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

4,702 homes + 196 early access

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome to Washington Heights! This stylishly updated 3-bed, 2-bath ranch is totally move-in ready. Step inside and you'll love the new hardwood floors, sleek floating vanities, and chic porcelain tile bathrooms. The kitchen pops with stainless steel appliances-perfect for cooking and entertaining. The fully finished basement doubles your living space with laundry hook-ups plus a flex room that works great as a media room, gym, or family hangout. Outside, enjoy a spacious backyard ready for summer BBQs, gardening, or just relaxing. All the updates are done-you just need to bring your vibe and make it home.

$223,000

3 beds2 baths1,295 sq ft

1024 W 103rd St, Chicago, IL 60643

Laundry hook-ups • Hardwood floors • Floating vanities

EARLY ACCESSCOMPASS COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Listen up. This isn't just another multifamily property. This is 7,100+ square feet of pure cash-flowing potential sitting on one of Chicago's most iconic boulevards. Built in 1898, this 9-bed, 6-bath beauty is a piece of Bronzeville history-and your ticket to serious ROI. Bronzeville crown jewel. We're talking historic architecture, proximity to downtown, and a neighborhood that's been on the rise for years. The smart money has already moved in. Are you next? Income-Producing Machine - 9 bedrooms, 6 bathrooms, multiple units. This property is designed to print money. Whether you're looking to rent, renovate, or reposition, the numbers work.

$650,000

9 beds6 baths7,095 sq ft

4507 S Michigan Ave, Chicago, IL 60653

Built 1898

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Nestled on a wide, tree-lined street, the property spans three Chicago lots and offers a perfect blend of size and privacy. The expansive great room is truly impressive. When family and friends come together for game nights or holiday celebrations, the warm wood-burning fireplace creates a welcoming atmosphere, perfect for entertaining and hosting guests. In the spacious, expanded kitchen, there is ample opportunity for everyone to participate in meal planning and preparation. The formal living room and dining room offer a warm feeling of being HOME. Relax and reenergize in the primary ensuite that features a private bathroom and shower. Comfortable bedrooms, ample storage spaces in the unf

$650,000

5 beds3 baths2,020 sq ft

3044 N Octavia Ave, Chicago, IL 60707

Three chicago lots • Unfinished basement • Primary ensuite

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Not a foreclosure, pre foreclosure, short sale or auction! This is a traditional sale with a engaged and available seller! Three levels of potential living space. Hookups for three kitchens and baths. Perfect for in-law arrangement or large family. Structurally sound with a new tear off roof. Carport and privacy fence. EZ 2 show.

$147,500

5 beds2 baths— sq ft

1424 W 72nd St, Chicago, IL 60636

Three levels • Carport • In-law arrangement

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Exciting opportunity! This frame 1 Story offers 2 bedrooms, 1 full bath, a 2-car detached garage and a basement that can be finished for added living space! This property is waiting for the right owner to unlock its full potential and turn it into a stunning home. Conveniently located near shopping, restaurants and transportation, this home is ideal for a first-time buyer ready to transform it into a fabulous living space or an investor looking to add to their rental portfolio.

