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 gorgeous views from this spacious 11th floor Hyde Park condo. Enter from 53rd street, go through the elegant, doorstaffed lobby, and up the elevator to the 11th floor. This is a NE corner unit with views of the Lake and downtown. On a clear day, you can see Indiana across the Lake. Walk all the way down the hall and enter on your left. Step inside, leave your coats and shoes in the hall closet and turn right into the primary bedroom. This extra large bedroom has an East facing view offering an unobstructed view of the Lake. There is a walk-in closet with professional organization and a primary bath with a stand alone shower. Keep going back to enter the central hub of the un

$285,000

4 beds3 baths2,350 sq ft

5300 S Shore Dr #111, Chicago, IL 60615

Ne corner unit • Galley kitchen • Walk-in closet

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Don't miss out on this irresistible and meticulously maintained gated condo situated in a very desirable area in the beautiful Woodlawn Neighborhood. This condo features two bedrooms and two bathrooms with centralized air and an in-unit European washer/dryer. Living Room is nice and open with high ceilings, decorative fireplace with mantel & side shelving which preserves the history of this vintage building. On the borderline of Hyde Park and the University; This is an ideal location for students. near shopping, dining and more; Newer windows throughout, quartz countertops in the updated kitchen. Schedule your private showing today! This GEM will not last long!!!

$170,000

2 beds2 baths— sq ft

6106 S Dorchester Ave Unit 2W, Chicago, IL 60637

Vintage building • Quartz countertops • Decorative fireplace

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
This is an AMAZING price for a FULLY RENOVATED mid-century unit in the heart of East Hyde Park, just steps from the lake within easy reach of the University of Chicago and its hospitals as well as the shopping, restaurants and all the fun to be had in Hyde Park. The story is that Mies van der Rohe designed the Chippewa Co-op building which is perched beside Harold Washington Park and overlooking Lake Michigan. The developer of the building (who paid all of the bills) decided that he didn't really need the huge wide open lobby space that Mies had designed. He preferred to use the space to add another two units into opposite ends of the first floor to maximize his profit. Mies was furious th

$125,000

2 beds1 bath1,110 sq ft

5050 S East End Ave Unit 4B, Chicago, IL 60615

Fully renovated • Steps from the lake • Mid-century unit

$720,000

16 beds10 baths— sq ft

2720 E 75th St, Chicago, IL 60649

Indoor parking space • Six unit opportunity • Modern appliances

ABOUT THIS HOME
Vintage Home for sale in South Side, IL:
Welcome to your future home in the desirable Hyde Park area! This freshly painted spacious 2 Bedroom, 1 Bath unit is conveniently located near public transportation, restaurants, shops, stores, and University of Chicago. The unit offers a spacious Living Room with a decorative Fireplace, Sun Room flooded with natural light perfect for office space or additional living space, large separate Dining Room, in-unit laundry, and hardwood floors throughout. Parking may be available for rent (waiting list). Schedule your showing today. Easy to show.

