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

4,700 homes + 197 early access

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
BRIGHTON PARK - FOR SALE: 7-unit multifamily property featuring a great unit mix consisting of two (3BD/1BA) units, two (2BD/1BA) units, two (1BD/1BA) units, and one studio unit. The property generates strong rental income and currently grossing $96,420 in annually. All units are equipped with individual furnaces and individual water heaters. Located in the excellent rental market of the Brighton Park neighborhood, this is a solid investment opportunity with stable income potential.

$859,000

13 beds7 baths— sq ft

4035 S Richmond St, Chicago, IL 60632

Individual furnaces • Multifamily property • Strong rental income

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Listing price $177,000 Great opportunity on this bungalow style home with detached 2 car garage. It offers approximately 1,866 square feet of living space with 4 bedrooms and 2 bathrooms. Basement. Built in 1908 repairs and updates are needed but has potential. Property sold "AS-IS" without contingencies, repairs, warranties, guarantees or representation as to listing accuracy, property information, photo or other depiction included or described herein. Inspect prior bidding!!! Auction.

$177,000

4 beds2 baths1,866 sq ft

7516 S Lafayette Ave, Chicago, IL 60620

Basement • Bungalow style home • 5,270 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Beautifully maintained Greystone multi-unit property offering 7 bedrooms, 3 bathrooms, and 2 kitchens. This spacious building features a 2-car garage and a roof that was replaced just 2 years ago. A great opportunity for investors or owner-occupants seeking a well-cared-for property with plenty of space and timeless character.

$480,000

7 beds3 baths— sq ft

2114 S Trumbull Ave, Chicago, IL 60623

2 kitchens • Roof replaced • 2,904 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
A solid opportunity for homeowners, investors, or anyone looking to add their personal touch. This property great bones and plenty of potential, requiring primarily cosmetic updates to bring it to its full value.

$175,000

3 beds2 baths1,168 sq ft

10812 S Vernon Ave, Chicago, IL 60628

3,600 sq ft lot • 2 garage spots • Built 1949

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Investor-friendly 2-flat duplex offering a fantastic opportunity to build wealth and generate income from day one! This property features solid bones and is ready for your vision with minor cosmetic updates. Whether you're an experienced investor looking to expand your portfolio or a buyer seeking a value-add opportunity, this property offers tremendous potential. Bring your ideas, add your personal touch, and start collecting rental income immediately. Conveniently located near schools, shopping, public transportation, and major expressways. Opportunities like this don't come around often. Schedule your showing today because this property won't last long! * * Package deal * * 11317 S E

