Southwest Side Homes under $400,000

Welcome to the vibrant Southwest Side of Chicago, a neighborhood that perfectly marries urban convenience with a welcoming community spirit. Nestled within Cook County, this area is known for its rich cultural heritage, diverse population, and a variety of amenities that cater to families, young professionals, and retirees alike.

One of the most appealing aspects of the Southwest Side is its affordability. Here, you can find charming homes under $400,000, making it an ideal choice for first-time homebuyers or those looking to downsize without compromising on quality of life. These homes often boast unique architectural details, spacious layouts, and well-maintained gardens, providing a perfect canvas for you to create your dream space.

The neighborhood is well-connected, with easy access to public transportation, major highways, and an array of local shops, restaurants, and parks. Whether you’re craving a cozy café, an eclectic eatery, or a tranquil green space for your weekend picnics, the Southwest Side has it all.

Additionally, the community prides itself on its strong sense of belonging and neighborly spirit. Local events and festivals bring residents together, fostering connections and celebrating the rich tapestry of cultures that make this area so special.

If you’re searching for a place that combines affordability, community, and convenience, the Southwest Side of Chicago awaits you. Discover your new home today, and become part of a neighborhood that truly feels like family!

Newest Southwest Side Homes under $400,000

$85,000

2 Beds ⋅ 1 Baths ⋅ 12776309 MLS ⋅ NEW Status

ATTEN: INVESTORS & BUILDERS- Prime opportunity to transform this property into a profitable investment or add it to your portfolio! Ideally located near Sherman Park and public transportation, this 2-bedroom, 1-bath home offers plenty of potential for the savvy investor or builder. Property features a full walk out basement, fenced-in yard, and detached garage. The interior has been gutted, providing a clean slate to bring your vision to life. Bring your ideas, creativity, and expertise and unlock the potential of this property! Great opportunity for a flip, renovation project, or investment portfolio addition. See this property today!

5247 S May Street, Chicago

$318,888

3 Beds ⋅ 3 Baths ⋅ 12776066 MLS ⋅ NEW Status

Charming 4-Bedroom Home with Flexible Living Space & Investment Potential. Welcome to this charming 4-bedroom, 3-full-bath home offering spacious living areas, a full basement, and plenty of flexibility for extended living or investment potential. The main level features hardwood floors, a functional kitchen with ceramic tile, and a bright sunroom at the rear of the home overlooking the yard. The second floor offers additional living space, a full bathroom, 1 bedroom , living room and kitchen, carpeted area, and vinyl flooring, providing privacy and versatility for bedrooms or a family retreat. The full basement includes an additional full bathroom , 1 bedroom and offers excellent potential for recreation, storage, office space, or additional living arrangements with laundry area. Outside, enjoy a brick patio, spacious yard, and a detached 2-car garage. Additional features include a new roof, two separate gas meters, and two separate electrical boxes, offering added flexibility for the property. Property is being sold AS-IS. Buyer is responsible for verifying room dimensions, permitted uses, zoning, utilities, and all property

4406 S Homan Avenue, Chicago

$295,500

4 Beds ⋅ 2 Baths ⋅ 12773200 MLS ⋅ NEW Status

Welcome to 4953 S. Artesian Ave., a spacious single-family home offering flexible living space in Chicago's Gage Park neighborhood. This property is officially configured as a 4-bedroom, 2-bath residence, with an additional finished room currently used as a fifth sleeping/bedroom space. The home's versatile layout provides multiple possibilities for today's buyer. The upper level has been arranged by the current occupants with additional living space, offering flexibility for a home office, guest accommodations, recreation space, or other uses to suit the next owner's needs. Inside, you'll find generous living space across multiple levels, and plenty of opportunity to personalize the home over time. The property is currently tenant-occupied and has been maintained as a functional residence, while still offering areas where a new owner can add value and make improvements. Outside, enjoy a private backyard and patio area with room for outdoor entertaining and relaxing, plus the convenience of garage parking. The Gage Park location adds another dimension to the property. Nearby Gage Park offers extensive recreational amenities including a fieldhouse, fitness center, playground, track, sports fields and courts, community garden and swimming facilities. Schedule your showing and explore everything 4953 S. Artesian has to offer.

4953 S Artesian Avenue, Chicago

$270,000

5 Beds ⋅ 2 Baths ⋅ 12775414 MLS ⋅ NEW Status

Welcome to this charming single-family home nestled in the fast-appreciating Gage Park neighborhood, surrounded by all the amenities this vibrant community has to offer. This spacious 2-story home features 5 large bedrooms with closets, 2 full baths, and a large eat-in kitchen - all designed for comfortable everyday living. The main floor bathroom has been beautifully remodeled and includes a whirlpool tub. Major updates throughout include new windows, new A/C, and a new boiler for year-round comfort and peace of mind. The full finished walkout basement offers even more living space with a full bath, family room, and bar - perfect for entertaining. Outside, enjoy a concrete patio, a front iron fence, a new private fence in the backyard, and a detached 2-car garage. Ideally located just minutes from Gage Park, Marquette Park, and several neighborhood schools, with Pete's Fresh Market and popular local restaurants nearby on Kedzie. Convenient access to I-55 and Midway Airport makes commuting a breeze. A wonderful opportunity in one of Chicago's most accessible and growing neighborhoods!

5730 S Washtenaw Avenue, Chicago

$350,000

4 Beds ⋅ 3 Baths ⋅ 12775185 MLS ⋅ NEW Status

Spacious home offering three levels of living space in a prime location within walking distance to Midway Airport and the Orange Line. This spacious residence features 4 bedrooms and 3 full baths, with refinished hardwood floors on the main level. The updated kitchen boasts stainless steel appliances and modern finishes. The second level includes two comfortable bedrooms, while the finished basement provides additional living space ideal for a family room, office, or guest suite. The backyard boasts an oversized concrete slab and Pergola, perfect for entertaining or relaxation. Seller is offering a one-year home warranty.

