Vintage homes for sale & real estate in Cook County, IL

4,698 homes + 198 early access

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Mixed-use opportunity for businesses, multi-family dwellings, and condominium or retail stores. It is located in a high-traffic area corner of Dempster and Waukegan. Retail shops and restaurants in the area are minutes from the highway. The building needs work or tear down. The property has 5 lots and is adjacent to a vacant lot that is also for sale.

$749,900

— beds— baths— sq ft

6950 Dempster St, Morton Grove, IL 60053

High-traffic area • 0.3 acre lot • Built 1948

$299,900

6 beds3 baths1,762 sq ft

4503 W Congress Pkwy, Chicago, IL 60624

Built 1893 • Listed 246 days

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Beautiful home to call your own; it has passed all village inspections! Fully renovated property with a full finished basement for all your laundry and storage needs. Property has been updated: new furnace, new roof, all new windows, kitchen, appliances, electrical upgrades, cabinetry, flooring, bath, front porch, drywall, paint, and refinished hardwood floors. 2 car garage with opener provides plenty of room for cars, bikes, and/or a workshop. Sizeable backyard that will be perfect for summer entertaining and bar-b-ques. Nothing to do but move in. Potential to add a third bedroom and another bathroom in the basement.

$164,000

2 beds1 bath1,234 sq ft

12532 S Throop St, Calumet Park, IL 60827

Updated appliances • Finished basement • Updated kitchen

$500,000

4 beds3 baths— sq ft

2948 N Narragansett Ave, Chicago, IL 60634

Fully updated • Newer kitchens • Outdoor deck space

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Clean stair free ranch. Home features bright open living room with vaulted ceiling and ceramic tile in the kitchen and living room. 2 car detached garage, central air, fenced yard and a nice long driveway for you and your guests. Freshly painted, newer roof, some newer windows, this is ready to be your home. Home has already passed the very stringent Cal City inspection process so is move in condition upon closing. Taxes do not currently include a homeowner's exemption so will be reduced upon a sale to an owner occupier. NOT in a flood zone as other houses south of this one are. Own cheaper than you can rent and start building equity today!

