Luxury homes for sale & real estate in South Side, IL

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NEW 15 HRS AGO

ABOUT THIS HOME
Luxury Home for sale in South Side, IL:
Home for the Holidays in this timeless Chicago remodeled Greystone in historic Bronzeville - a perfect blend of classic architecture and modern luxury. From the brand-new roof to the dual-zoned furnaces, no detail was overlooked in this top-to-bottom transformation. Boasting 5 bedrooms and 3.5 baths, this home welcomes you with gleaming hardwood floors throughout the main level and stairways, and plush carpeting in the bedrooms for a warm, inviting feel. The dream kitchen is a true showstopper - featuring sleek black and gold ZLINE professional appliances, a dual oven, elegant wood hood, and an enormous waterfall quartz island that anchors the space in style. Upstairs, the primary suite is

$875,000

5 beds3.5 baths3,439 sq ft

4938 S Vincennes Ave, Chicago, IL 60615

Brand-new roof • Plush carpeting • Dream kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in South Side, IL:
Presenting 7200-02 S. Stony Island Avenue, a 24-unit multifamily investment opportunity located in the rapidly appreciating South Shore neighborhood of Chicago. This stately brick walk-up offers a highly desirable unit mix of twelve (12) spacious 2 bed / 1 bath and twelve (12) 1 bed / 1 bath apartments. The property has been meticulously maintained with significant capital improvements, blending modern upgrades with timeless vintage character. Each unit features expansive floor plans, large living rooms, generous bedroom sizes, and abundant natural light. Interior renovations include condo-quality finishes such as stainless steel appliances, in-unit laundry, updated kitchens and baths, an

$3,300,000

36 beds24 baths— sq ft

7200 S Stony Island Ave, Chicago, IL 60649

Unit mix • Vintage character • Modern upgrades

NEW CONSTRUCTION

$1,250,700

9 beds6 baths— sq ft

4934 S Champlain Ave, Chicago, IL 60615

3,253 sq ft lot • 3 garage spots • Built 2025

ABOUT THIS HOME
Luxury Home for sale in South Side, IL:
7.5 CAP Welcome to TPAL, The Prairie Ave Lofts, a Crown Jewel of the Bronzeville Collection spans 125 x 160.58 just under a 1/2 acre perfectly positioned on a prime corner in well located high growth Bronzeville 1/4 block to Green Line and Pendleton Park. An Iconic Classic Chicago All Masonry 31-unit prominent walk up with distinctive 5 entrances, steel rear decks, private all masonry entertainment size front terraces plus 19 gated parking spaces. A complete gut renovation, electric, plumbing, roof, windows, unit interiors with meticulous attention to detail . The development team embraced this extensive undertaking showcasing superior craftsmanship and attention to detail with fully docume

$8,360,000

54 beds48 baths— sq ft

4358 S Prairie Ave, Chicago, IL 60653

Steel rear decks • Prime corner • 0.46 acre lot

ABOUT THIS HOME
Luxury 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. Their deep industry expertise is evident in the thoughtful capital improvements, superior tenant satisfaction, and consistent high-quality decisions that have become hallmarks of their ownership. Every property reflects an unwavering commitment to excellence. Their approach integrates a long-term vision

$3,160,000

30 beds22 baths— sq ft

4417 S Indiana Ave, Chicago, IL 60653

Meandering walkways • Extensively upgraded • Elevator building

Property at 4840 S Indiana Ave, Chicago, IL 60615, 38 beds, 23 baths

$4,240,000

38 beds23 baths— sq ft

4840 S Indiana Ave, Chicago, IL 60615

Property at 6316 S Evans Ave, Chicago, IL 60637, 9 beds, 6 baths

$860,000

9 beds6 baths— sq ft

6316 S Evans Ave, Chicago, IL 60637

Property at 1045 W 34th Pl, Chicago, IL 60608, 4 beds, 3.5 baths

$879,900

4 beds3.5 baths3,400 sq ft

1045 W 34th Pl, Chicago, IL 60608

Property at 3309 S Lowe Ave, Chicago, IL 60616, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths3,000 sq ft

3309 S Lowe Ave, Chicago, IL 60616

Property at 1201 E Madison Park #3, Chicago, IL 60615, 5 beds, 3 baths

$1,050,000

5 beds3 baths— sq ft

1201 E Madison Park #3, Chicago, IL 60615

Property at 4915 S Martin Luther King Dr, Chicago, IL 60615, 5 beds, 4.5 baths

$1,279,900

5 beds4.5 baths5,080 sq ft

4915 S Martin Luther King Dr, Chicago, IL 60615

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 4932 S Champlain Ave, Chicago, IL 60615, 9 beds, 6 baths

$1,250,700

9 beds6 baths— sq ft

4932 S Champlain Ave, Chicago, IL 60615

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 3222-3224 S Morgan St, Chicago, IL 60608

