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

$499,999

2 Beds ⋅ 2 Baths ⋅ 12707918 MLS ⋅ NEW Status

Sophisticated Corner Townhome with Private Rooftop Deck! Welcome to this beautifully updated 2-bedroom + den, 2-bath corner townhome offering over 2,080 square feet of stylish living in the heart of the South Loop. Ideally situated between South Loop, Bronzeville and McCormick Square, this spacious home combines modern updates, abundant natural light and exceptional indoor-outdoor living. The recently remodeled kitchen is a true showpiece, featuring quartz countertops, contemporary cabinetry, stainless steel appliances, a generous center island, and pantry; perfect for entertaining and everyday living. The main level flows effortlessly with an expansive living and dining area, highlighted by a dramatic walls of windows. Enjoy three private outdoor spaces, including a balcony off the kitchen for grilling, a private rooftop deck ideal for entertaining, or enjoying the skyline and views, plus an additional front outdoor space. The spacious primary suite offers triple-pane Pella windows for exceptional sound reduction and energy efficiency, while updated window treatments add style throughout the home. The versatile entry-level family room can easily serve as a home office, media room, workout space, or be converted into a third bedroom with a full bath nearby. Additional features include an attached two-car garage with EV charging capability, generous storage, abundant natural light, and a quiet interior courtyard location. Ideally located just minutes from: McCormick Place, Wintrust Arena, Soldier Field, 31st Street Beach, Lake Michigan, Museum Campus, parks, restaurants, shopping, public transportation, Lake Shore Drive, and I-55. This move-in-ready home offers the perfect combination of space, luxury, and convenience.

2502 S Calumet Avenue, Chicago

$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

$425,000

4 Beds ⋅ 3 Baths ⋅ 12526499 MLS ⋅ NEW Status

2819 S Michigan Avenue, 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

$400,000

4 Beds ⋅ 3 Baths ⋅ 12701689 MLS ⋅ ACTIVE Status

Amazing end unit TOWNHOUSE minutes from the U of CHICAGO, The OBAMA center, and the LAKEFRONT. This home feels like a single family home, as there's a fenced yard, an attached 2 car garage, and it has it's own entrance. The home was recently renovated with QUARTZ countertops, HARDWOOD flooring, and all new kitchen and bathrooms. Enjoy a gated community, with a large shared common area and yard. Low assessments, and low taxes make this ideal. 2 PRIMARY BEDROOMS with PRIVATE BATHS make this the perfect home. 24 hour notice at a minimum please. EMAIL only for further information

710 E 51St Street Unit #710, Chicago

$949,000

4 Beds ⋅ 4 Baths ⋅ 12698231 MLS ⋅ ACTIVE Status

Move-in ready new construction at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences on a quiet, tree-lined cul-de-sac in historic Kenwood. Designed as a full masonry build to deliver lasting quality, timeless curb appeal, and long-term value, this thoughtfully planned three-level residence offers the scale and privacy of a single-family home with the ease of modern new construction, featuring expansive living spaces, refined designer finishes, private outdoor living, and a 2-car garage included for added convenience and storage. Sun-filled interiors feature clean architectural lines and timeless finishes throughout. The beautifully appointed kitchen is designed for everyday living and effortless entertaining, with custom dark wood Studio 41 cabinetry, stainless steel appliances, an oversized quartz island, and ample storage. Limited opportunity remains for buyer customization and select finish selections. The open-concept main living spaces are designed for seamless indoor-outdoor living, with sliding glass doors opening directly to a private backyard retreat. Ideal for entertaining, dining al fresco, relaxing, or everyday enjoyment, this rare outdoor space adds a true single-family feel within a boutique new-construction setting. With no monthly HOA assessment, The Kenwood Reserve offers a rare combination of privacy, autonomy, and low-maintenance luxury. The lower level provides a warm and versatile secondary living space, perfect for a media room, lounge, playroom, fitness area, or home office, along with a private fourth bedroom ideal for guests. Located moments from Hyde Park, the University of Chicago, lakefront parks, dining, and major cultural institutions - including the Obama Presidential Center in nearby Jackson Park - The Kenwood Reserve offers full masonry new-construction living in one of Chicago's most historic and architecturally distinguished neighborhoods. Preferred lender program available. Only three residences available. Private tours now offered.

4719 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

$424,900

4 Beds ⋅ 3 Baths ⋅ 12696080 MLS ⋅ ACTIVE Status

Welcome to 8 on The Park in Washington Park! This premier 4 bedroom 2.1 bathroom three-story townhome was rehabbed in 2020 and has LOTS of features and amenities. The main level has an open floor plan with a living room/dining room combo, a gas fireplace in the living room and an eat-in kitchen with an island, custom oak cabinets, granite countertops and stainless steel appliances. The primary bedroom includes an en suite bathroom with double sinks, whirlpool tub and separate shower. There are white oak hardwood floors throughout, a 2-car attached garage and a second floor laundry area! Entertain and enjoy the city skyline views on your large PRIVATE rooftop deck! Conveniently located across from Washington Park and a short distance from the University of Chicago, Metra, Lake Shore Drive, I-90/94, public transportation, schools, restaurants and shopping. This unit is RARELY AVAILABLE and will not last long! Check out the 3D tour!

5210 S King Drive Unit #C, Chicago

$649,800

4 Beds ⋅ 4 Baths ⋅ 12694375 MLS ⋅ ACTIVE Status

Beautiful Townhome located off picturesque Drexel Blvd, available for immediate occupancy. This sophisticated home, crafted in 2023, offers a modern and impeccable design with top of the line finishes. Spanning three levels plus a private rooftop, this 4-bedroom, 3.5-bath residence is waiting for you. Additional highlights include a designer kitchen with contemporary custom cabinetry, an oversized island, quartz countertops, and LG stainless steel appliances. Hardwood floors flow throughout the main living areas and bedrooms, complemented by oversized windows, motorized window treatments and second-floor laundry. The spacious primary suite features a walk-in closet and a spa-inspired bath with heated floors, a soaking tub, and a separate shower. The versatile first-floor flex space is ideal as a fourth bedroom, office, or family room with an en-suite bath, plus an attached 2-car garage. Enjoy the best of city living with Lake Michigan, scenic parks, bike trails, shopping, presidential center and dining just minutes away-all within a 10-minute drive to downtown. Schedule your private showing today-we'd love to welcome you home!

4442 S Drexel Boulevard Unit #G, 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

$425,000

4 Beds ⋅ 2 Baths ⋅ 12675404 MLS ⋅ ACTIVE Status

For the first time in 47 years, a rare value-add opportunity in the heart of historic Kenwood Mansion District. This spacious 4-bedroom, 1.1-bath townhome offers three levels of living space, including a partially finished basement and a large private fenced yard. Solid brick and concrete construction provides the perfect foundation for renovation, with tremendous upside for investors or owner-occupants looking to build equity. Featuring 4 bedrooms on one level, this home offers a functional layout that can easily be reimagined for modern living. Ideally located just blocks from the neighborhood gem, Kenwood Community Park, and close proximity to Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the recently finalized Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this property presents a unique chance to renovate and live in one of the South Side's most sought-after neighborhoods.

4753 S Woodlawn Avenue, 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

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