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

459 homes

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Recommended

$175,000

2 beds1 bath1,037 sq ft

Close to the lake • Historic home • $165 HOA

NEW 31 HRS AGO

$430,000

5 beds2 baths— sq ft

Solid wood cabinets • Modern upgrades • Led lighting

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Stunning Rehabbed Brick 2-Flat in Auburn Park - Investor or Owner-Occupant Dream! Introducing an incredible opportunity to own a beautifully renovated 7-bedroom, 4-bathroom brick 2-flat nestled in the heart of Auburn Park-a growing and well-connected community on Chicago's South Side. Whether you're an investor seeking turnkey rental income or an owner-occupant looking to house-hack, this meticulously rehabbed property checks every box.

$464,999

7 beds4 baths— sq ft

7621 S Normal Ave, Chicago, IL 60620

6,534 sq ft lot • 2 garage spots • Built 1907

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Presenting 7200-02 S. Stony Island Avenue, a 24-unit multifamily investment opportunity located in the rapidly appreciating South Shore neighborhood of Chicago. This stately brick walk-up offers a highly desirable unit mix of twelve (12) spacious 2 bed / 1 bath and twelve (12) 1 bed / 1 bath apartments. The property has been meticulously maintained with significant capital improvements, blending modern upgrades with timeless vintage character. Each unit features expansive floor plans, large living rooms, generous bedroom sizes, and abundant natural light. Interior renovations include condo-quality finishes such as stainless steel appliances, in-unit laundry, updated kitchens and baths, an

$3,300,000

36 beds24 baths— sq ft

7200 S Stony Island Ave, Chicago, IL 60649

Unit mix • Vintage character • Modern upgrades

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Attention Investors & Rehabbers!!! Fantastic value-add opportunity to own a 4 bed, 1.5 bath home in Greater Grand Crossing. Solid bones with strong upside potential. Property is being sold As-Is with no repairs or credits. Clean title. Cash or hard money only. Bring your vision! Ideal for a fix-and-rent, fix-and-resell, or owner-occupant renovation strategy. Strong rental demand in the area with rents around $2,400. This property is available through online auction date Dec 10,2025.

