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

4,698 homes + 198 early access

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$185,000

3 beds1 bath1,597 sq ft

3133 Stafford Dr, Markham, IL 60428

3,750 sq ft lot • 2 garage spots • Built 1956

$313,000

4 beds2.5 baths1,388 sq ft

11056 S State Line Rd, Chicago, IL 60617

New carpeting • New flooring • Newer windows

$479,000

7 beds5 baths— sq ft

9655 S Commercial Ave, Chicago, IL 60617

Owner suite unit • Wrought iron gate • 4 unit building

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Roseland Mixed Use Property. Turnkey opportunity with a fully renovated restaurant (2022) and a flexible open space on the Second Floor. Parking for 4 Vehicles in the back of the Property. Since 1969, the property has been a Steakhouse with a loyal clientele. Some of the renovations include new flooring, tables, and chairs, a full kitchen, a waitress station, lighting, an ice maker, a water heater, and a point-of-sale system, just to name a few. The second level is currently set up for banquet use, but could easily be converted to residential use.

$374,900

— beds— baths— sq ft

11147 S Michigan Ave, Chicago, IL 60628

Flexible open space • 3,125 sq ft lot • Built 1909

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
BACK ON THE MARKET - A Second Opportunity at 10901 S Michigan! Sometimes an opportunity deserves another look. 10901 S Michigan is back on the market, giving buyers another chance to consider a property offering flexibility, visibility, and multiple possibilities along the Michigan Avenue corridor. The price was improved shortly before the property went under contract, and now that it has returned to the market, that improved price remains-creating a renewed opportunity for buyers who may have missed their chance the first time. If this property was previously on your radar, now is the time to take another look. Two Units. Former Storefront. Multiple Possibilities. Currently presenting as

