Vintage homes for sale & real estate in Chicago, IL

3,015 homes

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ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Beautifully rehabbed home featuring updated finishes and modern touches throughout. Enjoy a refreshed kitchen, upgraded bathrooms, new flooring, and fresh paint. This property combines style and comfort-perfect for today's buyer!

$429,900

4 beds3 baths1,754 sq ft

458 W 127th St, Chicago, IL 60628

7,627 sq ft lot • 2 garage spots • Built 1959

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Full brick JUMBO 7-unit building with great curb appeal in the Westridge/East Rogers Park neighborhood within steps to the WORLD district of Devon Ave. at Western Ave. /Oakley Ave. Large units throughout in immaculate condition with individual furnaces, water tanks, central AC, and in unit washers and dryers. Consisting of: A. 5-units, each is 3-bedrooms, 2-baths, B. 1-unit, is 5-bedrooms, 3-baths, and C. The 7th unit is 2-bedrooms, 2-baths, all with master bedrooms, fireplaces, and balcony. 4-Car garage and 3-parking spaces. Walking distance to public transportation on Devon Ave. Western Ave. bus stop. , Western Ave. , and Pratt Ave. , Park and Library, retailers, shops, restaurants, daily

$1,599,000

79 beds57 baths8,400 sq ft

6337 N Oakley Ave, Chicago, IL 60659

Central ac • Individual furnaces • Master bedrooms

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Discover this beautiful property that has been recently renovated. With a brick exterior, it features a detached garage for two cars, a total of five bedrooms, and two full bathrooms. Additionally, it boasts a fully finished basement that includes a laundry area. The property also has a lovely front garden and a well-maintained, beautiful backyard.

$364,900

5 beds2 baths1,300 sq ft

Brick exterior • Laundry area • Front garden

NEW 27 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Reabbers and Investors, lowest priced 2 flat in the area!!! Separate heating already in place, dry basement. Property is being sold AS_IS. Seller will not supply survey.

$59,900

5 beds2 baths— sq ft

11576 S State St, Chicago, IL 60628

Separate heating • Dry basement • 5,000 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Great opportunity to own this investment property . Beautiful Renovated from top to bottom brick 3- unit property . This property sits on an oversize Chicago lot. Features 2 spacious units with large living room/dining combo, 3 bedrooms , modern full bath, Gorgeous eat-in kitchen with white cabinets and quartz countertops. Hardwood flooring. The garden apartment has a living room, 2 bedrooms and 1 bath. Coin laundry washer and dryer. New three boiler furnaces. New tank less hot water heater . SEPARATE UTILITIES. All units included appliances . New electrical, lighting, drywall, and plumbing. Large size backyard. Detached 2 car garage with carport for 3rd vehicle.

