New Listings for Sale in South Side, IL

149 homes

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ABOUT THIS HOME
New Listing for sale in South Side, IL:
Welcome to 6619 South Maryland Avenue, a recently rehabbed gem in the East Woodlawn neighborhood near the University of Chicago! This versatile property features two distinct units, making it perfect for a variety of living arrangements or investment opportunities. Step into Unit 1, where you'll find a cozy layout with 2 bedrooms and 1 bathroom, offering a comfortable space to unwind. Unit 2 boasts 3 bedrooms and 1 bathroom, providing ample room for all your needs. Both units have been thoughtfully updated to blend modern charm with classic touches. Below, a full unfinished basement awaits your creativity, providing endless potential for storage or future expansion. Additionally, the unfini

$319,900

5 beds2 baths— sq ft

6619 S Maryland Ave, Chicago, IL 60637

Two distinct units • Recently rehabbed • Unfinished attic

ABOUT THIS HOME
New Listing for sale in South Side, IL:
Wonderful condo! Views of the Lake and downtown Chicago! Near White Sox Park, Transportation, and downtown Chicago!

$119,995

0 beds1 bath500 sq ft

2901 S Michigan Ave #908, Chicago, IL 60616

Downtown chicago • Near white sox park • Views of the lake

ABOUT THIS HOME
New Listing for sale in South Side, IL:
Stunning & Spacious South Shore Condo Near the Lake! Experience the best of South Shore living in this expansive 3-bedroom, 2-bathroom condo located just moments from the golf course, Lake Shore Drive, and the beach. This bright and airy unit offers an incredible amount of living space, perfect for entertaining and comfortable daily life. Enjoy a large living room, a separate formal dining area, and an additional sitting room/den for maximum flexibility. The main bedroom suite boasts an enormous walk-in closet (8x10) complete with custom built-ins, offering exceptional storage. Additionally, this home features hardwood floors throughout and a functional galley kitchen. In-unit washer

$230,000

3 beds2 baths2,200 sq ft

6724 S Paxton Ave #3, Chicago, IL 60649

Walk-in closet • Large living room • Custom built-ins

ABOUT THIS HOME
New Listing for sale in South Side, IL:
* * Incredible Investment Opportunity: 4-Unit Property for the Price of 2! * * Attention investors and renovators! This unique property offers an extraordinary chance to acquire a total of four units for the price of two. Situated on a sizable lot, this distressed, as-is 2-flat building features two units, each with 2 bedrooms and 1 bathroom. Adding significant value, the property includes a legal 2-unit coach house at the rear, boasting an additional 4 bedrooms and 2 bathrooms (2 bedrooms, 1 bathroom in each unit). Unlock the potential of this prime investment by bringing your vision and flashlight - please note, there are no utilities currently on the premises. This is your opportun

$185,000

9 beds4 baths— sq ft

5435 S Princeton Ave, Chicago, IL 60609

Profitable asset • 4 unit property • Sizable lot

ABOUT THIS HOME
New Listing for sale in South Side, IL:
Exclusively engaged to market for sale Drexel House [5017 S DrexelBlvd], an 8-unit, 38-bedroom multifamily property in Chicago's Hyde Park neighborhood. 5017 S Drexel is a gut-rehabbed property showcasing a rare and highly functional unit configuration: [7] spacious five-bedroom apartments and [1] three-bedroom unit, all equipped with three bathrooms. Each residence has been meticulously updated, offering modern, high-end finishes, quality furnishings, private furnaces, and in-unit laundry. These extensive upgrades support strong investment potential and market-leading returns in one of Chicago's most upward-trending submarkets. The building operates with both short-term rental flexibility

$4,700,000

38 beds24 baths— sq ft

5011 S Drexel Blvd, Chicago, IL 60615

In unit laundry • Private furnaces • Quality furnishings

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

$220,000

4 beds2 baths— sq ft

6618 S Marquette Rd, 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 2605 S Indiana Ave #708, Chicago, IL 60616, 1 bed, 1 bath

