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

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Fantastic opportunity for homeowners, builders, investors, and developers! Situated on a desirable 29' x 125' lot in a sought-after neighborhood, this two-bedroom detached home offers excellent potential for renovation, expansion, or redevelopment. Bring your vision and transform the existing home into a beautiful custom residence, or renovate the current layout to suit your needs. The property has significant floor damage, and interior showings are not permitted at this time. Property is being sold strictly AS-IS. An excellent opportunity for those seeking a project with long-term potential in a desirable location.

$230,000

2 beds1 bath— sq ft

3006 N Natoma Ave, Chicago, IL 60634

New construction

OPEN TODAY, 11AM TO 1PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome to this exceptional Greystone vintage 3-unit building offering 5 bedrooms, 5 full bathrooms, and 1 half bathroom, perfectly blending classic Chicago charm with modern comfort. Featuring beautiful landscaping, a fenced backyard, and thoughtfully designed living spaces, this remarkable property presents an outstanding opportunity for both homeowners and investors. A stunning hardwood staircase welcomes you through the main entrance, providing access to both the first- and second-floor units. Let's begin with the second-floor residence. As you enter, you're greeted by a bright and spacious living room, highlighted by a beautiful English skylight lantern above the foyer and oversized wi

$1,299,000

5 beds5.5 baths— sq ft

4448 N Tripp Ave, Chicago, IL 60630

Private balcony • Walk-in closet • Hardwood staircase

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
WELCOME TO THE RASCHER MANSION. Situated in the highly sought-after northwest corner of Lincoln Square in Budlong Woods, this home is the epitome of chic urban living-a captivating destination for those in search of a true standout residence. Set on an expansive 120' x 125' lot (no alley gives home added 10' in depth) and offering approximately 12,000 sq ft of luxurious living space, the mansion effortlessly blends grandeur, comfort, and sophisticated design. As you enter, you're greeted by two distinct living areas. One features soaring 18-foot ceilings, a European-crafted floor-to-ceiling fireplace mantle, and a custom wet bar-creating a dramatic gathering space. Adjacent, large south-fac

$1,800,000

6 beds6 baths12,000 sq ft

2851 W Rascher Ave, Chicago, IL 60625

Fitness center • Chef's dream kitchen • Full theater room

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
City-certified two-flat in the heart of Gladstone Park offering exceptional flexibility for investors, owner-occupants, or multi-generational living. Thoughtfully updated over the years, this well-maintained property features remodeled kitchens and bathrooms on both the first and second floors, along with an updated first-floor primary bedroom. Each unit offers comfortable living space, while the second-floor apartment features two private entrances and an expanded rear deck overlooking the beautifully landscaped yard. A partially finished basement includes an in-law suite, providing additional flexible living space. Outside, you'll find a true urban oasis with raised garden beds, fruit tre

$599,999

3 beds2 baths— sq ft

5942 W Thorndale Ave, Chicago, IL 60646

In-law suite • Remodeled kitchens • Raised garden beds

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Investors welcome! We have a 3 bedroom home with 1.5 baths and partially finished basement with extra bedroom and tons of storage space. Currently leased by a long term tenant who would prefer to stay. Or, you could fix and flip the choice is yours. Wonderfull location near West Ridge Nature Preserve, Green Briar Park and plenty of places to shop and dine.

