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

453 homes

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ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Where charm meets space and every detail says welcome home. This 4-bedroom stunner features 2 full spa-inspired baths, a first-floor bedroom, and an open kitchen that's perfect for cooking or mingling. Downstairs, enjoy a large finished basement made for entertaining - movie nights, game days, or celebrations Outside, you'll find a spacious yard, covered entertainment space, and a monster-size garage ready for your biggest truck or weekend toys. Come see this home today. This home qualifies for grants

$350,000

4 beds2 baths— sq ft

6724 S Kolin Ave, Chicago, IL 60629

Spacious yard • Finished basement • 3,746 sq ft lot

$430,000

5 beds3 baths— sq ft

7154 S Rockwell St, Chicago, IL 60629

3,125 sq ft lot • 2 garage spots • Built 1927

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
COURT ORDERS SALE. A two-unit brick building is available for sale in Chicago Lawn Great opportunity for investors. Property features two duplexed units, each with 4 bedrooms and 2 full bathrooms. Both units are separately metered for gas and electric, keeping operating costs low. Forced air and laundry in each unit. Strong rental potential with spacious layouts ideal for long-term tenants. Convenient location near public transportation, schools, and retail. Turn-key building ready to add to your portfolio or for an owner-occupant seeking rental income. This is an as-is, where is sale with no warranties, representations, prorations, or survey.

8 beds2 baths— sq ft

6953 S Artesian Ave, Chicago, IL 60629

Forced air • Duplexed units • Separately metered

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Prime Location Great Opportunity to own a Restaurant Business. with 2 Apartments Live in One. Rent the Other Prime Location Ample Parking For 28 Cars This is a Golden & Unique opportunity for Smart Investor. .. Building and Restaurant in Great Condition. For Sale Building and business license . .all current inventory and fixtures Included . .. Please Do Not Approach Clients Or Staff under any Circumstances. . for More Details Contact listing Agent

$875,000

— beds— baths— sq ft

5960 S Archer Ave, Chicago, IL 60638

Ample parking • 4,750 sq ft lot • Built 1955

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Discover an incredible opportunity for investors and owner-occupants in this versatile multi-unit property. Featuring two spacious units plus a nonconforming basement AND a coach house unlocks a ton of income potential. Units 1 and 2 offer 3 bedrooms and 1 bathroom, ideal for owner-occupants, investors, or those exploring short-term rental opportunities. Both units feature generous layouts with abundant natural light and separate utilities. A large unfinished attic offers additional storage or the potential to expand. .perfect for a duplex-up conversion, studio space, or guest suite. The recently updated second-floor unit is ready for a new tenant or owner, complete with a brand-new stove a