$100,000

— beds— baths2,808 sq ft

10901 S Michigan Ave, Chicago, IL 60628

3,402 sq ft lot • Built 1906

Property at 10429 S Indiana Ave, Chicago, IL 60628, 5 beds, 3 baths

$310,000

5 beds3 baths1,921 sq ft

10429 S Indiana Ave, Chicago, IL 60628

Property at 9800 S 51st Ave, Oak Lawn, IL 60453, 3 beds, 2 baths

$334,000

3 beds2 baths1,146 sq ft

9800 S 51st Ave, Oak Lawn, IL 60453

Property at 8700 Melvina Ave, Oak Lawn, IL 60453, 4 beds, 2 baths

$334,900

4 beds2 baths1,390 sq ft

8700 Melvina Ave, Oak Lawn, IL 60453

Property at 8609 W 121st St, Palos Park, IL 60464, 4 beds, 3 baths

$850,000

4 beds3 baths3,245 sq ft

8609 W 121st St, Palos Park, IL 60464

Property at 8039 S Marquette Ave, Chicago, IL 60617, 7 beds, 3 baths

$375,000

7 beds3 baths— sq ft

8039 S Marquette Ave, Chicago, IL 60617

Property at 8153 S Stewart Ave, Chicago, IL 60620, 3 beds, 3 baths

$149,900

3 beds3 baths1,200 sq ft

8153 S Stewart Ave, Chicago, IL 60620

Property at 3142 W Cermak Rd, Chicago, IL 60623

$995,000

— beds— baths7,496 sq ft

3142 W Cermak Rd, Chicago, IL 60623

Property at 401 S Cicero Ave, Chicago, IL 60644

$219,000

— beds— baths2,900 sq ft

401 S Cicero Ave, Chicago, IL 60644

Property at 2720 W Harrison St, Chicago, IL 60612, 5 beds, 3 baths

$499,900

5 beds3 baths1,934 sq ft

2720 W Harrison St, Chicago, IL 60612

Property at 1418 N Waller Ave, Chicago, IL 60651, 2 beds, 2 baths

$305,000

2 beds2 baths794 sq ft

1418 N Waller Ave, Chicago, IL 60651

Property at 1937 S 3rd Ave, Maywood, IL 60153, 4 beds, 2 baths

$365,995

4 beds2 baths1,224 sq ft

1937 S 3rd Ave, Maywood, IL 60153

Property at 114 Geneva Ave, Bellwood, IL 60104, 4 beds, 1 bath

$269,900

4 beds1 bath— sq ft

114 Geneva Ave, Bellwood, IL 60104

Property at 5820 Park Ave, Berkeley, IL 60163, 3 beds, 1.5 baths

$365,000

3 beds1.5 baths1,247 sq ft

5820 Park Ave, Berkeley, IL 60163

Property at 5544 W Belmont Ave, Chicago, IL 60641

$895,000

— beds— baths7,136 sq ft

5544 W Belmont Ave, Chicago, IL 60641

Property at 4054 N Western Ave, Chicago, IL 60618

$1,250,000

— beds— baths4,225 sq ft

4054 N Western Ave, Chicago, IL 60618

Property at 4827 N Harding Ave, Chicago, IL 60625, 5 beds, 2.5 baths

$768,000

5 beds2.5 baths3,472 sq ft

4827 N Harding Ave, Chicago, IL 60625

Property at 62 Woodley Rd, Winnetka, IL 60093, 6 beds, 5 baths

$2,569,900

6 beds5 baths7,000 sq ft

62 Woodley Rd, Winnetka, IL 60093

Property at 1201 Middlebury Ln, Wilmette, IL 60091, 5 beds, 3.5 baths

$899,000

5 beds3.5 baths2,369 sq ft

1201 Middlebury Ln, Wilmette, IL 60091

Property at 3843 Springdale Ave, Glenview, IL 60025, 3 beds, 2 baths

$615,000

3 beds2 baths2,323 sq ft

3843 Springdale Ave, Glenview, IL 60025

Property at 8000 S Hermitage Ave, Chicago, IL 60620, 5 beds, 2 baths

$1,050,000

5 beds2 baths— sq ft

8000 S Hermitage Ave, Chicago, IL 60620

Property at 7727 S Carpenter St, Chicago, IL 60620, 18 beds, 11 baths

$799,900

18 beds11 baths— sq ft

7727 S Carpenter St, Chicago, IL 60620

Property at 7200 S Vincennes Ave, Chicago, IL 60621, 36 beds, 24 baths

$349,999

36 beds24 baths— sq ft

7200 S Vincennes Ave, Chicago, IL 60621

Property at 1327 E 52nd St #302, Chicago, IL 60615, 3 beds, 2 baths

$335,000

3 beds2 baths1,600 sq ft

1327 E 52nd St #302, Chicago, IL 60615

Property at 4923 S Greenwood Ave, Chicago, IL 60615, 8 beds, 4.5 baths

$2,475,000

8 beds4.5 baths5,000 sq ft

4923 S Greenwood Ave, Chicago, IL 60615

Property at 3265 S Archer Ave, Chicago, IL 60608

$1,550,000

— beds— baths8,150 sq ft

3265 S Archer Ave, Chicago, IL 60608

Property at 1407 N Hoyne Ave, Chicago, IL 60622, 5 beds, 5.5 baths

$4,695,000

5 beds5.5 baths8,250 sq ft

1407 N Hoyne Ave, Chicago, IL 60622

Property at 32 E Bellevue Pl, Chicago, IL 60611, 6 beds, 5.5 baths

$4,500,000

6 beds5.5 baths6,000 sq ft

32 E Bellevue Pl, Chicago, IL 60611

Property at 3510 W 63rd St, Chicago, IL 60629

$450,000

— beds— baths— sq ft

3510 W 63rd St, Chicago, IL 60629

Property at 1417 S 48th Ct, Cicero, IL 60804, 5 beds, 3 baths

$405,000

5 beds3 baths— sq ft

1417 S 48th Ct, Cicero, IL 60804

Property at 6404 S Peoria St, Chicago, IL 60621, 7 beds, 2 baths

$339,900

7 beds2 baths— sq ft

6404 S Peoria St, Chicago, IL 60621

Property at 1908 E 79th St, Chicago, IL 60649

$575,000

— beds— baths— sq ft

1908 E 79th St, Chicago, IL 60649

Property at 5335 N California Ave #304, Chicago, IL 60625, 2 beds, 1 bath

$185,000

2 beds1 bath875 sq ft

5335 N California Ave #304, Chicago, IL 60625

Property at 7351 N Ridge Blvd Unit 1A, Chicago, IL 60645, 2 beds, 1 bath

$225,000

2 beds1 bath1,200 sq ft

7351 N Ridge Blvd Unit 1A, Chicago, IL 60645

Property at 600-606 S Pulaski Rd, Chicago, IL 60624

$199,500

— beds— baths6,000 sq ft

600-606 S Pulaski Rd, Chicago, IL 60624

Property at 15633 Lexington Ave, Harvey, IL 60426, 37 baths

$499,999

— beds37 baths6,948 sq ft

15633 Lexington Ave, Harvey, IL 60426

Property at 1120 N Lake Shore Dr Unit 18AB, Chicago, IL 60611, 4 beds, 3 baths

$895,000

4 beds3 baths3,500 sq ft

1120 N Lake Shore Dr Unit 18AB, Chicago, IL 60611

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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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