South Side Homes under $300,000

Welcome to the vibrant South Side of Chicago, a neighborhood steeped in rich history, cultural diversity, and a strong sense of community. Known for its iconic landmarks and spirited atmosphere, the South Side offers an array of experiences that cater to every lifestyle. From the lush expanses of Washington Park to the artistic flair of Hyde Park, this area is a mosaic of parks, galleries, and local eateries that celebrate the heart and soul of Chicago.

For those seeking an affordable entry into this dynamic neighborhood, homes under $300,000 are not just a possibility; they are a reality. The South Side boasts a variety of housing options, from charming bungalows to cozy condos, making it an ideal choice for first-time homebuyers, young families, or anyone looking to invest in a thriving community. With the cost of living in Chicago steadily rising, finding a home in this price range is a rare gem.

Living in the South Side means being part of a community that values connection and tradition. Residents enjoy easy access to public transportation, making commuting to downtown Chicago a breeze. The area is also home to renowned institutions such as the University of Chicago, the Museum of Science and Industry, and the historic Bronzeville neighborhood, which offers a rich cultural experience.

Whether you’re drawn to the South Side for its affordability, its community spirit, or its cultural vibrancy, you’ll find that this neighborhood has something special for everyone. Embrace the opportunity to call the South Side your home, and experience the warmth and charm of one of Chicago’s most beloved areas.

Newest South Side Homes under $300,000

$126,000

3 Beds ⋅ 2 Baths ⋅ 12785910 MLS ⋅ NEW Status

Great Investment Opportunity! A perfect opportunity for investors looking to generate rental income or renovate and resell for a profit! This classic 3-bedroom brick bungalow features a full finished basement with a family room and bathroom, plus a 2-car detached garage. Situated on an oversized Chicago lot, this property offers plenty of outdoor space for entertaining, gardening, or family gatherings. With a spacious layout and room for both large and small families, this home has tremendous potential for investors and homeowners alike. Bring your vision and unlock the possibilities! (room sizes approx)

1374 W 78Th Street, Chicago

$249,900

4 Beds ⋅ 2 Baths ⋅ 12785725 MLS ⋅ NEW Status

Spacious brick bungalow in the desirable Chatham neighborhood! This 4-bedroom, 2-bath home features a bright living room, separate dining area, generous bedroom sizes, central air conditioning, and a full partially finished basement with additional living and storage space. Conveniently located near schools, parks, shopping, public transportation, and major expressways. Great opportunity to own a classic Chicago home with endless potential. Property sold as-is. Seller does not provide survey. Buyer to verify zoning and take subject to municipal requirements, if any. *Property not rent - beware of rental scams. Security camera enforced*

8519 S King Drive, Chicago

$199,900

4 Beds ⋅ 2 Baths ⋅ 12742360 MLS ⋅ NEW Status

Great Opportunity for Homeowners and Investors! This spacious 4-bedroom, 1-bathroom property offers plenty of room and potential. The fully finished basement provides additional living space, perfect for a family room, entertainment area, or home office. Whether you're looking for your next home or an investment opportunity, this property is full of possibilities. Please note that roof replacement or repairs will be needed. The property is being sold in its current condition, AS-IS. Don't miss this opportunity to make it your own! Schedule your showing today.

6730 S Sangamon Street, Chicago

$300,000

10 Beds ⋅ 4 Baths ⋅ 12612273 MLS ⋅ NEW Status

An exciting opportunity to add value and grow your investment portfolio with this four-unit property situated on two lots! The building features a rented front first-floor unit with 2 bedrooms and 1 bathroom, a rear first-floor 2-bedroom, 1-bath unit that is currently gutted and ready for renovation, a second-floor 3-bedroom, 1-bath unit, and a third-floor 3-bedroom, 1-bath unit. The second- and third-floor units have recently been vacated, offering investors the opportunity to renovate, reposition, and maximize rental potential. Each unit has separate electricity and heating, and the property also includes an additional basement. Conveniently located near grocery stores, Miles Davis Magnet Academy, local businesses and just minutes from the Green Line. With four units, two lots, and plenty of potential to add value, this property is an opportunity worth exploring! Sold as-is.

6758 S Hermitage Avenue, Chicago

$104,500

2 Beds ⋅ 1 Baths ⋅ 12785253 MLS ⋅ NEW Status

Charming 1 story brick home located in the sought after Auburn Gresham neighborhood. This 2 bedroom, 1 bath residence offers a functional layout with great potential for homeowners looking to add their personal touch. Room sizes are estimates. Features include a detached 1 car garage and a cute backyard perfect for relaxing, gardening, or outdoor gatherings. Conveniently located near schools, parks, shopping, public transportation, and neighborhood amenities. With solid brick construction and endless possibilities, this property is ready for its next chapter. Property is being sold in AS IS condition, no surveys nor disclosures, taxes prorated. Don't miss this opportunity to own in a well-established Chicago neighborhood. This property is a HUD home,137-321852. HUD registered agents with a NAID can submit a bid at hudhomestore. No one may alter nor occupy the property until transfer of title. This property is HUD owned and is offered in "AS IS" condition with neither repairs nor warranties. Insurability code IE. Please see attached disclosures which provide excellent guidelines to follow. Thank you for your effort.