$240,000

2 beds1 bath1,200 sq ft

1155 E Hyde Park Blvd Unit 2F, Chicago, IL 60615

Decorative fireplace • Sun room • In-unit laundry

Property at 7225 S Woodlawn Ave, Chicago, IL 60619, 3 beds, 3 baths

$99,900

3 beds3 baths2,348 sq ft

7225 S Woodlawn Ave, Chicago, IL 60619

Property at 7830 S Merrill Ave, Chicago, IL 60649, 5 beds, 4 baths

$430,000

5 beds4 baths3,000 sq ft

7830 S Merrill Ave, Chicago, IL 60649

Property at 614 E Marquette Rd, Chicago, IL 60637, 3 beds, 1 bath

$128,900

3 beds1 bath1,152 sq ft

614 E Marquette Rd, Chicago, IL 60637

Property at 1059 E Hyde Park Blvd #1, Chicago, IL 60615, 3 beds, 2 baths

$300,000

3 beds2 baths2,425 sq ft

1059 E Hyde Park Blvd #1, Chicago, IL 60615

Property at 6840 S Indiana Ave, Chicago, IL 60637, 3 beds, 1.5 baths

$65,000

3 beds1.5 baths924 sq ft

6840 S Indiana Ave, Chicago, IL 60637

Property at 7833 S Kingston Ave, Chicago, IL 60649, 14 beds, 6 baths

$699,000

14 beds6 baths14,880 sq ft

7833 S Kingston Ave, Chicago, IL 60649

Property at 5001 S King Dr Unit GN, Chicago, IL 60615, 3 beds, 2 baths

$205,000

3 beds2 baths1,450 sq ft

5001 S King Dr Unit GN, Chicago, IL 60615

Property at 3428 S King Dr, Chicago, IL 60616

$1,200,000

— beds— baths12,000 sq ft

3428 S King Dr, Chicago, IL 60616

Property at 7627 S Prairie Ave, Chicago, IL 60619, 4 beds, 1.5 baths

$227,000

4 beds1.5 baths1,036 sq ft

7627 S Prairie Ave, Chicago, IL 60619

Property at 109 E 37th Pl, Chicago, IL 60653, 2 beds, 1.5 baths

$150,000

2 beds1.5 baths— sq ft

109 E 37th Pl, Chicago, IL 60653

Property at 2469 E 74th St, Chicago, IL 60649, 4 beds, 3 baths

$90,000

4 beds3 baths1,564 sq ft

2469 E 74th St, Chicago, IL 60649

Property at 601 E 32nd St Unit 210-211, Chicago, IL 60616, 5 beds, 4 baths

$325,000

5 beds4 baths3,112 sq ft

601 E 32nd St Unit 210-211, Chicago, IL 60616

Property at 6506 S Eberhart Ave, Chicago, IL 60637, 5 beds, 2 baths

$290,000

5 beds2 baths— sq ft

6506 S Eberhart Ave, Chicago, IL 60637

Property at 1527 E 66th Pl, Chicago, IL 60637, 9 beds, 6.5 baths

$874,900

9 beds6.5 baths— sq ft

1527 E 66th Pl, Chicago, IL 60637

Property at 7512 S Champlain Ave, Chicago, IL 60619, 8 beds, 4 baths

$505,000

8 beds4 baths— sq ft

7512 S Champlain Ave, Chicago, IL 60619

Property at 3017 E 78th St Unit 4B, Chicago, IL 60649, 1 bed, 1 bath

$57,900

1 bed1 bath900 sq ft

3017 E 78th St Unit 4B, Chicago, IL 60649

Property at 6440 S Eberhart Ave, Chicago, IL 60637, 8 beds, 4 baths

$480,000

8 beds4 baths— sq ft

6440 S Eberhart Ave, Chicago, IL 60637

Property at 5142 S Greenwood Ave #1, Chicago, IL 60615, 3 beds, 2 baths

$324,000

3 beds2 baths1,650 sq ft

5142 S Greenwood Ave #1, Chicago, IL 60615

Property at 7227 S Bennett Ave, Chicago, IL 60649, 3 beds, 3 baths

$285,000

3 beds3 baths1,883 sq ft

7227 S Bennett Ave, Chicago, IL 60649

Property at 7003 S Oglesby Ave, Chicago, IL 60649, 40 beds, 20 baths

$2,800,000

40 beds20 baths— sq ft

7003 S Oglesby Ave, Chicago, IL 60649

Property at 7327 S Kenwood Ave, Chicago, IL 60619, 3 beds, 1 bath

$75,000

3 beds1 bath1,020 sq ft

7327 S Kenwood Ave, Chicago, IL 60619

Property at 6827 S Langley Ave, Chicago, IL 60637, 5 beds, 2 baths

$339,000

5 beds2 baths— sq ft

6827 S Langley Ave, Chicago, IL 60637

Property at 7843 S Evans Ave, Chicago, IL 60619, 6 beds, 2 baths

$274,900

6 beds2 baths— sq ft

7843 S Evans Ave, Chicago, IL 60619

Property at 5943 S Indiana Ave, Chicago, IL 60637, 11 beds, 5 baths

$689,900

11 beds5 baths— sq ft

5943 S Indiana Ave, Chicago, IL 60637

Property at 211 W 23rd St, Chicago, IL 60616, 1 bath

$1,600,000

0 beds1 bath— sq ft

211 W 23rd St, Chicago, IL 60616

Property at 1225 E 71st Pl, Chicago, IL 60619, 2 beds, 1 bath

$170,000

2 beds1 bath1,282 sq ft

1225 E 71st Pl, Chicago, IL 60619

Property at 4800 S Chicago Beach Dr Unit 1202S, Chicago, IL 60615, 1 bed, 1 bath

$133,999

1 bed1 bath801 sq ft

4800 S Chicago Beach Dr Unit 1202S, Chicago, IL 60615

Property at 6712 S Wabash Ave, Chicago, IL 60637, 9 beds, 5 baths

$389,000

9 beds5 baths— sq ft

6712 S Wabash Ave, Chicago, IL 60637

Property at 512-516 E 47th St, Chicago, IL 60653

$399,000

— beds— baths5,000 sq ft

512-516 E 47th St, Chicago, IL 60653

Property at 5148 S King Dr Unit B3, Chicago, IL 60615, 1 bed, 1 bath

$83,000

1 bed1 bath800 sq ft

5148 S King Dr Unit B3, Chicago, IL 60615

Property at 1401 E 55th St Unit 602N, Chicago, IL 60615, 2 beds, 2 baths

$209,000

2 beds2 baths1,000 sq ft

1401 E 55th St Unit 602N, Chicago, IL 60615

Property at 1755 E 55th St #301, Chicago, IL 60615, 2 beds, 2 baths

$230,000

2 beds2 baths1,800 sq ft

1755 E 55th St #301, Chicago, IL 60615

Property at 7643 S Paxton Ave, Chicago, IL 60649, 4 beds, 1.5 baths

$244,000

4 beds1.5 baths1,440 sq ft

7643 S Paxton Ave, Chicago, IL 60649

Property at 5000 S East End Ave Unit 24A, Chicago, IL 60615, 3 beds, 2 baths

$329,900

3 beds2 baths1,865 sq ft

5000 S East End Ave Unit 24A, Chicago, IL 60615

Property at 6622 S Marquette Rd, Chicago, IL 60637, 5 beds, 2 baths

$280,000

5 beds2 baths— sq ft

6622 S Marquette Rd, Chicago, IL 60637

Property at 7839 S Kingston Ave, Chicago, IL 60649, 28 beds, 17 baths

$1,365,000

28 beds17 baths29,760 sq ft

7839 S Kingston 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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