South Side Homes for Sale

Welcome to the vibrant South Side of Chicago, a neighborhood rich in history, culture, and community spirit. Nestled in Cook County, this area is a tapestry of diverse cultures, offering an authentic Chicago experience that resonates with warmth and charm. The South Side boasts a variety of architectural styles, from classic bungalows to modern townhomes, making it an appealing choice for homebuyers seeking character and comfort.

One of the standout features of the South Side is its strong sense of community. Residents enjoy a tight-knit atmosphere, with local events, farmers' markets, and festivals that celebrate the neighborhood's unique heritage. Parks and green spaces, such as Washington Park and Jackson Park, provide ample opportunities for outdoor recreation, picnicking, and enjoying the beautiful Chicago skyline.

For those considering a move, the South Side offers a range of homes for sale that cater to different lifestyles and budgets. Whether you’re looking for a cozy single-family home, a spacious condo, or a charming vintage property, you’ll find options that fit your needs. The real estate market here is thriving, with properties that not only provide comfort but also serve as an investment in a community poised for growth.

With its convenient public transportation options, access to major highways, and proximity to downtown Chicago, the South Side is perfectly situated for both work and play. Explore the rich cultural landscape, from renowned museums to local eateries, and discover why the South Side is not just a place to live, but a place to call home. Your dream home awaits in this dynamic neighborhood!

Newest South Side Homes for Sale

$755,000

3 Beds ⋅ 4 Baths ⋅ 12718764 MLS ⋅ NEW Status

Welcome to Luxury Living at Its Finest! Prepare to be impressed by this stunning 4-bedroom, 3.5-bath two-story Greystone located in the historic Bronzeville area that blends sophisticated design with modern functionality. From the moment you enter, you'll be captivated by the open-concept layout, wired stereo system, designer finishes, and custom details throughout. The main level welcomes you with soaring ceilings and a striking granite feature wall showcasing a sleek electric fireplace, perfectly designed to accommodate your large-screen TV. The dramatic staircase serves as the home's centerpiece with custom decorative wall accents and elegant glass railings, creating a truly one-of-a-kind architectural statement. Designed for both everyday living and entertaining, the gourmet chef's kitchen boasts premium stainless steel appliances, including a 48-inch gas range with six sealed burners and grill, oversized refrigerator, dishwasher, built-in microwave, 54" cabinets and a professional stainless steel wall-mounted range hood. Sliding patio doors lead to the spacious deck custom pergola complete with sound, overlooking the backyard and detached two-car garage, making indoor-outdoor entertaining effortless. Upstairs, retreat to the luxurious primary suite featuring two custom walk-in closets and a spa-inspired ensuite complete with a freestanding soaking tub, oversized glass shower, and designer finishes. Two additional generously sized bedrooms, a full bath, and a conveniently located second-floor laundry room complete the upper level. The finished lower level is the ultimate entertainment space, offering a spacious family or theater room with a custom media wall, wet bar, second laundry area, and a large fourth bedroom with a convenient continental bathroom, ideal for guests, extended family, or a private home office. This home has been completely renovated with new electrical, plumbing, roof, dual HVAC systems, and all new fixtures, providing peace of mind for years to come. Conveniently located in the just steps from the CTA Red and Green Lines, the Dan Ryan Expressway (I-94), shopping, restaurants, parks, and schools. Enjoy being only 7 minutes from Lake Michigan and its beautiful beaches and 10 minutes from downtown Chicago. This exceptional home offers luxury, style, and convenience in one incredible package. Schedule your private tour today, this is one you won't want to miss!

4956 S Indiana Avenue, Chicago

$535,000

3 Beds ⋅ 3 Baths ⋅ 12719039 MLS ⋅ NEW Status

Prepare to be impressed by this meticulously renovated 5- bedroom, 2.1- bathroom brick bungalow on a well-maintained block in Washington Heights. Expansive floorplan offering over 2,400 sq/ft of perfectly crafted living space on 3 levels. The heart of the home is a stunning kitchen featuring new cabinetry, a custom backsplash, ss appliances, sleek quartz counters, and gorgeous tiled flooring. The enclosed porch off the kitchen is perfect for morning coffee or evening relaxation. Spacious living room and adjacent dining area with custom fireplace and gorgeous LVP flooring that flows seamlessly throughout the home. Flexible layout with two main level bedrooms and a beautifully remodeled powder room. The entire upper level features a primary suite with large walk-in closet and offers a spa-inspired ensuite full bathroom with a soaker tub, walk in shower, dual sink vanity and over the top custom tile work. The English lower level has spectacular epoxied flooring and features a sizeable recreation room, family room with wet bar, 2 bedrooms, another beautifully renovated full bathroom, laundry room and storage. Detached 2 car garage for convenience and additional storage. Highlights include new cabinetry, vanities, flooring, appliances, lighting, and paint throughout ensuring years of low maintenance living. Located on a quiet block in a great neighborhood close to parks, schools, shopping, the Metra and major expressways - this is one you do not want to miss!

