Vintage homes for sale & real estate in Southwest Side, IL

452 homes

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ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Come to the New Englewood, This Greystone is in move in condition with a two and three bedroom unit with hardwood floors. .This can be a cash cow. Cash or Hard money Loan. Showing Saturdays. 12-2 and Sundays 12-2 Highest and Best Due by 12/15

$215,000

5 beds2 baths— sq ft

6018 S Sangamon Ave, Chicago, IL 60621

2 parking spots • Built 1910 • Listed 42 days

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
* * SELLER IS HIGHLY MOTIVATED * * This spacious 4 bedroom, 2 1/2 bath hidden gem is nestled on an extremely quiet block. The house is priced to sell, and offers incredible potential. Whether you're and investor looking for your next project, or a buyer ready to bring a bit of "TLC" to the home, come take a look and make it your own. It has great "bones, " which includes a 4 year old roof, and a beautiful large staircase. The home offers a large full basement and finished open attic with endless possibilities including "frame out" work for an additional bathroom. Schedule your showing today. SOLD AS IS! 203K Loans Welcomes!

$115,000

4 beds2.5 baths2,464 sq ft

6738 S Normal Blvd, Chicago, IL 60621

Finished open attic • 4 year old roof • Large full basement

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Fully Rehabbed 4-Unit - Freshly renovated 4-unit building ready for a new owner. All major systems done in 2025: roof, plumbing, electrical, furnaces, and water heaters. Each unit has 2 beds/1 bath, stainless steel appliances, laundry hookup, and separate utilities. Asking $539,900. Showings by appointment only. Serious inquiries must have pre-approval or proof of funds. Set to be 100% complete November 1st

$539,900

8 beds4 baths— sq ft

4332 S Hermitage Ave, Chicago, IL 60609

Fully rehabbed • Separate utilities • Major systems done

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
Newly renovated 4-bedroom, 2-bath home featuring an open-concept kitchen and living room with skylight. Kitchen offers new cabinets, marble countertops, and brand-new appliances. Finished basement with in-law suite. Double lot provides plenty of outdoor space and a large driveway for ample parking. Move-in ready!

$310,000

4 beds2 baths1,300 sq ft

7011 S Aberdeen St, Chicago, IL 60621

In-law suite • Large driveway • Open-concept kitchen

ABOUT THIS HOME
Vintage Home for sale in Southwest Side, IL:
* * * Update * * * Seller is providing a Platinum warranty plan through American Home Shield Warranty for one year with the sale of this property. Sellers are long time owners, residing in the home for over 25 years with no major issues! Christmas has come early this year! This beautifully maintained 2-bedroom, 2-bathroom home has been lovingly and meticulously cared for by the same owners for over 25 years and is now ready for its next chapter. From the moment you step inside, you'll appreciate the inviting layout and the pride of ownership that shines throughout. The main level offers a spacious living room and dining room, perfect for gatherings or everyday living. The kitchen is co

