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

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ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Recently remodeled - 2 story unit @ Bronzeville Lofts! New kitchen, new bathrooms! New flooring and lighting throughout! Includes 2 bedrooms, 2 bathrooms, in-unit laundry, fireplace and private balcony with skyline view!! Features gorgeous exposed brick, 2 story living room, breakfast bar off kitchen, tons of natural light, rustic timber ceiling and exposed beams throughout! One exterior parking space included! Building has new roof. Conveniently located, close to lake Michigan, expressway, Lake Shore Drive, Green Line, Metra and South Loop. Building is pet friendly. Sold as-is.

$398,400

2 beds2 baths1,757 sq ft

50 E 26th St #406, Chicago, IL 60616

Remodeled • New kitchen • Private balcony

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Landmark restoration distinguishes this large 2-story with basement just waiting for you and your family to call it home. The remodeled, move-in ready interior begins with a welcoming enclosed front porch that doubles as a foyer, leading into a spacious living/dining room combo and continuing into a fully remodeled kitchen (refrigerator and oven/range to be installed prior to closing). The main level offers two bedrooms and a beautifully updated full bathroom. Upstairs features its own private side-porch entrance, opening into a second living or family room, two generously sized bedrooms, a second fully remodeled bathroom, and a spacious loft area. The semi-finished basement provides even m

$214,873

4 beds2 baths2,000 sq ft

6336 S Saint Lawrence Ave, Chicago, IL 60637

Second living room • Spacious loft area • Enclosed front porch

$50,000

2 beds1 bath800 sq ft

2212 E 70th St Unit 2D, Chicago, IL 60649

Cultural center • Turnkey rental • South shore beach

$119,000

3 beds3 baths1,710 sq ft

5140 S King Dr Unit A1, Chicago, IL 60615

In unit laundry • View of the park • $427 HOA

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
A ROOF OVER YOUR HEAD AND MONEY IN YOUR POCKETS. .. .. .. .. .RECENTLY RENOVATED 3 UNIT IN EAST WOODLAWN. 1ST FLOOR DUPLEX FEATURES 3 BED/3 BATH, PERFECT FOR OWNER'S UNIT. 2ND AND 3RD FLOORS HAVE 3 BED/2 BATH. HARDWOOD FLOORS THROUGHOUT. LAUNDRY IN EACH UNIT. INDIVIDUAL MECHANICALS. SECURED GATED PARKING. PERFECT INVESTMENT: RENT NOW AND SELL AS CONDOS LATER, OR LIVE-IN AND LET TENANTS PAY THE MORTGAGE. STEPS TO HYDE PARK, MUSEUM OF SCIENCE AND INDUSTRY AND OBAMA LIBRARY.