$115,000

2 beds1 bath1,064 sq ft

7 N State St, Glenwood, IL 60425

2 garage spots • Built 1916 • Listed 59 days

Property at 8407 S Wolcott Ave, Chicago, IL 60620, 4 beds, 2.5 baths

$390,000

4 beds2.5 baths5,000 sq ft

8407 S Wolcott Ave, Chicago, IL 60620

Property at 2506 N Clybourn Ave, Chicago, IL 60614

$1,475,000

— beds— baths5,500 sq ft

2506 N Clybourn Ave, Chicago, IL 60614

Property at 4300 Amelia Ave, Lyons, IL 60534, 6 beds, 4 baths

$499,900

6 beds4 baths— sq ft

4300 Amelia Ave, Lyons, IL 60534

Property at 5233 S Hermitage Ave, Chicago, IL 60609, 5 beds, 3 baths

$259,000

5 beds3 baths— sq ft

5233 S Hermitage Ave, Chicago, IL 60609

Property at 2922 E 78th Pl, Chicago, IL 60649, 2 beds, 1 bath

$87,500

2 beds1 bath740 sq ft

2922 E 78th Pl, Chicago, IL 60649

Property at 15439 Elm St, South Holland, IL 60473, 4 beds, 2 baths

$158,000

4 beds2 baths1,275 sq ft

15439 Elm St, South Holland, IL 60473

Property at 2037 N Tripp Ave, Chicago, IL 60639, 4 beds, 3 baths

$449,900

4 beds3 baths— sq ft

2037 N Tripp Ave, Chicago, IL 60639

Property at 440 N Hamlin Ave, Chicago, IL 60624, 6 beds, 4.5 baths

$599,000

6 beds4.5 baths— sq ft

440 N Hamlin Ave, Chicago, IL 60624

Property at 5402 W 23rd St, Cicero, IL 60804, 10 beds, 5 baths

$599,900

10 beds5 baths— sq ft

5402 W 23rd St, Cicero, IL 60804

Property at 1133 Parkview Ave, Chicago Heights, IL 60411, 4 beds, 1.5 baths

$163,000

4 beds1.5 baths1,463 sq ft

1133 Parkview Ave, Chicago Heights, IL 60411

Property at 10708 S Avenue E, Chicago, IL 60617, 5 beds, 2 baths

$330,000

5 beds2 baths3,300 sq ft

10708 S Avenue E, Chicago, IL 60617

Property at 461 Clyde Ave, Calumet City, IL 60409, 4 beds, 2 baths

$192,000

4 beds2 baths974 sq ft

461 Clyde Ave, Calumet City, IL 60409

Property at 7149 S Wood St, Chicago, IL 60636, 4 beds, 2 baths

$165,000

4 beds2 baths— sq ft

7149 S Wood St, Chicago, IL 60636

Property at 3950 N Lake Shore Dr Unit 317C, Chicago, IL 60613, 2 beds, 1 bath

$229,999

2 beds1 bath— sq ft

3950 N Lake Shore Dr Unit 317C, Chicago, IL 60613

Property at 17658 Lincoln Ave, Homewood, IL 60430, 3 beds, 2 baths

$251,000

3 beds2 baths2,001 sq ft

17658 Lincoln Ave, Homewood, IL 60430

Property at 4857 W Roscoe St #1, Chicago, IL 60641, 1 bed, 1 bath

$169,000

1 bed1 bath— sq ft

4857 W Roscoe St #1, Chicago, IL 60641

Property at 6337 Roosevelt Rd #107, Berwyn, IL 60402, 1 bed, 1 bath

$129,999

1 bed1 bath733 sq ft

6337 Roosevelt Rd #107, Berwyn, IL 60402

Property at 8 W Monroe St #1403, Chicago, IL 60603, 2 beds, 2 baths

$310,000

2 beds2 baths958 sq ft

8 W Monroe St #1403, Chicago, IL 60603

Property at 3726 N Christiana Ave, Chicago, IL 60618, 6 beds, 11 baths

$1,275,000

6 beds11 baths5,314 sq ft

3726 N Christiana Ave, Chicago, IL 60618

Property at 14424 S Lowe Ave, Riverdale, IL 60827, 2 beds, 1 bath

$105,000

2 beds1 bath891 sq ft

14424 S Lowe Ave, Riverdale, IL 60827

Property at 821-23 N Fairfield Ave, Chicago, IL 60622, 11 beds, 6 baths

$1,090,000

11 beds6 baths3,891 sq ft

821-23 N Fairfield Ave, Chicago, IL 60622

Property at 11443 S Longwood Dr, Chicago, IL 60643, 3 beds, 2 baths

$344,700

3 beds2 baths1,250 sq ft

11443 S Longwood Dr, Chicago, IL 60643

Property at 1109 W Fulton Market St, Chicago, IL 60607

$5,200,000

— beds— baths— sq ft

1109 W Fulton Market St, Chicago, IL 60607

Property at 6938 S Peoria St, Chicago, IL 60621, 6 beds, 2 baths

$300,000

6 beds2 baths— sq ft

6938 S Peoria St, Chicago, IL 60621

Property at 2058 Downey Rd, Homewood, IL 60430, 4 beds, 2 baths

$248,000

4 beds2 baths1,305 sq ft

2058 Downey Rd, Homewood, IL 60430

Property at 8453 S Aberdeen St, Chicago, IL 60620, 4 beds, 2 baths

$275,000

4 beds2 baths1,200 sq ft

8453 S Aberdeen St, Chicago, IL 60620

Property at 2120 W Belmont Ave, Chicago, IL 60618, 5 beds, 4 baths

$2,850,000

5 beds4 baths6,528 sq ft

2120 W Belmont Ave, Chicago, IL 60618

Property at 7706 S Saint Lawrence Ave, Chicago, IL 60619, 4 beds, 2.5 baths

$225,000

4 beds2.5 baths— sq ft

7706 S Saint Lawrence Ave, Chicago, IL 60619

Property at 1585 Ridge Ave #705, Evanston, IL 60201, 2 beds, 1 bath

$210,000

2 beds1 bath1,000 sq ft

1585 Ridge Ave #705, Evanston, IL 60201

Property at 1305 S 51st Ave, Cicero, IL 60804, 4 beds, 2 baths

$300,000

4 beds2 baths— sq ft

1305 S 51st Ave, Cicero, IL 60804

Property at 4934-36 W Jackson Blvd, Chicago, IL 60644, 19 beds, 7 baths

$975,000

19 beds7 baths11,040 sq ft

4934-36 W Jackson Blvd, Chicago, IL 60644

Property at 6706 16th St, Berwyn, IL 60402

$265,000

— beds— baths— sq ft

6706 16th St, Berwyn, IL 60402

Property at 1321 W 18th St, Chicago, IL 60608

$950,000

— beds— baths6,111 sq ft

1321 W 18th St, Chicago, IL 60608

Property at 1822 S 55th Ave, Cicero, IL 60804, 2 beds, 1 bath

$300,000

2 beds1 bath838 sq ft

1822 S 55th Ave, Cicero, IL 60804

Property at 728 W Jackson Blvd #724, Chicago, IL 60661, 1 bed, 1 bath

$340,000

1 bed1 bath850 sq ft

728 W Jackson Blvd #724, Chicago, IL 60661

Property at 4988 N Elston Ave, Chicago, IL 60630, 9 beds, 5 baths

$1,185,000

9 beds5 baths— sq ft

4988 N Elston Ave, Chicago, IL 60630

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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 4898 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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