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

459 homes

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ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Solid three-bedroom brick bungalow situated on a nice lot with side drive and 2-car garage. Interior features a traditional living room and dining room, 1.5 baths, and a spacious enclosed heated rear porch that leads to a deck. Full basement offers expansion possibilities. This property is ready for your vision-update, modernize, or restore to its original charm. Perfect for rehabbers and investors looking for their next project. Don't miss the opportunity to add value and maximize returns! Property is V. A. owned & sold in "as is/where is" condition. Seller will make no repairs. Property was built prior to 1978 and lead based paint may potentially exist. This property may q

$65,000

3 beds1.5 baths1,385 sq ft

7022 S Kimbark Ave, Chicago, IL 60637

Brick bungalow • Full basement • Deck

$174,999

3 beds2 baths1,149 sq ft

7846 S Maryland Ave, Chicago, IL 60619

Parking • Built 1920 • Listed 31 days

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Property sits on a nice size lot with an additional lot attached for your enjoyment. Located in Greater grand crossing with 2 stories of living space, 4 bedrooms, 2 1/2 bathrooms, wrought iron fence, privacy fence and 2 car garage. Home needs some TLC. Great schools and close to the expressway with easy access to the loop. Home needs some TLC and sold As Is. Schedule your appointment today and make this your home

$275,000

4 beds3.5 baths1,810 sq ft

7428 S Maryland St, Chicago, IL 60619

Nice size lot • Privacy fence • Additional lot

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
This is a unique opportunity to reside in the private residences of Lake Meadows Condo Units. This building is uniquely located moments away from downtown and seconds away from DuSable Lake Shore Drive, with plenty of shopping moments away! The Unit offers 2 spacious bedrooms and 2 Baths with ample closet space throughout. The location has a 24-hour doorperson for your security with a covered garage parking space to boot. Hardwood floors throughout with carpet in the bedrooms for that warm touch in the morning! This is the time to check this out because of the rarity of the corner unit coming available. For those investors that have interest, rentals are allowed! Property sold AS-IS. Sch

$150,000

2 beds2 baths— sq ft

601 E 32nd St #211, Chicago, IL 60616

Uniquely located • 24 hour doorperson • Corner unit

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Rehab Opportunity! This solid brick 2-flat offers incredible potential with much of the renovation already underway. Framing, new electrical service, plumbing rough-ins, and brand new back porches are already in place, saving time and upfront costs for the next owner. Each unit offers a spacious layout with classic Chicago architecture and great natural light. Full basement provides additional options for in-law/ family unit. Perfect for investors or owner-occupants looking to build equity. Conveniently located near public transportation, expressways, and local amenities. Sold as-is - finish the rehab and bring this property to full market value.

