South Side Townhomes for Sale

Welcome to the vibrant South Side of Chicago, a neighborhood rich in history, culture, and community spirit. Nestled within Cook County, the South Side is known for its diverse population and a strong sense of belonging among residents. This area boasts a unique blend of historic architecture and modern amenities, making it a sought-after destination for homebuyers looking for townhomes that offer both charm and convenience.

The South Side is home to beautiful parks, cultural institutions, and a variety of dining options that reflect the area's rich heritage. Residents can enjoy leisurely strolls through Washington Park or visit the historic Museum of Science and Industry, one of the largest science museums in the Western Hemisphere. The South Side's vibrant arts scene is also a highlight, with galleries, theaters, and music venues that showcase local talent and creativity.

For those seeking townhomes for sale, the South Side presents an excellent opportunity to invest in a community that is on the rise. With a variety of styles and sizes available, you can find the perfect townhome that meets your needs. Many of these properties feature modern designs, spacious layouts, and outdoor spaces, ideal for both entertaining and relaxation.

Additionally, the South Side's accessibility to public transportation and major highways makes commuting to downtown Chicago and other areas a breeze. With a strong sense of community and an array of amenities, the South Side of Chicago is not just a place to live; it’s a place to thrive. Explore the townhomes for sale and discover the perfect blend of urban living and neighborhood charm!

Newest South Side Townhomes for Sale

$999,000

4 Beds ⋅ 4 Baths ⋅ 12792798 MLS ⋅ NEW Status

Move-in ready new construction at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences nestled on a quiet, tree-lined cul-de-sac in historic Kenwood. Thoughtfully designed as a full masonry build, each three-level residence delivers the scale and privacy of a single-family home with the ease of modern new construction, offering expansive living spaces, refined designer finishes, private outdoor living, and a 2-car garage. Sun-filled interiors are complemented by clean architectural lines and timeless finishes throughout. The beautifully appointed kitchen is designed for both everyday living and effortless entertaining, featuring custom dark wood Studio 41 cabinetry, an oversized quartz island, and a spacious pantry offering exceptional storage. Limited opportunity remains for buyer customization and select finish selections. The open-concept main living spaces flow seamlessly into a rare private outdoor retreat, ideal for entertaining, relaxing, and indoor-outdoor living rarely found in the neighborhood. With no monthly HOA assessment, The Kenwood Reserve delivers a rare combination of privacy, autonomy, and boutique luxury living. The lower level offers a warm and versatile secondary living space perfect for a media room, lounge, playroom, or fitness area, alongside a private fourth bedroom ideal for guests or a home office. A unique additional 230 SF unfinished space presents endless possibilities for customization, including a wine cellar, creative studio, wellness room, or additional storage. Located moments from Hyde Park, the University of Chicago, lakefront parks, dining, and cultural institutions, The Kenwood Reserve offers a rare opportunity to own full masonry new construction with private outdoor space, garage parking, and boutique luxury living in one of Chicago's most historic neighborhoods.

4717 S Ingleside Avenue, Chicago

4818 S Drexel Boulevard Unit #A, Chicago

$184,900

2 Beds ⋅ 1 Baths ⋅ 12793251 MLS ⋅ NEW Status

Contemporary style meets comfortable everyday living in these newly rehabbed, two-bedroom, one-bath townhomes. Each home features laminate flooring throughout, bright interiors and recessed lighting. Open-concept kitchen features warm wood cabinetry, stainless appliances, and open shelving. Clean lines, neutral finishes, and fenced outdoor areas complete the appeal. AVAILABLE EXCLUSIVELY FOR OWNER OCCUPANTS ONLY.

