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Chicago 2-4 Flats at $400,000 or Less

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Browse Chicago properties advertised with two to four units and asking prices of $400,000 or less.

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Chicago 2-4 Flats at $400,000 or Less

8718 S Kingston Avenue, Chicago
$264,000
7 Beds ⋅ 3 Baths ⋅ 12747639 MLS ⋅ ACTIVE Status

8718 S Kingston Avenue, Chicago
7712 S Ridgeland Avenue, Chicago
$260,000
6 Beds ⋅ 4 Baths ⋅ 12797733 MLS ⋅ PRICE CHANGE Status
***ACCEPTING CASH OFFERS!!!! BUYER COULDN'T GET FINANCED. Will not pass FHA inspection. Mold present in the basement.*** Majestic beautiful legal 4 flat on serene tree lined street. These 3 units of 2 bed/1 bath have the largest footprint in all of South Shore!!! These are regal sun drenched units with huge formal living room, separate formal dining room, breakfast nook off the kitchen with walk-in pantry, 2 massive oversized bedrooms, and fabulous long hallways that make the perfect gallery for art or family photos!!! Hardwood floors throughout!!! Units are so oversized, you can easily add a 3rd bdrm and another full bath. Full unfinished english basement large enough for an additional 2 or 3 bedroom unit, lovely cemented backyard and a 3 car garage!!! Entry reception hall into each unit with glass door enclosed built-in bookshelves. Regal building entry vestibule that's large enough to hold 30 people comfortably. Amazing spaces!!! Updates needed throughout. AS-IS! Mold present in basement. ****Must sign hold harmless prior to viewing!!!!

7712 S Ridgeland Avenue, Chicago
5955 S Hermitage Avenue, Chicago
$260,000
5 Beds ⋅ 2 Baths ⋅ 12796609 MLS ⋅ ACTIVE Status

5955 S Hermitage Avenue, Chicago
7321 S Stewart Avenue, Chicago
$260,000
12 Beds ⋅ 4 Baths ⋅ 12758567 MLS ⋅ ACTIVE Status
GREAT INVESTMENT OPPORTUNITY -This rare 12bedroom, 4bath, 4,908 sq ft quadruplex built in 1900 offers exceptional income potential with 3 units currently vacant and 1 units rented monthtomonth. Whether you're expanding your portfolio or seeking a highyield valueadd property, this one stands out from the rest. Units are functional but would benefit from light "updating" during turnover and some fresh paint (one unit needs minimal drywall work)- Recent Updates / Systems & Exterior: heating units have systems approximately 10 years old, Cooling: No central air; window units used for cooling and back porches (all four porches) rebuilt ~12 years ago-AsIs Sale- Investment Highlights Estimated ARV around $440,000 based on area comps- Strong rental upside with 12 bedrooms across four units- 3 units ready for immediate renovation and leasing (1 unit is leased until 10/27), Unique charm and historic character not found in other local quadruplexes. This property offers tremendous potential for investors seeking cashflow, valueadd opportunities, or longterm appreciation. This won't last - don't miss out on a onceinalifetime opportunity! Cash buyers, Hard money buyers, Conventional financing buyers.

7321 S Stewart Avenue, Chicago
5932 S Parnell Avenue, Chicago
$259,800
5 Beds ⋅ 2 Baths ⋅ 12599972 MLS ⋅ ACTIVE Status

5932 S Parnell Avenue, Chicago
2652 S Komensky Avenue, Chicago
$259,000
4 Beds ⋅ 2 Baths ⋅ 12599708 MLS ⋅ ACTIVE Status
This well-maintained property features two units, each offering 2 bedrooms and 1 bathroom. Ideally located near local shopping centers and public transportation, perfect for commuters or savvy investors. Includes a 2-car garage and is located within the Whitney Elementary and Little Village High School districts. Sold "as-is"!. Bring your finishing touches to maximize equity. A solid addition to any portfolio or a perfect fix and flip opportunity. Whether you're looking for a long-term rental or a place to call home, this property delivers on location and value. Don't miss out on this versatile property in a high-demand area!

