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:
Newly Renovated Unique Loft in Historic OPERA LOFTS is an Exceptional Place to Call Home with Original Artifacts and Relics Displayed Throughout the Building. The Open Floorpan Features High Ceilings and Exposed Brick and Views of Downtown From Your Large Balcony. Newly Renovated Kitchen Features Brand New HIGH END BOSCH Stainless Steel Appliance Package, Stone Counters, Modern Tile Backsplash and Under Cabinet Lighting. Large Primary Suite Features Dressing Area with Excellent Closet Space. Luxurious Primary Bath Features Marble Slab Floor and Spa Tub Surround. Be Impressed by the Sleek New Kohler and Vigo Fixtures, Modern Commode and Spa Bath with New Glass Door. The Stunning Second Marbl

$415,000

2 beds2 baths— sq ft

2545 S Dearborn St #509, Chicago, IL 60616

Original artifacts • Newly renovated loft • Exposed brick

$619,000

6 beds2.5 baths3,300 sq ft

Mahogany woodwork • Oversized rooms • Period features

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Welcome to 7545, a beautifully updated South Shore brick bungalow that perfectly blends timeless charm with modern comfort. This 4-bedroom, 2-bath home offers three levels of living space, featuring designer tiling, modern light fixtures, and an open-concept living and dining area ideal for entertaining. The renovated kitchen showcases sleek finishes, ample cabinetry, and thoughtful design throughout. With two bedrooms on the main level, the layout is perfect for multi-generational living or anyone seeking convenience and flexibility. Enjoy an all-seasons front porch, mudroom off the kitchen, and a fully fenced backyard with a deck and two-car garage-perfect for gatherings and summer barbec

$339,000

4 beds2 baths2,200 sq ft

7545 S Merrill Ave, Chicago, IL 60649

Renovated kitchen • Deck • Open-concept living

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
7.5 CAP Breathe Rare Air. The sellers of this property portfolio are not just seasoned investors; they are passionate visionary stewards with over 45 years of experience in branded high quality property development and management. Since 2007, they have meticulously curated each asset in the Bronzeville collection, focusing on longevity, quality, and the future potential of every investment. Every property reflects an unwavering commitment to excellence. From intelligent design choices to extensive renovations and improvements that prioritize durability, modernity, and lifestyle, they ensured no detail is overlooked. Their approach integrates a long-term vision with a hands-on philosophy, ba

$4,240,000

38 beds23 baths— sq ft

4840 S Indiana Ave, Chicago, IL 60615

20 parking spaces • Extensive masonry • 0.46 acre lot

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Stunning Lakefront Condo in the Heart of Hyde Park - 5555 S Everett Ave Unit C14 Wake up every morning to breathtaking lakefront views from this beautifully updated 2-bedroom, 1.5-bath condo offering nearly 1,700 sq ft of bright, open living space in one of Hyde Park's most desirable lakefront buildings. Step inside and you'll immediately feel the warmth of natural sunlight pouring through oversized windows that frame the sparkling blue waters of Lake Michigan. The spacious living room is ideal for relaxing or entertaining, featuring gleaming hardwood floors and a seamless flow into the modern chef's kitchen-fully equipped with quartz countertops, mahogany cabinets, stainless steel applian

