South Side Homes under $400,000

Welcome to the vibrant and diverse South Side of Chicago, a neighborhood that perfectly blends rich history with modern living. Nestled in Cook County, the South Side is known for its unique cultural heritage, stunning architecture, and a strong sense of community. This area boasts a variety of parks, local eateries, and cultural institutions, making it a great place for families, young professionals, and anyone looking to experience the true essence of Chicago life.

For homebuyers seeking affordability without sacrificing charm, the South Side offers an impressive selection of homes under $400,000. Whether you’re looking for a cozy bungalow, a spacious multi-family unit, or a stylish condo, you’ll find a range of options to suit your needs. Many of these homes feature classic Chicago architecture, complete with beautiful hardwood floors, vintage details, and inviting outdoor spaces.

Living in the South Side means enjoying easy access to public transportation, allowing for a seamless commute to downtown Chicago and beyond. The neighborhood is also home to a number of renowned institutions, including the Museum of Science and Industry and the historic Bronzeville area, known for its influential African American heritage.

With its affordable housing market and vibrant community spirit, the South Side of Chicago is an ideal destination for those looking to invest in their future while enjoying the rich tapestry of city life. Explore the possibilities today and discover your dream home in this dynamic neighborhood!

Newest South Side Homes under $400,000

$77,000

3 Beds ⋅ 1 Baths ⋅ 12774408 MLS ⋅ NEW Status

Large 1.5 story Classic Brick Bungalow located in the Auburn Gresham neighborhood of the City. Features generous room sizes, beautiful Leaded Glass Bay Windows in the Living Room, formal Dining Room, Eat-In Kitchen, finished Attic, enclosed rear Porch, full unfinished Basement, fenced Yard and a 2 Car detached Garage off the Alley. Close to Shopping, Dining, Transportation, Parks and the Dan Ryan Woods. HUD Case 137-532578, Insured Status: UI (Uninsured). HUD owned Property. The Seller Is selling this property in "AS IS" condition. Seller nor its representatives make any representations or warranties regarding the property.

8119 S Wolcott Avenue, Chicago

$242,500

3 Beds ⋅ 2 Baths ⋅ 12775705 MLS ⋅ NEW Status

This beautiful condo qualifies for the City of Chicago HomeGrown assistance program of up to $70,000! It must be your primary residence, but you don't have to be a first-time home buyer. Welcome home to this meticulously maintained 3-bedroom, 2-bath garden unit offering an impressive 1,500 square feet of comfortable living space in the heart of Bronzeville. Hardwood floors flow throughout the home, while the spacious kitchen features stainless steel appliances and opens seamlessly to the living area, creating an inviting space for everyday living and entertaining. The private primary suite offers its own en-suite bath, and the convenience of in-unit laundry makes daily life even easier. Low monthly assessments and an investor-friendly association add exceptional value, whether you're searching for your next home or an investment opportunity. Ideally located near parks, restaurants, shopping, and public transportation, this move-in-ready home combines comfort, convenience, and a prime location. A wonderful place to call home-or a smart addition to your investment portfolio!

4520 S King Drive Unit #1B, Chicago

$350,000

6 Beds ⋅ 3 Baths ⋅ 12774609 MLS ⋅ NEW Status

6146 S California Avenue, Chicago

$124,900

3 Beds ⋅ 1 Baths ⋅ 12772762 MLS ⋅ NEW Status

A welcoming Chicago home with comfortable living spaces and plenty of flexibility to make it your own. The interior offers a bright, functional layout with room to relax, entertain, work from home, or create spaces that fit your lifestyle. The kitchen serves as a natural gathering point, while the bedrooms provide comfortable private retreats and the overall layout offers practical everyday living. Outdoor space adds another place to unwind or gather with guests. Conveniently located near neighborhood parks, schools, shopping, dining, public transportation, and major roadways with easy access throughout Chicago and the surrounding South Side communities.

8919 S Bishop Street, Chicago

$299,000

4 Beds ⋅ 3 Baths ⋅ 12771971 MLS ⋅ NEW Status

Welcome to 5735 S. Marshfield Ave! This brick two-unit property offers a versatile layout with a duplex-down first-floor unit and a spacious second-floor apartment, making it a great opportunity for an owner-occupant, house hacker, or investor looking to add to their portfolio. Both units offer functional layouts with separate living areas and plenty of opportunity to make the property your own. The duplex-down first-floor unit features 2 bedrooms, 2 bathrooms, living room, dining room, and kitchen. The second-floor unit features 2 bedrooms, 1 bathroom, living room, dining room, kitchen, and pantry. Both water heaters were replaced with new units in March 2024. Property is being sold as-is.

5735 S Marshfield Avenue, Chicago

$259,900

3 Beds ⋅ 2 Baths ⋅ 12524979 MLS ⋅ NEW Status

WOW!!! PROFESSIONAL GUT REHAB. EVERYTHING IS NEW!!! HUGE KITCHEN FEATURES 42 IN MAPLE CABINETS QUARTZ COUNTERTOPS W/ UNDERMOUNT SINK, GORGEOUS MOSAIC KITCHEN BACKSPLASH, BRAND NEW STAINLESS STEEL APPLIANCES, DISHWASHER, WINE RACK & COOLER, PLENTY OF CABINET AND COUNTERTOP SPACE. MARBLE BATH FLOOR TILES IN MAIN BATH. LIVING AREA IS OPEN, SPACIOUS FLOOR PLAN WITH GENEROUS SIZE LIVING ROOM, SEPARATE DINING ROOM. CAN LIGHTING THROUGHOUT. CROWN MOLDING, BEAUTIFUL OAK HARDWOOD FLOORS AND WAINSCOT WALL TRIMS. GENEROUS SIZED HARDWOOD FLOOR STAIRCASE LEADING TO 2ND FLOOR WHICH INCLUDES 2 LARGE BEDROOMS AND 2ND (1/2) BATH. BASEMENT FEATURES A 3RD BEDROOM, LAUNDRY AREA AND UTILITY ROOM. NEW PLUMBING AND ELECTRIC THROUGHOUT. CENTRAL AIR TO BE INSTALLED PRIOR TO CLOSE. 2 CAR PARKING IN REAR OF PROPERTY, BIG BACK YARD. LOW PROPERTY TAXES. DON'T MISS THIS ONE!

