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

4,660 homes + 194 early access

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Recommended

$619,900

4 beds2.5 baths2,663 sq ft

5625 N Menard Ave, Chicago, IL 60646

Renovated bungalow • Abundant cabinetry • Dedicated office

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Great investment opportunity on Chicago's West Side! This property offers strong potential for rehab or redevelopment and is ideal for investors or buyers looking to add value. In need of updates and repairs, but with a solid layout and plenty of upside. Bring your ideas and make it your own. Property is being sold as-is.

$179,900

4 beds1 bath924 sq ft

5009 W Chicago Ave, Chicago, IL 60651

2 garage spots • Built 1893 • Listed 6 days

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome to this exceptional Garfield Ridge residence where timeless craftsmanship meets modern luxury. Sitting on the original foundation, this home has been completely reimagined with a brand-new second story and expansive rear addition, offering the space, style, and functionality today's buyers demand. Step inside to discover an open and airy floor plan featuring wide-plank hardwood flooring, designer lighting, custom millwork, and high-end finishes throughout. The gourmet kitchen flows seamlessly into the main living areas, creating the perfect space for entertaining and everyday living. Luxurious bathrooms showcase contemporary fixtures, custom vanities, and striking tile work. The spa

$709,999

5 beds3.5 baths— sq ft

5721 S Newcastle Ave, Chicago, IL 60638

Custom wet bar • Gourmet kitchen • Massive backyard

$979,000

4 beds2.5 baths2,451 sq ft

3-car garage • Remodeled kitchen • Finished basement

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Check out this charming Canaryville 3 bedrooms, 2 full bath, and a finished basement with built-in bar! The main level features a functional floor plan with a spacious eat-in kitchen that flows into an enclosed porch, providing flexible space for a mudroom, home office, or additional storage. Ideally situated in the heart of Canaryville, this home is close to neighborhood parks, restaurants, schools, and public transportation. Enjoy easy access to both the Red and Orange Lines, downtown Chicago, and major expressways while still enjoying the charm and community feel that make Canaryville such a sought-after neighborhood. Welcome Home!

