South Side Real Estate

Welcome to the vibrant South Side of Chicago, a neighborhood steeped in rich history and cultural diversity. Nestled within Cook County, this dynamic area is a tapestry of communities, each offering its own unique charm and character. From the bustling streets of Hyde Park to the artistic enclaves of Bronzeville, the South Side is a place where tradition meets modernity.

One of the defining features of the South Side is its deep-rooted cultural heritage. The neighborhood is renowned for its contributions to music, art, and literature, having birthed legendary figures such as Louis Armstrong and Gwendolyn Brooks. You can stroll through the historic streets, where jazz and blues echo from local venues, or visit the DuSable Museum of African American History to immerse yourself in the rich narratives that have shaped this area.

The South Side is also home to beautiful parks and green spaces, including the expansive Washington Park and the picturesque Jackson Park, which hosted the 1893 World’s Columbian Exposition. These parks provide a perfect backdrop for outdoor activities, community events, and family gatherings.

For those seeking a sense of community, the South Side offers a variety of local businesses, farmers' markets, and eateries that reflect the neighborhood's culinary diversity. Whether you’re enjoying a classic Chicago-style deep-dish pizza or exploring the flavors of international cuisine, you’ll find something to tantalize your taste buds.

With its affordable housing options, strong community ties, and rich cultural offerings, the South Side of Chicago is not just a place to live; it’s a place to thrive. Discover the warmth and vibrancy of this extraordinary neighborhood today!

Newest Listings in South Side

$350,000

12799063 MLS ⋅ NEW Status

Bring your business vision to Chicago's 79th Street commercial corridor. Located at 255 W 79th St, Chicago, IL 60620, this approximately 7,125 SF retail building for sale offers entrepreneurs, owner-users, and developers the opportunity to establish their next destination in West Chatham. Picture a beauty and wellness destination combining salon suites with product retail. A neighborhood grocery or specialty food market serving nearby households. A medical, dental, or physical therapy practice offering convenient local care. Or a fitness, yoga, or personal-training studio built around a loyal membership community. C1-1 zoning accommodates a broad range of commercial uses, creating possibilities for these concepts as well as restaurants, coffee shops, professional offices, and retail showrooms. Formerly occupied by a beauty supply retailer, the building features a distinctive brick-and-stone facade, street-level exposure, and a rear overhead door. The existing interior presents an opportunity for a custom commercial renovation, allowing a buyer to plan sales areas, treatment rooms, studios, offices, or other business-specific spaces. For an owner-operator, this is an opportunity to build a brand while owning the real estate behind it. For a developer or investor, it offers a commercial property to renovate, reposition, and introduce to new occupants. Accessibility strengthens the opportunity. Nearby CTA #79 and #24 bus stops connect the property to surrounding neighborhoods, while the 79th Street Red Line station is approximately 0.4 mile away. Dan Ryan Expressway/I-94 access is approximately 0.3 mile away, supporting connections for customers, employees, and deliveries. Chatham Market is roughly 1 mile away, with Lowe's nearby, and Chatham Ridge Shopping Center is approximately 1.4 miles away. Area shopping destinations include Food 4 Less, Five Below, Foot Locker, and Starbucks. The property fronts a Neighborhood Opportunity Fund eligible commercial corridor and is mapped within the 79th/Vincennes SBIF district. Qualifying commercial projects may pursue NOF grants and potential SBIF assistance, subject to program eligibility, funding, application windows, and City approval. Create a storefront that reflects your vision and gives customers a reason to return. Schedule a tour to explore the property's retail, service-business, and commercial redevelopment possibilities.

255 W 79Th Street, Chicago

$389,900

5 Beds ⋅ 2 Baths ⋅ 12799062 MLS ⋅ NEW Status

Classic Chicago character meets updated living. Located along historic Martin Luther King Drive in Greater Grand Crossing, this beautifully maintained two-unit Greystone was remodeled in 2022 and offers an excellent opportunity for an owner-occupant or investor. Both residences feature separate living and dining rooms with original hardwood floors that showcase the building's timeless charm. The first-floor unit offers two bedrooms and one bathroom, while the second-floor unit features three bedrooms and one bathroom. The unfinished basement provides additional storage and a dedicated laundry area serving the building. Just steps from public transportation, this property combines neighborhood character with everyday convenience. Live in one unit and rent the other, or add this well-kept Greystone to your investment portfolio. Schedule your private showing today!