$60,000

4 beds1.5 baths1,435 sq ft

7829 S Champlain Ave, Chicago, IL 60619

Built 1908 • Listed 6 days

Property at 7412 S Phillips Ave, Chicago, IL 60649, 4 beds, 2 baths

$299,000

4 beds2 baths2,328 sq ft

7412 S Phillips Ave, Chicago, IL 60649

Property at 2935 S Emerald Ave, Chicago, IL 60616, 5 beds, 2 baths

$365,000

5 beds2 baths1,240 sq ft

2935 S Emerald Ave, Chicago, IL 60616

Property at 7127 S Saint Lawrence Ave, Chicago, IL 60619, 4 beds, 2.5 baths

$239,900

4 beds2.5 baths2,164 sq ft

7127 S Saint Lawrence Ave, Chicago, IL 60619

Property at 3329 S Racine Ave, Chicago, IL 60608, 3 beds, 2 baths

$399,900

3 beds2 baths— sq ft

3329 S Racine Ave, Chicago, IL 60608

Property at 4331 S Evans Ave, Chicago, IL 60653, 4 beds, 3 baths

$520,000

4 beds3 baths2,100 sq ft

4331 S Evans Ave, Chicago, IL 60653

Property at 7644 S Constance Ave, Chicago, IL 60649, 4 beds, 3 baths

$400,000

4 beds3 baths3,400 sq ft

7644 S Constance Ave, Chicago, IL 60649

Property at 7019 S Indiana Ave, Chicago, IL 60637, 5 beds, 2 baths

$89,000

5 beds2 baths2,100 sq ft

7019 S Indiana Ave, Chicago, IL 60637

Property at 7711 S Champlain Ave, Chicago, IL 60619, 4 beds, 2 baths

$85,000

4 beds2 baths1,797 sq ft

7711 S Champlain Ave, Chicago, IL 60619

Property at 1404 W Fuller St, Chicago, IL 60608, 5 beds, 2 baths

$319,900

5 beds2 baths2,500 sq ft

1404 W Fuller St, Chicago, IL 60608

Property at 7339 S Evans Ave, Chicago, IL 60619, 4 beds, 3 baths

$325,000

4 beds3 baths2,700 sq ft

7339 S Evans Ave, Chicago, IL 60619

Property at 7646 S Wabash Ave, Chicago, IL 60619, 4 beds, 4 baths

$360,000

4 beds4 baths2,867 sq ft

7646 S Wabash Ave, Chicago, IL 60619

Property at 5141 S Wabash Ave, Chicago, IL 60615, 4 beds, 3.5 baths

$610,000

4 beds3.5 baths3,100 sq ft

5141 S Wabash Ave, Chicago, IL 60615

Property at 2849 S Normal Ave, Chicago, IL 60616, 6 beds, 2.5 baths

$432,000

6 beds2.5 baths— sq ft

2849 S Normal Ave, Chicago, IL 60616

Property at 3240 S Parnell Ave, Chicago, IL 60616, 4 beds, 2 baths

$379,000

4 beds2 baths— sq ft

3240 S Parnell Ave, Chicago, IL 60616

Property at 7533 S Eberhart Ave, Chicago, IL 60619, 4 beds, 2 baths

$199,999

4 beds2 baths2,200 sq ft

7533 S Eberhart Ave, Chicago, IL 60619

Property at 809 E 40th St Unit 4-4, Chicago, IL 60653, 2 beds, 2 baths

$235,000

2 beds2 baths1,300 sq ft

809 E 40th St Unit 4-4, Chicago, IL 60653

Property at 6527 S Vernon Ave, Chicago, IL 60637, 7 beds, 3 baths

$499,500

7 beds3 baths— sq ft

6527 S Vernon Ave, Chicago, IL 60637

Property at 4507 S Michigan Ave, Chicago, IL 60653, 9 beds, 6 baths

$675,000

9 beds6 baths— sq ft

4507 S Michigan Ave, Chicago, IL 60653

Property at 7545 S Perry Ave, Chicago, IL 60620, 6 beds, 3 baths

$359,900

6 beds3 baths2,969 sq ft

7545 S Perry Ave, Chicago, IL 60620

Property at 3602 S Prairie Ave, Chicago, IL 60653, 6 beds, 4 baths

$699,000

6 beds4 baths2,700 sq ft

3602 S Prairie Ave, Chicago, IL 60653

Property at 7435 S Wentworth Ave, Chicago, IL 60621, 4 beds, 2 baths

$104,900

4 beds2 baths— sq ft

7435 S Wentworth Ave, Chicago, IL 60621

Property at 601 E 32nd St #400, Chicago, IL 60616, 2 beds, 2 baths

$139,900

2 beds2 baths1,500 sq ft

601 E 32nd St #400, Chicago, IL 60616

Property at Sign in for address, Chicago, IL 60649, 11 beds, 7 baths

$550,000

11 beds7 baths— sq ft

Property at 7437 S Merrill Ave, Chicago, IL 60649, 4 beds, 3 baths

$316,999

4 beds3 baths2,300 sq ft

7437 S Merrill Ave, Chicago, IL 60649

Property at 430 E 46th St, Chicago, IL 60653, 5 beds, 3.5 baths

$499,900

5 beds3.5 baths2,500 sq ft

430 E 46th St, Chicago, IL 60653

Property at 7449 S Vernon Ave, Chicago, IL 60619, 4 beds, 2.5 baths

$244,900

4 beds2.5 baths2,214 sq ft

7449 S Vernon Ave, Chicago, IL 60619

Property at 7535 S Vernon Ave, Chicago, IL 60619, 4 beds, 2 baths

$204,999

4 beds2 baths1,969 sq ft

7535 S Vernon Ave, Chicago, IL 60619

Property at 6731 S Cregier Ave, Chicago, IL 60649, 4 beds, 3 baths

$735,000

4 beds3 baths3,000 sq ft

6731 S Cregier Ave, Chicago, IL 60649

Property at 7841 S Burnham Ave, Chicago, IL 60649, 5 beds, 2 baths

$349,000

5 beds2 baths— sq ft

7841 S Burnham Ave, Chicago, IL 60649

Property at 2925 S Shields Ave, Chicago, IL 60616, 8 beds, 3 baths

$580,000

8 beds3 baths— sq ft

2925 S Shields Ave, Chicago, IL 60616

Property at 7408 S Maryland Ave, Chicago, IL 60619, 9 beds, 5 baths

$153,000

9 beds5 baths— sq ft

7408 S Maryland Ave, Chicago, IL 60619

Property at 6156 S Indiana Ave, Chicago, IL 60637, 7 beds, 2 baths

$429,900

7 beds2 baths— sq ft

6156 S Indiana Ave, Chicago, IL 60637

Property at 6150 S Ingleside Ave, Chicago, IL 60637, 4 beds, 3.5 baths

$599,000

4 beds3.5 baths2,943 sq ft

6150 S Ingleside Ave, Chicago, IL 60637

Property at 3309 S Lowe Ave, Chicago, IL 60616, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths3,000 sq ft

3309 S Lowe Ave, Chicago, IL 60616

Property at 7431 S Kimbark Ave, Chicago, IL 60619, 6 beds, 3 baths

$180,000

6 beds3 baths— sq ft

7431 S Kimbark Ave, Chicago, IL 60619

Property at 7804 S Burnham Ave, Chicago, IL 60649, 9 beds, 6 baths

$394,000

9 beds6 baths— sq ft

7804 S Burnham 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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