$110,000

3 beds1 bath999 sq ft

1469 Stanley Blvd, Calumet City, IL 60409

Fenced yard • Vaulted ceiling • Ceramic tile

Property at 18504 Wentworth Ave, Lansing, IL 60438, 4 beds, 1.5 baths

$245,000

4 beds1.5 baths1,660 sq ft

18504 Wentworth Ave, Lansing, IL 60438

Property at 1008 W 115th St, Chicago, IL 60643, 3 beds, 1.5 baths

$130,000

3 beds1.5 baths1,002 sq ft

1008 W 115th St, Chicago, IL 60643

Property at 11727 S Normal Ave, Chicago, IL 60628, 5 beds, 1 bath

$90,000

5 beds1 bath— sq ft

11727 S Normal Ave, Chicago, IL 60628

Property at 13719 S Spaulding Ave, Robbins, IL 60472, 4 beds, 2 baths

$50,000

4 beds2 baths1,370 sq ft

13719 S Spaulding Ave, Robbins, IL 60472

Property at 5802 S May St, Chicago, IL 60621, 5 beds, 2 baths

$10,000

5 beds2 baths— sq ft

5802 S May St, Chicago, IL 60621

Property at 2913 W 63rd St, Chicago, IL 60629

$259,900

— beds— baths— sq ft

2913 W 63rd St, Chicago, IL 60629

Property at 32 Woodley Rd, Winnetka, IL 60093, 5 beds, 5.5 baths

$4,950,000

5 beds5.5 baths9,908 sq ft

32 Woodley Rd, Winnetka, IL 60093

Property at 97 Harlem Ave, Oak Park, IL 60302

$449,000

— beds— baths— sq ft

97 Harlem Ave, Oak Park, IL 60302

Property at 5742 S Marshfield Ave, Chicago, IL 60636, 4 beds, 2 baths

$130,000

4 beds2 baths1,584 sq ft

5742 S Marshfield Ave, Chicago, IL 60636

Property at 1749 W North Shore Ave, Chicago, IL 60626, 10 beds, 3 baths

$760,000

10 beds3 baths— sq ft

1749 W North Shore Ave, Chicago, IL 60626

Property at 8225 S Manistee Ave, Chicago, IL 60617, 3 beds, 2.5 baths

$239,900

3 beds2.5 baths— sq ft

8225 S Manistee Ave, Chicago, IL 60617

Property at 1308 E 56th St #2, Chicago, IL 60637, 1 bed, 1 bath

$225,000

1 bed1 bath900 sq ft

1308 E 56th St #2, Chicago, IL 60637

Property at 880 N Lake Shore Dr Unit 16DH, Chicago, IL 60611, 2 beds, 2 baths

$475,000

2 beds2 baths1,545 sq ft

880 N Lake Shore Dr Unit 16DH, Chicago, IL 60611

Property at 246 Arrowhead St, Park Forest, IL 60466, 4 beds, 1 bath

$49,900

4 beds1 bath1,023 sq ft

246 Arrowhead St, Park Forest, IL 60466

Property at 3814 W Sherwin Ave, Lincolnwood, IL 60712, 3 beds, 2 baths

$549,000

3 beds2 baths1,372 sq ft

3814 W Sherwin Ave, Lincolnwood, IL 60712

Property at 1004 N California Ave, Chicago, IL 60622

$725,000

— beds— baths5,000 sq ft

1004 N California Ave, Chicago, IL 60622

Property at 201 S Ashland Ave, Chicago, IL 60607

$9,995,000

— beds— baths41,128 sq ft

201 S Ashland Ave, Chicago, IL 60607

Property at 11548 S State St, Chicago, IL 60628, 5 beds, 2 baths

$159,900

5 beds2 baths1,672 sq ft

11548 S State St, Chicago, IL 60628

Property at 1330 Webford Ave, Des Plaines, IL 60016

$399,900

— beds— baths4,268 sq ft

1330 Webford Ave, Des Plaines, IL 60016

Property at 3233 S Morgan St, Chicago, IL 60608, 4 beds, 4 baths

$499,500

4 beds4 baths— sq ft

3233 S Morgan St, Chicago, IL 60608

Property at 1319 Otto Blvd, Chicago Heights, IL 60411, 4 beds, 2 baths

$230,000

4 beds2 baths1,440 sq ft

1319 Otto Blvd, Chicago Heights, IL 60411

Property at 16705 Wolf Rd, Orland Park, IL 60467, 4 beds, 2 baths

$799,000

4 beds2 baths2,600 sq ft

16705 Wolf Rd, Orland Park, IL 60467

Property at 2916 W 25th Pl, Chicago, IL 60623, 8 beds, 5 baths

$489,000

8 beds5 baths— sq ft

2916 W 25th Pl, Chicago, IL 60623

Property at 17318 Walter St, Lansing, IL 60438, 4 beds, 2 baths

$200,000

4 beds2 baths1,890 sq ft

17318 Walter St, Lansing, IL 60438

Property at 72 W 19th St, Chicago Heights, IL 60411, 5 beds, 2 baths

$109,999

5 beds2 baths— sq ft

72 W 19th St, Chicago Heights, IL 60411

Property at Sign in for address, Chicago, IL 60660, 2 beds, 1 bath

$129,900

2 beds1 bath900 sq ft

Property at 2541 S Springfield Ave, Chicago, IL 60623, 6 beds, 4 baths

$395,000

6 beds4 baths— sq ft

2541 S Springfield Ave, Chicago, IL 60623

Property at 3222 N Drake Ave, Chicago, IL 60618, 4 beds, 1 bath

$865,000

4 beds1 bath— sq ft

3222 N Drake Ave, Chicago, IL 60618

Property at 4014 W 21st St, Chicago, IL 60623, 5 beds, 2 baths

$300,000

5 beds2 baths— sq ft

4014 W 21st St, Chicago, IL 60623

Property at 601 E 32nd St #400, Chicago, IL 60616, 2 beds, 2 baths

$131,900

2 beds2 baths1,500 sq ft

601 E 32nd St #400, Chicago, IL 60616

Property at 3522 W Armitage Ave, Chicago, IL 60647, 2 beds, 1.5 baths

$620,000

2 beds1.5 baths— sq ft

3522 W Armitage Ave, Chicago, IL 60647

Property at 10734 S Prairie Ave, Chicago, IL 60628, 5 beds, 2 baths

$200,000

5 beds2 baths— sq ft

10734 S Prairie Ave, Chicago, IL 60628

Property at 5330 S Union Ave, Chicago, IL 60609, 4 beds, 2 baths

$65,000

4 beds2 baths1,852 sq ft

5330 S Union Ave, Chicago, IL 60609

Property at 7042 S Laflin St, Chicago, IL 60636, 2 beds, 1 bath

$45,000

2 beds1 bath1,200 sq ft

7042 S Laflin St, Chicago, IL 60636

Property at 2567 S Emerald Ave, Chicago, IL 60616, 8 beds, 5 baths

$800,000

8 beds5 baths— sq ft

2567 S Emerald Ave, Chicago, IL 60616

Property at 1953 W Roscoe St, Chicago, IL 60657

$1,749,000

— beds— baths6,336 sq ft

1953 W Roscoe St, Chicago, IL 60657

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Based on information submitted to the MLS GRID as of Sun Aug 30 2026. 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 Cook County

There are currently 4896 vintage homes for sale in Cook County at a median listing price of $360K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Cook County stay on the market for 49 days and receive 3 offers. This map is refreshed with the newest listings in Cook County every 15 minutes.

In the past month, 5258 homes have been sold in Cook County. In addition to houses in Cook County, there were also 7081 condos, 1441 townhouses, and 2013 multi-family units for sale in Cook County last month. Find your dream home in Cook County 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 Cook County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Cook County. If you're looking to sell your home in the Cook County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Cook County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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