South Side Homes under $500,000

Welcome to the vibrant South Side of Chicago, a neighborhood rich in history, culture, and community spirit. Nestled within Cook County, this area boasts a unique blend of urban charm and suburban tranquility, making it an ideal place for families, young professionals, and anyone looking to embrace the Windy City lifestyle.

The South Side is renowned for its diverse architecture, featuring everything from classic bungalows to modern townhomes. For those seeking affordable housing options, you’ll be delighted to know that there are numerous homes available for under $500,000. This affordability does not compromise quality; many of these homes are well-maintained and situated in friendly neighborhoods, perfect for creating lasting memories.

Living in the South Side means you are never far from local attractions. Enjoy a leisurely stroll through the picturesque parks, explore the rich cultural heritage at the Museum of Science and Industry, or indulge in the culinary delights of local eateries that reflect the area’s diverse population. The community is also well-connected, with convenient public transportation options that make commuting to downtown Chicago a breeze.

As you explore the South Side, you’ll find a welcoming community that takes pride in its neighborhoods, making it an excellent place to call home. With homes under $500,000 readily available, now is the perfect time to discover what this dynamic area has to offer. Whether you’re a first-time homebuyer or looking to invest, the South Side is waiting for you to make it your own!

Newest South Side Homes under $500,000

$182,000

3 Beds ⋅ 1 Baths ⋅ 12776323 MLS ⋅ NEW Status

Foreclosure sold with non-paying tenant in place. Price agreed upon by foreclosure. 3 bedroom, 1 bath. Property was inherited and heir does not have access to interior but tenant is known. There are no interior pictures and no other information available. No inspections other than exterior of property. Survey must be paid for buy buyer. CASH ONLY as we do not have interior access. Great opportunity if you are willing to work out a lease or move-out with tenant. Absolutely no access will be granted to the interior unless you can convince the tenant to let you in. No disclosures as seller has no knowledge of condition of home.

8520 S Laflin Street, Chicago

$130,000

2 Beds ⋅ 2 Baths ⋅ 12776159 MLS ⋅ NEW Status

A Great Opportunity with Endless Potential! Whether you're an investor looking for your next project or a buyer ready to customize a home to fit your vision, this one-story property is worth a look! The main level features 2 bedrooms, 1 full bathroom, a living room, dining room, and kitchen, providing a comfortable layout with plenty of opportunity to make it your own. The home also includes an enclosed back porch, a fenced backyard, and a one-car garage, offering additional space and functionality. The full basement adds even more potential, featuring another full bathroom, a kitchen area, and an additional room that could be used as a bedroom, office, recreation space, or whatever best suits your needs. With its versatile layout, additional living space, and desirable features, this property is full of possibilities and ready for the right buyer to bring their vision to life. Don't miss this opportunity to create something special! Schedule your showing today.

6608 S Claremont Avenue, Chicago

$77,000

2 Beds ⋅ 1 Baths ⋅ 12774408 MLS ⋅ NEW Status

Large 1.5 story Classic Brick Bungalow located in the Auburn Gresham neighborhood of the City. Features generous room sizes, beautiful Leaded Glass Bay Windows in the Living Room, formal Dining Room, Eat-In Kitchen, finished Attic, enclosed rear Porch, full unfinished Basement, fenced Yard and a 2 Car detached Garage off the Alley. Close to Shopping, Dining, Transportation, Parks and the Dan Ryan Woods. HUD Case 137-532578, Insured Status: UI (Uninsured). HUD owned Property. The Seller Is selling this property in "AS IS" condition. Seller nor its representatives make any representations or warranties regarding the property.

8119 S Wolcott Avenue, Chicago

$242,500

3 Beds ⋅ 2 Baths ⋅ 12775705 MLS ⋅ NEW Status

This beautiful condo qualifies for the City of Chicago HomeGrown assistance program of up to $70,000! It must be your primary residence, but you don't have to be a first-time home buyer. Welcome home to this meticulously maintained 3-bedroom, 2-bath garden unit offering an impressive 1,500 square feet of comfortable living space in the heart of Bronzeville. Hardwood floors flow throughout the home, while the spacious kitchen features stainless steel appliances and opens seamlessly to the living area, creating an inviting space for everyday living and entertaining. The private primary suite offers its own en-suite bath, and the convenience of in-unit laundry makes daily life even easier. Low monthly assessments and an investor-friendly association add exceptional value, whether you're searching for your next home or an investment opportunity. Ideally located near parks, restaurants, shopping, and public transportation, this move-in-ready home combines comfort, convenience, and a prime location. A wonderful place to call home-or a smart addition to your investment portfolio!

