Vintage homes for sale & real estate in West Side, IL

498 homes

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ABOUT THIS HOME
Vintage Home for sale in West Side, IL:
Investor's Dream in Humboldt Park! This fully occupied 2-4 flat offers strong rental income with tons of upside. Features include a nonconforming basement-perfect for storage or a potential duplex-down conversion-plus a 2-car garage and backyard for added value. A rare opportunity to own a multi-unit in a desirable Chicago neighborhood with long-term growth potential.

$499,999

7 beds3 baths— sq ft

3333 W Pierce Ave, Chicago, IL 60651

Chicago neighborhood • Backyard • 2 car garage

$465,000

6 beds2 baths— sq ft

1242 S Sawyer Ave, Chicago, IL 60623

Rehabbed grey stone • Gutted and remodeled • Gorgeous quartz

ABOUT THIS HOME
Vintage Home for sale in West Side, IL:
Welcome to 4747 W Monroe St - Your Next Investment Opportunity! This spacious 5-bedroom, 3-bathroom home, is ready for your personal touch. Recently repainted and featuring beautiful hardwood floors throughout, it offers a fully finished basement, updated bathrooms, and sun-filled rooms perfect for living and entertaining. Enjoy the large backyard, two-car garage, and plenty of closet space in every bedroom. With so much potential, this property is ideal for investors or anyone looking to create their dream home. Don't miss out - sold AS IS, but full of possibilities!

$345,000

5 beds2.5 baths1,596 sq ft

4747 W Monroe St, Chicago, IL 60644

Large backyard • Updated bathrooms • Hardwood floors

ABOUT THIS HOME
Vintage Home for sale in West Side, IL:
Three-bedroom brick Georgian in appreciating Humboldt Park area. Hardwood floors throughout with new Boiler and newer front fence. Property in good condition but selling "As-Is".

$379,900

3 beds2 baths2,952 sq ft

3534 W Le Moyne St, Chicago, IL 60651

New boiler • Privacy fence • Brick georgian

ABOUT THIS HOME
Vintage Home for sale in West Side, IL:
This exquisitely restored Victorian residence is a true architectural gem, seamlessly blending timeless historic charm with contemporary luxury. The expansive main floor features high ceilings, exposed brick, and an open-layout with both the living and dining room flowing into a chef's kitchen that has been thoughtfully renovated with brand-new custom cabinetry and premium appliances. Step out of the kitchen into an outdoor oasis: the private backyard is an entertainer's dream, featuring a beautifully landscaped garden, two decks, and a tranquil patio. In addition to the expansive outdoor space, the backyard features a two-car garage and a storage shed. Upstairs, the second level presents a