7010 S King Drive, Chicago

$125,000

3 Beds ⋅ 1 Baths ⋅ 12798448 MLS ⋅ NEW Status

Affordable living at its best. Spacious main level with kitchen and living room. 3 nice sized bedrooms with bathroom upstairs. End unit with a concrete pad next to unit for parking. Nice yard for relaxing. FHA and VA buyers welcome! Text LA about ~60 property portfolio.

6442 S Yale Avenue Unit #A, Chicago

3021 S Michigan Avenue Unit #306, Chicago

$150,000

2 Beds ⋅ 2 Baths ⋅ 12798990 MLS ⋅ NEW Status

Discover spacious and comfortable city living at 3021 S Michigan Ave, Unit 306, a desirable corner unit with beautiful north and west exposures that bring abundant natural light throughout the home. This well-designed two-bedroom residence features heated flooring, generously sized bedrooms that can both comfortably accommodate king-size beds, and a large private balcony, perfect for relaxing or enjoying the city atmosphere. The functional kitchen offers exciting renovation potential, with the possibility of opening up the kitchen wall to create a modern, open-concept living and entertaining space. Ideally situated near downtown Chicago, the lakefront, parks, restaurants, shopping, public transportation, and major expressways, this home combines generous living space, everyday convenience, and excellent potential for personalization.

3021 S Michigan Avenue Unit #306, Chicago

$155,000

7 Beds ⋅ 3 Baths ⋅ 12798925 MLS ⋅ NEW Status

**INVESTOR SPECIAL - DOUBLE-WIDE LOT, TWO POSSIBILITIES, ENDLESS POTENTIAL!** Bring your vision and renovation expertise to 7011 S. Indiana Avenue! Situated on a generous 50' 125' lot (approximately 6,250 square feet), this property presents an exciting opportunity to complete the two-unit configuration or transform it into one spacious single-family residence, subject to zoning and city approvals. With interior preparation already underway, the clean slate is ready for your creative vision. The oversized lot provides additional possibilities for outdoor entertaining, landscaping, gardening, and future improvements. Conveniently situated near the Dan Ryan Expressway, CTA transportation, neighborhood shopping and dining, Washington Park, Grand Crossing Park, and the historic Stony Island Arts Bank. Whether your goal is to create an income-producing property or a substantial custom residence, this is an opportunity to reimagine the space and unlock its potential. Two possibilities. One oversized lot. Your vision! Property sold AS-IS. Buyer responsible for verifying zoning, permitted use, unit count, lot dimensions, permits, and property condition.

7011 S Indiana Avenue, Chicago

$304,900

4 Beds ⋅ 2 Baths ⋅ 12798809 MLS ⋅ NEW Status

Completely Remodeled Brick Bungalow in on upcoming Area. Beautifully Renovated Top -2-Bottom Transformation. From the moment you walk in You'll immediately will Notice the Quality Finishes; Brand new Vinal Plank Flooring, New Windows Throughout, Every Detail was Thoughtfully Done. Kitchen with 42in. Tall Cabinets, Granit Countertop, 4 Bedrooms, 2 Full Bath, All Stain Still Appliances, Brand New Electricity and Plumbing Installed, Newer 2 Car Garage, New Air Forced Heater System with Air Conditioner, Brend New Deck on the Back Porch. The Fully Finished Basement Adds Space for your Family Gatherings and much more to list.

8339 S Throop Street, Chicago

$187,900

12798688 MLS ⋅ NEW Status

EXCELLENT INVESTMENT OPPORTUNITY! OWN 3,000 square feet of versatile commercial and residential space in a high-visibility location just steps from the bustling 79th Street corridor, between Racine and Ashland. This property offers excellent potential for business owners, investors, or those seeking a combination of commercial space and rental income. The building features two separate units and a full unfinished basement. The first-floor open layout of commercial space is a blank canvas, offering endless possibilities for a variety of business ventures, including professional offices, service-based businesses, retail, or other commercial uses. The first floor also includes a private owner/manager's office. The second floor features a renovated apartment with a spacious living room, separate dining room, two bedrooms, one full bathroom, and an enclosed finished rear porch, an attractive feature for potential tenants. Additional highlights include a full unfinished basement, a deep brick two-car garage, separate utilities for the first-floor commercial space and basement versus the second-floor apartment, and rear parking for owners. Convenient street parking and easy commuting access add to the property's appeal. Whether you're an investor looking to expand your portfolio or an entrepreneur seeking the perfect location for your business, this property offers outstanding potential in a well-traveled commercial corridor. PRICED TO SELL! Don't miss this opportunity to bring your vision to life!

