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:
Welcome home to your City Haven South Condominium! Move in ready! 3 bedrooms 2 bathrooms condo in the Hyde Park- Kenwood historic district. This home sits on a quiet cul-de-sac street close to University of Chicago 10 minute bus ride to the Chicago Loop. This home has a spacious and well designed floor plan and offers an abundance of natural light with a SunRoom, featuring pristine hardwood floors, high ceilings, marble gas fireplace, full size washer and dryer in the unit. Kitchen has granite countertops, quality cabinetry with ample storage, stainless steel appliances and a beautiful backsplash. Primary Bathroom has a timeless design with slate tile and a separate shower with whirlpool

$265,000

3 beds2 baths— sq ft

4740 S Ingleside Ave Unit 2N, Chicago, IL 60615

Sunroom • Marble gas fireplace • Granite countertops

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
CORPORATE OWNED SINGLE-FAMILY HOME SOLD AS-IS WITH A MOTIVATED SELLER. GREAT OPPORTUNITY FOR RESTORATION AT THIS PRICE. VACANT AND EASY TO SHOW. PLEASE INSPECT PRIOR TO SUBMITTING AN OFFER SINCE WE ARE SELLING "AS-IS". Proof of funds required for access and for offers to be considered. PLEASE NOTE: THE SELLER WILL COVER CURRENT AND ALL PRIOR TAX BUT NO CREDIT FOR FUTURE BILLS. NO SURVEY. EXPERIENCED & QUALIFIED DEVELOPERS ONLY. NO wholesale or reselling before rehab is complete. Seller does not collect earnest money, but prefers accelerated closing dates. Property will be transferred via Quit Claim Deed and owners' policy will be provided to insure the transaction. Buyer res

$79,000

3 beds1.5 baths1,200 sq ft

7843 S Langley Ave, Chicago, IL 60619

3,125 sq ft lot • 2 garage spots • Built 1906

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Massive 3-unit building with additional garden unit in Chicago's South Shore, perfect for investors or owner-occupants looking to generate rental income. Each unit offers generous layouts with sun-filled living spaces, hardwood floors, and classic Chicago charm. The property includes three large apartments (approximately 1600 sq ft) plus a fully finished garden unit, providing flexible options for extended family, house hacking, or strong cash flow potential. Located just minutes from the lakefront, South Shore Cultural Center, and new neighborhood development projects, this property combines convenience with opportunity. Easy access to public transit, major roadways, and nearby shops and d

$700,000

9 beds5 baths— sq ft

7759 S Constance Ave, Chicago, IL 60649

Major roadways • Garden unit • Hardwood floors

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Classic brick 2-flat offering income, space, and long-term potential. Each unit features 3 bedrooms, 1.5 baths, and separate utilities with solid structure throughout. Great option for an owner occupant or anyone looking to start building wealth through real estate ownership.

$255,000

6 beds3 baths— sq ft

7407 S Kenwood Ave, Chicago, IL 60619

Built 1878 • Listed 55 days

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
GREAT LOCATION AND INVESTMENT OPPORTUNITY!!! Back of the yards neighborhood! This 2 flat has an unfinished basement with the opportunity to add a 3rd unit! 2 Large 4 Bedroom apartments. Great for live-in owner! First floor unit available for live-in owner! Long term tenant on 2nd floor. Rent is way under market value. Parking on property contains 2 car spots on carport. Large porches for out door space for tenants. Nice yard. Close to Red Line and other public transportation, beautiful parks and lots of shopping!