$280,000

2 beds2 baths855 sq ft

3920 W Marquette Rd, Chicago, IL 60629

Generous open layout • Plenty of storage • Laundry area

Property at 3641 W 57th St, Chicago, IL 60629, 6 beds, 3 baths

$409,900

6 beds3 baths— sq ft

3641 W 57th St, Chicago, IL 60629

Property at 5330 S California Ave, Chicago, IL 60632, 2 beds, 2 baths

$245,000

2 beds2 baths900 sq ft

5330 S California Ave, Chicago, IL 60632

Property at 420 W 65th Pl, Chicago, IL 60621, 4 beds, 2 baths

$199,999

4 beds2 baths— sq ft

420 W 65th Pl, Chicago, IL 60621

Property at 7318 S Aberdeen St, Chicago, IL 60621, 5 beds, 2.5 baths

$255,000

5 beds2.5 baths1,250 sq ft

7318 S Aberdeen St, Chicago, IL 60621

Property at 6155 S Whipple Ave, Chicago, IL 60629, 8 beds, 6 baths

$320,000

8 beds6 baths— sq ft

6155 S Whipple Ave, Chicago, IL 60629

Property at 2951 W 43rd St, Chicago, IL 60632

$160,000

— beds— baths2,277 sq ft

2951 W 43rd St, Chicago, IL 60632

Property at 4944 S Honore St, Chicago, IL 60609, 7 beds, 3 baths

$380,000

7 beds3 baths— sq ft

4944 S Honore St, Chicago, IL 60609

Property at 5042 S Laflin St, Chicago, IL 60609, 4 beds, 2 baths

$165,000

4 beds2 baths— sq ft

5042 S Laflin St, Chicago, IL 60609

Property at 5814 S Massasoit Ave, Chicago, IL 60638, 3 beds, 1.5 baths

$359,000

3 beds1.5 baths1,017 sq ft

5814 S Massasoit Ave, Chicago, IL 60638

Property at 5806 S Talman Ave, Chicago, IL 60629, 5 beds, 2 baths

$154,900

5 beds2 baths— sq ft

5806 S Talman Ave, Chicago, IL 60629

Property at 6830 S Honore St, Chicago, IL 60636, 4 beds, 2 baths

$239,999

4 beds2 baths1,378 sq ft

6830 S Honore St, Chicago, IL 60636

Property at 5237 S Long Ave, Chicago, IL 60638, 6 beds, 2.5 baths

$419,000

6 beds2.5 baths— sq ft

5237 S Long Ave, Chicago, IL 60638

Property at 6843 S Carpenter St, Chicago, IL 60621, 7 beds, 3 baths

$299,999

7 beds3 baths3,123 sq ft

6843 S Carpenter St, Chicago, IL 60621

Property at 7408 S Campbell Ave, Chicago, IL 60629, 4 beds, 1 bath

$240,000

4 beds1 bath1,152 sq ft

7408 S Campbell Ave, Chicago, IL 60629

Property at 7219 S Peoria St, Chicago, IL 60621, 6 beds, 3 baths

$360,000

6 beds3 baths2,000 sq ft

7219 S Peoria St, Chicago, IL 60621

Property at 7205 S Hamlin Ave, Chicago, IL 60629, 5 beds, 2 baths

$359,900

5 beds2 baths1,080 sq ft

7205 S Hamlin Ave, Chicago, IL 60629

Property at 5712 W 56th St, Chicago, IL 60638, 5 beds, 3 baths

$399,000

5 beds3 baths1,878 sq ft

5712 W 56th St, Chicago, IL 60638

Property at 5152 S Lawler St, Chicago, IL 60638, 4 beds, 2 baths

$399,000

4 beds2 baths1,300 sq ft

5152 S Lawler St, Chicago, IL 60638

Property at 2050 W 52nd St, Chicago, IL 60609, 2 beds, 1 bath

$199,900

2 beds1 bath1,344 sq ft

2050 W 52nd St, Chicago, IL 60609

Property at 6424 S Washtenaw Ave, Chicago, IL 60629, 3 beds, 1 bath

$259,000

3 beds1 bath1,188 sq ft

6424 S Washtenaw Ave, Chicago, IL 60629

Property at 6522 S Marshfield Ave, Chicago, IL 60636, 4 beds, 2 baths

$270,000

4 beds2 baths1,471 sq ft

6522 S Marshfield Ave, Chicago, IL 60636

Property at 5604 S Morgan St, Chicago, IL 60621, 5 beds, 2 baths

$149,900

5 beds2 baths1,489 sq ft

5604 S Morgan St, Chicago, IL 60621

Property at 3604 W 65th Pl, Chicago, IL 60629, 6 beds, 2 baths

$324,900

6 beds2 baths1,315 sq ft

3604 W 65th Pl, Chicago, IL 60629

Property at 4446 S Wood St, Chicago, IL 60609, 9 beds, 3 baths

$379,900

9 beds3 baths— sq ft

4446 S Wood St, Chicago, IL 60609

Property at 7144 S May St, Chicago, IL 60621, 3 beds, 1 bath

$57,500

3 beds1 bath880 sq ft

7144 S May St, Chicago, IL 60621

Property at 1809 W 71st St, Chicago, IL 60636, 4 beds, 1 bath

$104,900

4 beds1 bath1,780 sq ft

1809 W 71st St, Chicago, IL 60636

Property at 5749 S Kenneth Ave, Chicago, IL 60629, 4 beds, 2 baths

$425,000

4 beds2 baths2,100 sq ft

5749 S Kenneth Ave, Chicago, IL 60629

Property at 3502 W 58th Pl, Chicago, IL 60629, 5 beds, 2 baths

$389,900

5 beds2 baths1,400 sq ft

3502 W 58th Pl, Chicago, IL 60629

Property at 6045 S Peoria St, Chicago, IL 60621, 6 beds, 3 baths

$255,000

6 beds3 baths— sq ft

6045 S Peoria St, Chicago, IL 60621

Property at 6622 S Artesian Ave, Chicago, IL 60629, 3 beds, 1 bath

$365,896

3 beds1 bath1,248 sq ft

6622 S Artesian Ave, Chicago, IL 60629

Property at 712 W Marquette Rd, Chicago, IL 60621, 5 beds, 2 baths

$189,900

5 beds2 baths— sq ft

712 W Marquette Rd, Chicago, IL 60621

Property at 7324 S Oakley Ave, Chicago, IL 60636, 4 beds, 2 baths

$285,000

4 beds2 baths1,750 sq ft

7324 S Oakley Ave, Chicago, IL 60636

Property at 7130 S Richmond St, Chicago, IL 60629, 2 beds, 2 baths

$236,000

2 beds2 baths1,328 sq ft

7130 S Richmond St, Chicago, IL 60629

Property at 3711 W 56th Pl, Chicago, IL 60629, 4 beds, 2 baths

$279,000

4 beds2 baths1,368 sq ft

3711 W 56th Pl, Chicago, IL 60629

Property at 3406 W 74th St, Chicago, IL 60629, 4 beds, 3 baths

$339,900

4 beds3 baths2,080 sq ft

3406 W 74th St, Chicago, IL 60629

Property at 1244 W 74th Pl, Chicago, IL 60636, 4 beds, 1 bath

$110,000

4 beds1 bath— sq ft

1244 W 74th Pl, Chicago, IL 60636

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Based on information submitted to the MLS GRID as of Fri Nov 28 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Southwest Side

There are currently 452 vintage homes for sale in Southwest Side at a median listing price of $285K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Southwest Side stay on the market for 58 days and receive 3 offers. Popular neighborhoods include Beverly, Bronzeville, South Loop, Bridgeport, and Hyde Park. This map is refreshed with the newest listings in Southwest Side every 15 minutes.

In the past month, 195 homes have been sold in Southwest Side. In addition to houses in Southwest Side, there were also 55 condos, 13 townhouses, and 268 multi-family units for sale in Southwest Side last month. Find your dream home in Southwest Side using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Southwest Side are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Southwest Side. If you're looking to sell your home in the Southwest Side area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Southwest Side with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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