$179,900

5 beds2 baths— sq ft

6715 S Bishop St, Chicago, IL 60636

Near schools • Solid bones • Conveniently located

Property at 4212 Joliet Ave, Lyons, IL 60534, 3 beds, 2 baths

$520,000

3 beds2 baths3,235 sq ft

4212 Joliet Ave, Lyons, IL 60534

Property at 7646 S Merrill Ave, Chicago, IL 60649, 5 beds, 2.5 baths

$249,900

5 beds2.5 baths1,394 sq ft

7646 S Merrill Ave, Chicago, IL 60649

Property at Sign in for address, Chicago, IL 60621, 30 beds, 12 baths

$730,000

30 beds12 baths— sq ft

Property at 4839 S Vincennes Ave #1, Chicago, IL 60615, 4 beds, 3 baths

$420,000

4 beds3 baths2,500 sq ft

4839 S Vincennes Ave #1, Chicago, IL 60615

Property at 4026 W Monroe St, Chicago, IL 60624, 6 beds, 2 baths

$320,000

6 beds2 baths— sq ft

4026 W Monroe St, Chicago, IL 60624

Property at 738 E 155th St, Phoenix, IL 60426, 4 beds, 2.5 baths

$389,900

4 beds2.5 baths2,200 sq ft

738 E 155th St, Phoenix, IL 60426

Property at 6700 S Crandon Ave Unit 6A, Chicago, IL 60649, 4 beds, 2.5 baths

$220,000

4 beds2.5 baths2,100 sq ft

6700 S Crandon Ave Unit 6A, Chicago, IL 60649

Property at 5123 S Avers Ave, Chicago, IL 60632, 2 beds, 1 bath

$319,900

2 beds1 bath1,140 sq ft

5123 S Avers Ave, Chicago, IL 60632

Property at 2705 N Monitor Ave, Chicago, IL 60639, 5 beds, 3 baths

$520,000

5 beds3 baths— sq ft

2705 N Monitor Ave, Chicago, IL 60639

Property at 500 Engle St, Dolton, IL 60419, 2 beds, 1 bath

$129,900

2 beds1 bath700 sq ft

500 Engle St, Dolton, IL 60419

Property at 9815 S Clyde Ave, Chicago, IL 60617, 2 beds, 1 bath

$105,000

2 beds1 bath956 sq ft

9815 S Clyde Ave, Chicago, IL 60617

Property at 850 N Lake Shore Dr #406, Chicago, IL 60611, 2 beds, 2 baths

$1,037,000

2 beds2 baths1,701 sq ft

850 N Lake Shore Dr #406, Chicago, IL 60611

Property at 17719 Burnham Ave, Lansing, IL 60438, 3 beds, 1.5 baths

$195,000

3 beds1.5 baths1,100 sq ft

17719 Burnham Ave, Lansing, IL 60438

Property at 3535 W Flournoy St, Chicago, IL 60624, 12 beds, 3 baths

$450,000

12 beds3 baths— sq ft

3535 W Flournoy St, Chicago, IL 60624

Property at 15409 Dobson Ave, Dolton, IL 60419, 3 beds, 2 baths

$130,000

3 beds2 baths1,142 sq ft

15409 Dobson Ave, Dolton, IL 60419

Property at 2759 W 38th St, Chicago, IL 60632, 6 beds, 3 baths

$425,000

6 beds3 baths— sq ft

2759 W 38th St, Chicago, IL 60632

Property at 8324 Grand Ave, River Grove, IL 60171

$3,200,000

— beds— baths16,000 sq ft

8324 Grand Ave, River Grove, IL 60171

Property at 10201 S Princeton Ave, Chicago, IL 60628, 2 beds, 1 bath

$125,000

2 beds1 bath1,020 sq ft

10201 S Princeton Ave, Chicago, IL 60628

Property at 906 W 71st St, Chicago, IL 60621, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths954 sq ft

906 W 71st St, Chicago, IL 60621

Property at 4546 W Jackson Blvd, Chicago, IL 60624, 5 beds, 2.5 baths

$415,000

5 beds2.5 baths— sq ft

4546 W Jackson Blvd, Chicago, IL 60624

Property at 1013 W 63rd St, Chicago, IL 60621

$289,000

— beds— baths— sq ft

1013 W 63rd St, Chicago, IL 60621

Property at 407 Watseka St, Park Forest, IL 60466, 4 beds, 2 baths

$219,900

4 beds2 baths— sq ft

407 Watseka St, Park Forest, IL 60466

Property at 3900 W Jackson Blvd, Chicago, IL 60624, 15 beds, 6 baths

$550,000

15 beds6 baths— sq ft

3900 W Jackson Blvd, Chicago, IL 60624

Property at 6424 S Eberhart Ave, Chicago, IL 60637, 9 beds, 2 baths

$365,000

9 beds2 baths— sq ft

6424 S Eberhart Ave, Chicago, IL 60637

Property at 1755 E 55th St #605, Chicago, IL 60615, 1 bed, 1 bath

$109,900

1 bed1 bath850 sq ft

1755 E 55th St #605, Chicago, IL 60615

Property at 1509 N Avers Ave, Chicago, IL 60651, 17 beds, 6 baths

$1,129,000

17 beds6 baths— sq ft

1509 N Avers Ave, Chicago, IL 60651

Property at 2606 W Walter Zimny Dr, Posen, IL 60469, 3 beds, 2 baths

$299,000

3 beds2 baths1,650 sq ft

2606 W Walter Zimny Dr, Posen, IL 60469

Property at 6442 S Ingleside Ave, Chicago, IL 60637, 4 beds, 3.5 baths

$424,900

4 beds3.5 baths2,646 sq ft

6442 S Ingleside Ave, Chicago, IL 60637

Property at 360 Streamside Dr, Harvey, IL 60426, 3 beds, 2 baths

$208,000

3 beds2 baths1,493 sq ft

360 Streamside Dr, Harvey, IL 60426

Property at 10841 S Vernon Ave, Chicago, IL 60628, 4 beds, 2 baths

$199,500

4 beds2 baths1,000 sq ft

10841 S Vernon Ave, Chicago, IL 60628

Property at 7356 S Kenwood Ave, Chicago, IL 60619, 3 beds, 2.5 baths

$289,900

3 beds2.5 baths1,540 sq ft

7356 S Kenwood Ave, Chicago, IL 60619

Property at 1436 S Kenneth Ave, Chicago, IL 60623, 6 beds, 3 baths

$330,000

6 beds3 baths— sq ft

1436 S Kenneth Ave, Chicago, IL 60623

Property at 3056 E 87th St, Chicago, IL 60617, 10 beds, 3 baths

$460,000

10 beds3 baths— sq ft

3056 E 87th St, Chicago, IL 60617

Property at 2833 W Polk St, Chicago, IL 60612, 9 beds, 3 baths

$740,000

9 beds3 baths— sq ft

2833 W Polk St, Chicago, IL 60612

Property at 7924 S Peoria St, Chicago, IL 60620, 7 beds, 3 baths

$485,000

7 beds3 baths— sq ft

7924 S Peoria St, Chicago, IL 60620

Property at 265 W 107th St, Chicago, IL 60628, 4 beds, 1.5 baths

$159,000

4 beds1.5 baths1,050 sq ft

265 W 107th St, Chicago, IL 60628

Viewing page 95 of 120

Based on information submitted to the MLS GRID as of Sat Aug 29 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 4897 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, 5257 homes have been sold in Cook County. In addition to houses in Cook County, there were also 7070 condos, 1442 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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* Data from the last year

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