South Side Homes with Condo-Duplex Style

Welcome to the vibrant South Side of Chicago, a neighborhood rich in history, culture, and community spirit. Nestled in Cook County, this dynamic area boasts a unique blend of urban charm and residential comfort, making it an ideal place to call home.

The South Side is renowned for its diverse architectural styles, and among them, the condo-duplex homes stand out as a popular choice for residents seeking modern living with a touch of classic elegance. These homes offer spacious layouts, often featuring high ceilings and large windows that flood the interiors with natural light. With multiple levels, condo-duplexes provide both privacy and a sense of community, perfect for families and young professionals alike.

Living in the South Side means being part of a thriving community that embraces its rich heritage while looking towards the future. You'll find an array of local shops, eateries, and cultural institutions, including museums and theaters that celebrate the arts. The neighborhood is also home to beautiful parks and green spaces, providing ample opportunities for outdoor activities and relaxation.

Transportation is convenient, with easy access to public transit options, making commutes to downtown Chicago a breeze. The South Side is not just a place to live; it’s a vibrant community where neighbors become friends and memories are made.

Whether you’re looking for a cozy condo-duplex to start your journey or a spacious home to grow your family, the South Side of Chicago offers an inviting atmosphere and a sense of belonging that is hard to find elsewhere. Discover your new home in this remarkable neighborhood today!

Newest South Side Homes with Condo-Duplex Style

$369,000

4 Beds ⋅ 3 Baths ⋅ 12743607 MLS ⋅ ACTIVE Status

Massive Duplex in Bronzeville! Enjoy the feel of single-family living in this beautifully updated duplex down with a private entrance on a quiet residential street with all new kitchen appliances. This extra-large condo offers the perfect balance of comfort, charm, and convenience. Inside, rich hardwood floors run throughout the main level, where you'll find a bright and welcoming living room with an abundance of natural light and overlooking a serene tree-lined street. The open-concept kitchen and dining area create a seamless space for everyday living or entertaining, with ALL new quartz countertops, 42" cabinets. On the main level, you also have THREE well-sized bedrooms and two full baths, including the primary en-suite. The lower level with sleek luxury vinyl offers even more space with a very large family room with dry bar, one additional bedroom, a full bathroom, side by side laundry, and tons of storage-perfect for extra living space, guests, a gym, or creative space. Out back, you have a nice-sized deck and one private parking space. Located near all that we love about Bronzeville: it is within walking distance to coffee, restaurants, shops, the Hyde Park 53rd St commercial corridor, and the inviting community vibes only found in Bronzeville.

4759 S Forrestville Avenue Unit #1W, Chicago

$530,000

3 Beds ⋅ 2 Baths ⋅ 12753255 MLS ⋅ ACTIVE Status

Discover this newly renovated duplex-up condo in the heart of Bronzeville. Featuring three spacious bedrooms with a den and thoughtfully designed bathrooms, this home is part of an exclusive four-unit building that showcases contemporary style and attention to detail throughout. Enjoy your own private rooftop retreat with sweeping views-ideal for entertaining guests or relaxing in peace. A private one-car garage adds both convenience and comfort to this exceptional offering. Don't miss the chance to own this stunning, move-in-ready residence.

3330 S Indiana Avenue Unit #2N, Chicago

$279,900

3 Beds ⋅ 2 Baths ⋅ 12742172 MLS ⋅ ACTIVE Status

FULLY FURNISHED NEW REMODELED TURN KEY UNIT MINUTES FROM OBAMA CENTER PERFECT FOR OWNER OCCUPIED OR INVESTORS PREVIOUSLY USED TO GENERATE ADDITIONAL INCOME ON AIRBNB Spectacular 3-bedroom, 2-bath duplex-down condo with an additional flex room offering approximately 1,800 sq. ft. of living space, just steps from Washington Park, public transportation, the University of Chicago, and the Museum of Science and Industry. Features include hardwood floors, exposed brick, modern kitchen with quartz countertops, farmhouse sink, subway tile backsplash, and premium Samsung Smart appliances, including a double oven with air-fryer feature. The lower level offers a primary bedroom, two additional bedrooms, office area, and modern bath with jacuzzi tub. Both bathrooms feature Bluetooth speakers. Enjoy central air/heat, newer high-efficiency furnace, in-unit laundry, washer/dryer, recently cleaned air ducts, and UV air purification system. Best of all, this home comes fully furnished and includes everything you need to move right in!

231 E 59Th Street Unit #1, Chicago

$345,000

3 Beds ⋅ 3 Baths ⋅ 12726659 MLS ⋅ ACTIVE Status

Stunning Bronzeville Duplex-Down 3-Bed, 2.5-Bath with garage parking included. Beautifully updated and move-in ready, this Bronzeville gem features hardwood floors, soaring ceilings, and natural light throughout. The sleek kitchen boasts quartz countertops and backsplash, white cabinetry, and brand-new stainless appliances plus an extra nook perfect for a coffee or wet bar. The primary suite offers generous space and a spa-like ensuite with floor-to-ceiling porcelain tile. The lower level adds a family room, two bedrooms, full bath, and extra storage, ideal for guests or flex living. Enjoy a private deck for entertaining, a shared backyard, and one included garage space. All of this just blocks from Northwestern Medicine, minutes from the Obama Presidential Center, U of C, public transit, and more. Schedule your showing today.

