Vintage homes for sale & real estate in Chicago, IL

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ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Discover the potential of this classic brick 2-unit building in Chicago's West Garfield Park neighborhood. Each spacious unit features 3 bedrooms and 1 full bath, ideal for rental income or multigenerational living. A finished basement is also currently rented, offering additional income potential and enhancing the property's value. It is conveniently located just minutes from public transit, schools, and shopping. Whether you're a seasoned investor or first-time buyer, this is a great opportunity to build equity and cash flow!

$400,000

6 beds3 baths— sq ft

641 N Spaulding Ave, Chicago, IL 60624

Finished basement • Conveniently located • 3,750 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Don't miss this solid investment opportunity! This all-brick 6-unit building offers strong cash flow and spacious layouts in each unit-featuring 2 bedrooms, separate living and dining rooms, eat-in kitchens, and individual hot water tanks. Recent updates include a new exterior porch. The property is secured with a wrought iron fence. Four units are currently rented month-to-month, and two units are vacant-perfect for owner-occupants or immediate rental income. Schedule your private showing today!

$450,000

12 beds6 baths5,424 sq ft

1455 S Avers Ave, Chicago, IL 60623

Spacious layouts • Eat-in kitchens • New exterior porch

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Classic Greystone 2-Flat! This well-maintained property features a 2-bedroom unit on the first floor and a 3-bedroom unit on the second, both offering spacious living and dining rooms, updated cabinet kitchens, and full baths. The fully finished basement is perfect for related living or additional rental income. Enjoy a fenced yard and a 2-car garage. Prime location near shopping, dining, and parks-schedule your showing today!

$480,000

5 beds3 baths— sq ft

648 N Drake Ave, Chicago, IL 60624

Fenced yard • 3,049 sq ft lot • 2 garage spots

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Check out this brick 2-unit located on a tucked-away, quiet street. Each unit offers 2 bedrooms, 1 full bathroom, a kitchen, and a living room. The property includes a full unfinished basement with a laundry area, a detached 2-car garage, and a fenced backyard. Conveniently close to public transportation, minutes from Jackson Park, and near all the amenities the City of Chicago has to offer. Property is being sold as-is.

$255,000

4 beds2 baths— sq ft

750 E 69th Pl, Chicago, IL 60637

Near jackson park • Brick 2-unit • Fenced backyard

$220,000

3 beds1.5 baths— sq ft

10807 S Wentworth Ave, Chicago, IL 60628

Remodeled apartment • Quartz countertops • New cabinets

Property at 6440 S Kildare Ave, Chicago, IL 60629, 5 beds, 2 baths

$320,000

5 beds2 baths853 sq ft

6440 S Kildare Ave, Chicago, IL 60629

Property at 5700 N Maplewood Ave Unit G, Chicago, IL 60659, 2 beds, 1 bath

$189,900

2 beds1 bath— sq ft

5700 N Maplewood Ave Unit G, Chicago, IL 60659

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 7944 S Trumbull Ave, Chicago, IL 60652, 6 beds, 2 baths

$280,000

6 beds2 baths1,251 sq ft

7944 S Trumbull Ave, Chicago, IL 60652

Property at 2337 W Belden Ave, Chicago, IL 60647, 4 beds, 3.5 baths

$1,699,000

4 beds3.5 baths3,000 sq ft

2337 W Belden Ave, Chicago, IL 60647

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 3439 W Hirsch St, Chicago, IL 60651, 5 beds, 2 baths