$144,000

1 bed1 bath750 sq ft

2605 S Indiana Ave #708, Chicago, IL 60616

Property at 5637 S Prairie Ave, Chicago, IL 60637, 9 beds, 6 baths

$1,049,000

9 beds6 baths— sq ft

5637 S Prairie Ave, Chicago, IL 60637

Property at 2734 S Wentworth Ave Unit PS-38, Chicago, IL 60616

$19,500

— beds— baths— sq ft

2734 S Wentworth Ave Unit PS-38, Chicago, IL 60616

Property at 442 E 48th St Unit B1, Chicago, IL 60615, 3 beds, 3 baths

$360,000

3 beds3 baths1,400 sq ft

442 E 48th St Unit B1, Chicago, IL 60615

Property at 3700 N Lake Shore Dr #307, Chicago, IL 60613, 2 beds, 2.5 baths

$595,000

2 beds2.5 baths1,600 sq ft

3700 N Lake Shore Dr #307, Chicago, IL 60613

Property at 444 E 48th St Unit B3, Chicago, IL 60615, 3 beds, 2 baths

$345,000

3 beds2 baths1,300 sq ft

444 E 48th St Unit B3, Chicago, IL 60615

Property at 7208 S Eberhart Ave, Chicago, IL 60619, 6 beds, 3 baths

$389,000

6 beds3 baths— sq ft

7208 S Eberhart Ave, Chicago, IL 60619

Property at 442 E 48th St Unit 1E, Chicago, IL 60615, 4 beds, 3 baths

$500,000

4 beds3 baths1,873 sq ft

442 E 48th St Unit 1E, Chicago, IL 60615

Property at 444 E 48th St Unit B2, Chicago, IL 60615, 2 beds, 1 bath

$255,000

2 beds1 bath930 sq ft

444 E 48th St Unit B2, Chicago, IL 60615

Property at 446 E 48th St Unit 3E, Chicago, IL 60615, 4 beds, 3 baths

$597,000

4 beds3 baths3,000 sq ft

446 E 48th St Unit 3E, Chicago, IL 60615

Property at 444 E 48th St Unit 3W, Chicago, IL 60615, 4 beds, 2.5 baths

$597,000

4 beds2.5 baths2,000 sq ft

444 E 48th St Unit 3W, Chicago, IL 60615

Property at 444 E 48th St Unit 1W, Chicago, IL 60615, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths1,900 sq ft

444 E 48th St Unit 1W, Chicago, IL 60615

Property at 444 E 48th St Unit 2W, Chicago, IL 60615, 4 beds, 2.5 baths

$565,000

4 beds2.5 baths2,200 sq ft

444 E 48th St Unit 2W, Chicago, IL 60615

Property at 442 E 48th St Unit 2E, Chicago, IL 60615, 4 beds, 3 baths

$565,000

4 beds3 baths2,100 sq ft

442 E 48th St Unit 2E, Chicago, IL 60615

$120,500

2 beds2 baths1,100 sq ft

Property at 3529 S Prairie Ave, Chicago, IL 60653

$230,000

— beds— baths— sq ft

3529 S Prairie Ave, Chicago, IL 60653

Property at 3630 S Giles Ave, Chicago, IL 60653

$360,000

— beds— baths— sq ft

3630 S Giles Ave, Chicago, IL 60653

Property at 6827 S State St, Chicago, IL 60637

$20,000

— beds— baths— sq ft

6827 S State St, Chicago, IL 60637

Property at 7149 S Champlain Ave, Chicago, IL 60619

$25,000

— beds— baths— sq ft

7149 S Champlain Ave, Chicago, IL 60619

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Based on information submitted to the MLS GRID as of Mon Nov 24 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.

New Listings for Sale in South Side

There are currently 149 new listings for sale in South Side at a median listing price of $279K. 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 78 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, 168 homes have been sold in South Side. In addition to houses in South Side, there were also 479 condos, 49 townhouses, and 259 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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