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

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
This legal 2-flat with a non-conforming garden unit sits on a generous 37-foot-wide lot with garage parking in one of Chicago's most in-demand Northwest Side neighborhoods. Portage Park delivers everything income-focused buyers look for: easy access to CTA bus and nearby Metra service, walkable proximity to grocery stores and everyday retail, and several neighborhood parks within blocks - the kind of location that keeps rental demand steady and turnover low. The investment case is compelling: strong in-place cash flow with a clear, well-supported path to 7% cap rate. Numbers are available upon request for serious inquiries. Whether you're expanding a multi-family portfolio or acquiring your

$500,000

5 beds3 baths— sq ft

5730 W Windsor Ave, Chicago, IL 60630

Garage parking • Nearby metra service • Neighborhood parks

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Discover this newly renovated duplex-up condo in the heart of Bronzeville. Featuring three spacious bedrooms with a den and thoughtfully designed bathrooms, this home is part of an exclusive four-unit building that showcases contemporary style and attention to detail throughout. Enjoy your own private rooftop retreat with sweeping views-ideal for entertaining guests or relaxing in peace. A private one-car garage adds both convenience and comfort to this exceptional offering. Don't miss the chance to own this stunning, move-in-ready residence.

$545,000

3 beds2 baths2,674 sq ft

3330 S Indiana Ave Unit 2N, Chicago, IL 60616

$250 HOA • Garage • Built 1940

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Beautiful brick Cape Cod home located in desirable Southgate! This well-loved and cared-for home features four bedrooms, two full bathrooms, a full basement, and an attached one-car garage. The main level offers two spacious bedrooms, a full bathroom, dining room, kitchen, and inviting living room. Gorgeous oak-finished stairs lead to the second floor, where you'll find two additional large bedrooms, another full bathroom, and an incredible amount of storage. You'll be impressed by the beautiful woodworking and charming details throughout. The full basement provides endless possibilities and is ready for your finishing touches to create additional living space, a home office, recreation are

$315,000

4 beds2 baths1,147 sq ft

18524 Gladville Ave, Homewood, IL 60430

Full basement • Brick cape cod home • 7,840 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Excellent opportunity in this brick Chicago bungalow ! Main floor features spacious living room, formal dining room, 3 bedrooms, eat in kitchen, full bath and enclosed heated back porch. There is a staircase to the attic from one of the bedrooms. The full basement has a full bath and is ready to be finished for extra living space. Nice size yard and 2 car garage. Conveniently located in the Chicago Lawn / Marquette Park neighborhood near schools, parks, shopping, public transportation, and major expressways. Minutes from Midway Airport and Marquette Park! Sold as is. Property NOT FOR RENT- beware of rental scams!

$220,000

3 beds2 baths1,254 sq ft

6537 S Francisco Ave, Chicago, IL 60629

Staircase to attic • Formal dining room • Eat in kitchen

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome to this well-maintained home offering plenty of space and functional living areas you'll appreciate. With 4 bedrooms, 3 full bathrooms, and a detached 2-car brick garage, this home is ready for its next owner. The main level features a spacious family room, separate dining room, kitchen, a main-level bedroom, and a screened-in porch that's perfect for enjoying your morning coffee or relaxing in the evening. Upstairs, the primary suite offers a large walk-in closet, while the additional bedrooms provide plenty of space for family, guests, or a home office. Finished basement includes an additional room for guests or a home office and a full bathroom. Head outside to a large back deck

