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

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ABOUT THIS HOME
Vintage 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
Vintage Home for sale in Southwest Side, IL:
Great opportunity for investors or owner-occupants looking for a solid rehab project! This classic two-flat offers a 3-bedroom, 1-bath unit on the second floor and a 2-bedroom, 1-bath unit on the first floor, with the option to duplex down into the unfinished basement to add extra bedrooms and bathrooms. The property is structurally sound with a dry basement and ready for your renovation vision. Needs a full rehab but is currently occupiable. Cash or 203k financing preferred.

$160,000

5 beds2 baths— sq ft

7348 S Lowe Ave, Chicago, IL 60621

Unfinished basement • Structurally sound • Dry basement

ABOUT THIS HOME
Vintage 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

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
LISTED FOR SALE ONLY, NOT LISTED FOR RENT. So much space for the Money!! This 1.5 story home offers over 1700 sq ft of living space, 3 bedrooms and 2 full baths. The main level has a large living room, formal dining area and a ceramic tiled kitchen featuring white cabinetry and black appliances. The second level is fully finished complete with a huge primary bedroom and full bath. Additional den area on the 2nd level as well-perfect for a play area or office. 2 More bedrooms and full bath on the main level. White trim and doors throughout. Ceramic tiled floors and tub/shower surrounds in both baths. Full basement has plenty of storage area and laundry room. Other amenities include a front p

$349,900

3 beds2 baths1,744 sq ft

6152 S Austin Ave, Chicago, IL 60638

Black appliances • Front porch • Den area

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Incredible Investment Opportunity in Prime Chicago Location! This solid 4-unit building offers endless potential for investors or owner-occupants looking to build equity. Each unit boasts generous space and great natural light. The unfinished basement provides a blank canvas-perfect for adding additional living space, laundry, or storage. Enjoy a fully fenced-in yard, ideal for outdoor entertaining or potential garden use. Conveniently located near public transit, shops, and dining. Whether you're looking to renovate, rent, or live-in and lease the rest, this property is a must-see. Sold As-Is-bring your vision and make it yours!

$275,000

8 beds4 baths— sq ft

5517 S Justine St, Chicago, IL 60636

Unfinished basement • 4 unit building • Fully fenced in yard

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

$409,000

5 beds2 baths1,415 sq ft

6441 S Campbell Ave, Chicago, IL 60629

Property at 4634 S Sawyer Ave, Chicago, IL 60632, 5 beds, 4 baths

$419,000

5 beds4 baths— sq ft

4634 S Sawyer Ave, Chicago, IL 60632

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 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 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 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 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 5758 W 65th St, Chicago, IL 60638

$849,000

— beds— baths— sq ft

5758 W 65th St, Chicago, IL 60638

Property at 7338 S Stewart Ave, Chicago, IL 60621, 9 beds, 4 baths

$459,000

9 beds4 baths— sq ft

7338 S Stewart Ave, 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 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 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 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 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 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 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 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 6113 S Sacramento Ave, Chicago, IL 60629, 5 beds, 3 baths

$489,900

5 beds3 baths— sq ft

6113 S Sacramento Ave, Chicago, IL 60629

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 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 7137 S Carpenter St, Chicago, IL 60621, 7 beds, 3 baths

$83,900

7 beds3 baths— sq ft

7137 S Carpenter St, Chicago, IL 60621

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 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 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 3516 S Damen Ave, Chicago, IL 60609, 3 beds, 2.5 baths

$384,500

3 beds2.5 baths1,280 sq ft

3516 S Damen Ave, Chicago, IL 60609

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

$280,000

4 beds2 baths— sq ft

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 5622 S Oak Park Ave, Chicago, IL 60638, 4 beds, 4 baths

$699,900

4 beds4 baths2,163 sq ft

5622 S Oak Park Ave, Chicago, IL 60638

Property at 6929 S Loomis Blvd, Chicago, IL 60636, 5 beds, 3 baths

$255,900

5 beds3 baths1,000 sq ft

6929 S Loomis Blvd, Chicago, IL 60636

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Based on information submitted to the MLS GRID as of Fri Nov 28 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 454 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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