South Side Real Estate

The South Side of Chicago, located in Cook County, Illinois, is a vibrant and diverse neighborhood that offers a unique blend of history, culture, and community. Known for its rich heritage and iconic landmarks, the South Side is a sought-after destination for both residents and visitors alike.

One of the standout features of the South Side is its stunning architecture. From the historic brownstone buildings of Bronzeville to the grand mansions of Hyde Park, this area showcases a wide range of architectural styles that reflect the neighborhood's storied past. Additionally, the South Side is home to several renowned institutions, including the University of Chicago, which adds to the intellectual and cultural atmosphere.

The South Side also boasts an array of recreational opportunities. Nature enthusiasts can explore the sprawling green spaces of Washington Park or take a stroll along the picturesque Lake Michigan shoreline. Sports enthusiasts can catch a game at Guaranteed Rate Field, home to the Chicago White Sox, or enjoy a round of golf at one of the area's many golf courses.

In terms of amenities, the South Side offers a diverse range of shopping, dining, and entertainment options. From trendy boutiques and gourmet restaurants to lively music venues and art galleries, there is something for everyone to enjoy.

With its rich history, vibrant culture, and diverse community, the South Side of Chicago is a neighborhood that truly embodies the spirit of the city. Whether you're looking for a place to call home or planning a visit, the South Side offers a unique and exciting experience.

Newest Listings in South Side

$155,000

3 Beds ⋅ 2 Baths ⋅ 12796711 MLS ⋅ NEW Status

8842 S Michigan Avenue, Chicago

$1,295,000

12790264 MLS ⋅ NEW Status

Exceptional Gut Renovated Legal 5-Unit Greystone in booming Bronzeville. Fully occupied w/ annual gross income of $115,200 and NOI of over $96k. Building was completely rebuilt to the studs in 2020 under full architectural plans and permits, with City of Chicago Inspections. Features a premium unit mix of three 2BR/2BA units and two 1BR/1BA units. Thoughtfully designed with open layouts and upgraded finishes throughout. All with in unit laundry and individual mechanicals. Fully secured building with gated entry and security system. This renovation pairs the old-world character, aesthetic and craftsmanship of a classic Chicago Greystone solid brick building, with the infrastructure, systems and finishes of modern construction. A fully rebuilt, stabilized boutique multifamily in a highly sought after neighborhood, perfect turnkey investment opportunity. Offering Memorandum available by request.

5021 S Indiana Avenue, Chicago

$394,000

5 Beds ⋅ 3 Baths ⋅ 12796693 MLS ⋅ NEW Status

Beautifully updated and spacious brick bungalow offering a versatile layout with multiple living areas. The first floor features 3 bedrooms, 1 full bath, a living room, dining room, and a dedicated office, along with hardwood floors throughout and stainless steel appliances. The basement features an in-law unit with 3 bedrooms, 1 full bath, a laundry room, tile flooring, and its own separate exit, providing additional living space and flexibility. The attic offers even more space with a kitchen, 2 bedrooms, and 1 full bath. Exterior features include a 2-car garage and an additional concrete parking slab. With generous space and a flexible layout, this property offers plenty of possibilities for extended family living or investment potential. Property is being sold AS IS.

6540 S Artesian Avenue, Chicago

$419,900

5 Beds ⋅ 4 Baths ⋅ 12792510 MLS ⋅ NEW Status

Beautifully renovated in 2026, this spacious 3-story, 5-bedroom, 3.5-bathroom Chicago home blends modern luxury with comfortable living. The chef's kitchen features brand-new Samsung appliances, marble countertops and backsplash, and additional cabinetry. Enjoy 10-foot ceilings, oak hardwood floors, contemporary fixtures, and recessed LED lighting throughout. The spacious living room features an electric fireplace, creating a warm and inviting atmosphere. The expansive primary suite offers a separate sitting area and private deck, while the spa-inspired primary bathroom includes a soaking tub, separate shower, and double vanity. Two separate heating systems provide added comfort and flexibility. The finished walkout basement offers versatile space for an office, recreation, or fitness room. An additional 1-bedroom, 1-bathroom ADU offers flexibility for guests, extended family, or potential rental income, subject to applicable requirements. Outdoor entertaining space, ample storage, and three detached parking pads complete this exceptional property. Schedule your showing today!

7749 S Green Street, Chicago

$120,000

3 Beds ⋅ 1 Baths ⋅ 12791489 MLS ⋅ NEW Status

Calling all investors and experienced rehabbers! This single story, 3 bedroom,1 bathroom home presents an opportunity for buyers looking to renovate and add value. Situated on a corner lot, the property features a layout ready for a new vision. Property is being sold AS-IS.

