South Side Real Estate

Welcome to the vibrant and diverse South Side of Chicago, a neighborhood that beautifully blends rich history with modern urban living. Nestled in Cook County, this area is known for its cultural significance, stunning architecture, and a strong sense of community that welcomes newcomers with open arms.

The South Side boasts an impressive array of parks, including the sprawling Washington Park and the iconic Jackson Park, which was designed by the renowned landscape architect Frederick Law Olmsted. These green spaces offer residents a perfect escape from the hustle and bustle of city life, providing opportunities for outdoor activities, family picnics, and leisurely strolls.

Cultural enthusiasts will appreciate the South Side's rich heritage, highlighted by historic landmarks like the DuSable Museum of African American History and the renowned Bronzeville neighborhood, famously known as the "Black Metropolis." This area has been a hub for African American culture, art, and music, making it a vibrant place to explore and experience the city’s rich past.

Dining in the South Side is an adventure in itself, featuring an eclectic mix of local eateries, from soul food restaurants to trendy cafes. You can savor everything from classic Chicago deep-dish pizza to international cuisines that reflect the neighborhood's diversity.

With its affordable housing options, strong community ties, and a wealth of amenities, the South Side of Chicago is not just a place to live; it’s a place to thrive. Whether you’re looking for a family-friendly environment or a lively urban atmosphere, the South Side offers a unique blend of both, making it one of Chicago's most sought-after neighborhoods. Come discover your new home in this dynamic community!

Newest Listings in South Side

$139,900

3 Beds ⋅ 1 Baths ⋅ 12804110 MLS ⋅ NEW Status

Great 3 Bedroom 1 Bath starter home Situated on double lot. Updated with fresh paint, hardwood floors, new carpet and updated bath. The eat-in kitchen has lots of cabinets, stove and refrigerator. The fully excavated basement is ready for your ideas. Don't let this one get away!

8535 S Givins Court, Chicago

$255,000

3 Beds ⋅ 1 Baths ⋅ 12804279 MLS ⋅ NEW Status

Welcome to 6340 S Bell, a brick single-family home in the upcoming Chicago Lawn neighborhood with a newly installed front fence, exterior doors and windows to ensure security. This 3-bedroom and 1-bath property, features a brand new kitchen and bathroom. This traditional floor plan layout includes generously sized bedrooms and a full finished basement with enclosed laundry hook up ready to be set up come move-in day. New laminated floors have been installed throughout, but original floors have been sanded and polished in the Master bedroom and Living room. Basement can serve as family room or potential 4th bedroom. New furnace, hot water tank, sump pump and central air conditioning. Nice back yard with space to park up to two personal cars. Close to Public Transit Green Line train, Walmart/Sam's Club, 15 min from Midway airport, and 15 min from new Obama Presidential Center!

6340 S Bell Avenue, Chicago

$370,000

2 Beds ⋅ 3 Baths ⋅ 12796627 MLS ⋅ NEW Status

Luxury Turn-Key Living on Historic King Drive Welcome home to this impeccably fully renovated, large 2-bedroom, 2.5-bathroom luxury residence located in a highly desirable gated Bronzeville development. Spanning approximately 1,500 square feet of pristine, move-in-ready living space, this property effortlessly combines modern sophisticated design with absolute urban convenience. From the moment you arrive, the elegant gated entrance sets this Bronzeville oasis apart. Beyond the gates, you are immediately welcomed by a beautifully landscaped, newly installed lawn and impeccably maintained surroundings that create an unmistakable sense of elegance, exclusivity, and pride of ownership. Step inside to discover a flawless, completely reimagined interior featuring high end luxury finishes, fireplace, open concept living, flawless hardwood floors, in unit laundry, tons of closet and storage space, all new appliances, vaulted ceiling, and a private deck perfect for entertaining. Bring YOUR FURRY FAMILY MEMBERS!!!! An extraordinary financial highlight: this premium property carries unbelievably low annual taxes of just $1,488 paired with a stable $200 monthly HOA that covers insurance, exterior maintenance, lawn care, scavenger, and snow removal. Enjoy the ultimate peace of mind and significantly lower monthly mortgage payments compared to nearby new construction builds! Key Highlights: * Turn-Key Luxury: Brand new interior upgrades from top to bottom with absolutely zero work required. * Premier Curb Appeal: Completely renovated front yard and manicured landscaping inside a secure gated complex. * Unbeatable Tax Savings: Rare, low annual property taxes ($1,488) maximizing your purchasing power. * Outdoor Oasis: Your own private deck space overlooking the historic Bronzeville neighborhood. Schedule your private tour today and capture this rare combination of luxury, security, and financial value before it's gone!