4818 S Drexel Boulevard Unit #A, Chicago

$179,900

2 Beds ⋅ 1 Baths ⋅ 12784116 MLS ⋅ NEW Status

825 E 48Th Street Unit #D, Chicago

4840 S Dorchester Avenue Unit #11, Chicago

$1,150,000

4 Beds ⋅ 4 Baths ⋅ 12790678 MLS ⋅ NEW Status

The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A courtyard, a communal garden, and a landscape front yard support a total of 13 townhouses. This 4 bedroom, 3.5 bath townhome is a dream for anyone looking for something a little extra from their home. This stunning facade is restored, a 1904 church designed by nationally famed architect Solo Spencer Beman. The main level is an open-concept chef's kitchen featuring custom two-tone cabinetry, a quartz countertop/backsplash, and a Bosch appliance package. There is still an opportunity for the buyer to select finishes. The primary suite, located on the top floor, includes 2 walk-in closets and an en-suite bathroom highlighting a stunning white marble shower and a separate soaking tub. The second floor features 3 spacious bedrooms and two full bathrooms. All bathrooms feature porcelain tiles, custom cabinetry, quartz countertops, and Hans Grohe plumbing fixtures. The unit has an attached, heated, above-ground, oversized garage that fits 1.5 cars. This University of Chicago community is ideally located just 10 minutes from downtown and a short distance to grocery stores, nightlife, distinctive restaurants, and cafes on 53rd street. Access to the lake and museums, and immediately next to the tennis court, Kenwood Park, and Kenwood public library, make this townhouse development a must-see.

4840 S Dorchester Avenue Unit #11, Chicago

$550,000

3 Beds ⋅ 4 Baths ⋅ 12754286 MLS ⋅ ACTIVE Status

Welcome home to this spacious 4-bedroom, 3.5-bath home located in Chicago's Historic and Highly Sought-After Bronzeville neighborhood, offering comfort, character, and plenty of room to enjoy every level. Hardwood floors flow throughout the main and upper levels, while the living room's gas fireplace creates a warm and inviting place to gather and unwind. The kitchen is ready for everything from everyday meals to holiday cooking and baking, featuring a 5-burner gas cooktop, double oven, and pantry-plenty of space to prepare your favorites while entertaining family and friends. Upstairs are three bedrooms, including a primary suite that feels like its own retreat with a private en-suite bath, electric fireplace, and stackable washer and dryer. The basement adds even more flexibility with a fourth bedroom, half bath, full-size washer and dryer, carpeted living space, tile near the rear entrance, and both front and rear access. Additional storage is conveniently located just outside the basement's rear door. With central heating and cooling, a 2-car detached garage, and permit-only street parking, everyday convenience is covered. The location puts you near grocery stores, the lakefront, public transportation, and expressway access, making it easy to enjoy both the neighborhood and everything Chicago has to offer. Come home to Bronzeville, get comfortable, and imagine making this one your own.

3839 S Giles Avenue, Chicago

$249,900

4 Beds ⋅ 2 Baths ⋅ 12778653 MLS ⋅ ACTIVE Status

Vintage Charm, Architectural Character & Endless Possibilities in Chicago's Historic Bronzeville Neighborhood! Enter into a home filled with timeless craftsmanship, original architectural details, and incredible potential. This character-rich property showcases original hardwood floors, soaring 11 ft ceilings, French-doors with beveled glass, pocket doors, and classic beaded wainscoting. The home has three fireplaces, decorative hallway millwork while the dining room features built-in cabinetry that reflects the charm and craftsmanship of a bygone era. The kitchen features some modern touches with vintage appeal. Enjoy front and rear porches, perfect for relaxing or entertaining. A spacious basement with high ceilings offers exciting possibilities for additional living space or a potential one-bedroom apartment, subject to applicable permits and approvals. Whether you envision restoring its original beauty or blending historic character with modern updates, this home offers four generous size bedrooms 1.5 bath, a spacious foyer, living room, dining room and kitchen and a walkout basement with front and rear entrance....wonderful opportunity to create something truly special. Bring your vision and creativity! The property needs TLC, but its distinctive architectural features and potential make it a standout opportunity. Prime location is another highlight! Enjoy convenient access to neighborhood parks, grocery shopping just a block away, minutes to expressways, downtown Chicago, Guaranteed Rate Field, Hyde Park, museums, bike paths, the lakefront, and the Obama Presidential Center. Experience the convenience of city living while enjoying the character and neighborhood atmosphere of Bronzeville. Property is be sold as-is.

3824 S Calumet Avenue, Chicago

$80,000

2 Beds ⋅ 2 Baths ⋅ 12780874 MLS ⋅ ACTIVE Status

MASSIVE UPSIDE POTENTIAL - Unlock serious equity with this budget-friendly renovation opportunity! Offering low property taxes and a complete blank canvas, this property presents a high-margin value-add opportunity for savvy investors, flippers, or ambitious homeowners. Bring your contractor, your vision, and your offer. Cash or hard money required. ESTATE SALE. Sold strictly AS-IS, WHERE-IS. Buyer to conduct all due diligence and verify information. Offers must be on a Multi-Board 8.0 Contract with POFs, and Probate Rider under additional info are required. Court Approval is required, please allow time for response.