8456 S Damen Avenue, Chicago

$189,000

3 Beds ⋅ 1 Baths ⋅ 12783742 MLS ⋅ NEW Status

Great Looking Marquette Park (3) Bedroom (1) Bathroom (SINGLE FAMILY RANCH HOME) just hitting the market! This property is in Beyond great shape! The house is in great move-in condition. If someone were to do one thing to it, I would strip the floors and refinish them and that's it! It's in great moving condition. The roof, tuck pointing are about 10 years old. Same with furnace about 10 years old. There is no AC unit on site. The stove, microwave, washer and dryer are new in 2026. There's a ((NEW Sliding Electric Gate)) In the rear of the property that you can pull cars in from there. All new blinds 2026 (2) new windows by the kitchen were just replaced in 2026. Sump pumps from 2014. Great property to confidently come and show a property to your clients that they can move into immediately!

7131 S Hoyne Avenue, Chicago

$210,000

3 Beds ⋅ 2 Baths ⋅ 12785087 MLS ⋅ NEW Status

SPACE. VALUE. OPPORTUNITY! Situated on two spacious lots, this well-maintained oversized home offers 4 generously sized bedrooms, 1.5 baths, a 2-car garage with a breezeway, and a second-floor sunroom. Good, solid bones and lots of updates, which include: New Washer, 2024 New Dryer, 2024 New Refrigerator, 2024 New Stove, 2024 New Hot Water Heater, 2024 new Furnace 2024 New Roof 2023 New Gutters 2023 New Storm windows added in 2022 in the front of the house. Whether you're a first-time buyer, investor, or move-up buyer, this property offers the space, flexibility, and potential to make it your own. Bring your vision, add your personal touches, and unlock the equity potential! SOLD "AS IS" !

855 W 73Rd Street, Chicago

$159,900

3 Beds ⋅ 1 Baths ⋅ 12783342 MLS ⋅ NEW Status

Welcome to 7532 S. Indiana Avenue, a charming brick bungalow offering three bedrooms, one full bathroom, and classic character throughout. Hardwood floors flow through the spacious living and separate dining rooms, creating an inviting setting for everyday living and entertaining. Large windows bring in natural light, while a decorative brick fireplace with built-in shelving adds charm to the living room. The kitchen features ample cabinet space and room for a small dining table. Three bedrooms offer flexibility for sleeping, a home office, or additional personal space. A full unfinished basement provides generous storage, while the backyard offers room to relax and enjoy the outdoors. A two-car garage completes this Chicago home. Photos are prior to tenant. Seller is working on a few cosmetic updates. Home is being sold "as is".

7532 S Indiana Avenue, Chicago

$225,000

4 Beds ⋅ 3 Baths ⋅ 12784936 MLS ⋅ NEW Status

This handsome Single family is ready for a redo! Estate sale AS IS you have some work cut out for you but will a wonderful home when you finish it! Walk out basement with full kitchen in place. Please excuse the clutter. Clean out will be buyers responsibility but maybe negotiated based on offering price. Room count, bathroom count, heating system (none of this information is guaranteed/ buyers responsible to verify) Bronzeville location within steps of downtown, McCormick district, South Loop restaurants, etc

3645 S Indiana Avenue, Chicago

$155,000

4 Beds ⋅ 2 Baths ⋅ 12784881 MLS ⋅ NEW Status

Amazing opportunity! Already permitted expanded upstairs with huge potential expansion in the basement. Nice quiet block. Great home for a large family or flip after cosmetic improvements.

7638 S Rhodes Avenue, Chicago

4800 S Lake Park Avenue Unit #306, Chicago

$49,999

2 Beds ⋅ 1 Baths ⋅ 12784601 MLS ⋅ NEW Status

AFFORDABLE HYDE PARK LIVING WITH 2 COVERED GARAGE SPACES!!! Just Minutes away from the OBAMA PRESIDENTIAL COMPLEX!!! Large Recently renovated 2 Bedroom Co-op Unit with an Open Floor Plan. A Few of the Many Amenities Include Granite Counter Tops, Stainless Steel Appliances, Bamboo Flooring, 42 Inch Maple Cabinets With Crown Molding, Large Breakfast Bar and Island Combination, Custom Real Flame Fireplace, Contemporary Bathroom with 2 Oversized spacious bedrooms. The Monthly Carrying Charge Of $1,311.00 Includes, Taxes, 24 Hour Door Person, Lawn Care, Snow Removal, Heat, Central Air, Basic Cable, Water, Interior Maintenance and On-Site Management. You only pays for Lights. Cash Buyers Preferred. Unit Must Be Owner Occupied. Board Approval Required. Must Go Through Credit, Income and Back Ground Check With Management Office. Buyer Pays The Purchase Price, and additional $5,420 For The Share, and The Monthly Carrying Charge Of $1,311.00. SOLD AS-IS. A Property To Live In And Relax!

4800 S Lake Park Avenue Unit #306, Chicago

$168,500

4 Beds ⋅ 2 Baths ⋅ 12784585 MLS ⋅ NEW Status

Great investment opportunity! This brick 2-flat features two spacious units, each offering 2 bedrooms, 1 full bathroom, and a large living room. The property also includes a full basement with potential for a third unit, subject to city approval, and a detached 2-car garage. With some updates and improvements needed, this property offers great potential for investors looking to renovate or generate rental income. Don't miss this opportunity! Property does not meet FHA financing requirements due to its current condition.

7739 S Wood Street, Chicago

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