$275,000

8 beds3 baths— sq ft

5756 S Princeton Ave, Chicago, IL 60621

Generous layouts • Coach house • Multi-unit property

Property at 5205 S Linder Ave, Chicago, IL 60638, 3 beds, 2 baths

$320,000

3 beds2 baths1,200 sq ft

5205 S Linder Ave, Chicago, IL 60638

Property at 1705 W 35th St, Chicago, IL 60609, 6 beds, 2 baths

$498,000

6 beds2 baths— sq ft

1705 W 35th St, Chicago, IL 60609

Property at 5125 S Elizabeth St, Chicago, IL 60609, 7 beds, 4 baths

$469,000

7 beds4 baths— sq ft

5125 S Elizabeth St, Chicago, IL 60609

Property at 6227 S May St, Chicago, IL 60621, 6 beds, 3 baths

$199,900

6 beds3 baths— sq ft

6227 S May St, Chicago, IL 60621

Property at 4824 S Kildare Ave, Chicago, IL 60632, 4 beds, 2 baths

$345,000

4 beds2 baths— sq ft

4824 S Kildare Ave, Chicago, IL 60632

Property at 2733 W 38th St, Chicago, IL 60632, 5 beds, 2 baths

$419,887

5 beds2 baths2,200 sq ft

2733 W 38th St, Chicago, IL 60632

Property at 3439 W 66th Pl, Chicago, IL 60629, 3 beds, 2 baths

$348,500

3 beds2 baths2,080 sq ft

3439 W 66th Pl, Chicago, IL 60629

Property at 6339 S Troy St, Chicago, IL 60629, 4 beds, 2 baths

$307,900

4 beds2 baths1,890 sq ft

6339 S Troy St, Chicago, IL 60629

Property at 5142 S Mulligan Ave, Chicago, IL 60638, 4 beds, 2 baths

$425,000

4 beds2 baths1,962 sq ft

5142 S Mulligan Ave, Chicago, IL 60638

Property at 2735 W 36th St, Chicago, IL 60632, 5 beds, 2.5 baths

$369,000

5 beds2.5 baths1,070 sq ft

2735 W 36th St, Chicago, IL 60632

Property at 7342 S Aberdeen St, Chicago, IL 60621, 4 beds, 1.5 baths

$219,000

4 beds1.5 baths2,100 sq ft

7342 S Aberdeen St, Chicago, IL 60621

Property at 3801 W 69th St, Chicago, IL 60629, 4 beds, 3 baths

$399,900

4 beds3 baths1,500 sq ft

3801 W 69th St, Chicago, IL 60629

Property at 5225 S Wood St, Chicago, IL 60609, 3 beds, 2 baths

$85,000

3 beds2 baths672 sq ft

5225 S Wood St, Chicago, IL 60609

Property at 5626 S Maplewood Ave, Chicago, IL 60629, 4 beds, 2 baths

$199,000

4 beds2 baths1,566 sq ft

5626 S Maplewood Ave, Chicago, IL 60629

Property at 6642 S Wolcott Ave, Chicago, IL 60636, 5 beds, 1 bath

$235,000

5 beds1 bath1,100 sq ft

6642 S Wolcott Ave, Chicago, IL 60636

Property at 3814 W 69th St, Chicago, IL 60629, 2 beds, 1 bath

$189,950

2 beds1 bath4,125 sq ft

3814 W 69th St, Chicago, IL 60629

Property at 5919 S Rockwell St, Chicago, IL 60629, 5 beds, 2 baths

$420,000

5 beds2 baths— sq ft

5919 S Rockwell St, Chicago, IL 60629

Property at 7023 S Aberdeen St, Chicago, IL 60621, 4 beds, 2 baths

$255,000

4 beds2 baths— sq ft

7023 S Aberdeen St, Chicago, IL 60621

Property at 6336 S Ada St, Chicago, IL 60636, 4 beds, 4.5 baths

$225,000

4 beds4.5 baths— sq ft

6336 S Ada St, Chicago, IL 60636

Property at 7336 S Emerald Ave, Chicago, IL 60621, 6 beds, 3 baths

$399,900

6 beds3 baths— sq ft

7336 S Emerald Ave, Chicago, IL 60621

Property at 7216 S Green St, Chicago, IL 60621, 7 beds, 2 baths

$214,700

7 beds2 baths— sq ft

7216 S Green St, Chicago, IL 60621

Property at 3933 W 63rd St, Chicago, IL 60629, 9 beds, 3 baths

$850,000

9 beds3 baths7,037 sq ft

3933 W 63rd St, Chicago, IL 60629

Property at 6054 W 64th St, Chicago, IL 60638, 5 beds, 3 baths

$439,900

5 beds3 baths— sq ft

6054 W 64th St, Chicago, IL 60638

Property at Sign in for address, Chicago, IL 60629, 5 beds, 3 baths

$395,900

5 beds3 baths1,102 sq ft

Property at 6419 S Morgan St, Chicago, IL 60621, 4 beds, 4 baths

$395,000

4 beds4 baths— sq ft

6419 S Morgan St, Chicago, IL 60621

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 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 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 5317 S Campbell Ave, Chicago, IL 60632, 7 beds, 3 baths

$499,900

7 beds3 baths1,046 sq ft

5317 S Campbell Ave, Chicago, IL 60632

Property at 5935 S Elizabeth St, Chicago, IL 60636, 7 beds, 3 baths

$139,900

7 beds3 baths— sq ft

5935 S Elizabeth St, Chicago, IL 60636

Property at 6731 S Kolin Ave, Chicago, IL 60629, 3 beds, 2 baths

$350,000

3 beds2 baths1,262 sq ft

6731 S Kolin Ave, Chicago, IL 60629

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 4158 W 58th Pl #4158, Chicago, IL 60629, 3 beds, 2 baths

$354,000

3 beds2 baths1,108 sq ft

4158 W 58th Pl #4158, Chicago, IL 60629

Property at 4845 S Throop St, Chicago, IL 60609, 4 beds, 2 baths

$299,900

4 beds2 baths— sq ft

4845 S Throop St, Chicago, IL 60609

Property at Sign in for address, Chicago, IL 60636, 3 beds, 2 baths

$290,000

3 beds2 baths1,863 sq ft

Property at 6037 S Mason Ave, Chicago, IL 60638, 5 beds, 3 baths

$455,000

5 beds3 baths2,760 sq ft

6037 S Mason Ave, Chicago, IL 60638

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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 453 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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