chicago, IL 60636, 7 beds, 3 baths

$389,900

7 beds3 baths1,148 sq ft

7017 S Hermitage Ave, Chicago, IL 60636

Property at 6953 S Elizabeth St, Chicago, IL 60636, 5 beds, 2 baths

$75,000

5 beds2 baths960 sq ft

6953 S Elizabeth St, Chicago, IL 60636

Property at 6933 S Washtenaw Ave, Chicago, IL 60629, 4 beds, 2 baths

$450,000

4 beds2 baths— sq ft

6933 S Washtenaw Ave, Chicago, IL 60629

Property at 5656 S Marshfield Ave, Chicago, IL 60636, 2 baths

$565,000

0 beds2 baths7,788 sq ft

5656 S Marshfield Ave, Chicago, IL 60636

Property at 6144 S Bishop St, Chicago, IL 60636, 6 beds, 3 baths

$347,000

6 beds3 baths— sq ft

6144 S Bishop St, Chicago, IL 60636

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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.

Vintage Homes for Sale in Southwest Side

There are currently 447 vintage 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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