2652 S Komensky Avenue, Chicago
1511 N Kildare Avenue, Chicago
$255,000
4 Beds ⋅ 2 Baths ⋅ 12803650 MLS ⋅ NEW Status
2 unit all brick building; each unit features a 2 BR/1 bathroom. Semi finished basement. Two car garage.

1511 N Kildare Avenue, Chicago
4505 S Union Avenue, Chicago
$255,000
4 Beds ⋅ 2 Baths ⋅ 12742759 MLS ⋅ PRICE CHANGE Status
**Exceptional investment opportunity in desirable Canaryville!** This unique brick 2-flat sits on a **double lot** and features a spacious backyard and an **all-brick 4-car garage**. Conveniently located near the Dan Ryan Expy I-90/94, parks, schools, and shopping**. The property has been **fully stripped to the studs**, offering a blank canvas for a complete renovation and customization. Whether you're an investor or homeowner looking for a redevelopment project, this property offers tremendous potential. $$Sold strictly "as-is." No repairs or credits will be provided by the seller.** Schedule your private showing today and explore the possibilities!

4505 S Union Avenue, Chicago
8325 S Saginaw Avenue, Chicago
$254,900
6 Beds ⋅ 3 Baths ⋅ 12710823 MLS ⋅ ACTIVE Status
Value-add opportunity in the South Chicago neighborhood. This fully occupied legal two-unit building is ideal for investors, rehabbers, or owner-occupants looking to build equity. The first-floor unit features 3 bedrooms and 1 bath, while the second-floor unit offers 2 bedrooms and 1 bath. Situated on an oversized 37-foot-wide Chicago lot with a side driveway and detached 2-car garage, the property offers additional outdoor space and convenient off-street parking. Sold AS-IS. Conveniently located near the future Illinois Quantum & Microelectronics Park, with easy access to transportation, shopping, and neighborhood amenities.

8325 S Saginaw Avenue, Chicago
7828 S Greenwood Avenue, Chicago
$254,000
5 Beds ⋅ 2 Baths ⋅ 12689065 MLS ⋅ ACTIVE Status
Welcome home to this beautifully renovated gem located on a peaceful, quiet block! Every inch of this home has been thoughtfully updated, allowing you to move in with confidence and enjoy modern living from day one. Step inside to discover stylish luxury vinyl flooring throughout, fresh paint, abundant natural light, and a bright, open feel. Both levels feature completely remodeled kitchens with new cabinetry, modern countertops, updated sinks, faucets, and plumbing-perfect for multi-generational living, entertaining, or potential related living. The bathrooms have been beautifully redesigned with new tubs, toilets, vanities, elegant tile work, painted and contemporary finishes that create a spa-like atmosphere.

7828 S Greenwood Avenue, Chicago
7416 S Luella Avenue, Chicago
$250,000
4 Beds ⋅ 2 Baths ⋅ 12801027 MLS ⋅ NEW Status
Don't miss this opportunity: stately brick 2 flat on premium South Shore block. Nestled on quiet treelined street, this solid building sits on an oversized lot with two car garage. Each unit features spacious, bright living rooms, separate dining rooms, two bedrooms, a tandem room and one bath. Lovingly cared for by family for many years, but in need of some updates. New hot water tank. Welcome!

7416 S Luella Avenue, Chicago
7929 S Harvard Avenue, Chicago
$250,000
6 Beds ⋅ 3 Baths ⋅ 12797897 MLS ⋅ ACTIVE Status
Great opportunity to own this classic brick 2-unit building in the West Chatham neighborhood! Perfect for investors or owner-occupants looking to generate rental income while building equity. Boiler and Water Heater completed replaced in 2020. Each unit features 2 bedrooms and 1 bathroom, spacious living areas, hardwood floors, beautiful original woodwork, and charming architectural details throughout. The property offers generously sized rooms, kitchens with ample cabinet space, and plenty of potential for updates and customization. The basement provides additional space and includes an extra bathroom. Outside, enjoy a fenced backyard, and 2-car detached garage. Whether you're looking to live in one unit while renting the other or expand your investment portfolio, this property offers an excellent opportunity to add value while preserving its original charm. Bring your vision and make this property your own. Schedule your showing today!