$485,000

3 beds1.5 baths— sq ft

6018 N Campbell Ave, Chicago, IL 60659

Extra bedroom • 4,092 sq ft lot • Built 1953

Property at 2114 N 74th Ave, Elmwood Park, IL 60707, 3 beds, 2 baths

$469,000

3 beds2 baths2,075 sq ft

2114 N 74th Ave, Elmwood Park, IL 60707

Property at 4129 N Oketo Ave, Norridge, IL 60706, 4 beds, 3.5 baths

$639,000

4 beds3.5 baths2,500 sq ft

4129 N Oketo Ave, Norridge, IL 60706

Property at 1820 Brophy Ave, Park Ridge, IL 60068, 4 beds, 4 baths

$1,199,900

4 beds4 baths3,600 sq ft

1820 Brophy Ave, Park Ridge, IL 60068

Property at 4940 Estes Ave, Skokie, IL 60077, 4 beds, 2.5 baths

$499,999

4 beds2.5 baths1,704 sq ft

4940 Estes Ave, Skokie, IL 60077

Property at 4825 W Jarlath St, Lincolnwood, IL 60712, 4 beds, 4.5 baths

$700,000

4 beds4.5 baths2,800 sq ft

4825 W Jarlath St, Lincolnwood, IL 60712

Property at 9139 Kedvale Ave, Skokie, IL 60076, 4 beds, 3.5 baths

$1,250,000

4 beds3.5 baths5,700 sq ft

9139 Kedvale Ave, Skokie, IL 60076

Property at 1912 Emerson St, Evanston, IL 60201, 5 beds, 3.5 baths

$562,500

5 beds3.5 baths2,632 sq ft

1912 Emerson St, Evanston, IL 60201

Property at 644 S 4th Ave, Des Plaines, IL 60016, 4 beds, 1.5 baths

$478,500

4 beds1.5 baths2,014 sq ft

644 S 4th Ave, Des Plaines, IL 60016

Property at 3420 Greenbriar Dr, Glenview, IL 60025, 3 beds, 1 bath

$417,500

3 beds1 bath1,077 sq ft

3420 Greenbriar Dr, Glenview, IL 60025

Property at 100 Woodcrest Ln, Elk Grove Village, IL 60007, 3 beds, 2 baths

$419,900

3 beds2 baths1,544 sq ft

100 Woodcrest Ln, Elk Grove Village, IL 60007

Property at 49 King Ln, Des Plaines, IL 60016, 3 beds, 2 baths

$495,000

3 beds2 baths1,306 sq ft

49 King Ln, Des Plaines, IL 60016

Property at 2324 Sumac Cir, Glenview, IL 60025, 3 beds, 2.5 baths

$777,500

3 beds2.5 baths1,463 sq ft

2324 Sumac Cir, Glenview, IL 60025

Property at 1450 Sanders Rd, Northbrook, IL 60062, 5 beds, 2 baths

$650,000

5 beds2 baths2,628 sq ft

1450 Sanders Rd, Northbrook, IL 60062

Property at 7836 S Marshfield Ave, Chicago, IL 60620, 4 beds, 2 baths

$269,900

4 beds2 baths— sq ft

7836 S Marshfield Ave, Chicago, IL 60620

Property at 7653 S Saint Lawrence Ave, Chicago, IL 60619, 4 beds, 2 baths

$264,000

4 beds2 baths1,102 sq ft

7653 S Saint Lawrence Ave, Chicago, IL 60619

Property at 1229 E 71st St, Chicago, IL 60619, 6 beds, 2 baths

$330,000

6 beds2 baths— sq ft

1229 E 71st St, Chicago, IL 60619

Property at 6723 S Euclid Ave, Chicago, IL 60649, 4 beds, 2.5 baths

$614,900

4 beds2.5 baths3,240 sq ft

6723 S Euclid Ave, Chicago, IL 60649

Property at 6245 S Damen Ave, Chicago, IL 60636, 5 beds, 3 baths

$259,900

5 beds3 baths2,100 sq ft

6245 S Damen Ave, Chicago, IL 60636

Property at 5445 S Dorchester Ave, Chicago, IL 60615, 3 beds, 2.5 baths

$689,000

3 beds2.5 baths2,078 sq ft

5445 S Dorchester Ave, Chicago, IL 60615

Property at 4318 S Hermitage Ave, Chicago, IL 60609, 8 beds, 4 baths

$384,900

8 beds4 baths— sq ft

4318 S Hermitage Ave, Chicago, IL 60609

Property at 4507 S Prairie Ave, Chicago, IL 60653, 5 beds, 2.5 baths

$635,000

5 beds2.5 baths5,500 sq ft

4507 S Prairie Ave, Chicago, IL 60653

Property at 6158 S Normandy Ave, Chicago, IL 60638, 4 beds, 1 bath

$325,000

4 beds1 bath1,510 sq ft

6158 S Normandy Ave, Chicago, IL 60638

Property at 3916 W 59th Pl, Chicago, IL 60629, 4 beds, 2 baths

$385,000

4 beds2 baths1,696 sq ft

3916 W 59th Pl, Chicago, IL 60629

Property at 7632 S Oketo Ave, Bridgeview, IL 60455, 4 beds, 2 baths

$299,900

4 beds2 baths1,445 sq ft

7632 S Oketo Ave, Bridgeview, IL 60455

Property at 7630 Odell Ave, Bridgeview, IL 60455, 4 beds, 2 baths

$310,000

4 beds2 baths1,719 sq ft

7630 Odell Ave, Bridgeview, IL 60455

Property at 6231 Linden Ln, La Grange Highlands, IL 60525, 3 beds, 1.5 baths

$490,000

3 beds1.5 baths1,436 sq ft

6231 Linden Ln, La Grange Highlands, IL 60525

Property at 8130 45th Pl, Lyons, IL 60534, 4 beds, 1.5 baths

$295,000

4 beds1.5 baths1,320 sq ft

8130 45th Pl, Lyons, IL 60534

Property at 850 N Dewitt Pl Unit 7K, Chicago, IL 60611, 2 beds, 2 baths

$399,000

2 beds2 baths1,530 sq ft

850 N Dewitt Pl Unit 7K, Chicago, IL 60611

Property at 3548 Clinton Ave, Berwyn, IL 60402, 4 beds, 3.5 baths

$669,000

4 beds3.5 baths1,823 sq ft

3548 Clinton Ave, Berwyn, IL 60402

Property at 3239 Wesley Ave, Berwyn, IL 60402, 5 beds, 4 baths

$717,000

5 beds4 baths4,200 sq ft

3239 Wesley Ave, Berwyn, IL 60402

Property at 4926 W 30th Pl, Cicero, IL 60804, 5 beds, 3 baths

$314,900

5 beds3 baths— sq ft

4926 W 30th Pl, Cicero, IL 60804

Property at 5214 W 24th St, Cicero, IL 60804, 5 beds, 2 baths

$440,000

5 beds2 baths1,786 sq ft

5214 W 24th St, Cicero, IL 60804

Property at 4834 W Henderson St Unit 2B, Chicago, IL 60641, 2 beds, 1 bath

$184,000

2 beds1 bath— sq ft

4834 W Henderson St Unit 2B, Chicago, IL 60641

Property at 5812 Reba St, Morton Grove, IL 60053, 2 beds, 2 baths

$349,000

2 beds2 baths1,100 sq ft

5812 Reba St, Morton Grove, IL 60053

Property at 3800 Saint Paul Ave, Bellwood, IL 60104, 6 beds, 2 baths

$399,999

6 beds2 baths— sq ft

3800 Saint Paul Ave, Bellwood, IL 60104

Property at 1408 N Central Park Ave, Chicago, IL 60651, 7 beds, 2 baths

$599,000

7 beds2 baths— sq ft

1408 N Central Park Ave, Chicago, IL 60651

Viewing page 71 of 120

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 4907 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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