$575,000

8 beds3 baths— sq ft

1329 N Latrobe Ave, Chicago, IL 60651

Oversize chicago lot • Modern full bath • White cabinets

Property at 750 E 69th Pl, Chicago, IL 60637, 4 beds, 2 baths

$255,000

4 beds2 baths— sq ft

750 E 69th Pl, Chicago, IL 60637

Property at 6221 S Wolcott Ave, Chicago, IL 60636, 4 beds, 2 baths

$187,000

4 beds2 baths— sq ft

6221 S Wolcott Ave, Chicago, IL 60636

Property at 3332 W 108th St, Chicago, IL 60655, 3 beds, 2 baths

$325,000

3 beds2 baths1,210 sq ft

3332 W 108th St, Chicago, IL 60655

Property at 12018 S Loomis St, Chicago, IL 60643, 3 beds, 3 baths

$230,000

3 beds3 baths2,599 sq ft

12018 S Loomis St, Chicago, IL 60643

Property at 2948 N Narragansett Ave, Chicago, IL 60634, 10 beds, 3 baths

$500,000

10 beds3 baths— sq ft

2948 N Narragansett Ave, Chicago, IL 60634

Property at 1350 N Astor St Unit 4C, Chicago, IL 60610, 1 bed, 1 bath

$315,000

1 bed1 bath956 sq ft

1350 N Astor St Unit 4C, Chicago, IL 60610

Property at 1953 W Roscoe St, Chicago, IL 60657

$1,799,000

— beds— baths6,336 sq ft

1953 W Roscoe St, Chicago, IL 60657

Property at 10812 S Vincennes Ave, Chicago, IL 60643, 3 beds, 3 baths

$330,900

3 beds3 baths1,300 sq ft

10812 S Vincennes Ave, Chicago, IL 60643

Property at 4322 N Monticello Ave, Chicago, IL 60618, 5 beds, 3 baths

$575,000

5 beds3 baths— sq ft

4322 N Monticello Ave, Chicago, IL 60618

Property at 6441 S Campbell Ave, Chicago, IL 60629, 5 beds, 2 baths

$389,000

5 beds2 baths1,415 sq ft

6441 S Campbell Ave, Chicago, IL 60629

Property at Sign in for address, Chicago, IL 60603, 2 beds, 2 baths

$330,000

2 beds2 baths1,100 sq ft

Property at 12432 S State St, Chicago, IL 60628, 4 beds, 2 baths

$282,500

4 beds2 baths1,634 sq ft

12432 S State St, Chicago, IL 60628

Property at 7006 S Woodlawn Ave, Chicago, IL 60637, 3 beds, 1 bath

$135,000

3 beds1 bath1,013 sq ft

7006 S Woodlawn Ave, Chicago, IL 60637

Property at Sign in for address, Chicago, IL 60647, 6 beds, 2 baths

$600,000

6 beds2 baths— sq ft

Property at 7344 S Langley Ave, Chicago, IL 60619, 5 beds, 2 baths

$147,000

5 beds2 baths2,000 sq ft

7344 S Langley Ave, Chicago, IL 60619

Property at 8005 S Blackstone Ave, Chicago, IL 60619, 4 beds, 2 baths

$295,000

4 beds2 baths— sq ft

8005 S Blackstone Ave, Chicago, IL 60619

Property at 4447 S Leamington Ave, Chicago, IL 60638, 4 beds, 3 baths

$399,000

4 beds3 baths3,780 sq ft

4447 S Leamington Ave, Chicago, IL 60638

Property at 4256 W Kamerling Ave, Chicago, IL 60651, 8 beds, 3 baths

$510,000

8 beds3 baths— sq ft

4256 W Kamerling Ave, Chicago, IL 60651

Property at 1755 E 55th St #1201, Chicago, IL 60615, 3 beds, 3 baths

$289,500

3 beds3 baths1,800 sq ft

1755 E 55th St #1201, Chicago, IL 60615

Property at 8228 S Clyde Ave, Chicago, IL 60617, 3 beds, 2.5 baths

$295,000

3 beds2.5 baths1,200 sq ft

8228 S Clyde Ave, Chicago, IL 60617

Property at 850 N Kildare Ave, Chicago, IL 60651, 6 beds, 3 baths

$409,900

6 beds3 baths— sq ft

850 N Kildare Ave, Chicago, IL 60651

Property at 11127 S Wallace St, Chicago, IL 60628, 6 beds, 3 baths

$374,900

6 beds3 baths2,500 sq ft

11127 S Wallace St, Chicago, IL 60628

Property at 5317 N Kenmore Ave Unit 2A, Chicago, IL 60640, 2 beds, 1 bath

$300,000

2 beds1 bath— sq ft

5317 N Kenmore Ave Unit 2A, Chicago, IL 60640

Property at 4813 W West End Ave, Chicago, IL 60644, 6 beds, 3 baths

$575,000

6 beds3 baths— sq ft

4813 W West End Ave, Chicago, IL 60644

Property at 8100 S Houston Ave, Chicago, IL 60617, 5 beds, 3 baths

$310,000

5 beds3 baths2,597 sq ft

8100 S Houston Ave, Chicago, IL 60617

Property at 9017 S Exchange Ave, Chicago, IL 60617, 12 beds, 6 baths

$575,000

12 beds6 baths— sq ft

9017 S Exchange Ave, Chicago, IL 60617

Property at 6525 S Fairfield Ave, Chicago, IL 60629, 4 beds, 2.5 baths

$215,000

4 beds2.5 baths2,400 sq ft

6525 S Fairfield Ave, Chicago, IL 60629

Property at 2225 W Carmen Ave, Chicago, IL 60625, 5 beds, 3.5 baths

$1,775,000

5 beds3.5 baths— sq ft

2225 W Carmen Ave, Chicago, IL 60625

Property at 9250 S Ada St, Chicago, IL 60620, 6 beds, 3 baths

$249,900

6 beds3 baths1,318 sq ft

9250 S Ada St, Chicago, IL 60620

Property at Sign in for address, Chicago, IL 60633, 4 beds, 2 baths

$250,000

4 beds2 baths— sq ft

Property at 1323 S 51 Ct, Cicero, IL 60804, 4 beds, 2 baths

$394,999

4 beds2 baths— sq ft

1323 S 51 Ct, Cicero, IL 60804

Property at 3826 N Whipple St, Chicago, IL 60618, 5 beds, 3 baths

$700,000

5 beds3 baths— sq ft

3826 N Whipple St, Chicago, IL 60618

Property at 6123 S Meade Ave, Chicago, IL 60638, 2 beds, 1.5 baths

$379,900

2 beds1.5 baths1,285 sq ft

6123 S Meade Ave, Chicago, IL 60638

Property at 10230 S Yates Blvd, Chicago, IL 60617, 9 beds, 4 baths

$191,900

9 beds4 baths— sq ft

10230 S Yates Blvd, Chicago, IL 60617

Property at 5117 S Luna Ave, Chicago, IL 60638, 3 beds, 2 baths

$299,900

3 beds2 baths859 sq ft

5117 S Luna Ave, Chicago, IL 60638

Property at 529 N Wood St, Chicago, IL 60622, 3 beds, 2 baths

$599,000

3 beds2 baths— sq ft

529 N Wood St, Chicago, IL 60622

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Based on information submitted to the MLS GRID as of Fri Dec 05 2025. 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 Chicago

There are currently 3015 vintage homes for sale in Chicago at a median listing price of $350K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chicago stay on the market for 62 days and receive 3 offers. Popular neighborhoods include Lincoln Park, Lake View, Beverly, Logan Square, and West Loop. This map is refreshed with the newest listings in Chicago every 15 minutes.

In the past month, 1534 homes have been sold in Chicago. In addition to houses in Chicago, there were also 3737 condos, 268 townhouses, and 1482 multi-family units for sale in Chicago last month. Chicago is a fairly walkable city in Cook County with a Walk Score of 77. Chicago is home to approximately 2,691,070 people and 1,261,210 jobs. Find your dream home in Chicago 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 Chicago are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chicago. Our Chicago real estate stats and trends will give you more information about home buying and selling trends in Chicago. If you're looking to sell your home in the Chicago area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chicago with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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