$199,900

6 beds4.5 baths— sq ft

4752 S Princeton Ave, Chicago, IL 60609

Solid brick • New back porches • Spacious layout

Property at 6922 S Jeffery Blvd Unit 5N, Chicago, IL 60649, 3 beds, 3 baths

$185,000

3 beds3 baths2,500 sq ft

6922 S Jeffery Blvd Unit 5N, Chicago, IL 60649

Property at 307 E 50th St Unit 307A, Chicago, IL 60615, 2 beds, 1 bath

$167,500

2 beds1 bath850 sq ft

307 E 50th St Unit 307A, Chicago, IL 60615

Property at 6540 S Ingleside Ave, Chicago, IL 60637, 3 beds, 3 baths

$624,900

3 beds3 baths2,880 sq ft

6540 S Ingleside Ave, Chicago, IL 60637

Property at 6832 S South Shore Dr #1, Chicago, IL 60649, 2 beds, 2 baths

$119,000

2 beds2 baths1,500 sq ft

6832 S South Shore Dr #1, Chicago, IL 60649

Property at 3222-3224 S Morgan St, Chicago, IL 60608

$1,475,000

— beds— baths6,660 sq ft

3222-3224 S Morgan St, Chicago, IL 60608

Property at 7853 S South Shore Dr, Chicago, IL 60649, 1 bed

$135,000

1 bed— baths2,393 sq ft

7853 S South Shore Dr, Chicago, IL 60649

Property at 7121 S Yale Ave, Chicago, IL 60621, 6 beds, 2 baths

$375,000

6 beds2 baths2,655 sq ft

7121 S Yale Ave, Chicago, IL 60621

Property at 7832 S Eberhart Ave, Chicago, IL 60619, 5 beds, 2 baths

$307,900

5 beds2 baths3,282 sq ft

7832 S Eberhart Ave, Chicago, IL 60619

Property at 4829 S Champlain Ave, Chicago, IL 60615, 5 beds, 2 baths

$475,000

5 beds2 baths— sq ft

4829 S Champlain Ave, Chicago, IL 60615

Property at 3353 S Aberdeen St, Chicago, IL 60608, 7 beds, 3 baths

$538,800

7 beds3 baths— sq ft

3353 S Aberdeen St, Chicago, IL 60608

Property at 7521 S Ridgeland Ave, Chicago, IL 60649, 4 beds, 2.5 baths

$249,900

4 beds2.5 baths— sq ft

7521 S Ridgeland Ave, Chicago, IL 60649

Property at 7208 S Eberhart Ave, Chicago, IL 60619, 6 beds, 3 baths

$389,000

6 beds3 baths— sq ft

7208 S Eberhart Ave, Chicago, IL 60619

Property at 7125 S University Ave, Chicago, IL 60619, 4 beds, 2 baths

$100,000

4 beds2 baths1,938 sq ft

7125 S University Ave, Chicago, IL 60619

Property at 6511 S Vernon Ave, Chicago, IL 60637, 4 beds, 2 baths

$221,000

4 beds2 baths1,559 sq ft

6511 S Vernon Ave, Chicago, IL 60637

Property at 2115 E 72nd Pl, Chicago, IL 60649, 6 beds, 2.5 baths

$125,000

6 beds2.5 baths— sq ft

2115 E 72nd Pl, Chicago, IL 60649

Property at 2221 E 68th St #3, Chicago, IL 60649, 3 beds, 2 baths

$127,500

3 beds2 baths1,750 sq ft

2221 E 68th St #3, Chicago, IL 60649

Property at 7825 S St Lawrence Ave, Chicago, IL 60619, 3 beds, 2.5 baths

$259,000

3 beds2.5 baths1,700 sq ft

7825 S St Lawrence Ave, Chicago, IL 60619

Property at 2310 S Canal St #210, Chicago, IL 60616, 1 bed, 1 bath

$225,000

1 bed1 bath900 sq ft

2310 S Canal St #210, Chicago, IL 60616

Property at 2310 S Canal St #212, Chicago, IL 60616, 1 bed, 1 bath

$249,900

1 bed1 bath— sq ft

2310 S Canal St #212, Chicago, IL 60616

Property at 5317 S Prairie Ave, Chicago, IL 60615, 3 beds, 3.5 baths

$479,900

3 beds3.5 baths3,109 sq ft

5317 S Prairie Ave, Chicago, IL 60615

Property at 450 W 29th St, Chicago, IL 60616, 9 beds, 6 baths

$680,000

9 beds6 baths— sq ft

450 W 29th St, Chicago, IL 60616

Property at 2906 S Lowe Ave, Chicago, IL 60616, 6 beds, 2 baths

$520,000

6 beds2 baths— sq ft

2906 S Lowe Ave, Chicago, IL 60616

Property at 5410 S Indiana Ave, Chicago, IL 60615, 18 beds, 6 baths

$899,000

18 beds6 baths14,841 sq ft

5410 S Indiana Ave, Chicago, IL 60615

Property at 7642 S Merrill Ave, Chicago, IL 60649, 5 beds, 3.5 baths

$439,900

5 beds3.5 baths1,870 sq ft

7642 S Merrill Ave, Chicago, IL 60649

Property at 4537 S Drexel Blvd #503, Chicago, IL 60653, 1 bed, 1 bath

$215,000

1 bed1 bath900 sq ft

4537 S Drexel Blvd #503, Chicago, IL 60653

Property at 6959 S Calumet Ave, Chicago, IL 60637, 5 beds, 2 baths

$310,000

5 beds2 baths— sq ft

6959 S Calumet Ave, Chicago, IL 60637

Property at 7246 S East End Ave, Chicago, IL 60649, 7 beds, 3 baths

$175,000

7 beds3 baths— sq ft

7246 S East End Ave, Chicago, IL 60649

Property at 2828 S Emerald Ave, Chicago, IL 60616, 6 beds, 3 baths

$599,000

6 beds3 baths— sq ft

2828 S Emerald Ave, Chicago, IL 60616

Property at 7712 S Evans Ave, Chicago, IL 60619, 4 beds, 2 baths

$285,000

4 beds2 baths2,035 sq ft

7712 S Evans Ave, Chicago, IL 60619

Property at 6812 S Saint Lawrence Ave, Chicago, IL 60637, 4 beds, 2 baths

$330,000

4 beds2 baths1,500 sq ft

6812 S Saint Lawrence Ave, Chicago, IL 60637

Property at 765 E 41st St Unit 1A, Chicago, IL 60653, 4 beds, 3 baths

$430,000

4 beds3 baths3,600 sq ft

765 E 41st St Unit 1A, Chicago, IL 60653

Property at 5133 S Greenwood Ave #2, Chicago, IL 60615, 3 beds, 2 baths

$329,000

3 beds2 baths1,700 sq ft

5133 S Greenwood Ave #2, Chicago, IL 60615

Property at 2234 E 70th Pl #1, Chicago, IL 60649, 3 beds, 2 baths

$90,000

3 beds2 baths1,200 sq ft

2234 E 70th Pl #1, Chicago, IL 60649

Property at 1502 E Marquette Rd, Chicago, IL 60637, 5 beds, 3.5 baths

$599,000

5 beds3.5 baths3,700 sq ft

1502 E Marquette Rd, Chicago, IL 60637

Property at 7337 S South Shore Dr #406, Chicago, IL 60649, 1 bed, 1 bath

$63,000

1 bed1 bath— sq ft

7337 S South Shore Dr #406, Chicago, IL 60649

Property at 7450 S Colfax Ave, Chicago, IL 60649, 6 beds, 3 baths

$195,000

6 beds3 baths2,711 sq ft

7450 S Colfax Ave, Chicago, IL 60649

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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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