1358 W 79Th Street, Chicago

$360,000

7 Beds ⋅ 3 Baths ⋅ 12792860 MLS ⋅ NEW Status

Freshly renovated and ready for its next chapter! This Chicago two-unit building offers three bedrooms, one bathroom, and convenient in-unit laundry in each unit, plus a finished basement for additional space. Extensive updates include brand-new windows, a new roof, new kitchens, new bathrooms, new electrical, new furnace, A/C and new plumbing. Both units are vacant, giving you the flexibility to move into one and rent out the other, or rent both as an investment property. With major updates already completed, this is an exciting opportunity to own, invest, and build equity. Schedule your showing today! Sold As-Is

2053 W 70Th Place, Chicago

$374,900

5 Beds ⋅ 2 Baths ⋅ 12798550 MLS ⋅ NEW Status

Welcome to this beautifully renovated Chicago-style bungalow located in historic Auburn Gresham. The first floor of this home features an updated LIVING ROOM with an electric fireplace and a spacious DINING ROOM. The expanded KITCHEN has stainless steel appliances, quartz countertops, and an island with a butcher block countertop that compliments the other wood features in the room. The MAIN FLOOR BEDROOM is a generous size, and the main floor BATHROOM is both practical and elegant. The second level consists of TWO SPACIOUS YET COZY BEDROOMS with carpeted floors. The basement is completely finished and has a FAMILY ROOM with a feature wall, TWO ADDITIONAL BEDROOMS, a sleek BATHROOM, and a finished LAUNDRY ROOM. The home also has solar panels, and other solar lighting features. The NEW WINDOWS and the benefits of the solar panels should provide energy efficiencies that you will appreciate for years to come. Seller will include a home warranty and is willing to offer closing cost assistance. Do yourself a favor and schedule an appointment today so that you may be Home For the Holidays!

8441 S Aberdeen Street, Chicago

$390,000

6 Beds ⋅ 5 Baths ⋅ 12798587 MLS ⋅ NEW Status

Classic brick charm, generous space, and exceptional versatility come together in this two-unit property, located in Chatham on a quiet, well-cared-for block! Each unit offers three generously sized bedrooms, one-and-a-half bathrooms, and separate heating. Central air conditioning adds comfort and appeal. Picture windows and distinctive masonry create striking curb appeal, while the interior showcases light-toned flooring, recessed lighting, a separate dining area, and a stylish kitchen with gray cabinetry and stainless steel appliances. The finished basement provides additional space for related living, including a standout shower with dramatic marble-look tile, rainfall fixtures, and built-in seating. Enjoy backyard gatherings and unwind in the hot tub, which stays with the building. A three-car garage adds valuable parking and storage, and a roof completed in April 2026 rounds out the highlights. An appealing opportunity for an owner-occupant or investor-schedule your private showing and explore the possibilities!

7921 S Prairie Avenue, Chicago

$330,000

3 Beds ⋅ 1 Baths ⋅ 12797979 MLS ⋅ NEW Status

Welcome to this beautifully rehabbed and meticulously maintained home in the desirable Midway area! This property offers a wonderful combination of modern finishes, comfort, and space. The main level features three spacious bedrooms and a beautifully updated kitchen with luxurious cabinetry. The full basement provides two additional bedrooms, offering flexibility for extended living, guests, or a home office. Enjoy the added outdoor space with a generously sized backyard. Whether you're a first-time buyer or looking for your next home, this property is a must-see!

3456 W 61St Place, Chicago

$59,500

3 Beds ⋅ 2 Baths ⋅ 12798571 MLS ⋅ NEW Status

CALLING ALL REHABBERS!! - HERE'S YOUR NEXT GREAT REHAB PROJECT! Chicago single family frame bungalow in need of loving care, GREAT FIXER UPPER! - Priced to sell fast! Property sold in "as-is" condition, Seller makes no repairs or offers any repair credits. Conveyed with Special Warranty Deed and tax proration at 100%. No survey and no termite provided by Seller. Schedule your showing today! Please submit all offers in writing with full set of disclosures and proof of funds.

330 W 60Th Place, Chicago

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South Side Real Estate

Newest Listings in South Side

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