$324,950

8 beds2 baths— sq ft

4452 S Shields Ave, Chicago, IL 60609

3,900 sq ft lot • 2 parking spots • Listed 112 days

Property at 7321 S South Shore Dr Unit 5A, Chicago, IL 60649, 3 beds, 2.5 baths

$179,900

3 beds2.5 baths2,000 sq ft

7321 S South Shore Dr Unit 5A, Chicago, IL 60649

Property at 7115 S Champlain Ave, Chicago, IL 60619, 7 beds, 2 baths

$415,999

7 beds2 baths— sq ft

7115 S Champlain Ave, Chicago, IL 60619

Property at 5169 S Michigan Ave, Chicago, IL 60615, 9 beds, 3 baths

$699,500

9 beds3 baths— sq ft

5169 S Michigan Ave, Chicago, IL 60615

Property at 6111 S Eberhart Ave, Chicago, IL 60637, 7 beds, 2 baths

$569,900

7 beds2 baths— sq ft

6111 S Eberhart Ave, Chicago, IL 60637

Property at 7220 S Rhodes Ave, Chicago, IL 60619, 7 beds, 2 baths

$235,000

7 beds2 baths— sq ft

7220 S Rhodes Ave, Chicago, IL 60619

Property at 7516 S Lafayette Ave, Chicago, IL 60620, 4 beds, 2 baths

$211,000

4 beds2 baths2,000 sq ft

7516 S Lafayette Ave, Chicago, IL 60620

Property at 7732 S Normal Ave, Chicago, IL 60620, 5 beds, 3 baths

$129,000

5 beds3 baths— sq ft

7732 S Normal Ave, Chicago, IL 60620

Property at 142 W Swann St, Chicago, IL 60609, 5 beds, 2 baths

$329,000

5 beds2 baths798 sq ft

142 W Swann St, Chicago, IL 60609

Property at 7842 S Evans Ave, Chicago, IL 60619, 5 beds, 3 baths

$289,000

5 beds3 baths2,529 sq ft

7842 S Evans Ave, Chicago, IL 60619

Property at 1308 E 56th St #2, Chicago, IL 60637, 1 bed, 1 bath

$250,000

1 bed1 bath900 sq ft

1308 E 56th St #2, Chicago, IL 60637

Property at 7554 S Perry Ave, Chicago, IL 60620, 5 beds, 3 baths

$345,000

5 beds3 baths3,268 sq ft

7554 S Perry Ave, Chicago, IL 60620

Property at 4530 S Prairie Ave Unit 1S, Chicago, IL 60653, 3 beds, 3 baths

$430,000

3 beds3 baths2,076 sq ft

4530 S Prairie Ave Unit 1S, Chicago, IL 60653

Property at 7042 S Eberhart Ave, Chicago, IL 60637, 6 beds, 2.5 baths

$355,000

6 beds2.5 baths2,500 sq ft

7042 S Eberhart Ave, Chicago, IL 60637

Property at 7845 S Yates Blvd, Chicago, IL 60649, 3 beds, 1.5 baths

$139,000

3 beds1.5 baths1,296 sq ft

7845 S Yates Blvd, Chicago, IL 60649

Property at 6830 1/2 S King Dr, Chicago, IL 60637, 3 beds, 2 baths

$49,900

3 beds2 baths1,480 sq ft

6830 1/2 S King Dr, Chicago, IL 60637

Property at 7744 S Rhodes Ave, Chicago, IL 60619, 5 beds, 2.5 baths

$189,000

5 beds2.5 baths— sq ft

7744 S Rhodes Ave, Chicago, IL 60619

Property at 7100 S Prairie Ave, Chicago, IL 60619, 7 beds, 3 baths

$355,000

7 beds3 baths— sq ft

7100 S Prairie Ave, Chicago, IL 60619

Property at 7414 S Colfax Ave, Chicago, IL 60649, 4 beds, 1 bath

$159,000

4 beds1 bath1,224 sq ft

7414 S Colfax Ave, Chicago, IL 60649

Property at 5469 S Ingleside Ave Unit 2N, Chicago, IL 60615, 2 beds, 1 bath

$299,000

2 beds1 bath1,100 sq ft

5469 S Ingleside Ave Unit 2N, Chicago, IL 60615

Property at 5455 S Ingleside Ave Unit 2W, Chicago, IL 60615, 2 beds, 1 bath

$230,000

2 beds1 bath1,100 sq ft

5455 S Ingleside Ave Unit 2W, Chicago, IL 60615

Property at 6619 S Champlain Ave, Chicago, IL 60637, 6 beds, 2 baths

$150,000

6 beds2 baths— sq ft

6619 S Champlain Ave, Chicago, IL 60637

Property at 6620 S Rhodes Ave, Chicago, IL 60637, 6 beds, 2 baths

$200,000

6 beds2 baths— sq ft

6620 S Rhodes Ave, Chicago, IL 60637

Property at 7337 S South Shore Dr #515, Chicago, IL 60649, 2 beds, 1 bath

$81,900

2 beds1 bath1,000 sq ft

7337 S South Shore Dr #515, Chicago, IL 60649

Property at 5900 S King Dr Unit C-3, Chicago, IL 60637, 3 beds, 2 baths

$204,995

3 beds2 baths1,220 sq ft

5900 S King Dr Unit C-3, Chicago, IL 60637

Property at 5900 S King Dr Unit C2, Chicago, IL 60637, 2 beds, 2 baths

$113,040

2 beds2 baths1,220 sq ft

5900 S King Dr Unit C2, Chicago, IL 60637

Property at 5110 S Woodlawn Ave Unit 3H, Chicago, IL 60615, 2 beds, 1 bath

$220,000

2 beds1 bath— sq ft

5110 S Woodlawn Ave Unit 3H, Chicago, IL 60615

Property at 1534 E Marquette Rd, Chicago, IL 60637, 18 beds, 12 baths

$1,460,000

18 beds12 baths— sq ft

1534 E Marquette Rd, Chicago, IL 60637

Property at 638 E 65th St, Chicago, IL 60637, 5 beds, 3.5 baths

$499,000

5 beds3.5 baths3,808 sq ft

638 E 65th St, Chicago, IL 60637

Property at 7245 S Evans Ave, Chicago, IL 60619, 4 beds, 2 baths

$162,000

4 beds2 baths2,000 sq ft

7245 S Evans Ave, Chicago, IL 60619

Property at 6811 S Langley Ave, Chicago, IL 60637, 6 beds, 2 baths

$275,000

6 beds2 baths— sq ft

6811 S Langley Ave, Chicago, IL 60637

Property at 6234 S Rhodes Ave, Chicago, IL 60637, 7 beds, 3 baths

$550,000

7 beds3 baths— sq ft

6234 S Rhodes Ave, Chicago, IL 60637

Property at 7134 S University Ave, Chicago, IL 60619, 4 beds, 2 baths

$265,000

4 beds2 baths— sq ft

7134 S University Ave, Chicago, IL 60619

Property at 115 E 60th St #2, Chicago, IL 60637, 2 beds, 1 bath

$94,900

2 beds1 bath950 sq ft

115 E 60th St #2, Chicago, IL 60637

Property at 2706 E 78th St, Chicago, IL 60649, 4 beds, 2 baths

$249,999

4 beds2 baths1,800 sq ft

2706 E 78th St, Chicago, IL 60649

Property at 6008 S Wabash Ave, Chicago, IL 60637, 10 beds, 4 baths

$559,000

10 beds4 baths— sq ft

6008 S Wabash Ave, Chicago, IL 60637

Property at 7642 S Dante Ave, Chicago, IL 60619, 3 beds, 2 baths

$299,900

3 beds2 baths1,656 sq ft

7642 S Dante Ave, Chicago, IL 60619

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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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