7929 S Greenwood Avenue, Chicago

4530 S Woodlawn Avenue Unit #305, Chicago

$569,900

3 Beds ⋅ 3 Baths ⋅ 12780124 MLS ⋅ ACTIVE Status

One of the largest and most distinctive townhomes in the Shakespeare community! This exceptional and meticulously maintained 3-bedroom, 3-full-bath A-unit offers 2,126 square feet across three levels, combining generous living space, thoughtful updates, and a peaceful courtyard setting. The beautifully updated main level features a stunning kitchen with custom cabinetry, oversized island, stainless appliances and upgraded finishes, opening to spacious living and dining areas with hardwood floors, a wood-burning fireplace and abundant natural light. The flexible first level includes a full bath and private sauna-perfect for a home office, gym, guest suite or additional living space. Upstairs, the spacious primary suite features vaulted ceilings, two custom walk-in closets and a private Juliet balcony, while two additional bedrooms, a full bath and convenient laundry complete the upper level. Additional highlights include custom built-ins and trim, crown molding, custom closets, Marvin windows and an attached 2.5-car garage with custom storage. Recent improvements include a new furnace blower and inducer (2026), Trane A/C and humidifier (2023), and an extensively renovated kitchen. Enjoy a quiet, private community just steps from the lakefront, beach, Lakefront Trail and 47th Street Metra, with easy access to downtown Chicago, Lake Shore Drive, the University of Chicago and the Obama Presidential Center. A rare combination of space, updates, privacy and location-come see why this home is so special.

4530 S Woodlawn Avenue Unit #305, Chicago

$200,000

2 Beds ⋅ 1 Baths ⋅ 12778884 MLS ⋅ ACTIVE Status

Welcome to 9323 S Calumet Ave! This move-in-ready 2-bedroom townhome offers comfortable living with a functional layout and plenty of natural light. The property is in move-in condition, making it a great option for a buyer looking to settle in without taking on a major renovation project. Enjoy the convenience of dedicated parking for one vehicle, along with easy access to neighborhood amenities, shopping, transportation, and major roadways. Whether you are a first-time homebuyer, downsizing, or simply looking for an affordable place to call home, 9323 S Calumet Ave is ready for its next owner. Schedule your showing today!

9323 S Calumet Avenue, Chicago

$139,900

2 Beds ⋅ 1 Baths ⋅ 12646108 MLS ⋅ ACTIVE Status

Welcome home! This 2-bedroom, 1-bath, two-story townhouse offers a great opportunity for a buyer looking to make a home their own. Major mechanical and energy-efficiency improvements have already been completed, including upgraded electrical wiring and panel, furnace, water heater, insulation/weatherization, bathroom exhaust fan, energy-efficient lighting, and central air, leaving the next owner the opportunity to personalize the cosmetic finishes. Recent inspections have been completed. Conveniently located near Chicago State University, shopping, public transportation, and neighborhood amenities. Bring your finishing touches and make this home yours. Sold As-Is.

9148 S Burnside Avenue, Chicago

$486,000

3 Beds ⋅ 3 Baths ⋅ 12763358 MLS ⋅ ACTIVE Status

Newly remodeled 3-story end-unit townhouse in a prime location, just minutes from the Loop, Chinatown, major expressways, public transportation, and the White Sox stadium. As an end unit, this home offers extra windows and abundant natural light throughout. The property features brand-new luxury vinyl flooring, fresh paint, a spacious living room with an open-concept layout, and a large kitchen with abundant cabinetry, a pantry closet, granite countertops, and brand-new stainless steel appliances, including a dishwasher, stove, washer, and dryer. This home offers 3 bedrooms and 3 full bathrooms. The first level provides flexible additional living space, ideal for an entertainment area, home office, or additional bedroom. Enjoy stunning Chicago skyline and White Sox stadium views from the rooftop. Additional features include an attached 1-car garage and a beautifully maintained community with green space, trees, and a children's playground.

3560 S Federal Street, Chicago

$484,000

3 Beds ⋅ 4 Baths ⋅ 12734398 MLS ⋅ ACTIVE Status

3544 S Federal Street, Chicago

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South Side Townhomes for Sale

Newest South Side Townhomes for Sale

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