$294,900

2 beds1.5 baths1,700 sq ft

5555 S Everett Ave Unit C14, Chicago, IL 60637

On site security • Updated kitchen • 24 hour door staff

Property at 6806 S Crandon Ave #2, Chicago, IL 60649, 3 beds, 3 baths

$150,000

3 beds3 baths2,200 sq ft

6806 S Crandon Ave #2, Chicago, IL 60649

Property at 7357 S Saint Lawrence Ave, Chicago, IL 60619, 8 beds, 11 baths

$675,000

8 beds11 baths— sq ft

7357 S Saint Lawrence Ave, Chicago, IL 60619

Property at 6318 S Greenwood Ave #1, Chicago, IL 60637, 4 beds, 3 baths

$364,900

4 beds3 baths2,056 sq ft

6318 S Greenwood Ave #1, Chicago, IL 60637

Property at 6415 S Eberhart Ave, Chicago, IL 60637, 3 beds, 1 bath

$110,000

3 beds1 bath714 sq ft

6415 S Eberhart Ave, Chicago, IL 60637

Property at 6320 S Greenwood Ave Unit G, Chicago, IL 60637, 2 beds, 2 baths

$184,900

2 beds2 baths1,100 sq ft

6320 S Greenwood Ave Unit G, Chicago, IL 60637

Property at 6961 S Eberhart Ave, Chicago, IL 60637, 7 beds, 2 baths

$449,900

7 beds2 baths— sq ft

6961 S Eberhart Ave, Chicago, IL 60637

Property at 7345 S Bennett Ave, Chicago, IL 60649, 6 beds, 2 baths

$371,900

6 beds2 baths3,463 sq ft

7345 S Bennett Ave, Chicago, IL 60649

Property at Sign in for address, Chicago, IL 60637, 5 beds, 2 baths

$360,000

5 beds2 baths— sq ft

Property at 7430 S Luella Ave, Chicago, IL 60649, 3 beds, 1 bath

$150,000

3 beds1 bath1,700 sq ft

7430 S Luella Ave, Chicago, IL 60649

Property at 7817 S Eberhart Ave, Chicago, IL 60619, 3 beds, 1.5 baths

$260,000

3 beds1.5 baths1,319 sq ft

7817 S Eberhart Ave, Chicago, IL 60619

Property at 5011 S Drexel Blvd, Chicago, IL 60615, 38 beds, 24 baths

$4,700,000

38 beds24 baths— sq ft

5011 S Drexel Blvd, Chicago, IL 60615

Property at 7443 S Wabash Ave, Chicago, IL 60619, 3 beds, 1 bath

$189,000

3 beds1 bath1,200 sq ft

7443 S Wabash Ave, Chicago, IL 60619

Property at 6520 S Ellis Ave, Chicago, IL 60637, 7 beds, 3 baths

$575,000

7 beds3 baths— sq ft

6520 S Ellis Ave, Chicago, IL 60637

Property at 7701 S Eggleston Ave, Chicago, IL 60620, 16 beds, 10 baths

$440,000

16 beds10 baths6,528 sq ft

7701 S Eggleston Ave, Chicago, IL 60620

Property at 5611 S Kenwood Ave, Chicago, IL 60637, 6 beds, 3.5 baths

$1,950,000

6 beds3.5 baths— sq ft

5611 S Kenwood Ave, Chicago, IL 60637

Property at 7650 S Cregier Ave, Chicago, IL 60649, 6 beds, 4 baths

$499,000

6 beds4 baths3,200 sq ft

7650 S Cregier Ave, Chicago, IL 60649

Property at 1520 E Marquette Rd Unit 2B, Chicago, IL 60637, 3 beds, 2 baths

$255,000

3 beds2 baths1,400 sq ft

1520 E Marquette Rd Unit 2B, Chicago, IL 60637

Property at 2916 S Union Ave, Chicago, IL 60616, 6 beds, 2 baths

$650,000

6 beds2 baths— sq ft

2916 S Union Ave, Chicago, IL 60616

Property at 6953 S Michigan Ave, Chicago, IL 60637, 3 beds, 1 bath

$125,000

3 beds1 bath— sq ft

6953 S Michigan Ave, Chicago, IL 60637

Property at 7329 S Coles Ave, Chicago, IL 60649, 10 beds, 5 baths

$650,000

10 beds5 baths— sq ft

7329 S Coles Ave, Chicago, IL 60649

Property at 318 W 75th St, Chicago, IL 60620, 6 beds, 2 baths

$94,999

6 beds2 baths2,126 sq ft

318 W 75th St, Chicago, IL 60620

Property at 2963 S Archer Ave, Chicago, IL 60608

$499,900

— beds— baths2,640 sq ft

2963 S Archer Ave, Chicago, IL 60608

Property at 928 E 46th St, Chicago, IL 60653, 4 beds, 2 baths

$489,000

4 beds2 baths3,200 sq ft

928 E 46th St, Chicago, IL 60653

Property at 5419 S Wabash Ave, Chicago, IL 60615, 8 beds, 6 baths

$715,000

8 beds6 baths— sq ft

5419 S Wabash Ave, Chicago, IL 60615

Property at 4808 S Dorchester Ave Unit 3N, Chicago, IL 60615, 4 beds, 3 baths

$312,000

4 beds3 baths2,138 sq ft

4808 S Dorchester Ave Unit 3N, Chicago, IL 60615

Property at 1615 E Hyde Park Blvd #2, Chicago, IL 60615, 3 beds, 2 baths

$347,000

3 beds2 baths1,800 sq ft

1615 E Hyde Park Blvd #2, Chicago, IL 60615

Property at 7356 S Champlain Ave, Chicago, IL 60619, 5 beds, 2 baths

$199,900

5 beds2 baths— sq ft

7356 S Champlain Ave, Chicago, IL 60619

Property at 3408 S Carpenter St, Chicago, IL 60608, 4 beds, 2.5 baths

$800,000

4 beds2.5 baths2,633 sq ft

3408 S Carpenter St, Chicago, IL 60608

Property at 7725 S Champlain Ave, Chicago, IL 60619, 4 beds, 2 baths

$166,000

4 beds2 baths1,200 sq ft

7725 S Champlain Ave, Chicago, IL 60619

Property at 2631 S Shields Ave, Chicago, IL 60616, 8 beds, 4 baths

$398,000

8 beds4 baths— sq ft

2631 S Shields Ave, Chicago, IL 60616

Property at 601 E 32nd St #210, Chicago, IL 60616, 3 beds, 2 baths

$175,000

3 beds2 baths2,100 sq ft

601 E 32nd St #210, Chicago, IL 60616

Property at 7825 S Ingleside Ave, Chicago, IL 60619, 3 beds, 3 baths

$259,000

3 beds3 baths1,800 sq ft

7825 S Ingleside Ave, Chicago, IL 60619

Property at 6430 S Eberhart Ave, Chicago, IL 60637, 7 beds, 3 baths

$575,000

7 beds3 baths— sq ft

6430 S Eberhart Ave, Chicago, IL 60637

Property at 7811 S Wabash Ave, Chicago, IL 60619, 4 beds, 3 baths

$210,000

4 beds3 baths1,500 sq ft

7811 S Wabash Ave, Chicago, IL 60619

Property at 7622 S Normal Ave, Chicago, IL 60620, 5 beds, 2 baths

$329,000

5 beds2 baths— sq ft

7622 S Normal Ave, Chicago, IL 60620

Property at 7037 S Crandon Ave #219, Chicago, IL 60649, 2 beds, 2 baths

$124,900

2 beds2 baths1,250 sq ft

7037 S Crandon Ave #219, 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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