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:
Top-Floor Condo in the Heart of Bronzeville Experience city living in this beautifully designed 2-bedroom, 2-bathroom condo. This top-floor unit offers abundant natural light, perfect for both relaxing and entertaining. The kitchen features granite countertops, stainless steel appliances, and plenty of cabinetry. a private balcony for morning coffee or evening unwinding. The primary suite includes a en-suite bathroom with a double vanity and whirlpool tub, providing the ideal space to recharge. Conveniently situated near public transportation, Mariano's shopping, and just minutes from the lakefront and Soldier Field. This home offers the perfect blend of comfort, convenience, and style.

$219,900

2 beds2 baths1,064 sq ft

3704 S King Dr Unit 3C, Chicago, IL 60653

Double vanity • Private balcony • Top-floor condo

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Don't miss this spacious 5 bedroom, 3.5 bathroom property located in the highly sough after South Shore neighborhood. This home offers exceptional potential for investors, rehabbers, or buyers looking to customize a spacious residence to their own style. Renovation work has begun but is not complete, giving you the flexibility to finish the project as you desire. One bedroom on first floor, 2 bedrooms on second floor and 2 bedrooms in the basement. Whether you're looking for your next investment or a property to make your own, this South Shore gem has endless potential. Bring your bright ideas and vision--this one won't last long. Property being sold in AS IS condition, no surveys nor discl

$179,000

5 beds3.5 baths1,288 sq ft

7133 S Constance Ave, Chicago, IL 60649

3,750 sq ft lot • Garage • Built 1916

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Stunning, Fully Renovated Sun-Drenched Residence in Historic Madison Park!Step into this exquisite 3rd-floor home featuring 45 oversized new windows that fill every room with natural light. Solid oak floors flow throughout expansive living spaces, including two bright sunrooms perfect for relaxing or entertaining. Elegant moldings and crown details highlight the home's graceful architecture, blending vintage charm with modern luxury. Enjoy radiant heat, central air, and supplemental GFA heating for year-round comfort. The designer chef's kitchen impresses with a large island, quartz countertops, abundant cabinetry, and a walk-in pantry. The spa-inspired primary bath showcases marble tile, a

$995,000

5 beds3 baths— sq ft

1201 E Madison Park #3, Chicago, IL 60615

Quartz countertops • Solid oak floors • Large island

$399,999

6 beds2.5 baths3,300 sq ft

7832 S Paxton Ave, Chicago, IL 60649

7,500 sq ft lot • Garage • Built 1921

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
This large single-family home boasts an expansive layout with over 2600+ square feet of finished living space, providing ample room for a large multi-generational or extended family to flourish. Stepping through the front door into the closeted foyer, you are greeted by a sprawling living room bathed in natural light streaming through the large windows. This residence a remarkable 10+ rooms, there are 3 bedrooms upstairs and 2 extra rooms and wet bar downstairs. There are 3 and a half baths (bath and half downstairs) as well. Whether it's aging parents, adult/teen children, or guests, the home's layout offers flexibility and privacy for every family member. The add'l rooms can be transforme