$759,000

9 beds7 baths— sq ft

6406 S Ingleside Ave, Chicago, IL 60637

Steps to hyde park • Recently renovated • Hardwood floors

Property at 1424 E Hyde Park Blvd #2, Chicago, IL 60615, 2 beds, 1 bath

$325,000

2 beds1 bath1,315 sq ft

1424 E Hyde Park Blvd #2, Chicago, IL 60615

Property at 7045 S Wabash Ave, Chicago, IL 60637, 4 beds, 2 baths

$155,000

4 beds2 baths— sq ft

7045 S Wabash Ave, Chicago, IL 60637

Property at 143 W 74th St, Chicago, IL 60621, 5 beds, 2.5 baths

$144,900

5 beds2.5 baths— sq ft

143 W 74th St, Chicago, IL 60621

Property at 2948 S Lyman St, Chicago, IL 60608, 4 beds, 2 baths

$405,000

4 beds2 baths1,400 sq ft

2948 S Lyman St, Chicago, IL 60608

Property at 7431 S Perry Ave, Chicago, IL 60621, 3 beds, 2 baths

$139,000

3 beds2 baths851 sq ft

7431 S Perry Ave, Chicago, IL 60621

Property at 737 E 50th St #4, Chicago, IL 60615, 4 beds, 4 baths

$324,900

4 beds4 baths2,412 sq ft

737 E 50th St #4, Chicago, IL 60615

Property at 5050 S East End Ave Unit 7A, Chicago, IL 60615, 2 beds, 1 bath

$165,000

2 beds1 bath1,190 sq ft

5050 S East End Ave Unit 7A, Chicago, IL 60615

Property at 2212 E 70th St Unit 3A, Chicago, IL 60649, 2 beds, 1 bath

$50,000

2 beds1 bath1,000 sq ft

2212 E 70th St Unit 3A, Chicago, IL 60649

Property at 7836 S Saint Lawrence Ave, Chicago, IL 60619, 4 beds, 2.5 baths

$295,000

4 beds2.5 baths1,002 sq ft

7836 S Saint Lawrence Ave, Chicago, IL 60619

Property at 5000 S East End Ave Unit 2D, Chicago, IL 60615, 2 beds, 2 baths

$235,000

2 beds2 baths1,600 sq ft

5000 S East End Ave Unit 2D, Chicago, IL 60615

Property at 1640 E 50th St Unit 13B, Chicago, IL 60615, 3 beds, 3 baths

$319,900

3 beds3 baths2,200 sq ft

1640 E 50th St Unit 13B, Chicago, IL 60615

Property at 6726 S Merrill Ave, Chicago, IL 60649, 3 beds, 2.5 baths

$235,000

3 beds2.5 baths1,668 sq ft

6726 S Merrill Ave, Chicago, IL 60649

Property at 5942 S Calumet Ave, Chicago, IL 60637, 12 beds, 4 baths

$585,000

12 beds4 baths— sq ft

5942 S Calumet Ave, Chicago, IL 60637

Property at 7000 S Eberhart Ave, Chicago, IL 60637, 4 beds, 2.5 baths

$299,995

4 beds2.5 baths2,000 sq ft

7000 S Eberhart Ave, Chicago, IL 60637

Property at 1725 E 67th St Unit 1F, Chicago, IL 60649, 2 beds, 2 baths

$149,900

2 beds2 baths— sq ft

1725 E 67th St Unit 1F, Chicago, IL 60649

Property at 6834 S Lafayette Ave, Chicago, IL 60621, 5 beds, 2 baths

$70,000

5 beds2 baths— sq ft

6834 S Lafayette Ave, Chicago, IL 60621

Property at 7337 S University Ave, Chicago, IL 60619, 3 beds, 2 baths

$232,500

3 beds2 baths984 sq ft

7337 S University Ave, Chicago, IL 60619

Property at 4014 S Drexel Blvd Unit 4R, Chicago, IL 60653, 3 beds, 2 baths

$310,000

3 beds2 baths1,900 sq ft

4014 S Drexel Blvd Unit 4R, Chicago, IL 60653

Property at 1234 E Madison Park Ave Unit 3W, Chicago, IL 60615, 4 beds, 3 baths

$685,000

4 beds3 baths2,400 sq ft

1234 E Madison Park Ave Unit 3W, Chicago, IL 60615

Property at 5140 S Kimbark Ave, Chicago, IL 60615, 27 beds, 18 baths

$2,990,000

27 beds18 baths— sq ft

5140 S Kimbark Ave, Chicago, IL 60615

Property at 5200 S Woodlawn Ave, Chicago, IL 60615, 47 beds, 37 baths

$6,290,000

47 beds37 baths65,000 sq ft

5200 S Woodlawn Ave, Chicago, IL 60615

Property at 7047 S Eberhart Ave, Chicago, IL 60637, 5 beds, 2.5 baths

$134,900

5 beds2.5 baths2,400 sq ft

7047 S Eberhart Ave, Chicago, IL 60637

Property at 7734 S Langley Ave, Chicago, IL 60619, 4 beds, 3 baths

$349,000

4 beds3 baths4,647 sq ft

7734 S Langley Ave, Chicago, IL 60619

Property at 5341 S Wabash St #5347, Chicago, IL 60615, 2 beds, 2 baths

$124,900

2 beds2 baths600 sq ft

5341 S Wabash St #5347, Chicago, IL 60615

Property at 1526 E 72nd Pl, Chicago, IL 60619, 12 beds, 6 baths

$315,000

12 beds6 baths5,736 sq ft

1526 E 72nd Pl, Chicago, IL 60619

Property at 1226 W 31st Pl, Chicago, IL 60608, 22 beds, 11 baths

$1,295,000

22 beds11 baths— sq ft

1226 W 31st Pl, Chicago, IL 60608

Property at 541 E 60th St Unit 1A, Chicago, IL 60637, 2 beds, 1 bath

$115,000

2 beds1 bath900 sq ft

541 E 60th St Unit 1A, Chicago, IL 60637

Property at 3405 S Union St, Chicago, IL 60616, 12 beds, 6 baths

$1,199,000

12 beds6 baths— sq ft

3405 S Union St, Chicago, IL 60616

Property at 442-444 E 48th St, Chicago, IL 60615, 29 beds, 23 baths

$4,000,000

29 beds23 baths— sq ft

442-444 E 48th St, Chicago, IL 60615

Property at 6442 S Ingleside Ave, Chicago, IL 60637, 4 beds, 3.5 baths

$509,900

4 beds3.5 baths2,646 sq ft

6442 S Ingleside Ave, Chicago, IL 60637

Property at 7628 S Evans Ave, Chicago, IL 60619, 4 beds, 3 baths

$290,000

4 beds3 baths1,762 sq ft

7628 S Evans Ave, Chicago, IL 60619

Property at 5742 S King Dr #3, Chicago, IL 60637, 3 beds, 2 baths

$175,000

3 beds2 baths1,375 sq ft

5742 S King Dr #3, Chicago, IL 60637

Property at 7444 S Merrill Ave, Chicago, IL 60649, 4 beds, 2.5 baths

$179,900

4 beds2.5 baths1,350 sq ft

7444 S Merrill Ave, Chicago, IL 60649

Property at 6121 S Woodlawn Ave #2, Chicago, IL 60637, 4 beds, 2 baths

$399,000

4 beds2 baths— sq ft

6121 S Woodlawn Ave #2, Chicago, IL 60637

Property at 6605 S Maryland Ave, Chicago, IL 60637, 9 beds, 3 baths

$474,999

9 beds3 baths— sq ft

6605 S Maryland Ave, Chicago, IL 60637

Property at 4940 S East End Ave Unit 2C, Chicago, IL 60615, 1 bed, 1 bath

$149,900

1 bed1 bath860 sq ft

4940 S East End Ave Unit 2C, Chicago, IL 60615

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Based on information submitted to the MLS GRID as of Sun Dec 07 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 South Side

There are currently 459 vintage homes for sale in South 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 South Side stay on the market for 79 days and receive 1 offers. Popular neighborhoods include Bronzeville, South Loop, West Loop, Bridgeport, and Hyde Park. This map is refreshed with the newest listings in South Side every 15 minutes.

In the past month, 98 homes have been sold in South Side. In addition to houses in South Side, there were also 412 condos, 47 townhouses, and 235 multi-family units for sale in South Side last month. Find your dream home in South 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 South Side are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in South Side. If you're looking to sell your home in the South Side area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in South 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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