4414 S King Drive Unit #A, Chicago

$400,000

6 Beds ⋅ 3 Baths ⋅ 12804067 MLS ⋅ NEW Status

Impressive All-Brick Two-Flat with Finished Basement! Discover the space, charm, and versatility this beautiful brick multi-unit property has to offer! Each of the two generously sized apartments features 3 spacious bedrooms, a formal dining room, an oversized living room, and hardwood floors throughout, offering comfortable living with plenty of room to spread out. The finished basement provides additional living space, complete with 2 bedrooms, a full bathroom, and a convenient summer kitchen, creating endless possibilities for extended living arrangements or additional recreational space. Step outside and enjoy a spacious backyard featuring a covered patio, perfect for summer barbecues, entertaining guests, or simply relaxing outdoors. With its solid brick construction, generous floor plans, and versatile layout, this property presents an excellent opportunity for owner-occupants and investors alike. A fantastic opportunity to own a spacious Chicago two-flat with so much to offer. Schedule your private showing today!

6217 S Whipple Street, Chicago

$270,000

3 Beds ⋅ 2 Baths ⋅ 12804042 MLS ⋅ NEW Status

Welcome to 5740 S. Paulina Street. This beautifully transformed home offers over 1,500 square feet of living space, featuring 3 spacious bedrooms and 2 bathrooms. Completely renovated from floor to ceiling, inside and out, this home showcases modern finishes, crisp updates, and attention to detail throughout. The updates kitchen features sleek stainless-steel appliances bringing both style and functionality to the heart of the home. An open layout basement provides additional versatile living space, perfect for entertaining, a recreation area, home office, or whatever fits your lifestyle! From the interior finishes to the exterior facelift, this home offers the perfect opportunity to enjoy a beautifully updated property without taking on the renovation work. Move-in ready, waiting for its new owners and next chapter... schedule your showing today!

5740 S Paulina Street, Chicago

$689,900

5 Beds ⋅ 4 Baths ⋅ 12803938 MLS ⋅ NEW Status

WHAT IF OWNING A BRAND-NEW LUXURY HOME CAME WITH $20,000 TO HELP MAKE IT HAPPEN? Welcome to DEUX ON EVANS, where qualified buyers automatically receive a $20,000 grant toward eligible closing costs and funds needed to purchase their new home! AND THERE'S MORE! Doctors, nurses, attorneys, CPAs, actuaries, architects, and pilots-your profession opens doors to exclusive mortgage programs offering up to 100 financing! Imagine owning a spectacular new construction two-unit property with zero down while creating an opportunity to generate rental income and build long-term wealth. Let's talk about making homeownership a reality! LIVE BEAUTIFULLY. GENERATE INCOME. BUILD WEALTH. Welcome to Deux on Evans, a striking new construction two-unit property where contemporary architecture, sophisticated design, and financial opportunity come together in the heart of West Woodlawn. FROM THE MOMENT YOU ARRIVE, PREPARE TO BE IMPRESSED! Bold modern architecture, expansive European-style windows, soaring ceilings, wide-plank hardwood flooring, and thoughtfully curated finishes create an atmosphere of effortless sophistication. Natural light pours into the open-concept living and dining areas, creating the perfect setting for quiet mornings, lively gatherings, and unforgettable celebrations. THE KITCHEN IS AN ABSOLUTE SHOWSTOPPER! Rich wood-toned cabinetry, gorgeous quartz countertops, dramatic pendant lighting, premium appliances, and an oversized island create a space where beautiful design meets everyday living. Imagine Sunday brunch with family, holiday dinners with friends, or simply enjoying your morning coffee in a kitchen that makes every day feel extraordinary. BUT HERE'S WHERE THIS HOME BECOMES AN EVEN GREATER OPPORTUNITY! The beautifully appointed garden residence offers the flexibility to generate rental income while enjoying the luxury of your own home. Welcome a long-term tenant, offer furnished accommodations, explore corporate housing, or consider short-term rental opportunities where permitted. Imagine owning a property that not only provides an exceptional lifestyle but also creates opportunities to build lasting wealth! THE LOCATION MAKES THE POSSIBILITIES EVEN MORE EXCITING! With the University of Chicago, the Obama Presidential Center, Jackson Park, and the Museum of Science and Industry nearby, the surrounding area attracts visiting professors, physicians, researchers, graduate students, traveling medical professionals, executives, and families seeking convenient accommodations. From extended stays to traditional leasing, the separate garden home offers remarkable versatility. AND LET'S TALK ABOUT THE NEIGHBORHOOD! Located in West Woodlawn, Deux on Evans places you near the University of Chicago, Hyde Park, the South Shore lakefront, beautiful parks, golf courses, neighborhood restaurants, cultural attractions, and convenient transportation. With continued investment and development throughout the surrounding community, this is an exciting place to call home. NOW LET'S TALK ABOUT THE FINANCIAL OPPORTUNITIES! Qualified buyers automatically receive a $20,000 grant toward eligible closing costs and qualifying purchase funds. Plus, professional mortgage programs offer up to 100 financing for doctors, nurses, attorneys, CPAs, actuaries, architects, and pilots. Your profession could open the door to owning a beautiful new construction property while creating opportunities for additional income! TWO BEAUTIFULLY DESIGNED HOMES. ONE EXTRAORDINARY OPPORTUNITY. Live in one. Generate income from the other. Create flexibility for family, guests, or tenants. Enjoy the sophistication of new construction while exploring the financial advantages of owning a two-unit property. Some homes simply provide a place to live. Others create opportunities that can change your financial future. LUXURY WITHOUT COMPROMISE. OPPORTUNITY WITHOUT LIMITS. LIVE BEAUTIFULLY TODAY. BUILD WEALTH FOR TOMORROW. WELCOME TO DEUX ON EVANS

