South Side Real Estate

The South Side of Chicago, located in Cook County, Illinois, is a vibrant and diverse neighborhood that offers a unique blend of history, culture, and community. Known for its rich heritage and iconic landmarks, the South Side is a sought-after destination for both residents and visitors alike.

One of the standout features of the South Side is its stunning architecture. From the historic brownstone buildings of Bronzeville to the grand mansions of Hyde Park, this area showcases a wide range of architectural styles that reflect the neighborhood's storied past. Additionally, the South Side is home to several renowned institutions, including the University of Chicago, which adds to the intellectual and cultural atmosphere.

The South Side also boasts an array of recreational opportunities. Nature enthusiasts can explore the sprawling green spaces of Washington Park or take a stroll along the picturesque Lake Michigan shoreline. Sports enthusiasts can catch a game at Guaranteed Rate Field, home to the Chicago White Sox, or enjoy a round of golf at one of the area's many golf courses.

In terms of amenities, the South Side offers a diverse range of shopping, dining, and entertainment options. From trendy boutiques and gourmet restaurants to lively music venues and art galleries, there is something for everyone to enjoy.

With its rich history, vibrant culture, and diverse community, the South Side of Chicago is a neighborhood that truly embodies the spirit of the city. Whether you're looking for a place to call home or planning a visit, the South Side offers a unique and exciting experience.

Newest Listings in South Side

$190,000

3 Beds ⋅ 2 Baths ⋅ 12716058 MLS ⋅ NEW Status

Spacious 3 bedroom and 2 full bath condominium features a large open living area with balcony access, mantel fireplace and kitchen with oak cabinetry, granite countertops and peninsula. New Frigidaire Gallery series stainless steel wall oven, range top, dishwasher and microwave oven. Recessed lighting throughout with exposed brick. Master suite also has a private full bath and rear deck access. In unit washer/dryer hook-up, nice closet space and central air. Gated parking. Steps to green line and Washington Park. Easy access to the expressway, Hyde Park and the lakefront.

5928 S Prairie Street Unit #3, Chicago

$1,875,000

12716218 MLS ⋅ NEW Status

CRER is pleased to present 4930 S Indiana, an 8-unit multifamily offering in Chicago's historic Bronzeville neighborhood. The building was built as a condominium in 2005 and includes a unit mix of (6) three-bedroom, two bath units and (2) four-bedroom, three bath units. Each unit features spacious layouts with condo quality finishes, central heat and air, hardwood floors, and the convenience of in-unit laundry. Other on-site amenities include eight gated parking spaces and 24-hour surveillance.

4930 S Indiana Avenue, Chicago

$409,999

4 Beds ⋅ 3 Baths ⋅ 12716212 MLS ⋅ NEW Status

Come see this beautifully renovated, move-in-ready home. It features a brand-new roof, soffit, fascia, gutters, windows, tuckpointing, updated flooring, high efficiency furnace and genuine wood moldings throughout. The main level boasts a spacious living room, a formal dining room, three bedrooms, a full bathroom, a den and a large kitchen with a full pantry. Upstairs, you will find a private primary bedroom suite complete with its own wet bar area and a separate den. The fully finished basement offers a massive open family room, an ample recreation room, a full bathroom, a utility room, and a laundry room. For extra convenience, the garage includes a rear overhead door that opens directly to the backyard and pavers patio, perfect for entertaining. A truly unique feature of this home is that every floor has its own direct exit to the backyard. Conveniently located near public transportation, restaurants, expressways, and shopping, this home has absolutely everything you need. Don't miss out!

3507 W 60Th Place, Chicago

$259,900

7 Beds ⋅ 3 Baths ⋅ 12716205 MLS ⋅ NEW Status

Completely Reimagined & Move-In Ready: Expansive 7-Bedroom Gem! Welcome home to this breathtaking, fully gut-rehabbed 2-story residence offering an incredibly rare 7 bedrooms, 3 full bathrooms, and an expansive layout designed for modern living. Stripped down and completely reimagined in 2026, this turn-key property seamlessly blends historic charm with sleek, contemporary upgrades. Step inside to discover a bright, airy main level boasting high ceilings, brilliant modern lighting, and gleaming new flooring throughout. The flowing floor plan is perfect for hosting gatherings of any size. The modern aesthetic continues with fresh, designer-curated paint and the perfect finishing touches. Need space? You'll love the fully finished basement, offering incredible flexibility for multigenerational living. Enjoy total peace of mind with brand-new central heating and A/C, updated plumbing and electric, and brand-new energy-efficient windows that flood the home with natural light. Situated on a generous 3,123 sq. ft. lot, the exterior features an easy-access rear entry with a dedicated off-alley parking pad. With every detail meticulously updated, all that's left to do is move in! Schedule your private tour today.