1244 W 96Th Street, Chicago

$250,000

4 Beds ⋅ 2 Baths ⋅ 12718792 MLS ⋅ NEW Status

8750 S Princeton Avenue, Chicago

$240,000

3 Beds ⋅ 2 Baths ⋅ 12718756 MLS ⋅ NEW Status

Welcome to this charming mid-century brick home in the heart of Chicago's Southwest Side. Well maintained and full of character, this solid residence offers comfortable living with great potential for customization. The functional layout features a natural flow between living, dining, and kitchen areas, along with three bedrooms ideal for family, guests, or a home office. Situated on a full lot with space for outdoor entertaining or gardening, the property also includes a rare 2-car garage. Located in the Marquette Park / Chicago Lawn area, this home offers convenient access to schools, parks, shopping, and public transportation. A great opportunity to own a classic Chicago home in a well-established neighborhood.

7326 S Francisco Avenue, Chicago

$275,000

2 Beds ⋅ 2 Baths ⋅ 12716403 MLS ⋅ NEW Status

Step inside this move-in-ready gem! The main level greets you with hardwood flooring, ample natural light, and a cozy focal point living area highlighted by an elegant electric fireplace-perfect for relaxing or entertaining. The open layout flows right into a contemporary kitchen equipped with sleek stainless steel appliances and modern cabinetry. Two spacious main-level bedrooms and a full bathroom offer effortless main-floor living. Head downstairs to the fully finished basement, featuring durable vinyl flooring throughout. This lower level adds exceptional living space, complete with two additional bedrooms and a full second bathroom-ideal for a primary suite, guest rooms, a home office, or an entertainment room. Every inch of this home has been thoughtfully renovated from top to bottom. Don't miss this turnkey South Side beauty.

623 E 88Th Place, Chicago

$319,000

3 Beds ⋅ 2 Baths ⋅ 12718618 MLS ⋅ NEW Status

Step into comfort, confidence, and a complete peace of mind with a stunning, fully renovated 5-bedroom, 2 full-bath residence where everything has been completely updates from top to bottom with high-end finishes just for you. From the moment you walk in, you'll appreciate the quality craftsmanship and attention to detail assuring that you'll know the difference-this is not just a house, it's the fresh start that you've been looking for! Every major system is brand new, from HVAC to plumbing, electrical, windows, doors, washer and dryer. This open, bright spacious layout features all-new flooring through out and a stunningly remodeled interior designed for todays lifestyle including a kitchen that comes equipped with brand-new smart appliances that pairs with android and iOS smartphones. Both full bathrooms have been transformed into spa-like sanctuaries, boasting pristine tile work, modern vanities, and all-new, high-end fixtures. This home has all new, energy-efficient windows that floods the home with natural light, while gorgeous new doors and contemporary light fixtures add a touch of upscale elegance to every single room. The excellence continues outside, where the property boasts fantastic curb appeal and enhanced privacy. A detached 2-car garage providing plenty of parking and additional storage space. The backyard serves as your own secure outdoor oasis, ideal for weekend barbecues, letting pets run freely, or creating a safe playground for children. While location is everything, and this property delivers a lifestyle of ultimate convenience. For daily commuters, your travel times will be slashed because you are in immediate, close proximity to the CTA Red Line station, making trips into the heart of downtown Chicago fast and effortless. Driving to work is just as simple, with lightning-fast access to both I-57 and I-94 corridors right around the corner. Everything you need for daily life is right at your doorstep-the surrounding area is packed with an abundance of excellent dining options, diverse restaurants, local cafes, and fully stocked grocery stores, making errands a breeze. This is not just a house; it is a brand-new lifestyle waiting for you to move right in. Schedule your private showing today before this turn-key masterpiece is gone!

9606 S Eggleston Avenue, Chicago

$229,500

4 Beds ⋅ 2 Baths ⋅ 12693417 MLS ⋅ NEW Status

Welcome home to this beautifully updated 4-bedroom, 2-bath residence offering the perfect blend of comfort, style, and functionality. Whether you're a first-time buyer, a growing family, or seeking a home that comfortably accommodates multigenerational living, this property offers the flexibility to fit your lifestyle. Step inside to a bright, open-concept living area featuring fresh paint and durable laminate flooring throughout. The modern kitchen flows seamlessly into the main living space, creating an inviting setting for everyday living and entertaining. Four generously sized bedrooms, two full bathrooms, and a spacious finished basement provide plenty of room for family, guests, a home office, recreation area, or additional living space. Enjoy the confidence that comes with major recent improvements, including new plumbing, electrical, furnace, and some windows, allowing you to move in with peace of mind. Outside, relax on the welcoming front porch or entertain family and friends in the fully fenced backyard, offering ample space for children, pets, gardening, or summer gatherings. Beautifully updated, move-in ready, and offering the space today's buyers are searching for, this is an opportunity you won't want to miss. Come experience all that this wonderful home has to offer and imagine yourself making it your own.

