South Side Homes with Townhouse-2 Story Style

Welcome to the vibrant South Side of Chicago, a neighborhood rich in history, culture, and community spirit. Nestled within Cook County, this area is a tapestry of diverse cultures, offering a unique blend of urban living and local charm. The South Side is known for its beautiful parks, historic landmarks, and a strong sense of community, making it an ideal place for families, young professionals, and anyone looking to experience the heart of Chicago.

One of the most appealing aspects of the South Side is its stunning array of homes, particularly the charming 2-story townhouses that dot the landscape. These residences capture the essence of classic Chicago architecture while providing modern conveniences that today’s homeowners desire. With spacious layouts, these townhouses often feature inviting living areas, generous bedrooms, and cozy outdoor spaces perfect for entertaining or relaxing after a long day.

Living in a 2-story townhouse in the South Side means more than just a beautiful home; it’s about embracing a lifestyle. Residents enjoy easy access to local amenities, including trendy cafes, boutique shops, and vibrant cultural institutions. The neighborhood is also home to several parks and recreational areas, providing ample opportunities for outdoor activities and community events.

Whether you’re sipping coffee at a local café or taking a leisurely stroll through one of the nearby parks, the South Side offers an inviting atmosphere that makes you feel right at home. Explore the possibilities of townhouse living in this dynamic neighborhood, where every street has a story, and every resident is part of a larger community narrative. Come discover your new home in the South Side of Chicago!

Newest South Side Homes with Townhouse-2 Story Style

$135,000

2 Beds ⋅ 2 Baths ⋅ 12717797 MLS ⋅ NEW Status

Beautifully maintained 2-bedroom, 1.5-bath townhouse plus full basement, offering over 1,100 sq. ft. of comfortable living space. The main level features a spacious living room and and ample eat in kitchen with plenty of cabinetry. Upstairs, you'll find two generously sized bedrooms with gleaming hardwood floors and a full bath. The finished basement provides additional living space, laundry hookups, and plenty of storage. Enjoy the privacy of a fenced patio, perfect for relaxing. Recent updates include newer furnace and A/C, windows, doors, electrical, water heater, sump pump, roof improvements, and a resurfaced bathtub-all completed within the last few years. Conveniently located near shopping, restaurants, parks, public transportation, and expressways for an easy commute.

9155 S Cottage Grove Avenue Unit #B, Chicago

$99,900

3 Beds ⋅ 2 Baths ⋅ 12710745 MLS ⋅ ACTIVE Status

Great Investment or Homeownership Opportunity! All brick two-story townhouse featuring 3 bedrooms, 1.5 bathrooms, full basement, and large, fenced yard. Conveniently located just north of the 87th Street corridor in East Chatham, this spacious corner unit offers easy access to schools, shopping, dining, services, transportation, and more. Inside, the open living and dining area combine original hardwood flooring with bright natural light from east and south facing windows. A recently updated kitchen provides a western exposure, along with access to a private covered deck and massive fenced yard, perfect for outdoor entertaining or--for added value--potential parking. Upstairs, a welcome retreat showcases a generously sized main bedroom, two secondary bedrooms, and a bathroom with full amenities. Additional features include a half bathroom on the main level plus a full unfinished basement with laundry on the lower level, an ideal location for future expansion or current storage needs. No HOA fees. Repairs and updates needed. Sold AS IS.

8610 S Ingleside Avenue, Chicago

$79,900

3 Beds ⋅ 2 Baths ⋅ 12696637 MLS ⋅ ACTIVE Status

Come see this 2-story townhome with fenced backyard, central AC and W/D hook-up in basement. This townhome boasts 3 bedrooms (BRs on 2nd level) and 1.5 bathrooms, eat-in kitchen with newer cabinets and separate living room and dining room. On a quiet street, blocks from Dan Ryan expressway, public transportation, shopping and restaurants. NO HOA FEES and low property tax. Don't wait, come see and make an offer! Make this home your own with your ideas and upgrades! Investors may also appreciate this property as similar rentals in the area may lease between $1500 - $1800 per month or more.

7410 S Wentworth Avenue, Chicago

$108,000

2 Beds ⋅ 1 Baths ⋅ 12679569 MLS ⋅ ACTIVE Status

Don't miss this nice two (2) bedroom townhome in this spacious, quiet area of Chatham. Freshly painted, rehabbed bath room, and laminated floors. Priced just right, and perfect for first time home buyers. Thanks in advanced for touring.

7931 S Dobson Avenue Unit #A, Chicago

$164,000

2 Beds ⋅ 1 Baths ⋅ 12670926 MLS ⋅ ACTIVE Status

Attention Buyers! What a bargain. This home is located in the Kenwood Historic district, and the area is federally targeted for home ownership. Some features that impact this home's values include: a new roof, exterior doors, new windows, granite countertop, new kitchen and bathroom fixtures and new carpet. A washing machine, electric dryer, dishwasher, stove, central air and a new refrigerator are included. A front and back yard add to your comfort. Lake Shore drive, the Dan Ryan expressway and the beaches along the Lakefront add to the value of this property. The bus stop on Cottage Grove is 1/2 block away from the residence. Public transportation in the area is easy and accessible. Northwestern hospital is across the street, and the University of Chicago is 6 blocks away. The Kenwood area is home to President Obama and other famous leaders. Seller may assist with closing costs.

827 E 48Th Street Unit #C, Chicago

$115,000

2 Beds ⋅ 2 Baths ⋅ 12668322 MLS ⋅ ACTIVE Status

Affordable beautifully rehabbed 2 bedrooms, 1 and half bathrooms Townhouse. The kitchen has brand new cabinets and granite countertops with stainless steel appliances. Microwave, washer and dryer are also included. Motivated seller is willing to assist buyer with closing costs.

7939 S Ingleside Avenue Unit #C, Chicago

$249,900

3 Beds ⋅ 2 Baths ⋅ 12658397 MLS ⋅ ACTIVE Status

Beautiful 3 levels Corner piece Townhome. Recently updated in 2026. and featuring a brand-new Samsung stainless steel appliance package. Offers stylish living across three levels in this beautifully updated corner townhome. Featuring 3 bedrooms and 2 full baths, this spacious home blends modern finishes with functional living space throughout. The bright contemporary kitchen showcases sleek cabinetry, updated finishes, and stainless-steel appliances. The lower level provides additional versatile living space ideal for recreation, entertainment, a home office, fitness area, or guest setup, along with a separate laundry area and generous storage options including multiple closets and walk-in storage space. Enjoy outdoor living with a large, fenced backyard, lively lawn, concrete walkway, gravel driveway, and detached 2-car garage. Situated on a quiet cul-de-sac in a serene, family-friendly neighborhood with convenient access to schools, parks, transportation, and city amenities.

46 E 91St Street, 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.