$1,475,000

— beds— baths6,660 sq ft

3222-3224 S Morgan St, Chicago, IL 60608

Property at 4730 S Greenwood Ave, Chicago, IL 60615, 6 beds, 5.5 baths

$2,400,000

6 beds5.5 baths4,200 sq ft

4730 S Greenwood Ave, Chicago, IL 60615

Property at 5114 S Kenwood Ave Unit 3B, Chicago, IL 60615, 3 beds, 2.5 baths

$850,000

3 beds2.5 baths1,881 sq ft

5114 S Kenwood Ave Unit 3B, Chicago, IL 60615

Property at 4827 S Saint Lawrence Ave, Chicago, IL 60615, 9 beds, 6.5 baths

$1,395,000

9 beds6.5 baths— sq ft

4827 S Saint Lawrence Ave, Chicago, IL 60615

Property at 5114 S Kenwood Ave Unit PHA, Chicago, IL 60615, 3 beds, 2.5 baths

$1,000,000

3 beds2.5 baths1,898 sq ft

5114 S Kenwood Ave Unit PHA, Chicago, IL 60615

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 922 E 42nd Pl, Chicago, IL 60653, 6 beds, 4.5 baths

$999,900

6 beds4.5 baths— sq ft

922 E 42nd Pl, Chicago, IL 60653

Property at 4537 S Evans Ave, Chicago, IL 60653, 10 beds, 8 baths

$1,189,000

10 beds8 baths— sq ft

4537 S Evans Ave, Chicago, IL 60653

Property at 5410 S Indiana Ave, Chicago, IL 60615, 18 beds, 6 baths

$899,000

18 beds6 baths14,841 sq ft

5410 S Indiana Ave, Chicago, IL 60615

Property at 4244 S Prairie Ave, Chicago, IL 60653, 6 beds, 5 baths

$899,999

6 beds5 baths— sq ft

4244 S Prairie Ave, Chicago, IL 60653

Property at 5200 S Woodlawn Ave, Chicago, IL 60615, 47 beds, 37 baths

$6,290,000

47 beds37 baths65,000 sq ft

5200 S Woodlawn Ave, Chicago, IL 60615

Property at 442-444 E 48th St, Chicago, IL 60615, 29 beds, 23 baths

$4,000,000

29 beds23 baths— sq ft

442-444 E 48th St, Chicago, IL 60615

Property at 5140 S Kimbark Ave, Chicago, IL 60615, 27 beds, 18 baths

$2,990,000

27 beds18 baths— sq ft

5140 S Kimbark Ave, Chicago, IL 60615

Property at 1226 W 31st Pl, Chicago, IL 60608, 22 beds, 11 baths

$1,295,000

22 beds11 baths— sq ft

1226 W 31st Pl, Chicago, IL 60608

Property at 3405 S Union St, Chicago, IL 60616, 12 beds, 6 baths

$1,199,000

12 beds6 baths— sq ft

3405 S Union St, Chicago, IL 60616

Property at 1422 E 66th Pl, Chicago, IL 60637, 9 beds, 6 baths

$880,000

9 beds6 baths— sq ft

1422 E 66th Pl, 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 3214 S Canal St, Chicago, IL 60616, 5 beds, 6 baths

$1,849,999

5 beds6 baths8,800 sq ft

3214 S Canal St, Chicago, IL 60616

Property at 4553 S Ellis Ave, Chicago, IL 60653, 7 beds, 4.5 baths

$975,000

7 beds4.5 baths3,852 sq ft

4553 S Ellis Ave, Chicago, IL 60653

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 5333 S Calumet Ave, Chicago, IL 60615, 12 beds, 8 baths

$1,077,500

12 beds8 baths— sq ft

5333 S Calumet Ave, Chicago, IL 60615

Property at 339 W 23rd Pl, Chicago, IL 60616, 9 beds, 4 baths

$915,000

9 beds4 baths— sq ft

339 W 23rd Pl, Chicago, IL 60616

Property at 5114 S Kenwood Ave Unit PHB, Chicago, IL 60615, 3 beds, 2.5 baths

$1,000,000

3 beds2.5 baths1,881 sq ft

5114 S Kenwood Ave Unit PHB, Chicago, IL 60615

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 7270 S South Shore Dr, Chicago, IL 60649, 28 beds, 20 baths

$7,000,000

28 beds20 baths40,000 sq ft

7270 S South Shore Dr, Chicago, IL 60649

Property at 5114 S Kenwood Ave Unit 4B, Chicago, IL 60615, 3 beds, 2.5 baths

$925,000

3 beds2.5 baths1,881 sq ft

5114 S Kenwood Ave Unit 4B, Chicago, IL 60615

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

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Based on information submitted to the MLS GRID as of Wed Dec 03 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.

Luxury Homes for Sale in South Side

There are currently 71 luxury homes for sale in South Side at a median listing price of $280K. 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 477 condos, 49 townhouses, and 257 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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