8836 S Carpenter Street, Chicago

$1,695,000

6 Beds ⋅ 6 Baths ⋅ 12705893 MLS ⋅ NEW Status

An extraordinary Kenwood greystone where historic craftsmanship takes center stage. Designed by celebrated Chicago builder Horatio Wilson, this remarkable 7-bedroom, 6-bath residence showcases more than 5,000 square feet of gracious living space, blending the grandeur of Chicago's architectural past with the comforts of modern living. Rich hardwood floors, extraordinary original millwork, handcrafted built-in cabinetry, decorative columns, pocket doors, and intricate wood detailing reflect a level of craftsmanship rarely found today. Formal living and dining rooms provide elegant spaces for entertaining and everyday living. Just beyond the dining room, a cozy lounge invites morning coffee or evening cocktails, while the adjoining butler's pantry offers a timeless transition into the kitchen. Tucked discreetly behind the kitchen, the original servant's staircase provides a charming connection between the home's first and second floors. Throughout the residence, seven fireplaces further celebrate its architectural heritage. The spacious primary suite serves as a private retreat with abundant closet space and a spa-inspired ensuite featuring a steam shower, soaking tub, dual vanities, and a walk-in closet. A finished lower level lives like a residence of its own with a second full kitchen, dining area, expansive family room, additional bedroom, and full bath-ideal for extended family, guests, or flexible living. Outside, a lush private garden offers a peaceful escape with mature landscaping and seasonal blooms. Ideally situated on a picturesque, tree-lined block in Kenwood near Hyde Park and the University of Chicago, this exceptional residence places you among one of Chicago's most architecturally significant neighborhoods, surrounded by historic homes, cultural institutions, acclaimed dining, and everyday conveniences. Homes of this caliber rarely become available, offering the opportunity to own not simply a remarkable residence, but an enduring chapter in Chicago's architectural story.

4942 S Ellis Avenue, Chicago

$254,900

2 Beds ⋅ 2 Baths ⋅ 12707579 MLS ⋅ NEW Status

Remodeled 4 bedroom 2 bathroom brick bungalow with PLENTY to offer in Chatham! Situated on a corner lot, this home features a living room and dining room with an electric fireplace in the living room, a remodeled kitchen with white cabinets, granite countertops and stainless steel appliances, remodeled bathrooms and a new 2-car garage! The primary bedroom has a huge walk-in closet. The loft style finished basement includes the 3rd and 4th bedrooms, a laundry room and storage. This home won't last long. Move in before the end of the Summer! Within a short distance to the expressway, shopping, schools, parks and public transportation.

8301 S Maryland Avenue, Chicago

$125,000

4 Beds ⋅ 2 Baths ⋅ 12718280 MLS ⋅ NEW Status

Great opportunity for investors and rehabbers looking for a large and affordable home in the Brainerd neighborhood. This home has 4 spacious bedrooms, 2 bathrooms, and beautiful hardwood floors. There is also a huge family room in the basement. Located close to commerce, schools, and parks. All room sizes are estimated. All room sizes are estimated. This property is being sold as-is where-is.

9355 S Throop Street, Chicago

$295,000

3 Beds ⋅ 3 Baths ⋅ 12717991 MLS ⋅ NEW Status

Well maintained solid brick raised ranch in Chicago's desirable Washington Heights neighborhood, this property is ready for you to make it your own. Natural light shines through large picture windows in the freshly painted open-concept living and dining rooms, 3 main-level bedrooms all generously sized, and 2.5 baths is just the beginning. Thoughtful upgrades include exquisite curb appeal with the concrete overlay front porch, new LED light fixtures in the eat-in kitchen, deck overlooking a well manicured backyard, a walk-in cedar closet, built-in bar in the expansive recreation room, shuttered windows and doors, wrought iron fencing around the perimeter. Schedule a tour of this beauty today.

9424 S Union Avenue, Chicago

$257,000

3 Beds ⋅ 3 Baths ⋅ 12717707 MLS ⋅ NEW Status

Welcome Home! This 2 Story 3Bed/2.5Bath Home is Waiting For Your Family. First Floor Features an Open Concept Living & Dining Area with Big Bay Windows for Plenty of Natural Sunlight. Boutique Inspired Powder Room for Guest. Kitchen is Nicely Appointed with Stainless Steel Appliances, Custom Butchers Block Countertops & Breakfast Bar. Refinished Hardwood Steps Lead You Upstairs to 3 Bedrooms & Bathroom with Floating Sink & Double Shower Head. Finished Basement Has Ample Space for Entertaining, Washer/Dryer & an Additional Full Bathroom. 2 Car Parking Pad Located in the Rear with Privacy Fence. This Home Shows Owners Pride with Many 2022 Updates that Include, New Roof, New Paint, Refinished Hardwood Floors, New Central A/C (2020), Furnace & Water Heater (5 years old) & Newer Washer/Dryer. Make Your Appointment Today!

7803 S Champlain Avenue, Chicago

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