$437,900

5 beds2 baths1,735 sq ft

3439 W Hirsch St, Chicago, IL 60651

Property at 3530 N Lake Shore Dr Unit 11B, Chicago, IL 60657, 2 beds, 2 baths

$600,000

2 beds2 baths2,000 sq ft

3530 N Lake Shore Dr Unit 11B, Chicago, IL 60657

Property at Sign in for address, Chicago, IL 60618, 5 beds, 4.5 baths

$1,325,000

5 beds4.5 baths3,900 sq ft

Property at 11224 S Fairfield Ave, Chicago, IL 60655, 3 beds, 2 baths

$229,900

3 beds2 baths1,056 sq ft

11224 S Fairfield Ave, Chicago, IL 60655

Property at 3430 W Lyndale St, Chicago, IL 60647, 5 beds, 3.5 baths

$1,299,999

5 beds3.5 baths3,200 sq ft

3430 W Lyndale St, Chicago, IL 60647

Property at 5700 N Orange Ave, Chicago, IL 60631, 4 beds, 2 baths

$455,000

4 beds2 baths2,531 sq ft

5700 N Orange Ave, Chicago, IL 60631

Property at 5834 N Maplewood Ave, Chicago, IL 60659, 7 beds, 3 baths

$649,900

7 beds3 baths— sq ft

5834 N Maplewood Ave, Chicago, IL 60659

Property at 3107 W Flournoy St, Chicago, IL 60612, 7 beds, 3 baths

$590,000

7 beds3 baths— sq ft

3107 W Flournoy St, Chicago, IL 60612

Property at 8626 S Kingston Ave, Chicago, IL 60617, 5 beds, 2 baths

$147,000

5 beds2 baths1,832 sq ft

8626 S Kingston Ave, Chicago, IL 60617

Property at 4852 W Hirsch St, Chicago, IL 60651, 3 beds, 1 bath

$314,900

3 beds1 bath2,154 sq ft

4852 W Hirsch St, Chicago, IL 60651

Property at 321 S Richmond St, Chicago, IL 60612, 6 beds, 3 baths

$699,999

6 beds3 baths— sq ft

321 S Richmond St, Chicago, IL 60612

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

$330,000

2 beds2 baths1,100 sq ft

Property at 5708 N Austin Ave, Chicago, IL 60646, 3 beds, 2 baths

$470,000

3 beds2 baths1,500 sq ft

5708 N Austin Ave, Chicago, IL 60646

Property at 4920 W Cortez St, Chicago, IL 60651, 4 beds, 2 baths

$184,700

4 beds2 baths— sq ft

4920 W Cortez St, Chicago, IL 60651

Property at 7206 S Lafayette Ave, Chicago, IL 60621, 3 beds, 1 bath

$124,700

3 beds1 bath1,105 sq ft

7206 S Lafayette Ave, Chicago, IL 60621

Property at 9417 S Racine Ave, Chicago, IL 60620, 4 beds, 1.5 baths

$200,000

4 beds1.5 baths1,074 sq ft

9417 S Racine Ave, Chicago, IL 60620

Property at 6547 S Langley Ave, Chicago, IL 60637, 4 beds, 3.5 baths

$550,000

4 beds3.5 baths3,000 sq ft

6547 S Langley Ave, Chicago, IL 60637

Property at 900 N Kingsbury St #1025, Chicago, IL 60610, 2 beds, 2 baths

$449,900

2 beds2 baths1,256 sq ft

900 N Kingsbury St #1025, Chicago, IL 60610

Property at 10656 S Oakley Ave, Chicago, IL 60643, 6 beds, 3.5 baths

$749,900

6 beds3.5 baths3,076 sq ft

10656 S Oakley Ave, 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 6643 S Laflin St, Chicago, IL 60636, 5 beds, 2 baths

$220,000

5 beds2 baths— sq ft

6643 S Laflin St, Chicago, IL 60636

Property at 5827 S Austin Ave, Chicago, IL 60638, 2 beds, 1 bath

$289,914

2 beds1 bath1,231 sq ft

5827 S Austin Ave, Chicago, IL 60638

Property at 4351 N Western Ave, Chicago, IL 60618

$889,500

— beds— baths— sq ft

4351 N Western Ave, Chicago, IL 60618

Property at Sign in for address, Calumet Park, IL 60827, 3 beds, 1.5 baths

$264,000

3 beds1.5 baths1,800 sq ft

Property at 5154 S Nordica Ave, Chicago, IL 60638, 4 beds, 2 baths

$390,000

4 beds2 baths1,022 sq ft

5154 S Nordica Ave, Chicago, IL 60638

Property at 7036 S Artesian Ave, Chicago, IL 60629, 6 beds, 2 baths

$245,000

6 beds2 baths— sq ft

7036 S Artesian Ave, Chicago, IL 60629

Property at 7705 S Paulina St, Chicago, IL 60620, 5 beds, 2 baths

$290,000

5 beds2 baths— sq ft

7705 S Paulina St, Chicago, IL 60620

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 5555 N Mango Ave, Chicago, IL 60630, 5 beds, 3 baths

$630,000

5 beds3 baths— sq ft

5555 N Mango Ave, Chicago, IL 60630

Property at 315 E 87th St, Chicago, IL 60619, 4 beds, 2 baths

$199,999

4 beds2 baths1,104 sq ft

315 E 87th St, Chicago, IL 60619

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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 3014 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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