Vintage homes for sale & real estate in Chicago, IL

3,019 homes

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ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Irving Park living at its finest-this standout 4-bedroom / 2.5-bath home offers generous space, modern updates, and flexible living options throughout. Warm and inviting, the main level welcomes you into a bright living room with 9-ft+ ceilings and bamboo flooring that flows seamlessly into the open kitchen and dining area. The updated kitchen features stainless steel appliances, custom cabinets, and a walk-in pantry. Two comfortable bedrooms and a full bath complete this level. The private second floor includes a serene primary suite with half bath and an expansive multi-purpose area with a 20' closet-perfect for a home office, nursery or workout zone. The lower level functions as a flexib

$479,900

4 beds2.5 baths2,193 sq ft

4046 N Saint Louis Ave, Chicago, IL 60618

Private second floor • Multi-purpose area • Serene primary suite

OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Truly extraordinary Bucktown home built with quality and character throughout! Loaded with custom details and innovative design elements, this artfully crafted property is one of a kind and unmistakably special. Equally impressive as the home's craftsmanship is its livability, with generous room sizes throughout, including a spacious family room addition that provides a primary living area with openness and width seldom seen in similar homes. The entry level is warm and welcoming, with its decorative foyer lit by oversized transom windows that lead to a formal front living room with herringbone floors, custom millwork, stonework, lighting, and tile. A beautiful marble fireplace anchors the

$1,699,000

4 beds3.5 baths3,000 sq ft

2337 W Belden Ave, Chicago, IL 60647

2,400 sq ft lot • 2 garage spots • Built 1885

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Set on an oversized lot in the highly sought-after Old Irving Park neighborhood, this meticulously maintained historic home offers the ideal blend of vintage character and modern convenience. Owned by the same family for over twenty-five years, this property has been thoughtfully updated throughout with both comfort and entertaining in mind. A welcoming front yard and covered porch with custom seating leads into a warm and inviting main level. The living and dining areas flow seamlessly together and feature beautifully preserved built-ins, rich moldings, and a custom stain glass window. The chef-designed kitchen is both beautiful and highly functional, featuring a custom bar area, prep sink

$899,999

4 beds2.5 baths2,150 sq ft

4033 W Waveland Ave, Chicago, IL 60641

Covered porch • Oversized lot • Welcoming front yard

OPEN SAT, 12PM TO 2PMHOT HOME

$440,000

3 beds1 bath977 sq ft

5542 N Osceola Ave, Chicago, IL 60656

4,641 sq ft lot • 2 garage spots • Built 1945

NEW 1 DAY AGO

ABOUT THIS HOME
Vintage Home for sale in Chicago, IL:
Beautifully Renovated 2 unit with finished basement features two - 3 bedroom apartments, first floor duplexed to basement for extended living. All separate heat Electric and H20 plus brand new roof top central air units. Custom kitchens with 42 inch cabinets quartz countertops in Kitchen and baths. Brand new Hardwood floors throughout and Stainless steel Appliances for both apartments. Located one block from I290 for easy access downtown and western suburbs

$465,000

6 beds3 baths— sq ft

4832 W Harrison St, Chicago, IL 60644

Quartz countertops • Separate heat • Brand new roof

Property at 6820 W Raven St Unit 1B, Chicago, IL 60631, 2 beds, 2 baths

$249,000

2 beds2 baths1,000 sq ft

6820 W Raven St Unit 1B, Chicago, IL 60631

Property at 948 W Sheridan Rd Unit 2D, Chicago, IL 60613, 2 beds, 2 baths

$429,900

2 beds2 baths1,300 sq ft

948 W Sheridan Rd Unit 2D, Chicago, IL 60613

Property at 8007 S Paulina St, Chicago, IL 60620, 3 beds, 1.5 baths

$109,900

3 beds1.5 baths1,376 sq ft

8007 S Paulina St, Chicago, IL 60620

Property at 7425 S Vernon Ave, Chicago, IL 60619, 5 beds, 4 baths

$330,000

5 beds4 baths2,800 sq ft

7425 S Vernon Ave, Chicago, IL 60619

Property at 3116 W 101st Pl, Evergreen Park, IL 60805, 3 beds, 2 baths

$310,000

3 beds2 baths1,258 sq ft

3116 W 101st Pl, Evergreen Park, IL 60805

Property at 10646 S Saint Louis Ave, Chicago, IL 60655, 4 beds, 3 baths

$464,900

4 beds3 baths1,831 sq ft

10646 S Saint Louis Ave, Chicago, IL 60655

Property at 1956 W Melrose St #102, Chicago, IL 60657, 1 bed, 1 bath

$270,000

1 bed1 bath— sq ft

1956 W Melrose St #102, Chicago, IL 60657

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 1904 S Fairview Ave, Park Ridge, IL 60068, 4 beds, 2 baths

$639,000

4 beds2 baths2,520 sq ft

1904 S Fairview Ave, Park Ridge, IL 60068

Property at 2947 S Farrell St, Chicago, IL 60608, 4 beds, 2 baths

$384,900

4 beds2 baths1,508 sq ft

2947 S Farrell St, Chicago, IL 60608

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 Sign in for address, Chicago, IL 60636, 5 beds, 3 baths

