Southwest Side Real Estate

Welcome to the Southwest Side of Chicago, a vibrant neighborhood steeped in rich history and cultural diversity. Nestled within Cook County, this area is known for its tight-knit community, making it an inviting place for families, young professionals, and retirees alike.

The Southwest Side boasts a unique blend of residential charm and urban convenience. Tree-lined streets are adorned with an eclectic mix of classic bungalows, modern townhomes, and spacious single-family houses, providing a variety of options for prospective homeowners. The neighborhood is also home to several parks, such as Marquette Park and McKinley Park, where residents can enjoy outdoor activities, picnics, and community events throughout the year.

Cultural influences are palpable here, with an array of restaurants offering everything from authentic Mexican cuisine to classic Chicago-style deep-dish pizza. The local shops and markets reflect the neighborhood's diversity, making it a delightful place to explore and support small businesses.

Transportation is a breeze, with easy access to public transit options and major highways, allowing residents to commute seamlessly to downtown Chicago and beyond. The Southwest Side is also known for its excellent schools and community programs, making it an ideal choice for families looking for a nurturing environment.

In summary, the Southwest Side of Chicago is a neighborhood that offers a perfect balance of community spirit, cultural richness, and urban accessibility. Whether you’re looking to buy your first home or seeking a welcoming community to settle down in, this charming area has something for everyone. Come and discover the warmth and character of the Southwest Side!

Newest Listings in Southwest Side

$545,000

5 Beds ⋅ 3 Baths ⋅ 12805751 MLS ⋅ NEW Status

Excellent opportunity for an owner-occupant or investor! This MULTI UNIT FEATURES 3 levels of living space. This property offers 2 units with an ADDITIONAL finished basement with in-law arrangement, a 2-car garage, strong existing tenants, and a VACANT main-floor unit-perfect for a buyer looking to move in while generating rental income. The building generates about $4,275.00 of monthly rent when it is fully occupied. The upper unit features a spacious 1-bedroom layout with a large living room, eat-in kitchen, and its own laundry room with washer and dryer. The main-floor unit offers 2 bedrooms, a combined living/dining area, and a kitchen. The finished basement in-law arrangement adds 2 bedrooms, 1 full bath, and access to a shared coin-operated Speed Queen laundry system with convenient PayRange digital payment capability. Major improvements make this property even more attractive, including a NEW ROOF AND GUTTERS, newly installed drain-tile/flood-control system, central heating and cooling, newer water heater, remodeled basement bathroom, updated main-floor kitchen with newer appliances, cabinets and countertops, exterior motion lighting, and a newer rear exterior/storm door. With great tenants already in place, a vacant main unit ready for an owner-occupant, multiple living spaces, a 2-car garage, and significant recent improvements, this is a turnkey opportunity with flexibility and income potential. Schedule your showing today!

5922 S Karlov Avenue, Chicago

$404,900

3 Beds ⋅ 3 Baths ⋅ 12805701 MLS ⋅ NEW Status

Rare find in the Clearing neighborhood, an updated, three-story townhouse. You won't want to miss seeing this one. The first level boasts a living room with cathedral ceiling, hardwood flooring, and electric fireplace; the second level features a formal dining room, large eat-in kitchen filled with sunlight, breakfast bar, and granite countertops, and a half bath. There is a nice-sized balcony off the kitchen to enjoy your morning coffee. The third level has a master bedroom suite with master bath and walk-in closet and two additional bedrooms and full bath. There also is an additional room on the lower level with heated floors that can be used as a family room, office, or playroom. This townhome is perfect for anyone looking for a spacious home with low maintenance.

6619 W 64Th Place, Chicago

$429,000

5 Beds ⋅ 2 Baths ⋅ 12803810 MLS ⋅ NEW Status

Legal 2 flats in the heart of Bridgeport. LOCATION LOCATION LOCATION. Very well kept building occupied by 2 generation owners. Features 3 bedrooms each unit, updated cabinets, in building washer and dryer, spacious living room, hardwood floor, stainless steel appliances, open kitchen with extra finsihed porch space. huge back yard for summer BBQ fun, full unfinsihed basement for extra storage or living space.7 year old tear off roof. Newer Vinyl windows. property is price to be sold as is condition. In walking distance to 27 acre community Palmisano Park 26.60-acre community park in the Bridgeport neighborhood Stearns Quarry Park, #8 bus, orange line, bank, grocery store, Walgreens, CVS, gas station and more.

