South Side Real Estate

Welcome to the vibrant South Side of Chicago, a neighborhood steeped in rich history and cultural diversity. Nestled within Cook County, this dynamic area is a tapestry of communities, each offering its own unique charm and character. From the bustling streets of Hyde Park to the artistic enclaves of Bronzeville, the South Side is a place where tradition meets modernity.

One of the defining features of the South Side is its deep-rooted cultural heritage. The neighborhood is renowned for its contributions to music, art, and literature, having birthed legendary figures such as Louis Armstrong and Gwendolyn Brooks. You can stroll through the historic streets, where jazz and blues echo from local venues, or visit the DuSable Museum of African American History to immerse yourself in the rich narratives that have shaped this area.

The South Side is also home to beautiful parks and green spaces, including the expansive Washington Park and the picturesque Jackson Park, which hosted the 1893 World’s Columbian Exposition. These parks provide a perfect backdrop for outdoor activities, community events, and family gatherings.

For those seeking a sense of community, the South Side offers a variety of local businesses, farmers' markets, and eateries that reflect the neighborhood's culinary diversity. Whether you’re enjoying a classic Chicago-style deep-dish pizza or exploring the flavors of international cuisine, you’ll find something to tantalize your taste buds.

With its affordable housing options, strong community ties, and rich cultural offerings, the South Side of Chicago is not just a place to live; it’s a place to thrive. Discover the warmth and vibrancy of this extraordinary neighborhood today!

Newest Listings in South Side

$180,000

4 Beds ⋅ 2 Baths ⋅ 12801436 MLS ⋅ NEW Status

Spacious 4-Bedroom Home in Chicago's Historic Brainerd Community (Sold AS-IS) Welcome to this solid single-family home, perfectly situated on a peaceful street in the highly desirable Brainerd neighborhood. This 4-bedroom, 2-full-bathroom property offers ample space, solid structural integrity, and excellent value. Please note: This property is being sold strictly in AS-IS condition. The home will require some work, fresh paint, new flooring on the main level, basement, and bathrooms need upgrades. This presents a straightforward opportunity for savvy buyers or investors looking to add their own finishing touches and build immediate equity. Key Property Highlights: * Generous 1,972 sq. Ft. Layout: 4 large bedrooms and 2 full bathrooms * Oak Kitchen cabinets: Are salvageable and will provide the storage and workflow to suit most needs. * Flexible Partially Finished Basement: Features one versatile bonus room-perfect for a gym or playroom-plus a dedicated, separate storage area. * Detached 2-Car Garage: A massive perk for Chicago winters, offering private parking and extra space for tools, hobbies, or more storage. *Mechanical & Security: While cosmetic updates are needed, the most expensive and heavy-lifting have already been taken care of for you: * Brand New boiler Heating System: High-efficiency climate control for worry-free winters. * Brand New Water Heater: Excellent hot water capacity for a busy household. * Enhanced Safety: heavy-duty steel security doors at the entrances. * Modern Windows: Updated vinyl double-hung tilt windows for maximum insulation. The Location Benefit: Nestled in the heart of Brainerd, this home puts you minutes away from vibrant neighborhood staples like Brainerd Park and Robichaux Park, excellent local library resources at the Carter G. Woodson Regional Library and convenient commuting options via the Metra Rock Island District line or Interstate 94. This property is a rare find that combines modern mechanical infrastructure, private garage space, and a fantastic neighborhood atmosphere. Bring your vision, refresh the surfaces, and unlock this home's full potential!

9416 S Elizabeth Street, Chicago

$429,999

10 Beds ⋅ 4 Baths ⋅ 12801434 MLS ⋅ NEW Status

Excellent investment or owner-occupant opportunity! This solid brick 3-unit property offers immediate income with two occupied units generating $1,420 and $1,620 per month, while the third unit is vacant and ready for a new tenant or perfect for house hacking. The property also features a detached brick garage, generous outdoor space, and is conveniently located near the Cottage Grove shopping plaza, restaurants, public transportation, and everyday amenities. Whether you're looking to expand your portfolio or this property offers strong cash flow potential in a convenient South Side location. Outside pictures may be slightly enhanced! Schedule your private showing today!

8755 S Cottage Grove Avenue, Chicago

$314,900

5 Beds ⋅ 2 Baths ⋅ 12801330 MLS ⋅ NEW Status

Step inside and fall for classic Chicago all over again. This beautifully remodeled 5 bed, 2 bath home pairs the timeless character of Chicago architecture with sleek, contemporary finishes, creating a space that feels both established and brand new. Thoughtfully updated from top to bottom, every room invites you to settle in. Upstairs, the expansive primary suite is a true private retreat, with an impressive sense of space and comfort you'll look forward to coming home to. Downstairs, the beautifully finished basement is made for entertaining, with room for game days, movie nights, and gatherings that turn into memories. With generous living spaces, stylish updates, and character you simply can't replicate, this is a rare blend of elegance, function, and classic Chicago appeal. Schedule your showing today!