$445,000

3 beds3.5 baths4,000 sq ft

3727 S Lowe Ave, Chicago, IL 60609

3,125 sq ft lot • Built 1890 • Listed 28 days

Property at 7801 S Eberhart Ave, Chicago, IL 60619, 5 beds, 4 baths

$445,900

5 beds4 baths4,082 sq ft

7801 S Eberhart Ave, Chicago, IL 60619

Property at 1755 E 55th St #503, Chicago, IL 60615, 2 beds, 2 baths

$114,000

2 beds2 baths1,750 sq ft

1755 E 55th St #503, Chicago, IL 60615

Property at 7541 S Rhodes Ave, Chicago, IL 60619, 2 beds, 1 bath

$65,000

2 beds1 bath1,643 sq ft

7541 S Rhodes Ave, Chicago, IL 60619

Property at 6437 S Eberhart Ave, Chicago, IL 60637, 3 beds, 1 bath

$115,000

3 beds1 bath3,050 sq ft

6437 S Eberhart Ave, Chicago, IL 60637

Property at 5330 S Wabash Ave, Chicago, IL 60615, 12 beds, 5 baths

$770,000

12 beds5 baths— sq ft

5330 S Wabash Ave, Chicago, IL 60615

Property at 7514 S Rhodes Ave, Chicago, IL 60619, 3 beds, 1 bath

$79,900

3 beds1 bath1,200 sq ft

7514 S Rhodes Ave, Chicago, IL 60619

Property at 6742 S Clyde Ave Unit 1S, Chicago, IL 60649, 3 beds, 4.5 baths

$190,000

3 beds4.5 baths1,392 sq ft

6742 S Clyde Ave Unit 1S, Chicago, IL 60649

Property at 6617 S Vernon Ave, Chicago, IL 60637, 4 beds, 2 baths

$199,900

4 beds2 baths— sq ft

6617 S Vernon Ave, Chicago, IL 60637

Property at 7859 S Eggleston Ave, Chicago, IL 60620, 8 beds, 4 baths

$130,000

8 beds4 baths— sq ft

7859 S Eggleston Ave, Chicago, IL 60620

Property at 6135 S Greenwood Ave #2, Chicago, IL 60637, 3 beds, 2 baths

$319,000

3 beds2 baths1,591 sq ft

6135 S Greenwood Ave #2, Chicago, IL 60637

Property at 7128 S Champlain Ave, Chicago, IL 60619, 6 beds, 1 bath

$79,900

6 beds1 bath— sq ft

7128 S Champlain Ave, Chicago, IL 60619

Property at 7824 S Euclid Ave, Chicago, IL 60649, 9 beds, 3 baths

$600,000

9 beds3 baths— sq ft

7824 S Euclid Ave, Chicago, IL 60649

Property at 6601 S St Lawrence Ave, Chicago, IL 60637, 14 beds, 4 baths

$499,999

14 beds4 baths— sq ft

6601 S St Lawrence Ave, Chicago, IL 60637

Property at 7225 S Princeton Ave, Chicago, IL 60621, 5 beds, 3 baths

$259,900

5 beds3 baths6,200 sq ft

7225 S Princeton Ave, Chicago, IL 60621

Property at 3217 S May St, Chicago, IL 60608, 6 beds, 3 baths

$589,000

6 beds3 baths— sq ft

3217 S May St, Chicago, IL 60608

Property at 7738 S Wabash Ave, Chicago, IL 60619, 6 beds, 2 baths

$299,900

6 beds2 baths— sq ft

7738 S Wabash Ave, Chicago, IL 60619

Property at 6511 S Evans Ave, Chicago, IL 60637, 4 beds, 3.5 baths

$539,500

4 beds3.5 baths3,400 sq ft

6511 S Evans Ave, Chicago, IL 60637

Property at 6506 S Saint Lawrence Ave, Chicago, IL 60637, 9 beds, 3 baths

$335,000

9 beds3 baths— sq ft

6506 S Saint Lawrence Ave, Chicago, IL 60637

Property at 1327 E 52nd St #202, Chicago, IL 60615, 4 beds, 2 baths

$375,000

4 beds2 baths1,700 sq ft

1327 E 52nd St #202, Chicago, IL 60615

Property at 6149 S Rhodes Ave, Chicago, IL 60637, 8 beds, 3 baths

$465,000

8 beds3 baths— sq ft

6149 S Rhodes Ave, Chicago, IL 60637

Property at 618 E 50th Pl, Chicago, IL 60615, 5 beds, 3 baths

$599,000

5 beds3 baths— sq ft

618 E 50th Pl, Chicago, IL 60615

Property at 2046 E 72nd Pl Unit 2w, Chicago, IL 60649, 2 beds, 1 bath

$97,500

2 beds1 bath1,000 sq ft

2046 E 72nd Pl Unit 2w, Chicago, IL 60649

Property at 5435 S Princeton Ave, Chicago, IL 60609, 9 beds, 4 baths

$149,900

9 beds4 baths— sq ft

5435 S Princeton Ave, Chicago, IL 60609

Property at 7749 S Muskegon Ave, Chicago, IL 60649, 10 beds, 3 baths

$284,900

10 beds3 baths— sq ft

7749 S Muskegon Ave, Chicago, IL 60649

Property at 6933 S Michigan Ave, Chicago, IL 60637, 7 beds, 2 baths

$275,000

7 beds2 baths1,173 sq ft

6933 S Michigan Ave, Chicago, IL 60637

Property at 7726 S Maryland Ave, Chicago, IL 60619, 4 beds, 1 bath

$95,000

4 beds1 bath1,221 sq ft

7726 S Maryland Ave, Chicago, IL 60619

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

$400,000

11 beds7 baths— sq ft

Property at 4358 S Prairie Ave, Chicago, IL 60653, 54 beds, 48 baths

$8,360,000

54 beds48 baths— sq ft

4358 S Prairie Ave, Chicago, IL 60653

Property at 6035 S St Lawrence Ave Unit GS, Chicago, IL 60637, 2 beds, 1 bath

$145,000

2 beds1 bath1,200 sq ft

6035 S St Lawrence Ave Unit GS, Chicago, IL 60637

Property at 6450 S Greenwood Ave, Chicago, IL 60637, 4 beds, 3.5 baths

$699,900

4 beds3.5 baths1,988 sq ft

6450 S Greenwood Ave, Chicago, IL 60637

Property at Sign in for address, Chicago, IL 60637, 7 beds, 2 baths

$465,000

7 beds2 baths— sq ft

Property at 7157 S Yale Ave, Chicago, IL 60621, 15 beds, 12 baths

$400,000

15 beds12 baths— sq ft

7157 S Yale Ave, Chicago, IL 60621

Property at 1765 E 55th St Unit J2, Chicago, IL 60615, 1 bed, 1 bath

$139,500

1 bed1 bath1,050 sq ft

1765 E 55th St Unit J2, Chicago, IL 60615

Property at 7716 S Kingston Ave, Chicago, IL 60649, 8 beds, 3 baths

$515,000

8 beds3 baths— sq ft

7716 S Kingston Ave, Chicago, IL 60649

Property at 6618 S Marquette Rd, Chicago, IL 60637, 4 beds, 2 baths

$210,000

4 beds2 baths— sq ft

6618 S Marquette Rd, Chicago, IL 60637

Property at 7821 S Oglesby Ave, Chicago, IL 60649, 3 beds, 1 bath

$109,900

3 beds1 bath748 sq ft

7821 S Oglesby 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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