$299,000

3 beds2 baths1,855 sq ft

539 W 44th St, Chicago, IL 60609

Finished basement • Downtown chicago • Enclosed porch

Property at 1916 Ridgeland Ave, Berwyn, IL 60402, 5 beds, 3 baths

$494,500

5 beds3 baths— sq ft

1916 Ridgeland Ave, Berwyn, IL 60402

Property at 609 E 89th St, Chicago, IL 60619, 5 beds, 3.5 baths

$345,000

5 beds3.5 baths2,350 sq ft

609 E 89th St, Chicago, IL 60619

Property at 3810 N Fremont St Unit 2B, Chicago, IL 60613, 2 beds, 2 baths

$750,000

2 beds2 baths1,858 sq ft

3810 N Fremont St Unit 2B, Chicago, IL 60613

Property at 1222 S Karlov Ave, Chicago, IL 60623, 6 beds, 3 baths

$609,000

6 beds3 baths— sq ft

1222 S Karlov Ave, Chicago, IL 60623

Property at 330 W Diversey Pkwy Unit 902-04, Chicago, IL 60657, 5 beds, 4 baths

$849,000

5 beds4 baths2,800 sq ft

330 W Diversey Pkwy Unit 902-04, Chicago, IL 60657

Property at 7959 S Michigan Ave, Chicago, IL 60619, 4 beds, 2.5 baths

$369,900

4 beds2.5 baths1,500 sq ft

7959 S Michigan Ave, Chicago, IL 60619

Property at 14545 Laporte Ave, Midlothian, IL 60445, 4 beds, 2 baths

$379,900

4 beds2 baths2,110 sq ft

14545 Laporte Ave, Midlothian, IL 60445

Property at 1310 N 20th Ave, Melrose Park, IL 60160, 3 beds, 1.5 baths

$319,900

3 beds1.5 baths2,300 sq ft

1310 N 20th Ave, Melrose Park, IL 60160

Property at 801 S 16th Ave, Maywood, IL 60153, 4 beds, 3 baths

$419,999

4 beds3 baths1,800 sq ft

801 S 16th Ave, Maywood, IL 60153

Property at 5105 W School St, Chicago, IL 60641, 5 beds, 3 baths

$624,000

5 beds3 baths— sq ft

5105 W School St, Chicago, IL 60641

Property at 7414 S Chappel Ave, Chicago, IL 60649, 9 beds, 6 baths

$550,000

9 beds6 baths— sq ft

7414 S Chappel Ave, Chicago, IL 60649

Property at 6455 S California Ave, Chicago, IL 60629, 8 beds, 2 baths

$346,900

8 beds2 baths1,600 sq ft

6455 S California Ave, Chicago, IL 60629

Property at 842 N Memorial Dr, Chicago Heights, IL 60411, 4 beds, 2.5 baths

$225,000

4 beds2.5 baths1,500 sq ft

842 N Memorial Dr, Chicago Heights, IL 60411

Property at 1631 S Michigan Ave #506, Chicago, IL 60616, 2 beds, 2 baths

$399,900

2 beds2 baths1,350 sq ft

1631 S Michigan Ave #506, Chicago, IL 60616

Property at 4923 N Mason Ave, Chicago, IL 60630, 4 beds, 3 baths

$579,000

4 beds3 baths— sq ft

4923 N Mason Ave, Chicago, IL 60630

Property at 9615 S Bensley Ave, Chicago, IL 60628, 2 beds, 1 bath

$150,000

2 beds1 bath— sq ft

9615 S Bensley Ave, Chicago, IL 60628

Property at 614 S Loomis St #2, Chicago, IL 60607, 3 beds, 1 bath

$330,000

3 beds1 bath1,000 sq ft

614 S Loomis St #2, Chicago, IL 60607

Property at 6559 S Eberhart Ave, Chicago, IL 60637, 9 beds, 3 baths

$350,000

9 beds3 baths— sq ft

6559 S Eberhart Ave, Chicago, IL 60637

Property at 530 N Lawler Ave, Chicago, IL 60644, 6 beds, 2 baths

$365,000

6 beds2 baths— sq ft

530 N Lawler Ave, Chicago, IL 60644

Property at 16068 Richmond Ave, Markham, IL 60428, 4 beds, 1.5 baths

$209,000

4 beds1.5 baths1,048 sq ft

16068 Richmond Ave, Markham, IL 60428

Property at 1621 S 60th Ct, Cicero, IL 60804, 4 beds, 1 bath

$379,900

4 beds1 bath1,200 sq ft

1621 S 60th Ct, Cicero, IL 60804

Property at 10554 S Avenue L St, Chicago, IL 60617, 3 beds, 2 baths

$165,000

3 beds2 baths1,038 sq ft

10554 S Avenue L St, Chicago, IL 60617

Property at 3002 Miller Ave, South Chicago Heights, IL 60411, 3 beds, 2 baths

$139,900

3 beds2 baths1,408 sq ft

3002 Miller Ave, South Chicago Heights, IL 60411

Property at 4671 185th Pl, Country Club Hills, IL 60478, 4 beds, 2 baths

$230,000

4 beds2 baths1,600 sq ft

4671 185th Pl, Country Club Hills, IL 60478

Property at 1415 N 14th Ave, Melrose Park, IL 60160, 4 beds, 3 baths

$578,000

4 beds3 baths2,016 sq ft

1415 N 14th Ave, Melrose Park, IL 60160

Property at 8340 S Yates Blvd, Chicago, IL 60617, 3 beds, 1.5 baths

$260,000

3 beds1.5 baths1,437 sq ft

8340 S Yates Blvd, Chicago, IL 60617

Property at Sign in for address, Hazel Crest, IL 60429, 3 beds, 1.5 baths

$174,900

3 beds1.5 baths1,485 sq ft

Property at 9952 S Vincennes Ave, Chicago, IL 60643, 2 beds, 1 bath

$115,000

2 beds1 bath1,040 sq ft

9952 S Vincennes Ave, Chicago, IL 60643

Property at 606 S 2nd Ave, Maywood, IL 60153, 3 beds, 2.5 baths

$385,000

3 beds2.5 baths2,000 sq ft

606 S 2nd Ave, Maywood, IL 60153

Property at 4035-37 W Harrison St, Chicago, IL 60624, 12 beds, 5 baths

$499,900

12 beds5 baths— sq ft

4035-37 W Harrison St, Chicago, IL 60624

Property at 10228 S Carpenter St, Chicago, IL 60643, 2 beds, 1 bath

$155,000

2 beds1 bath1,079 sq ft

10228 S Carpenter St, Chicago, IL 60643

Property at 15117 Vine Ave, Harvey, IL 60426, 5 beds, 3 baths

$219,999

5 beds3 baths1,912 sq ft

15117 Vine Ave, Harvey, IL 60426

Property at 7021 S Cregier Ave, Chicago, IL 60649, 3 beds, 1.5 baths

$575,000

3 beds1.5 baths3,000 sq ft

7021 S Cregier Ave, Chicago, IL 60649

Property at 2417 S Troy St, Chicago, IL 60623, 2 beds, 3 baths

$230,000

2 beds3 baths660 sq ft

2417 S Troy St, Chicago, IL 60623

Property at 7526 S Honore St, Chicago, IL 60620, 5 beds, 2 baths

$329,900

5 beds2 baths3,200 sq ft

7526 S Honore St, Chicago, IL 60620

Property at 5357 W Waveland Ave, Chicago, IL 60641, 6 beds, 3 baths

$575,000

6 beds3 baths— sq ft

5357 W Waveland Ave, Chicago, IL 60641

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Based on information submitted to the MLS GRID as of Fri Aug 28 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 4854 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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