8624 S Justine Street, Chicago

$499,999

12801285 MLS ⋅ NEW Status

DON'T MISS THIS EXCEPTIONAL OPPORTUNITY TO OWN A WELL-MAINTAINED, FULLY OCCUPIED SIX-UNIT INVESTMENT PROPERTY IN THE DESIRABLE CHATHAM NEIGHBORHOOD OF CHICAGO! THIS INCOME-PRODUCING PROPERTY FEATURES A DESIRABLE UNIT MIX OF THREE SPACIOUS 3-BEDROOM, 1-BATHROOM UNITS AND THREE WELL-MAINTAINED 2-BEDROOM, 1-BATHROOM UNITS. WITH ALL SIX UNITS CURRENTLY OCCUPIED, INVESTORS CAN BENEFIT FROM AN ESTABLISHED TENANT BASE AND RENTAL INCOME FROM DAY ONE. WHETHER YOU'RE AN EXPERIENCED INVESTOR LOOKING TO EXPAND YOUR PORTFOLIO OR ENTERING THE MULTIFAMILY MARKET, THIS PROPERTY PRESENTS AN EXCELLENT OPPORTUNITY TO INVEST IN CHICAGO'S SOUTH SIDE. CONVENIENTLY LOCATED NEAR PUBLIC TRANSPORTATION, SHOPPING, AND EVERYDAY AMENITIES, THIS PROPERTY OFFERS IMMEDIATE INCOME POTENTIAL AND LONG-TERM INVESTMENT APPEAL.

8142-8146 S Maryland Avenue, Chicago

$250,000

12801240 MLS ⋅ NEW Status

Outstanding Mixed-Use Investment Opportunity in Chicago! This substantial two-story mixed-use property offers tremendous potential for an investor, developer, or owner-user looking to bring their vision to life. Featuring a large footprint with commercial space on the main level and additional space on the second level, the property presents numerous possibilities for future use, renovation, or redevelopment. A major highlight is the property's excellent location near the CTA Green Line Ashland/63rd Station, providing convenient public transportation and accessibility to the surrounding community and greater Chicago area. The property also benefits from a prominent urban location with strong street presence and easy access to major thoroughfares. Whether you're looking for a mixed-use investment, commercial opportunity, or a property with significant value-add potential, this is a unique chance to acquire a large and versatile building in an established Chicago neighborhood.

1550 W 63Rd Street, Chicago

$328,900

3 Beds ⋅ 3 Baths ⋅ 12801236 MLS ⋅ NEW Status

Welcome to this beautifully rehabbed brick bungalow in the heart of Auburn Gresham! This spacious 4-bedroom, 3-full-bath home is ready for a new owner! Interior offers generous living space, well-appointed bedrooms, and three full bathrooms designed for everyday convenience. The full basement provides additional flexible space and features drain tile, offering added peace of mind and functionality. Outside, enjoy the convenience of a brand-new 2-car garage. A great opportunity to own a substantially updated home with the space, features, and convenience you've been looking for. Close to transportation, expressway, shopping, restaurants and more.

7522 S Carpenter Street, Chicago

$10,000

12801227 MLS ⋅ NEW Status

BANKRUPTCY SALE! Priced to sell quickly. This is a CASH for Deed sale. Minimum of 60 days closing for court approval; Bankruptcy court order to remove liens and back taxes. The full purchase price funds are due within 10 days of acceptance of an offer. No survey, no title insurance provided.

1339 W Marquette Road, Chicago

$110,000

2 Beds ⋅ 2 Baths ⋅ 12801146 MLS ⋅ NEW Status

This well maintained single family has lots of space. 2 bedrooms 1st floor, full partially finished basement with an additional room, and unfinished attic. Hardwood floors living/dining. 2 bathrooms and lots of storage. Basement was previously used as a hair salon. Call for your showing today. This will not last. Great investment! Properties are going fast. Get in NOW.