2836 S Union Avenue, Chicago

$375,000

3 Beds ⋅ 3 Baths ⋅ 12790218 MLS ⋅ NEW Status

Welcome to this charming home situated on a rarely available double lot in Chicago's Clearing neighborhood, offering generous indoor living space and an expansive backyard perfect for outdoor entertaining! Notable recent improvements include a new roof and gutters in 2023, a new furnace in 2023, fresh interior paint in 2026, brand new carpeting in 2026, 2nd floor AC/furnace unit installed in 2026, and a new pool liner in 2026. Step inside to discover a freshly painted interior and beautiful hardwood floors that flow through the inviting living room and adjoining dining room. The living room features a large bay window that fills the space with natural light, while the dining room provides a great setting for everyday meals and gatherings. The eat-in kitchen offers Corian countertops, can lighting, and a newer sliding glass door installed in 2021 that provides direct access to the backyard. Two conveniently located main-level bedrooms offer flexible living arrangements. Upstairs, the spacious primary bedroom features two closets, including one with built-in organizers, and a private full bathroom complete with double sinks, a separate shower, and a whirlpool tub. An additional upstairs office with built-in bookshelves provides an ideal space for working from home or studying. The finished basement expands the living space with a large family room perfect for entertaining, movie nights, or recreation. A full basement bathroom and a dedicated laundry room with plenty of additional storage complete the lower level. Step outside and enjoy the exceptional outdoor space that comes with owning a double lot! The fully fenced backyard features a spacious deck with built-in bench seating and a 24-foot above-ground pool with a brand-new liner installed in 2026, creating the perfect setting for summer gatherings and relaxation. A 2.5-car detached garage provides ample parking and additional storage. With its versatile floor plan, finished basement, and oversized outdoor space, this home offers a wonderful opportunity in Chicago's Clearing neighborhood!

6223 S Nashville Avenue, Chicago

$1,100,000

3 Beds ⋅ 5 Baths ⋅ 12802676 MLS ⋅ NEW Status

Welcome to this beautifully newly constructed two-story single-family residence with a full basement in Bridgeport. This home features 5 bedrooms and 4.5 bathrooms with stylish finishes. The spacious kitchen features beautiful natural wood-tone cabinetry with sleek black hardware, elegant quartz-style countertops, a modern white tile backsplash, and a famous Fotile range hood. The second floor features three spacious private bedroom suites, offering exceptional comfort, privacy, and convenience for family members and guests alike. Finished basement with wet bar and closet great for entertainment and party. Two-car detached garage, landscaped and fenced front and back yard. Offering two levels of living space plus a basement, this newly built residence combines contemporary style, quality design details, and functional living spaces. A wonderful opportunity to own a beautiful new construction home with modern appeal and timeless finishes!

1019 W 32Nd Street, Chicago

$475,000

5 Beds ⋅ 3 Baths ⋅ 12805030 MLS ⋅ NEW Status

Great opportunity with this well-maintained 2-unit property offering flexible living space and plenty of storage. The first unit features 3 bedrooms, 11/2 baths and a full kitchen, while the second unit offers 2 bedroom, 1 bath and its own full kitchen. Each unit has separate electric, making this a practical option for an owner-occupant or investor. The property also features a full basement with an additional sub-basement, plus a full walk-in attic providing plenty of room for storage. Recent mechanical updates include a boiler installed in 2025 and a furnace approximately 4 years old, while the roof and windows are approximately 10 years old. Outside, you'll find a new fenced yard and 2-car garage and new gutters with leaf guard- no more cleaning your gutters! A solid Chicago 2-unit with multiple levels of usable space and many of the major improvements already completed.