6635 S Evans Avenue, Chicago

$475,000

6 Beds ⋅ 3 Baths ⋅ 12607211 MLS ⋅ NEW Status

Exceptional Multi-Unit Investment Opportunity - Three Units Plus Additional In-Law Suite! Welcome to 9115 S. Ada, a spacious brick multi-unit property offering an excellent opportunity for investors or owner-occupants looking to maximize flexibility and income potential. This property features three traditional residential units plus an additional in-law suite, providing multiple possibilities for extended family living or rental opportunities, subject to applicable zoning and municipal requirements. The building showcases classic Chicago brick architecture, generous living spaces, hardwood flooring, large windows that bring in plenty of natural light, and spacious bedrooms. The interior features comfortable living and dining areas, functional kitchens with updated cabinetry and appliances, and refreshed bathroom finishes. Each level offers its own living space, creating flexibility for multi-generational households or an investor seeking multiple income streams. The additional in-law suite adds another layer of versatility rarely found in traditional multi-unit properties. Whether you're expanding your investment portfolio, looking for an owner-occupied property with additional rental income potential, or seeking a property that accommodates extended family, 9115 S. Ada presents an opportunity worth exploring. Three residential units. One additional in-law suite (Potentially add an ADU to legalize a 4th unit). Multiple possibilities. Don't miss this opportunity!

9115 S Ada Street, Chicago

$374,900

4 Beds ⋅ 2 Baths ⋅ 12803903 MLS ⋅ NEW Status

This well-maintained 2-flat presents a great opportunity for both homeowners and investors, with numerous important updates already completed. Each unit is equipped with forced air heat and central A/C, providing comfort throughout every season. Over the past 5 years, several major improvements have been made, including the roof, garage, tuckpointing, and windows, giving added peace of mind. The exterior has also been enhanced with an updated porch and newer concrete sidewalk, adding both charm and practicality. The unfinished basement features an open layout and offers plenty of potential for added living space, storage, or future customization. Ideally situated near schools, parks, shopping, and public transportation, this property combines location, functionality, and long-term value. A truly well-cared-for building ready for its next chapter.