6843 S Carpenter Street, Chicago

$369,500

4 Beds ⋅ 3 Baths ⋅ 12716185 MLS ⋅ NEW Status

ABSOLUTELY STUNNING RECENTLY REHABBED FIVE BEDROOM HOME JUST MINUTES AWAY FROM 90/94 AND WALKING DISTANCE TO SHOPPING, RETAIL, SCHOOLS, PARKS, AND ALL THAT THE AREA HAS TO OFFER. THE MAIN LEVEL OF THIS METICULOUSLY MAINTAINED HOME FEATURES AN OPEN CONCEPT LIVING ROOM/DINING ROOM, UPDATED KITCHEN WITH AMPLE CABINET AND COUNTERTOP SPACE, TWO SPACIOUS BEDROOMS, AND FULL BATH. THE UPSTAIRS INCLUDES THE PRIMARY SUITE FEATURING A HUGE WALK-IN CLOSET/SITTING ROOM, FULLY REHABBED SHARED BATH, AND ADDITIONAL OVERSIZED BEDROOM. THE LOWER LEVEL OF THIS GEM INCLUDES A MASSIVE DEN/LIVING ROOM, ADDITIONAL BEDROOM WITH WALK-IN CLOSET, FULL BATH WITH BEAUTIFUL FULLY TILED SHOWER, ADDITIONAL STORAGE SPACE, AND LAUNDRY AREA. THIS HOME ALSO FEATURES UPDATED PLUMBING, ELECTRICAL, HVAC, NEWER DECK/PORCH, AND TWO CAR GARAGE.

7643 S Eberhart Avenue, Chicago

$975,000

9 Beds ⋅ 6 Baths ⋅ 12716170 MLS ⋅ NEW Status

Turnkey 3 Unit on an oversized lot. Each luxury simplex is an oversized 3-bedroom, 2-bathroom condo-quality unit; each features a beautiful 1,500 sq ft open floorplan, each kitchen with high-end stainless steel appliances, quartz counters, and in-unit laundry. Extra insulation for noise reduction between floors and from the outside. Unbeatable location walking distance to the CTA Green Line station and two blocks from Washington Park. Fully rented at $8,400/month. Developed by Woodlawn's premier New Construction builder, this home is ready for the savvy investor and comes with a one-year builder warranty. This is an opportunity to own a trophy investment property in a rapidly appreciating neighborhood. Schedule a private showing today.

5643 S Prairie Avenue, Chicago

$10,000

12716169 MLS ⋅ NEW Status

ATTENTION DEVELOPERS/BUILDERS/INVESTORS. EXCELLENT OPPORTUNITY TO BUY AND BUILD ALSO LISTED FOR SALE SEPARATELY ARE LOTS 6447/6449

6451 S Laflin Street, Chicago

$10,000

12716168 MLS ⋅ NEW Status

ATTENTION DEVELOPERS/BUILDERS/INVESTORS. EXCELLENT OPPORTUNITY TO BUY AND BUILD ALSO LISTED FOR SALE SEPARATELY ARE LOTS 6447/6451

6449 S Laflin Street, Chicago

$10,000

12716165 MLS ⋅ NEW Status

ATTENTION DEVELOPERS/BUILDERS/INVESTORS. EXCELLENT OPPORTUNITY TO BUY AND BUILD ALSO LISTED FOR SALE SEPARATELY ARE LOTS 6449 and 6451

6447 S Laflin Street, Chicago

$975,000

9 Beds ⋅ 6 Baths ⋅ 12716167 MLS ⋅ NEW Status

BRAND NEW CONSTRUCTION 3 Unit on an oversized lot. Each luxury simplex is an oversized 3 bedroom, 2 bathroom Condo Quality Unit; each features a beautiful 1,500 sq ft open floorplan, each kitchen with high-end stainless steel appliances, quartz counters, and in-unit laundry. Extra insulation for noise reduction between floors and from the outside. Unbeatable location walking distance to the CTA Green Line station and two blocks from Washington Park. Projected rent roll is $8,400. Developed by Woodlawn's premier New Construction builder, this home is ready for immediate occupancy and comes with a one-year builder warranty. This is an opportunity to own a trophy investment property in a rapidly appreciating neighborhood. Schedule a private showing today to experience the exceptional craftsmanship and modern design firsthand.

5637 S Prairie Avenue, Chicago

$2,899,000

12716166 MLS ⋅ NEW Status

New Construction 9 Unit Building by one of the Southside's Premium Developers & the Opportunity to own a trophy investment property in a rapidly appreciating neighborhood. Perfect for a 1031 Investor looking for a property with over $25,000/month in projected income (with rental and sale comps already proven by the same developer in the same area), low maintenance, and steady year-on-year upside appreciation. Each building is on an oversized lot. Each luxury simplex is a 3 bedroom, 2 bathroom Condo Quality Unit; each features a beautiful 1,500 sq ft open floorplan, each kitchen with high-end stainless steel appliances, quartz counters, and in-unit laundry. Extra insulation for noise reduction between floors and from the outside. Unbeatable location walking distance to the CTA Green Line station and two blocks from Washington Park. Projected rent roll is $8,400.

5637-43 S Prairie Avenue, Chicago

$100,000

12716161 MLS ⋅ NEW Status

ATTENTION DEVELOPERS/BUILDERS/INVESTORS. EXCELLENT OPPORTUNITY TO BUY AND BUILD

6407 S Justine Street, Chicago

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