$1,299,000

4 beds3.5 baths— sq ft

1636 W Julian St, Chicago, IL 60622

Private backyard • Two decks • Expansive main floor

Property at 3902 W Fillmore St, Chicago, IL 60624, 5 beds, 2 baths

$180,000

5 beds2 baths— sq ft

3902 W Fillmore St, Chicago, IL 60624

Property at 2854 S Central Park Ave, Chicago, IL 60623, 5 beds, 2 baths

$387,546

5 beds2 baths896 sq ft

2854 S Central Park Ave, Chicago, IL 60623

Property at 1657 N Monticello Ave, Chicago, IL 60647, 4 beds, 2 baths

$669,000

4 beds2 baths— sq ft

1657 N Monticello Ave, Chicago, IL 60647

Property at 3903 W Monroe St, Chicago, IL 60624, 7 beds, 2 baths

$375,000

7 beds2 baths— sq ft

3903 W Monroe St, Chicago, IL 60624

Property at 5943 W Huron St, Chicago, IL 60644, 3 beds, 2 baths

$265,000

3 beds2 baths700 sq ft

5943 W Huron St, Chicago, IL 60644

Property at 1934 S Saint Louis Ave, Chicago, IL 60623, 6 beds, 2 baths

$449,999

6 beds2 baths— sq ft

1934 S Saint Louis Ave, Chicago, IL 60623

Property at 32 S Menard Ave, Chicago, IL 60644, 21 beds, 9 baths

$1,100,000

21 beds9 baths— sq ft

32 S Menard Ave, Chicago, IL 60644

Property at 1070 W 15th St #251, Chicago, IL 60608, 2 beds, 2 baths

$309,999

2 beds2 baths1,300 sq ft

1070 W 15th St #251, Chicago, IL 60608

Property at 4016 W Crystal St, Chicago, IL 60651, 6 beds, 3 baths

$580,000

6 beds3 baths— sq ft

4016 W Crystal St, Chicago, IL 60651

Property at 2838 S Keeler Ave, Chicago, IL 60623, 8 beds, 4 baths

$479,000

8 beds4 baths— sq ft

2838 S Keeler Ave, Chicago, IL 60623

Property at 2228 W Cermak Rd, Chicago, IL 60608, 9 beds, 2 baths

$899,000

9 beds2 baths— sq ft

2228 W Cermak Rd, Chicago, IL 60608

Property at 4510 W Adams St, Chicago, IL 60624, 6 beds, 3 baths

$545,000

6 beds3 baths— sq ft

4510 W Adams St, Chicago, IL 60624

Property at 1141 S Saint Louis Ave, Chicago, IL 60624, 7 beds, 2 baths

$217,500

7 beds2 baths— sq ft

1141 S Saint Louis Ave, Chicago, IL 60624

Property at 2815 W 25th St, Chicago, IL 60623, 10 beds, 5 baths

$695,000

10 beds5 baths— sq ft

2815 W 25th St, Chicago, IL 60623

Property at 1900 S Throop St, Chicago, IL 60608, 23 beds, 13 baths

$1,899,999

23 beds13 baths— sq ft

1900 S Throop St, Chicago, IL 60608

Property at 949 N Lockwood Ave, Chicago, IL 60651, 4 beds, 3.5 baths

$429,000

4 beds3.5 baths1,426 sq ft

949 N Lockwood Ave, Chicago, IL 60651

Property at 2109 W 18th Pl, Chicago, IL 60608, 6 beds, 5 baths

$799,000

6 beds5 baths— sq ft

2109 W 18th Pl, Chicago, IL 60608

Property at 1017 W Washington Blvd Unit 6F, Chicago, IL 60607, 2 beds, 2 baths

$799,000

2 beds2 baths2,200 sq ft

1017 W Washington Blvd Unit 6F, Chicago, IL 60607

Property at 3916 W Grand Ave, Chicago, IL 60651, 3 beds, 3 baths

$320,000

3 beds3 baths900 sq ft

3916 W Grand Ave, Chicago, IL 60651

Property at 1735 N Latrobe Ave, Chicago, IL 60639, 5 beds, 3 baths

$427,770

5 beds3 baths1,177 sq ft

1735 N Latrobe Ave, Chicago, IL 60639

Property at 4146 W Jackson Blvd, Chicago, IL 60624, 10 beds, 3 baths

$380,000

10 beds3 baths— sq ft

4146 W Jackson Blvd, Chicago, IL 60624

Property at 1613 S Central Park Ave, Chicago, IL 60623, 8 beds, 3 baths

$380,000

8 beds3 baths— sq ft

1613 S Central Park Ave, Chicago, IL 60623

Property at 3158 S Harding Ave, Chicago, IL 60623

$320,000

— beds— baths2,100 sq ft

3158 S Harding Ave, Chicago, IL 60623

Property at 2518 S Homan Ave, Chicago, IL 60623

$99,000

0 beds— baths— sq ft

2518 S Homan Ave, Chicago, IL 60623

Property at 411 N Lawler Ave, Chicago, IL 60644, 5 beds, 2 baths

$465,900

5 beds2 baths— sq ft

411 N Lawler Ave, Chicago, IL 60644

Property at 1400 N Lawndale Ave, Chicago, IL 60651, 5 beds, 3 baths

$487,000

5 beds3 baths— sq ft

1400 N Lawndale Ave, Chicago, IL 60651

Property at 4626 W Monroe St, Chicago, IL 60644, 5 beds, 3 baths

$499,000

5 beds3 baths— sq ft

4626 W Monroe St, Chicago, IL 60644

Property at 2324 W Warren Blvd, Chicago, IL 60612, 5 beds, 3.5 baths

$600,000

5 beds3.5 baths2,728 sq ft

2324 W Warren Blvd, Chicago, IL 60612

Property at 1371 S California Ave, Chicago, IL 60608, 17 beds, 9 baths

$1,995,000

17 beds9 baths11,584 sq ft

1371 S California Ave, Chicago, IL 60608

Property at 130 S Canal St #217, Chicago, IL 60606, 2 beds, 2 baths

$399,000

2 beds2 baths1,300 sq ft

130 S Canal St #217, Chicago, IL 60606

Property at 2738 S Christiana Ave, Chicago, IL 60623, 4 beds, 2 baths

$259,900

4 beds2 baths— sq ft

2738 S Christiana Ave, Chicago, IL 60623

Property at 1000 W 15th St #234, Chicago, IL 60608, 2 beds, 2 baths

$324,900

2 beds2 baths1,000 sq ft

1000 W 15th St #234, Chicago, IL 60608

Property at 2338 W 18th Pl, Chicago, IL 60608, 7 beds, 3 baths

$738,900

7 beds3 baths— sq ft

2338 W 18th Pl, Chicago, IL 60608

Property at 1842 S Drake Ave, Chicago, IL 60623, 10 beds, 3 baths

$380,000

10 beds3 baths— sq ft

1842 S Drake Ave, Chicago, IL 60623

Property at 1000 W Washington Blvd #517, Chicago, IL 60607, 3 beds, 3 baths

$785,000

3 beds3 baths2,500 sq ft

1000 W Washington Blvd #517, Chicago, IL 60607

Property at 3907 W Monroe St, Chicago, IL 60624, 5 beds, 2 baths

$315,000

5 beds2 baths— sq ft

3907 W Monroe St, Chicago, IL 60624

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Based on information submitted to the MLS GRID as of Sat Nov 29 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 West Side

There are currently 498 vintage homes for sale in West Side at a median listing price of $460K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in West Side stay on the market for 52 days and receive 2 offers. Popular neighborhoods include Lincoln Park, Lake View, Bucktown, Logan Square, and West Loop. This map is refreshed with the newest listings in West Side every 15 minutes.

In the past month, 298 homes have been sold in West Side. In addition to houses in West Side, there were also 682 condos, 43 townhouses, and 486 multi-family units for sale in West Side last month. Find your dream home in West Side 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 West Side are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in West Side. If you're looking to sell your home in the West Side area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in West Side with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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