735 E 50Th Street Unit #2, Chicago

$439,900

4 Beds ⋅ 3 Baths ⋅ 12552430 MLS ⋅ ACTIVE Status

At nearly 3,000 square feet, this spacious duplex-down condo offers the comfort and feel of a single-family home in the heart of Bronzeville. The home reflects normal wear and presents a wonderful opportunity for the next owner to add their own style through a few cosmetic updates. This 4 bedroom, 3 bath open-concept condo welcomes you with hardwood floors throughout the main floor and a beautiful walnut inlay that highlights the fireplace. A spacious kitchen with stainless steel appliances, granite countertops, and a center island that flows seamlessly into the dining and living areas perfect for everyday living and entertaining. The oversized primary suite includes a private deck and a spa-like bath with a whirlpool tub, separate shower, and double vanity. A second bedroom and full bath, along with flexible space for a home office or sitting area, complete the main level.The lower level offers 10-foot ceilings, a large family room with a second fireplace, two additional bedrooms, a full bath, in-unit laundry, and extra space for a home gym, playroom, or media room. Private storage and one gated parking space are included in this low monthly assessments, self-managed building. Located on a quiet, tree-lined block surrounded by historic and newer homes, you're just steps from King Drive and the annual Bud Billiken Parade. Enjoy easy access to the CTA Green Line, Metra, major expressways, Mariano's, Jewel-Osco, Guaranteed Rate Field, McCormick Place, the lakefront, downtown Chicago, restaurants, coffee shops, and Bronzeville's vibrant arts and cultural scene. Front and back exterior security cameras are included with this unit, a new owner monitoring subscription will be required. Come see why this isn't just another condo-it's a home with room to live.

435 E 42Nd Street Unit #1, Chicago

$344,900

3 Beds ⋅ 3 Baths ⋅ 12685324 MLS ⋅ ACTIVE Status

Welcome to this marvelous over-sized duplex condo in the picturesque sought after neighborhood of historic Bronzeville. Featuring 3 bedrooms and 3 full bathrooms, this beautifully updated duplex offers an abundance of space that is drenched with natural light. The gleaming luxury hardwood floors welcome you in the spacious living room with a grandiose patio door that offers wonderful views of the beautiful tree lined streets. The living room guides you into the spectacular kitchen with amazing high end cabinets, elegant quartz countertops that boast a breakfast bar and stainless steel appliances. The living room offers a serene setting that features a breathtaking fireplace. The main floor also offers a conveniently located full bathroom and a guest bedroom, perfect for when entertaining family and friends. The lower level features two expansive master bedrooms with new carpet, new light fixtures, large walk-in closets and full master baths. The unit also offers plenty of storage space throughout and in-unit laundry room. Enjoy some fresh air on those spring and summer days on your own private balcony. Updates include: New paint throughout, new light fixtures, refinished hardwood floors, new carpet, new kitchen faucet, and new cabinet pulls. The unit includes 1 parking space conveniently located steps away from the backdoor entrance, intercom system, and a private storage locker. Walking distance to the beautiful Oakwood Beach. The proximity to golfing, parks, shopping and dining is outstanding. Pets are welcome.

4105 S Drexel Boulevard Unit #1SR, Chicago

$420,000

4 Beds ⋅ 3 Baths ⋅ 12661298 MLS ⋅ ACTIVE Status

Gorgeous, well-maintained 4 beds/3 full baths duplex down grey-stone avail now in Historic Grand Boulevard! Main level has hardwood floors in living/dining/kitchen, stainless steel appliances, granite countertops, recessed lighting and ceiling fans throughout. Living area has electric fireplace w/mantle and beautiful bay windows for plenty of sunlight. 2 nice-sized carpeted bedrooms on main level w/main bath which has soaking tub/shower. Master suite has large bedroom w/full private bath w/double sinks, European shower, and heated floors. Cozy walk-in closet w/custom shelves, steel shutters on back windows for privacy/security. Below level has huge family room/den w/wet-bar, side-by-side washer/dryer in separate closet, huge bedroom w/wall to wall closet, and full shared bath w/shower/tub! Unit includes one assigned garage parking space w/remote, storage unit and semi-private deck on first level! Truly, a gem on a nice tree-lined block! Don't miss your opportunity to own a piece of history in the heart of Bronzeville!

4839 S Vincennes Avenue Unit #1, Chicago

$159,900

3 Beds ⋅ 2 Baths ⋅ 12599397 MLS ⋅ ACTIVE Status

3 bed 2 bath condo-duplex located on the southern end of the historic Bronzeville neighborhood. With over 2200 sq ft of living space spread across 2 floors this condo feels like a house. On main floor- spacious living room with access to personal east-facing front balcony perfect for view of the sunrise, updated eat-in kitchen with stainless steel appliances and plenty of cabinet space and 2 bedrooms. Lower level consists of an additional bedroom, an additional bathroom family room, another finished room that could be used as an office and in-unit laundry. Assigned garage parking space for secure car storage, just minutes from the Dan Ryan expressway for easy commute. Within walking distance of CTA bus and Train (Green & Red lines).

5016 S Prairie Avenue Unit #1, 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.