3805 S Honore Street, Chicago

$420,000

3 Beds ⋅ 2 Baths ⋅ 12802588 MLS ⋅ NEW Status

Welcome to 5326 S. Merrimac Ave.! Offering an impressive 2,351 square feet of living space, this spacious 5-bedroom, 2-bathroom home provides the perfect blend of comfort, functionality, and versatility. The main level features beautiful hardwood floors, a bright and inviting living room, a modern kitchen complete with a stylish island, a spacious primary bedroom, and two additional bedrooms. The fully finished basement expands your living possibilities with a generous family room, a second kitchen, and two additional bedrooms-ideal for extended family, guests, or additional living space. Step outside to enjoy the expansive yard, offering plenty of room for entertaining, relaxing, and outdoor activities. With abundant living space and a flexible layout, this home offers endless possibilities. Don't miss the opportunity to make this wonderful property your own!

5326 S Merrimac Avenue, Chicago

$235,000

5 Beds ⋅ 2 Baths ⋅ 12804865 MLS ⋅ NEW Status

FLEXIBILITY & INCREDIBLE VALUE! Welcome to this 5-bedroom, 2-bath home in Chicago's Gage Park neighborhood, offering plenty of room to grow and make it your own! Featuring two levels of living space, a generous eat-in kitchen, and a beautifully updated main-floor bathroom with a whirlpool tub, this home offers a versatile layout for everyday living. The full finished walkout basement provides additional recreational space, complete with a family room, a second full bathroom, and a bar-ideal for entertaining or relaxing. Enjoy valuable improvements including newer windows, central A/C, and a boiler. Outside, you'll find a private fenced backyard, concrete patio, and detached 2-car garage. Conveniently located near Gage Park, Marquette Park, schools, shopping, restaurants, Midway Airport, and I-55. With 5 bedrooms, additional finished basement space, and so much potential, this is an opportunity you don't want to miss. Schedule your showing today!

5730 S Washtenaw Avenue, Chicago

$385,000

4 Beds ⋅ 2 Baths ⋅ 12804627 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

$199,900

12804532 MLS ⋅ NEW Status

***Attention all investor and rehabbers*** Add instant sweat equity to this solid and massive 4,675 square foot brick mixed-use structure. Prime Back Of The Yards location just steps to Sherman Park. This property needs a full renovation and has excellent income potential. ***NOTE - A previous zoning certification indicates that property is a legal 1-unit (single-family). Buyer must take subject to the SFR zoning cert. Sold strictly as-is. No survey. Must take subject to all violations and code compliance requirements.

1114 W 51St Street, Chicago

$2,200,000

12804352 MLS ⋅ NEW Status

Attention Builders/Developers/Investors!! Large lot with a large building for sale in the heart of Bridgeport. The building included commercial on the first floor and residential units on the 2nd-floor. Zoned B1-1. Many new developments around the area.

3700-3716 S Halsted Street, Chicago

$325,000

4 Beds ⋅ 2 Baths ⋅ 12804311 MLS ⋅ NEW Status

Spacious 4-Bedroom Home on an Oversized Double Lot with a Sought-After Side Driveway! Welcome to this spacious 4-bedroom, 2-full-bath home offering an abundance of room, comfort, and endless possibilities! Featuring two separate formal dining rooms, this home is perfect for hosting family gatherings and entertaining guests. The generously sized kitchen provides plenty of space for cooking, dining, and everyday living. Additional highlights include a full unfinished basement offering excellent potential for additional living space, storage, or customization to suit your needs. Enjoy year-round comfort with central heating and air conditioning systems that are less than two years old! Situated on an oversized double lot, this property features a desirable side driveway and plenty of outdoor space to entertain family and friends, enjoy outdoor activities, or simply relax. Conveniently located near public transportation, including bus routes and the Orange Line, with an approximately 20-minute train commute to downtown. Easy access to I-55, as well as nearby shopping, restaurants, and everyday conveniences. A wonderful opportunity to own a spacious home with a desirable side driveway, generous outdoor space, and incredible potential in a convenient location!

4827 S Lotus Avenue, Chicago

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Southwest Side Real Estate

Newest Listings in Southwest Side

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