South Side Homes with Townhouse-2 Story Style

Welcome to the vibrant South Side of Chicago, a neighborhood rich in culture, history, and community spirit. Nestled within Cook County, this area is renowned for its diverse population and unique blend of urban living and green spaces. The South Side is home to a variety of attractions, from the stunning views along Lake Michigan to the bustling streets filled with local shops, eateries, and cultural landmarks.

One of the most appealing aspects of the South Side is its charming architectural landscape, particularly the inviting Townhouse-2 Story style homes that grace the streets. These residences offer a perfect combination of modern comforts and classic design, making them ideal for families and young professionals alike. With spacious layouts, high ceilings, and ample natural light, these townhouses provide a warm and welcoming atmosphere. Many feature private outdoor spaces, perfect for enjoying the vibrant Chicago summers or hosting gatherings with friends and family.

The South Side is not just about beautiful homes; it boasts a strong sense of community and an array of amenities. Residents can enjoy access to parks, schools, and public transportation, ensuring that everything you need is just a stone's throw away. Whether you're exploring the rich history of the area or indulging in the local culinary scene, the South Side offers a lifestyle that is both dynamic and fulfilling.

Discover your dream home in this lively neighborhood, where the charm of Townhouse-2 Story residences meets the heart of Chicago living. Embrace the South Side, and become part of a community that celebrates diversity and connection.

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

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