$329,000

5 beds3 baths— sq ft

Property at 5250 S Nagle Ave, Chicago, IL 60638, 4 beds, 2 baths

$389,900

4 beds2 baths1,330 sq ft

5250 S Nagle Ave, Chicago, IL 60638

Property at 4938 S Vincennes Ave, Chicago, IL 60615, 5 beds, 3.5 baths

$875,000

5 beds3.5 baths3,439 sq ft

4938 S Vincennes Ave, Chicago, IL 60615

Property at 921 W Addison St Unit 3B, Chicago, IL 60613, 2 beds, 2 baths

$550,000

2 beds2 baths1,650 sq ft

921 W Addison St Unit 3B, Chicago, IL 60613

Property at 3642 N Albany Ave, Chicago, IL 60618, 4 beds, 2 baths

$585,000

4 beds2 baths— sq ft

3642 N Albany Ave, Chicago, IL 60618

Property at 4827 N Spaulding Ave, Chicago, IL 60625, 8 beds, 4 baths

$679,000

8 beds4 baths— sq ft

4827 N Spaulding Ave, Chicago, IL 60625

Property at 6724 S Kolin Ave, Chicago, IL 60629, 4 beds, 2 baths

$350,000

4 beds2 baths— sq ft

6724 S Kolin Ave, Chicago, IL 60629

Property at 645 E 113th St, Chicago, IL 60628, 7 beds, 4 baths

$89,999

7 beds4 baths— sq ft

645 E 113th St, Chicago, IL 60628

Property at 5813 S Wabash Ave, Chicago, IL 60637, 15 beds, 4 baths

$499,000

15 beds4 baths— sq ft

5813 S Wabash Ave, Chicago, IL 60637

Property at 7826 S Marshfield Ave, Chicago, IL 60620, 7 beds, 3 baths

$119,900

7 beds3 baths— sq ft

7826 S Marshfield Ave, Chicago, IL 60620

Property at 2236 N Lockwood Ave, Chicago, IL 60639, 4 beds, 2 baths

$349,000

4 beds2 baths— sq ft

2236 N Lockwood Ave, Chicago, IL 60639

Property at 10436 S Eberhart Ave, Chicago, IL 60628, 5 beds, 3 baths

$319,900

5 beds3 baths2,239 sq ft

10436 S Eberhart Ave, Chicago, IL 60628

Property at 5218 W Patterson Ave, Chicago, IL 60641, 4 beds, 1 bath

$389,900

4 beds1 bath— sq ft

5218 W Patterson Ave, Chicago, IL 60641

Property at 2502 W Augusta Blvd, Chicago, IL 60622, 9 beds, 4 baths

$975,000

9 beds4 baths— sq ft

2502 W Augusta Blvd, Chicago, IL 60622

Property at 1703 N Monticello Ave, Chicago, IL 60647, 6 beds, 3 baths

$450,000

6 beds3 baths— sq ft

1703 N Monticello Ave, Chicago, IL 60647

Property at 10333 S Millard Ave, Chicago, IL 60655, 2 beds, 1 bath

$249,900

2 beds1 bath852 sq ft

10333 S Millard Ave, Chicago, IL 60655

Property at 4653 N Lawndale Ave Unit 3S, Chicago, IL 60625, 3 beds, 2 baths

$299,900

3 beds2 baths1,500 sq ft

4653 N Lawndale Ave Unit 3S, Chicago, IL 60625

Property at 7618 S Yates Blvd, Chicago, IL 60649, 4 beds, 3 baths

$99,900

4 beds3 baths2,200 sq ft

7618 S Yates Blvd, Chicago, IL 60649

Property at 5639 S Emerald Ave, Chicago, IL 60621, 6 beds, 1.5 baths

$214,900

6 beds1.5 baths— sq ft

5639 S Emerald Ave, Chicago, IL 60621

Property at 3951 W Waveland Ave #2, Chicago, IL 60618, 2 beds, 1.5 baths

$325,000

2 beds1.5 baths1,000 sq ft

3951 W Waveland Ave #2, Chicago, IL 60618

Property at 9716 S Prairie Ave, Chicago, IL 60628, 3 beds, 2 baths

$140,000

3 beds2 baths1,200 sq ft

9716 S Prairie Ave, Chicago, IL 60628

Property at 6116 S Neenah Ave, Chicago, IL 60638, 2 beds, 1 bath

$265,000

2 beds1 bath922 sq ft

6116 S Neenah Ave, Chicago, IL 60638

Property at 5131 W Roscoe St, Chicago, IL 60641, 6 beds, 3 baths

$790,000

6 beds3 baths— sq ft

5131 W Roscoe St, Chicago, IL 60641

Property at 1520 S Christiana Ave, Chicago, IL 60623, 7 beds, 3 baths

$469,000

7 beds3 baths— sq ft

1520 S Christiana Ave, Chicago, IL 60623

Property at 2103 W 52nd St, Chicago, IL 60609, 5 beds, 3 baths

$180,000

5 beds3 baths— sq ft

2103 W 52nd St, Chicago, IL 60609

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Based on information submitted to the MLS GRID as of Sat Dec 06 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 3019 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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