7929 S Harvard Avenue, Chicago
414 N Lawler Avenue, Chicago
$250,000
5 Beds ⋅ 2 Baths ⋅ 12797627 MLS ⋅ ACTIVE Status
Bring Your Vision to This Spacious Two-Flat! An opportunity for investors and rehabbers ready to take on their next renovation project. Roof and siding (2023), Windows on 2nd floor (2023). This frame two-unit property features generous living rooms, separate dining rooms, and eat-in kitchens, plus a full unfinished basement and detached two-car garage. Explore the layout, envision the possibilities, and see how you can transform this property. Updates and repairs are needed throughout. Schedule your showing today! Cash or rehab financing only. Sold AS IS; AS IS rider required. Seller will not provide a survey or termite inspection.

414 N Lawler Avenue, Chicago
8329 S Burnham Avenue, Chicago
$250,000
6 Beds ⋅ 2 Baths ⋅ 12796097 MLS ⋅ ACTIVE Status
Explore the potential of this two-flat property featuring six bedrooms and two full bathrooms across two units. The property offers an opportunity for investors looking to expand their portfolio or buyers interested in a multi-unit investment. The lower unit features updates and is vacant, offering a starting point for an owner-occupant or investor. The upper unit is tenant-occupied, and access to assess its current condition has not yet been obtained. The property also features a full basement and additional potential for buyers looking to add value. Conveniently located in Chicago's South Shore area, this property presents an opportunity for buyers prepared to evaluate the existing condition, occupancy, and renovation needs. Due diligence is encouraged. Schedule your showing today!

8329 S Burnham Avenue, Chicago
8012 S Rhodes Avenue, Chicago
$250,000
4 Beds ⋅ 2 Baths ⋅ 12790393 MLS ⋅ ACTIVE Status
Brick Chatham 2 Flat on a real nice block! This building has lots to offer. Each unit is 2 Bed, 1 Bath with Dining Rooms and Enclosed Back Porches giving expansion options. Separate heat systems for each floor. 2 car garage and unfinished basement with 2 doors and utilities off to the side. This building is good as a rental property or for an owner occupant. Priced to build equity! Make your appointment for a private viewing to see if this is the building you have been waiting for!

8012 S Rhodes Avenue, Chicago
4425 W Carroll Avenue, Chicago
$250,000
6 Beds ⋅ 2 Baths ⋅ 12780558 MLS ⋅ ACTIVE Status
***Incredible Value-Add Opportunity in West Garfield Park!*** This spacious, owner-occupied home offers approximately 1,200 sq ft per floor, and is conveniently located just 3 blocks from the Green Line. The turnkey upper level features a functional layout with 4 bedrooms, 1 full bathroom, and fresh paint in 6 rooms. Enjoy the newly-updated luxury bathroom featuring a Jacuzzi tub (2026), along with major improvements, including new radiator piping, a newer roof approximately 4-years old, and a beautifully-constructed deck and patio completed in 2024. The finished lower level offers 2 additional bedrooms, a 2nd full bathroom, a dedicated laundry room, and extra storage space. The lower-level bathroom and some walls need minor cosmetic finishing, providing an excellent opportunity to personalize the space and add value. A premium Swann security system with 5 motion-sensor cameras is also included. Enjoy outdoor living on the deck and patio, along with convenient access to public transportation. Whether you are an owner-occupant, a value-add buyer, or an investor looking to maximize rental potential, this property offers plenty of possibilities. Buyers may explore conventional financing or FHA 203(k) rehabilitation financing, subject to lender approval and property eligibility. Property is being sold strictly "as-is." Please review the property details before scheduling a showing and note that the lower level requires minor cosmetic finishes. Come see the potential this property has to offer!