$199,900

4 beds3 baths1,331 sq ft

3761 215th St, Matteson, IL 60443

6,098 sq ft lot • 2 garage spots • Built 1953

Property at 8129 S Winchester Ave, Chicago, IL 60620, 3 beds, 2.5 baths

$233,900

3 beds2.5 baths1,156 sq ft

8129 S Winchester Ave, Chicago, IL 60620

Property at 1337 Degener Ave, Elmhurst, IL 60126, 5 beds, 3 baths

$525,000

5 beds3 baths1,692 sq ft

1337 Degener Ave, Elmhurst, IL 60126

Property at 4956 N Winchester Ave #2, Chicago, IL 60640, 1 bed, 1 bath

$301,000

1 bed1 bath— sq ft

4956 N Winchester Ave #2, Chicago, IL 60640

Property at 4936 Greenwood St, Evanston, IL 60077, 14 beds, 6 baths

$1,725,000

14 beds6 baths— sq ft

4936 Greenwood St, Evanston, IL 60077

Property at 3509 W Lexington St, Chicago, IL 60624, 8 beds, 2 baths

$300,000

8 beds2 baths— sq ft

3509 W Lexington St, Chicago, IL 60624

Property at 10518 S Artesian Ave Unit 2S, Chicago, IL 60655, 2 beds, 1 bath

$200,000

2 beds1 bath950 sq ft

10518 S Artesian Ave Unit 2S, Chicago, IL 60655

Property at 4839 Crain St, Skokie, IL 60077, 2 beds, 2.5 baths

$365,000

2 beds2.5 baths1,542 sq ft

4839 Crain St, Skokie, IL 60077

Property at 2505 W 45th St, Chicago, IL 60632, 4 beds, 2.5 baths

$299,900

4 beds2.5 baths760 sq ft

2505 W 45th St, Chicago, IL 60632

Property at 3800 N Lake Shore Dr Unit 3G, Chicago, IL 60613, 2 beds, 2 baths

$560,000

2 beds2 baths— sq ft

3800 N Lake Shore Dr Unit 3G, Chicago, IL 60613

Property at 1330 S Lawndale Ave, Chicago, IL 60623, 11 beds, 6 baths

$424,000

11 beds6 baths— sq ft

1330 S Lawndale Ave, Chicago, IL 60623

Property at 7030 W Wrightwood Ave, Chicago, IL 60707, 5 beds, 4 baths

$590,000

5 beds4 baths— sq ft

7030 W Wrightwood Ave, Chicago, IL 60707

Property at 1517 N Laramie Ave, Chicago, IL 60651, 4 beds, 2 baths

$350,000

4 beds2 baths— sq ft

1517 N Laramie Ave, Chicago, IL 60651

Property at 805 E Palatine Rd, Palatine, IL 60074, 3 beds, 1 bath

$360,000

3 beds1 bath1,650 sq ft

805 E Palatine Rd, Palatine, IL 60074

Property at 753 E 156th Pl, South Holland, IL 60473, 3 beds, 2 baths

$169,900

3 beds2 baths— sq ft

753 E 156th Pl, South Holland, IL 60473

Property at 6031 S Merrimac Ave, Chicago, IL 60638, 4 beds, 3 baths

$370,000

4 beds3 baths1,465 sq ft

6031 S Merrimac Ave, Chicago, IL 60638

Property at 2626 W Wilcox St, Chicago, IL 60612, 4 beds, 2 baths

$499,999

4 beds2 baths1,800 sq ft

2626 W Wilcox St, Chicago, IL 60612

Property at 5915 W Roscoe St, Chicago, IL 60634, 3 beds, 2.5 baths

$510,000

3 beds2.5 baths1,417 sq ft

5915 W Roscoe St, Chicago, IL 60634

Property at 4923 S Komensky Ave, Chicago, IL 60632, 3 beds, 2 baths

$354,900

3 beds2 baths1,300 sq ft

4923 S Komensky Ave, Chicago, IL 60632

Property at 2051 N Kilbourn Ave, Chicago, IL 60639, 7 beds, 3 baths

$549,000

7 beds3 baths— sq ft

2051 N Kilbourn Ave, Chicago, IL 60639

Property at 4052 S Campbell Ave, Chicago, IL 60632, 6 beds, 3 baths

$329,999

6 beds3 baths— sq ft

4052 S Campbell Ave, Chicago, IL 60632

Property at 4553 S Ellis Ave, Chicago, IL 60653, 7 beds, 4.5 baths

$935,000

7 beds4.5 baths3,852 sq ft

4553 S Ellis Ave, Chicago, IL 60653

Property at 6506 S Sacramento Ave, Chicago, IL 60629, 4 beds, 2 baths

$155,100

4 beds2 baths1,325 sq ft

6506 S Sacramento Ave, Chicago, IL 60629

Property at 208 W Washington St #910, Chicago, IL 60606, 2 beds, 2 baths

$325,000

2 beds2 baths1,300 sq ft

208 W Washington St #910, Chicago, IL 60606

Property at 5330 W Melrose St, Chicago, IL 60641, 4 beds, 1.5 baths

$475,000

4 beds1.5 baths1,732 sq ft

5330 W Melrose St, Chicago, IL 60641

Property at 1418 Western Ave, Flossmoor, IL 60422, 6 beds, 7 baths

$925,000

6 beds7 baths7,881 sq ft

1418 Western Ave, Flossmoor, IL 60422

Property at 2040 W Charleston St, Chicago, IL 60647, 8 beds, 4 baths

$1,200,000

8 beds4 baths— sq ft

2040 W Charleston St, Chicago, IL 60647

Property at 1150 W 112th Pl, Chicago, IL 60643, 4 beds, 1 bath

$145,000

4 beds1 bath1,404 sq ft

1150 W 112th Pl, Chicago, IL 60643

Property at 3303 W 38th Pl, Chicago, IL 60632, 5 beds, 3 baths

$344,898

5 beds3 baths— sq ft

3303 W 38th Pl, Chicago, IL 60632

Property at 6647 N Lawndale Ave, Lincolnwood, IL 60712, 3 beds, 2 baths

$640,000

3 beds2 baths1,053 sq ft

6647 N Lawndale Ave, Lincolnwood, IL 60712

Property at 3805 Euclid Ave, Berwyn, IL 60402, 4 beds, 2 baths

$359,000

4 beds2 baths1,516 sq ft

3805 Euclid Ave, Berwyn, IL 60402

Property at 5916 W Byron St, Chicago, IL 60634, 5 beds, 4 baths

$899,900

5 beds4 baths2,900 sq ft

5916 W Byron St, Chicago, IL 60634

Property at 165 N Canal St #809, Chicago, IL 60606, 2 beds, 2 baths

$525,000

2 beds2 baths1,166 sq ft

165 N Canal St #809, Chicago, IL 60606

Property at 17717 Bernadine St, Lansing, IL 60438, 4 beds, 1.5 baths

$224,900

4 beds1.5 baths1,407 sq ft

17717 Bernadine St, Lansing, IL 60438

Property at 12718 S Justine St, Calumet Park, IL 60827, 3 beds, 1 bath

$199,900

3 beds1 bath1,155 sq ft

12718 S Justine St, Calumet Park, IL 60827

Property at 6329 W School St, Chicago, IL 60634, 5 beds, 3 baths

$439,900

5 beds3 baths1,928 sq ft

6329 W School St, Chicago, IL 60634

Property at Undisclosed address, Chicago, IL 60628, 5 beds, 2.5 baths

$159,500

5 beds2.5 baths1,575 sq ft

Undisclosed address, Chicago, IL 60628

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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 4907 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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