5647 S Keeler Avenue, Chicago

$225,000

4 Beds ⋅ 3 Baths ⋅ 12775100 MLS ⋅ NEW Status

Incredible investment opportunity awaits in the heart of Brighton Park! Located at 4441 S. Trumbull Ave, this classic Chicago brick bungalow is a historic gem awaiting your creative vision. While the property requires plenty of TLC and updating, it boasts excellent structural bones, a solid foundation, and the timeless architectural charm that makes Chicago bungalows highly coveted. Legally classified as a single-family home, this property offers an opportunity for savvy buyers: it is uniquely configured with the possibility to be utilized as a two-unit property or related-living space, complete with two separate electric meters already in place. Whether you are looking to build out an expansive multi-generational estate or explore a flexible layout, this property offers incredible equity potential.

4441 S Trumbull Avenue, Chicago

$385,000

4 Beds ⋅ 2 Baths ⋅ 12774615 MLS ⋅ NEW Status

Welcome to 5801 S Talman Ave! This well-maintained single-family home features 6 bedrooms and 2 bathrooms with a functional layout and plenty of space for comfortable living. The main level offers a spacious living area, kitchen, and bedrooms, while the full basement provides additional room for storage, recreation, a home office, or future use. The property sits on a generous lot and offers a great combination of space, functionality, and potential. The home is in good overall condition and has been well cared for, making it a great opportunity for a homeowner or investor looking for a solid property in Chicago's Marquette Park area. Conveniently located near shopping, dining, schools, parks, and transportation. Whether you're looking for your next home or an investment opportunity, this property is definitely worth a look. Property is being sold AS-IS. Schedule your showing today!

5801 S Talman Avenue, Chicago

$379,000

3 Beds ⋅ 3 Baths ⋅ 12774500 MLS ⋅ NEW Status

Welcome to Garfield Ridge! This gorgeous 2-story Georgian features gleaming hardwood floors throughout and 3 bedrooms and 3 baths. This classic home has been thoughtfully expanded to offer the space today's families are looking for, including a larger kitchen, a full bathroom on the main level, and a separate dining room perfect for everyday living and entertaining. Upstairs, you'll find three spacious bedrooms and an additional full bathroom, offering comfort and privacy for the whole household. The finished basement adds incredible versatility, complete with a full bath and kitchenette. Making it ideal for extended living, guests, or additional entertaining space. Major updates provide peace of mind, including a roof replaced in 2019, a newer water heater, and a 2025 HVAC and AC system. The fully fenced backyard offers privacy and room to enjoy the outdoors, plus a 2-car garage for added convenience. Recently rehabbed and move-in ready, this Garfield Ridge gem combines timeless Georgian charm with modern upgrades in one of the neighborhood's most desirable locations.

5227 S Neenah Avenue, Chicago

$319,900

3 Beds ⋅ 1 Baths ⋅ 12774385 MLS ⋅ NEW Status

Must see! Spacious well maintained home in the West Lawn neighborhood, Main floor feature Living room, Kitchen with newer appliances and 3 bedrooms with hardwood flooring. Full unfinished attic with lots of space for more bedrooms and rough inn plumbing for a bathroom. Basement is full unfinished perfect for more living space and ready for your ideas. Located near School, Shopping, and transportation minutes away from the Orange Line. Set up your showing before its Sold!!!!!

6221 S Tripp Avenue, Chicago

$355,000

3 Beds ⋅ 2 Baths ⋅ 12760269 MLS ⋅ NEW Status

Welcome home to this charming brick Georgian in the heart of Garfield Ridge! Warm, inviting, and filled with natural lighting and thoughtful updates, this home features a spacious primary suite, beautifully updated bathrooms, birch cabinetry, stainless steel appliances, and modern finishes throughout. Enjoy added comfort with updated electrical and plumbing, a purifier, a humidifier, ejector pump, washer and dryer, and soundproof windows. The spacious backyard is ready for summer gatherings, gardening, or simply relaxing outdoors, while the large 2.5-car garage offers plenty of parking and storage. Close to shopping, dining, transportation, and expressway access! More pictures coming this week

5110 S Monitor Avenue, Chicago

$65,000

3 Beds ⋅ 1 Baths ⋅ 12773257 MLS ⋅ NEW Status

1 Story 3 Bedroom Bungalow located in the New City neighborhood of the City. Close to Shopping, Transportation and the I-90/94 Expressway. Features Hardwood Floors, formal Dining Room and a full unfinished Basement. HUD Case 137-474607, 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.

5140 S Emerald Avenue, Chicago

$329,999

3 Beds ⋅ 2 Baths ⋅ 12772855 MLS ⋅ NEW Status

Welcome home to this spacious and beautifully updated property offering 5 generously sized bedrooms and 2 full bathrooms, with plenty of room for comfortable living and entertaining. The main level features a welcoming living room, separate dining room, and an updated kitchen with a functional layout. The finished basement provides additional living space with tile flooring throughout, a full bathroom, and a flexible layout ideal for related living, a recreation area, home office, or guest space. Outside, enjoy a 2-car garage, spacious yard, and a covered concrete patio-perfect for relaxing, entertaining, and enjoying the outdoors. With generous living space inside and out, this home offers versatility, comfort, and plenty of possibilities for its next owner. Schedule your showing today!

6506 S Keating Avenue, Chicago

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