4520 S King Drive Unit #1B, Chicago

$435,000

7 Beds ⋅ 2 Baths ⋅ 12747469 MLS ⋅ NEW Status

Welcome to 7322 S Langley Ave! Situated on a desirable **double lot** in Chicago's Greater Grand Crossing neighborhood, this updated 2-unit property offers space, versatility, and excellent investment potential. First floor unit features 3 bedrooms and 1 bathroom with access to additional finished lower-level space. Second Floor unit features 4 bedrooms and 1 bathroom. Both units are vacant, providing flexibility for owner-occupants and investors alike. Enjoy the expansive outdoor space, a neighborhood elementary school directly across the street, and convenient access to public transportation, shopping, and local amenities. An attractive opportunity to house hack, generate rental income, or expand your investment portfolio. Schedule your showing today!

7322 S Langley Avenue, Chicago

$350,000

6 Beds ⋅ 3 Baths ⋅ 12774609 MLS ⋅ NEW Status

6146 S California Avenue, Chicago

$124,900

3 Beds ⋅ 1 Baths ⋅ 12772762 MLS ⋅ NEW Status

A welcoming Chicago home with comfortable living spaces and plenty of flexibility to make it your own. The interior offers a bright, functional layout with room to relax, entertain, work from home, or create spaces that fit your lifestyle. The kitchen serves as a natural gathering point, while the bedrooms provide comfortable private retreats and the overall layout offers practical everyday living. Outdoor space adds another place to unwind or gather with guests. Conveniently located near neighborhood parks, schools, shopping, dining, public transportation, and major roadways with easy access throughout Chicago and the surrounding South Side communities.

8919 S Bishop Street, Chicago

$490,000

7 Beds ⋅ 2 Baths ⋅ 12774941 MLS ⋅ NEW Status

4737 S Langley Avenue, Chicago

$299,000

4 Beds ⋅ 3 Baths ⋅ 12771971 MLS ⋅ NEW Status

Welcome to 5735 S. Marshfield Ave! This brick two-unit property offers a versatile layout with a duplex-down first-floor unit and a spacious second-floor apartment, making it a great opportunity for an owner-occupant, house hacker, or investor looking to add to their portfolio. Both units offer functional layouts with separate living areas and plenty of opportunity to make the property your own. The duplex-down first-floor unit features 2 bedrooms, 2 bathrooms, living room, dining room, and kitchen. The second-floor unit features 2 bedrooms, 1 bathroom, living room, dining room, kitchen, and pantry. Both water heaters were replaced with new units in March 2024. Property is being sold as-is.

5735 S Marshfield Avenue, Chicago

$259,900

3 Beds ⋅ 2 Baths ⋅ 12524979 MLS ⋅ NEW Status

WOW!!! PROFESSIONAL GUT REHAB. EVERYTHING IS NEW!!! HUGE KITCHEN FEATURES 42 IN MAPLE CABINETS QUARTZ COUNTERTOPS W/ UNDERMOUNT SINK, GORGEOUS MOSAIC KITCHEN BACKSPLASH, BRAND NEW STAINLESS STEEL APPLIANCES, DISHWASHER, WINE RACK & COOLER, PLENTY OF CABINET AND COUNTERTOP SPACE. MARBLE BATH FLOOR TILES IN MAIN BATH. LIVING AREA IS OPEN, SPACIOUS FLOOR PLAN WITH GENEROUS SIZE LIVING ROOM, SEPARATE DINING ROOM. CAN LIGHTING THROUGHOUT. CROWN MOLDING, BEAUTIFUL OAK HARDWOOD FLOORS AND WAINSCOT WALL TRIMS. GENEROUS SIZED HARDWOOD FLOOR STAIRCASE LEADING TO 2ND FLOOR WHICH INCLUDES 2 LARGE BEDROOMS AND 2ND (1/2) BATH. BASEMENT FEATURES A 3RD BEDROOM, LAUNDRY AREA AND UTILITY ROOM. NEW PLUMBING AND ELECTRIC THROUGHOUT. CENTRAL AIR TO BE INSTALLED PRIOR TO CLOSE. 2 CAR PARKING IN REAR OF PROPERTY, BIG BACK YARD. LOW PROPERTY TAXES. DON'T MISS THIS ONE!

6812 S Green Street, Chicago

$413,500

10 Beds ⋅ 4 Baths ⋅ 12775221 MLS ⋅ NEW Status

This affordable 4 units multifamily building located in the Washington Park neighborhood is priced to sell. Excellent cash flow opportunity for homebuyers and investors. Three of the apartments have 3 spacious bedrooms, large living rooms and family rooms. The tenants pay for their electric and gas. Located close to the University of Chicago campus, Washington Park, Jackson Park, the Obama Presidential Center, and Lake Michigan. This property is being sold as-is and where-is.

5920 S Calumet Avenue, Chicago

$150,000

1 Beds ⋅ 1 Baths ⋅ 12773683 MLS ⋅ NEW Status

Spacious 1 bedroom condo, filled with natural light and lake views. Move in ready! Beautiful South/East views, located on the top floor. Walking distance to Lake Michigan. Close to Hospital, llT, McCormick Place Convention Center, MotorRow restaurants and shops and centrally located next to I-55 , 90, and 290. Elevator building. PARKING permit is available within the condo community. Great for owner or investor. RENTALS ALLOWED.

345 E Eastgate Place Unit #604, Chicago

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