1843 W 71St Street, Chicago

$575,000

3 Beds ⋅ 3 Baths ⋅ 12794838 MLS ⋅ NEW Status

Luxury Elevated. City Living Reimagined. Prepare to be impressed by this extraordinary and rare triplex residence at Flats on the Drive, where contemporary design, sophisticated style, and exceptional space converge in the heart of Bronzeville. Offering approximately 2,400 square feet, 3 bedrooms, and 3 full bathrooms, this distinctive residence was built in 2019 and delivers the scale and privacy of single-family living with the convenience of condominium ownership. The moment you enter the main level, dramatic 14-foot ceilings and expansive open-concept living and dining areas create an unforgettable first impression. Hardwood flooring, sleek finishes, and an abundance of natural light establish a refined yet welcoming atmosphere. A private balcony just off the living room extends the entertaining space outdoors, offering the perfect spot to enjoy your morning coffee or unwind. Designed for both effortless everyday living and elevated entertaining, the stylish kitchen features premium stainless-steel appliances, generous counter space, and an island with ample seating perfect for casual mornings, intimate dinners, or gathering with guests. Thoughtfully designed across three distinct levels, this exceptional home offers a desirable separation of living, entertaining, and private retreat spaces. The lower level features three (3) bedrooms, including a spacious primary suite, while the upper level family room provides an inviting retreat for movie nights, relaxation, or hosting friends. Glass doors lead to your private rooftop deck, creating the perfect setting for morning coffee, sunset cocktails, and memorable evenings beneath the Chicago skyline. Beyond the impressive interiors, the lifestyle is just as compelling. Enjoy the convenience of garage parking, in-unit laundry, and a pet-friendly building. Ideally located along historic and picturesque King Drive, you are moments from the lakefront, Mariano's, Wintrust Arena, McCormick Place, and the vibrant dining, cultural, and entertainment destinations of Chicago's South Side. With convenient access to Hyde Park and downtown Chicago, this location puts the best of city living within reach. More than a condominium, this is a statement in modern urban living. Sophisticated, spacious, and designed to impress, this exceptional residence offers the perfect blend of architectural character, contemporary comfort, and private outdoor living. Your next chapter deserves an extraordinary address. Welcome home to Flats on the Drive. Please note that some photos are virtually staged.

3918 S King Drive Unit #3S, Chicago

$575,000

4 Beds ⋅ 4 Baths ⋅ 12801172 MLS ⋅ NEW Status

Welcome to WOODLAWN "SAME AS" NEW CONSTRUCTION 3-STORY, 5 BEDROOM 3.5 BATH SINGLE FAMILY HOME. WITH OVER 2,000 OF ADDITIONAL NEWLY BUILT SQUARE FOOTAGE, FOR A TOTAL OF 3,808 SQFT - THIS IS A BRAND NEW HOME! This exquisite modern-style home has been completed with over 350k in expansion, redesign, renovation and is ready for the discerning Buyer seeking luxury, comfort and convenience. This is a well curated floor plan with an expansive main level, featuring new hardwood flooring throughout, 10ft ceilings, plenty of natural sunlight, separate living/dining room combo, Butler's pantry with wine cooler, walk-in kitchen pantry, half bath and storage room! However, that's not it! Keep walking and you'll notice a beautiful chef kitchen with custom-built soft close cabinetry, over-sized 11ft waterfall island with breakfast bar overhangs, Calacatta white quartz countertops with ceramic tile backsplash, professional series stainless steel appliances with double oven, eat-in breakfast nook large enough for 6-chair table, and a spacious family room! The entire second floor is a family oasis that includes primary bedroom with walk-in closet, spa-like master suite with separate soaker tub, massive shower and double vanity sinks. 3 additional bedrooms and another full bath with double vanity sinks for all the kids, laundry has been added to the 2nd floor for your convenience, dual controlled heating and cooling, and hardwood floors throughout. Can't wait to see your face drop with all the space in the basement! Drain-tile zero flooding system, vinyl flooring, an additional bedroom, full bath with more storage and utility room. The wrought iron fence and wood fenced yard provides privacy and professional landscaping brings urban oasis to life. New cement patio and sidewalk and new 2.5 car garage. This home is surrounded by new construction, The Obama Library, University of Chicago, Jackson Park Golf Course, Children's Hospital, Museum of Science & Industry and Lake Shore Beaches ALL are within a few miles away! Come take a tour and fall in love!! Inquire about Buyer Credits for rate assistance!! Seller is motivated

638 E 65Th Street, Chicago

$205,000

3 Beds ⋅ 2 Baths ⋅ 12795136 MLS ⋅ NEW Status

Welcome to this nicely updated home offering the perfect combination of comfort, style, and convenience! Step inside to discover attractive laminate wood flooring, modern recessed lighting, and a spacious kitchen featuring granite countertops, a stylish backsplash, and a generous pantry for additional storage. Recent improvements include newer windows adding to the home's overall appeal. This property does have an additional bedroom in the basement along with laundry area to add additional living space. Please note the basement has lower ceiling heights. Enjoy outdoor living in the expansive, fully fenced backyard situated on a wide lot, perfect for entertaining, relaxing, or outdoor activities. A detached 2-car garage provides additional convenience and storage. Nestled on a quiet residential street in the Washington Heights neighborhood, this home offers easy access to I-90/94 Don't miss this fantastic opportunity to own a move-in ready home with plenty of space, updates, and potential! Schedule your private showing today! Please note PROPERTY IS BEING SOLD AS-IS.

9020 S Carpenter Street, Chicago

$322,000

3 Beds ⋅ 2 Baths ⋅ 12799861 MLS ⋅ NEW Status

3347 W 65Th Place, Chicago

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South Side Real Estate

Newest Listings in South Side

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