6225 S Seeley Avenue, Chicago

$699,900

8 Beds ⋅ 4 Baths ⋅ 12803880 MLS ⋅ NEW Status

STUNNING FULLY RENOVATED BRICK 3-FLAT IN CHICAGO'S BRONZEVILLE AREA! An exceptional opportunity to own a beautifully reimagined multifamily property offering 8 bedrooms, 4 full bathrooms, and modern luxury finishes throughout. Extensively renovated in 2026, this impressive property blends timeless architectural character with today's most desirable design elements. Step inside to discover gorgeous hardwood flooring, expansive open-concept living spaces, elegant custom wainscoting, recessed lighting, designer fixtures, and stunning kitchens featuring shaker-style cabinetry, quartz countertops, stainless steel appliances, and oversized islands perfect for entertaining. Beautifully appointed bathrooms showcase large-format porcelain tile, contemporary vanities, and sleek black fixtures. The first and second floors each offer spacious 3-bedroom, 1-bathroom layouts, while the finished walkout lower level features an additional 2-bedroom, 2-bathroom unit. Outside, enjoy a generous 25 x 150 lot complete with a fenced backyard, outdoor deck, and detached 2-car garage. Conveniently located near parks, public transportation, shopping, dining, and major expressways. Whether you're an investor looking to expand your portfolio or an owner-occupant seeking a move-in-ready property with income potential, this is a rare opportunity to own a turnkey, beautifully renovated Chicago multifamily property. Schedule your private showing today!

5250 S Indiana Avenue, Chicago

$649,900

3 Beds ⋅ 4 Baths ⋅ 12802090 MLS ⋅ NEW Status

Space, style, location, AND $10,000 toward closing costs! Your opportunity to own a beautifully updated home in the heart of Bronzeville just got better! Offering nearly 3,000 square feet of living space, this stunning home features soaring 10-foot ceilings, hardwood floors, abundant natural light, a cozy fireplace, and an open-concept layout perfect for entertaining. The chef-inspired kitchen boasts an oversized granite island, custom cabinetry, and designer lighting. Retreat to the spacious primary suite featuring a soaking tub and spa-inspired shower. Enjoy generously sized bedrooms, a finished basement, and the convenience of laundry on two levels! Major updates include: Full rehab (2016), roofs (2021), furnace (2018), microwave (2025), new A/C (2026), and tuckpointing (2026). Conveniently located near the lakefront, Hyde Park, parks, beaches, shopping, dining, and downtown Chicago.

4009 S Vincennes Avenue, Chicago

$280,000

3 Beds ⋅ 3 Baths ⋅ 12803733 MLS ⋅ NEW Status

Brand new roof & freshly staged! Beautifully renovated 4-bedroom (3 +1), 2.1 baths single-family home offering a massive amount of living space across multiple levels. The bright, modern interior showcases new luxury vinyl plank floors and is anchored by a sleek kitchen featuring contemporary cabinetry, quartz countertops, and stainless steel appliances. Upstairs, you'll find three exceptionally spacious bedrooms. Downstairs, the expansive, fully finished basement provides even more room to entertain, featuring a large family room, full bath, and a fourth bedroom or private home office you can easily partition off. Throughout the home, the bathrooms have been completely updated with elegant tile and modern fixtures to create a spa-like feel. Complete with a brand-new central A/C system, a detached 2-car garage, and a prime location near shopping, parks, and tollways, this move-in-ready home truly has it all.

7000 S Eberhart Avenue, Chicago

$149,900

3 Beds ⋅ 3 Baths ⋅ 12803751 MLS ⋅ NEW Status

Welcome to this classic Chicago brick bungalow, perfectly situated in the desirable West Chatham neighborhood. Just steps away from beautiful West Chatham Park. This home offers an incredible opportunity for a savvy investor, experienced contractor, or live-in DIY homeowner ready to bring their vision to life. Featuring three spacious bedrooms and three full bathrooms, this property provides a solid foundation with plenty of room to customize and add value. The traditional bungalow layout offers generous living and dining spaces, original architectural details, and large windows that fill the home with natural light. The full basement offers excellent potential for additional living space or a recreation area, and it includes convenient walk-out access to the backyard. Outside, you'll find a large deck, perfect for entertaining or relaxing. and a two-car detached garage for secure parking and extra storage. Located within walking distance of Simeon Career Academy, local shopping, restaurants, and public transportation, this home is ideally positioned for daily commuting and urban living. Whether you're looking to renovate and resell, build long-term equity, or design your dream home, this property is full of potential. Sold As-Is. Don't miss this fantastic opportunity to own a piece of classic Chicago architecture in a thriving community!

8153 S Stewart Avenue, Chicago

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South Side Real Estate

Newest Listings in South Side

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