4425 W Carroll Avenue, Chicago
4053 W 16Th Street, Chicago
$250,000
4 Beds ⋅ 3 Baths ⋅ 12756411 MLS ⋅ ACTIVE Status
Sold as is, home needs work.

4053 W 16Th Street, Chicago
6451 S Vernon Avenue, Chicago
$250,000
4 Beds ⋅ 2 Baths ⋅ 12646322 MLS ⋅ ACTIVE Status
Beautifully-maintained 2-story brick building located in a rapidly-developing area of Chicago, conveniently situated near I-94 and just west of the future Obama Presidential Center. This well-kept investment property features two spacious 2-bedroom units, each offering generous living and dining areas with functional layouts. Both kitchens are in good condition and include newer stoves and refrigerators replaced within the past year. The property also offers rear patios and a detached 2-car garage. The building is currently occupied by long-term tenants who have resided in the property for over 4 years, consistently pay rent on time, and take pride in maintaining their units. A solid investment opportunity in an area experiencing continued growth and redevelopment.

6451 S Vernon Avenue, Chicago
3332 W Congress Parkway, Chicago
$249,900
4 Beds ⋅ 2 Baths ⋅ 12801938 MLS ⋅ NEW Status
**VACANT CHICAGO GREYSTONE | POTENTIAL THREE-UNIT CONVERSION | VALUE-ADD OPPORTUNITY NEAR MAJOR WEST SIDE REDEVELOPMENT | ESTIMATED RENOVATED 3-UNIT ARV $590K-$699K.** Delivered completely vacant, this 1903 limestone-front Classical Revival greystone in East Garfield Park, on a 25x125 RM-5 lot, is a true value-add canvas: two existing units (each 2 bed/1 bath; 9 rooms, 4 beds total), a full unfinished basement, original stone facade, and 2 exterior parking spaces. **The property requires a complete gut renovation, including extensive interior demolition and rehabilitation, and is best suited for experienced investors and contractors prepared to undertake a major restoration project.** The building is being sold as-is, and the property cleanout has been completed. Interior photos are available for buyers to review the property's current condition. **THE THIRD-UNIT PLAY:** Chicago's Additional Dwelling Unit ordinance, citywide since April 1, 2026, allows one conversion unit in eligible 1-4 unit buildings at least 20 years old in RM districts, with no added parking required and an exemption from minimum lot area per unit. Owner-occupancy and block-face limits may apply in the City's West ADU zone, and Department of Housing pre-certification, permits, and building-code compliance (including basement ceiling height and egress) are required. A third unit is not currently permitted or guaranteed; buyers should verify eligibility with the City and their architect. **WHY THE UPSIDE MATTERS:** Within one mile in the last six months, fully renovated vintage 3-flats closed at $589,000-$635,000 (3169 W Monroe, $635K), a fully remodeled 3-flat closed at $699,000, and renovated 2-flats with finished lower-level duplexes closed at $590,000-$610,000. Based on those closed sales, we estimate a fully renovated legal 3-unit after-repair value of approximately $590,000-$699,000, or roughly $500,000-$610,000 as a renovated 2-flat with a finished lower level. These are estimates only, not an appraisal or guarantee, and depend on renovation scope, condition, permits, and City approvals. **LOCATION:** East Garfield Park, steps from the Kedzie-Homan Blue Line and the I-290 Eisenhower, about 1.3 miles to the Illinois Medical District, and roughly 1.9 miles from the United Center on the Near West Side, where the $7 billion, 55-acre 1901 Project broke ground in June 2026 and received a full building permit for its 6,000-capacity Music Hall in November 2026 (Phase 1 targeted for 2028). Close to Garfield Park and the Conservatory, with fast access to downtown. **STRATEGIES:** Full renovation and resale, a long-term hold with potential three-unit income, or owner-occupancy with rental income, subject to financing and legal-use requirements. Cash or renovation financing recommended. Vacant and easy to show: schedule a private showing through ShowingTime. The property has been fully cleaned out, and interior photos are now available to showcase its existing condition and renovation potential.