8801 S Wood Street, Chicago

$160,000

5 Beds ⋅ 2 Baths ⋅ 12795389 MLS ⋅ NEW Status

Located in West Englewood on historic Marquette BLVD just blocks from Ogden Park you will find this spacious bungalow style two unit which offers an expansive layout and a great opportunity to live in one unit and rent the other out or rent them both out while collecting passive income. This home feels larger than it looks with classic modern updates while preserving the classic bungalow feel so many have grown to love. The first-floor unit features hardwood floors throughout, a large living room with decorative fireplace, formal dining room and two bedrooms with a modern kitchen offering newer cabinets/counters. The second-floor unit is slightly larger with similar layout while providing three bedrooms. Bathrooms in both units are newer and clean, each unit has individual HVAC, and the basement is finished offering additional living space with rental income potential! Off the rear of the home you will find space for two cars in the parking pad, the location is ideal being so close to the Red Line and Dan Ryan, this home offers tremendous upside and should not be overlooked!

1044 W Marquette Road, Chicago

$249,900

7 Beds ⋅ 2 Baths ⋅ 12796645 MLS ⋅ NEW Status

A property that offers more than just a place to call home! This well-maintained, classic Chicago greystone two-unit building offers timeless character and an excellent opportunity to enjoy homeownership while benefiting from rental income. Live in one unit and rent the other, or add a promising property to your investment portfolio. Well cared for and ready for its next chapter, this greystone offers both charm and versatility. Don't miss the opportunity to make it yours!

6542 S Peoria Street, Chicago

$249,000

4 Beds ⋅ 3 Baths ⋅ 12794568 MLS ⋅ NEW Status

6022 S Vernon Avenue, Chicago

$339,900

3 Beds ⋅ 4 Baths ⋅ 12795862 MLS ⋅ NEW Status

Located in historic North Kenwood, just blocks from the lakefront, this three-story vintage brownstone offers a rare opportunity to create something truly special. With nearly 3,000 square feet, a spacious layout, and renovations already underway, this property is ready for someone to bring their vision to life. The main level features an open floor plan with soaring ceilings over 10 feet, creating a great foundation for a beautiful living and entertaining space. The second floor offers three bedrooms, including a large primary suite at the front of the home and two additional bedrooms at the rear with a shared Jack-and-Jill bathroom. The third floor provides additional flexible space that could be finished to suit your needs, whether as a family room, home office, or extra living area. A large unfinished basement offers even more possibilities. Outside, enjoy a private yard and a brick two-car garage, adding to the appeal of this spacious property. The location is hard to beat. Directly across from Dr. Martin Luther King College Preparatory High School, the home is just blocks from lakefront access and minutes from everything Hyde Park has to offer. Properties with this much space and potential in North Kenwood are hard to find. Whether you're an investor or a buyer looking to create a home tailored to your style, this is an opportunity to bring new life to a classic Chicago brownstone in a location that continues to stand out.

4421 S Ellis Avenue, Chicago

$360,000

4 Beds ⋅ 3 Baths ⋅ 12795351 MLS ⋅ NEW Status

Fully renovated 2.5 story brick bungalow featuring 5 bedrooms and 3 full bathrooms. The main level offers separate living and dining rooms, hardwood flooring, 3 bedrooms and a full bathroom. The updated kitchen features upgraded finishes and a full stainless steel appliance package. The second level includes a primary suite with a private ensuite bathroom and an additional adjoining room ideal for a home office, sitting area or flex space. The basement houses additional living space for a family room or entertainment area, has a 5th bedroom, full bathroom and laundry area. Hardwood flooring extends throughout the main and second levels. Exterior features include a fenced backyard and detached 2Car garage. A spacious layout with flexible living areas and updated finishes throughout.

8542 S Ada Street, Chicago

$284,900

3 Beds ⋅ 2 Baths ⋅ 12796559 MLS ⋅ NEW Status

Welcome to 8231 Wentworth! This spacious 5-bedroom, 2-bath home offers plenty of room and stylish updates throughout. The updated kitchen features crisp white cabinetry, beautiful countertops, subway tile backsplash, stainless steel appliances, and modern finishes. Both bathrooms have been updated, adding to the home's fresh, move-in-ready feel. With five generously sized bedrooms, flexible living space, and a large backyard perfect for entertaining, relaxing, or outdoor activities, this home has plenty to offer. Schedule your showing today!

8231 S Wentworth Avenue, Chicago

$129,900

4 Beds ⋅ 2 Baths ⋅ 12796500 MLS ⋅ NEW Status

Fantastic opportunity for investors or owner occupants. This classic 2 Flat brick property in the heart of Englewood features two spacious, well maintained units. Each unit offers a functional layout with 2 generous bedrooms, 1 full bathroom, bright living and dining areas, and ample natural light throughout. The building includes a full unfinished basement providing substantial space for storage, laundry set up, or potential expansion. Solid structure with endless potential. Conveniently located near schools, parks, shopping and public transportation. Property being sold in AS IS condition, no surveys nor disclosures, taxes prorated.

6237 S Ada Street, Chicago

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South Side Real Estate

Newest Listings in South Side

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