6812 S Green Street, Chicago

$150,000

1 Beds ⋅ 1 Baths ⋅ 12773683 MLS ⋅ NEW Status

Spacious 1 bedroom condo, filled with natural light and lake views. Move in ready! Beautiful South/East views, located on the top floor. Walking distance to Lake Michigan. Close to Hospital, llT, McCormick Place Convention Center, MotorRow restaurants and shops and centrally located next to I-55 , 90, and 290. Elevator building. PARKING permit is available within the condo community. Great for owner or investor. RENTALS ALLOWED.

345 E Eastgate Place Unit #604, Chicago

3001 S Michigan Avenue Unit #809, Chicago

$120,000

1 Beds ⋅ 1 Baths ⋅ 12758463 MLS ⋅ NEW Status

Bright north-facing 1 bedroom at South Commons with a skyline view that stretches to the lake. Floor-to-ceiling windows fill the open living and dining area with natural light, and the private balcony is the perfect spot for morning coffee or evening city lights. The fully remodeled kitchen features new cabinetry, counters, and stainless appliances, and opens to the main living space. The generous bedroom offers ample closet space, with a full bath nearby. South Commons is a 6-building community with 24-hour security, on-site management, two outdoor pools, a bike room, storage, and parking available. Assessments include heat, gas, water, pool, and common insurance. Coin laundry in building. Recent building improvements include full water riser replacement, new roofs on the low-rise buildings, resurfaced parking lots, and LED lighting throughout. Steps to the 31st Street Beach and lakefront trail, Mariano's, IIT, and McCormick Place, with the Red Line, Metra Electric, I-55, and Lake Shore Drive minutes away. An easy downtown commute in a neighborhood that keeps getting better.

3001 S Michigan Avenue Unit #809, Chicago

$125,000

5 Beds ⋅ 2 Baths ⋅ 12774916 MLS ⋅ NEW Status

Two Unit on a double lot with space in the back for 4 cars (brand new concrete slab) Fully gutted and ready for your ideas. Top floor is currently a 3 bed/1bath with the potential to duplex up, dormer out and finish the attic space. First level is a 2 bed/1 bath with basement access. Insulation, some dry wall, Brand new plywood/subflooring has been added throughout. New Framing has been added throughout. Great opportunity to build in some equity while cash flowing from the start. Sold "As Is, Where Is" information deemed reliable but not guaranteed. All measurements are estimates. Container will be included with the home.

736 E 90Th Street, Chicago

$279,000

3 Beds ⋅ 2 Baths ⋅ 12767563 MLS ⋅ NEW Status

A beautifully remodeled, fully furnished duplex-down condo in a prime South Side location. This spacious 3-bedroom, 2-bath home features approximately 1,800 square feet of stylish living space with an additional flex room ideal for an office, guest area, workout space, or creative studio. The main level offers a warm, modern feel with hardwood flooring, exposed brick, and an updated kitchen featuring quartz countertops, farmhouse sink, subway tile backsplash, and premium Samsung Smart appliances, including a double oven with air-fryer feature. The lower level expands the home with generous bedroom space, a modern bath with jacuzzi tub, and excellent flexibility for everyday living or hosting. Additional highlights include central heat and air, newer high-efficiency furnace, in-unit laundry, washer and dryer, recently cleaned air ducts, UV air purification system, and Bluetooth speakers in both bathrooms. Designed as a true turnkey furnished residence, the home includes 2 luxury king sleigh beds, 6 massive 4K TVs, a PS5 gaming lounge, a Kobe Bryant-themed room, LED mirrors, and a 6-jet bathtub. **This home has previously been used as a furnished income-producing rental, including Airbnb use. With all furnishings included, it offers strong leasing potential while also serving as a comfortable move-in-ready residence.** Ideally located near Washington Park, public transportation, the University of Chicago, UChicago Medicine, Hyde Park, Lake Michigan, the Obama Presidential Center, and the Griffin Museum of Science and Industry. Schedule your private showing today!

231 E 59Th Street Unit #1, Chicago

$130,000

4 Beds ⋅ 2 Baths ⋅ 12767603 MLS ⋅ NEW Status

4 BR/2 bath SFH. Full unfinished basement. Two car detached garage.

7343 S Prairie Avenue, Chicago

$75,000

4 Beds ⋅ 2 Baths ⋅ 12770827 MLS ⋅ NEW Status

Located on the south after West Englewood comunity, this brick tudor style home offers an expansive floor plan, solid bones with tremendous upside. This home features a large open living room upon entry with eastern exposure which allows natural sunlight to shine all day into the home. There is a formal dining room and a first-floor bedroom which is a huge upside to have a first-floor bedroom. The second level features 3 additional bedrooms with a second bathroom, can easily convert two of those bedrooms into one and create a large master suite while building equity! IF more space is something you are in need of the basement was previously finished, offers plenty of room for 2 more bedrooms and tons of equity upside! Add a two-car garage and a private fenced yard, this is a diamond in the rough waiting to be shined! Get inside today as this one will not last long!

6120 S Loomis Boulevard, Chicago

Start Your Search

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED 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.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.