3332 W Congress Parkway, Chicago
5246 W Congress Parkway, Chicago
$249,900
5 Beds ⋅ 2 Baths ⋅ 12789808 MLS ⋅ RE-ACTIVATED Status
Distinctive architectural character and versatile living spaces highlight this classic Chicago two-unit property, offering an excellent opportunity for homeowners and investors alike. Featuring 5 bedrooms and 2 full bathrooms across both units, the building showcases spacious living rooms with large bay windows, hardwood flooring, original wood trim, and separate dining areas that reflect its timeless charm. Each unit offers a functional kitchen with cabinetry and room for future improvements. The generous layouts provide flexibility for comfortable living or rental opportunities, while the full unfinished basement offers additional storage space. A detached two-car garage adds everyday convenience. With its striking stone facade and traditional details, this property presents plenty of potential for personalized updates. Conveniently located near neighborhood parks, shopping, dining, public transportation, and major roadways with easy access throughout Chicago's West Side and surrounding communities.

5246 W Congress Parkway, Chicago
4930 W Washington Boulevard, Chicago
$249,000
6 Beds ⋅ 3 Baths ⋅ 12776435 MLS ⋅ PRICE CHANGE Status
LARGE BRICK 3 FLAT WITH ADDITIONAL SIDE DOOR ENTRANCE GARDEN-BASEMENT UNIT. PROPERTY BEING SOLD AS IS CONDITION, NO SURVEYS NOR DISCLOSURES. BUYER TO TAKE OVER BUILDING CODE VIOLATIONS (ROOM COUNTS / SIZES ARE ESTIMATES). THERE IS A FULL BASEMENT WITH HIGH CEILINGS. DONT MISS THIS ONE.

4930 W Washington Boulevard, Chicago
6820 S Prairie Avenue, Chicago
$249,000
5 Beds ⋅ 2 Baths ⋅ 12764521 MLS ⋅ ACTIVE Status
Attention Investors! This fully occupied 2-flat features a 2-bedroom, 1-bath on the first floor unit and a 3-bedroom, 1-bath second floor unit. The property also offers a full basement with washer and dryer, a spacious fenced backyard, and additional rear space for parking. With tenants already in place, this property presents an opportunity for investors seeking an income-producing 2-unit property. Property is being sold AS-IS and is priced to sell!

6820 S Prairie Avenue, Chicago
8152 S Escanaba Avenue, Chicago
$245,000
6 Beds ⋅ 2 Baths ⋅ 12796227 MLS ⋅ NEW Status
Investor Opportunity - Short Sale | Two-Unit Building Attention savvy investors and buyers with construction experience! This two-unit property at 8152 S. Escanaba presents an excellent opportunity to add value and unlock its full potential. Each unit offers 3 bedrooms and 1 bathroom, providing a solid foundation for an investment portfolio or future income-producing property. The property requires some renovations, including work on the second-floor rear sun porch making this an ideal opportunity for an investor ready to bring their vision and expertise to the table. Enjoy the added convenience of rear parking and a desirable location just steps from Chicago's beautiful Lake Michigan shoreline. Whether you're looking to renovate, reposition, or expand your investment portfolio, this property offers tremendous potential in a sought-after location. Property is being sold as a short sale. Sale is subject to lender approval. Property is being sold as-is. Bring your vision and explore the possibilities

8152 S Escanaba Avenue, Chicago
4942 S Racine Avenue, Chicago
$245,000
4 Beds ⋅ 2 Baths ⋅ 12781220 MLS ⋅ ACTIVE Status
Motivated Seller! 2 flat features large apartments, 4 bedrooms, 2 bathrooms including a full, unfinished basement with 4 parking spaces. Perfect for an owner occupied buyer, or investor looking for cash flow. For an owner occupied buyer this building would be cheaper than paying rent since the income covers a portion of the mortgage and expenses.

4942 S Racine Avenue, Chicago
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