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

4,698 homes + 198 early access

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Presenting an unparalleled opportunity to acquire one of Chicago's most distinguished estates - an historic residence offering over 25,000 square feet of total living space, set on nearly one-third of an acre along the Gold Coast's prestigious Astor Street. This is an exceptionally wide and long lot like no other. Originally designed by acclaimed architect Howard Van Doren Shaw for the Goodman Family, this extraordinary property is being offered for the first time in 40 years. A true masterpiece, this estate stands as a defining example of neo-classical and Georgian Revival design and spans an impressive 80 feet across and embodying Chicago's rich architectural heritage. At the center of th

$21,000,000

6 beds5.5 baths25,000 sq ft

1355 N Astor St, Chicago, IL 60610

Historic residence • Formal gardens • Private courtyard

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
NEW PRICE - take another look at the opportunity this Berwyn property has to offer! With strong upside potential and a newly adjusted price, this property presents an opportunity for buyers looking to renovate, personalize, or invest. Property is being sold subject to inspection report - current inspection report is in file. Convenient location near schools, parks, shopping, dining, and transportation. Buyer to verify all information and complete their own due diligence.

$209,900

3 beds1 bath949 sq ft

2323 Highland Ave, Berwyn, IL 60402

Near schools • Near dining • Near shopping

FLOOR PLAN

$360,000

3 beds1.5 baths1,152 sq ft

7220 N Hamilton Ave, Chicago, IL 60645

Built 1910 • Listed 110 days

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
EXCELLENT OPPORTUNITY IN THIS ALL BRICK RAISED RANCH LOCATED IN CHICAGO LAWN NEIGHBORHOOD. THE MAIN LEVEL OFFERS LIVING ROOM, KITCHEN WITH DINETTE AREA, 3 BEDROOMS AND FULL BATH. THERE IS A FULL BASEMENT FOR ADDITIONAL LIVING SPACE AND STORAGE. OVERSIZED LOT. CONVINIENT ACCESS TO SCHOOLS, PUBLIC TRANSPORTATION AND MAJOR HIGHWAYS. NEAR MARQUETTE PARK AND PULASKI ROAD'S SHOPPING AND RESTAURANTS. CLOSE PROXIMITY TO MIDWAY AIRPORT. SOLD AS IS. READY FOR THE RIGHT BUYER TO RESTORE IT TO ITS FULL POTENTIAL ! Sold as is. Property NOT FOR RENT- beware of rental scams!

$195,000

3 beds1 bath1,038 sq ft

3709 W 66th Pl, Chicago, IL 60629

Full basement • Oversized lot • Major highways

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Exceptional move-in ready residence offering extensive updates throughout, including renovated walls, newer flooring, updated bathrooms, and a beautifully remodeled kitchen with modern finishes. The maintenance-free exterior provides both convenience and lasting curb appeal, complemented by a 1.5-car garage. The fully finished basement expands the living space substantially and features a full bath along with a spacious 4th bedroom, ideal for related living, guests, or a private office suite. Conveniently situated near shopping centers, dining, schools, and major highways, this home combines comfort, style, and accessibility. A truly impressive property certain to satisfy even the most disc

$430,000

3 beds3 baths— sq ft

3935 Birchwood Ave, Skokie, IL 60077

Newer flooring • Renovated walls • Remodeled kitchen

Property at 9200 Kedvale Ave, Skokie, IL 60076, 4 beds, 1.5 baths

$459,000

4 beds1.5 baths— sq ft

9200 Kedvale Ave, Skokie, IL 60076

Property at 400 W Milburn Ave, Mount Prospect, IL 60056, 2 beds, 1.5 baths

$535,000

2 beds1.5 baths1,786 sq ft

400 W Milburn Ave, Mount Prospect, IL 60056

Property at 8035 Wolf Rd, La Grange, IL 60525, 3 beds, 2.5 baths

$635,000

3 beds2.5 baths2,964 sq ft

8035 Wolf Rd, La Grange, IL 60525

Property at 2836 S Union Ave, Chicago, IL 60616, 5 beds, 2 baths

$550,000

5 beds2 baths— sq ft

2836 S Union Ave, Chicago, IL 60616

Property at 7338 N Overhill Ave, Chicago, IL 60631, 3 beds, 2.5 baths

$489,000

3 beds2.5 baths— sq ft

7338 N Overhill Ave, Chicago, IL 60631

Property at 7330 N Kilbourn Ave, Lincolnwood, IL 60712, 4 beds, 2.5 baths

$544,900

4 beds2.5 baths1,290 sq ft

7330 N Kilbourn Ave, Lincolnwood, IL 60712

Property at 325 Gentry St, Park Forest, IL 60466, 3 beds, 1.5 baths

$100,000

3 beds1.5 baths1,209 sq ft

325 Gentry St, Park Forest, IL 60466

Property at 3424 Kenilworth Ave, Berwyn, IL 60402, 3 beds, 2 baths

$298,000

3 beds2 baths1,195 sq ft

3424 Kenilworth Ave, Berwyn, IL 60402

Property at 6754 S 78th Ave, Bridgeview, IL 60455, 4 beds, 2 baths

$332,900

4 beds2 baths1,451 sq ft

6754 S 78th Ave, Bridgeview, IL 60455

Property at 12524 S 71st Ct, Palos Heights, IL 60463, 3 beds, 2 baths

$406,000

3 beds2 baths1,970 sq ft

12524 S 71st Ct, Palos Heights, IL 60463

Property at 4136 N Sacramento Ave, Chicago, IL 60618, 5 beds, 2 baths

$500,000

5 beds2 baths1,774 sq ft

4136 N Sacramento Ave, Chicago, IL 60618

Property at 9217 S Perry Ave, Chicago, IL 60628, 4 beds, 3 baths

$79,900

4 beds3 baths1,372 sq ft

9217 S Perry Ave, Chicago, IL 60628

Property at 5819 S Fairfield Ave, Chicago, IL 60629, 4 beds, 2 baths

$239,998

4 beds2 baths3,300 sq ft

5819 S Fairfield Ave, Chicago, IL 60629

Property at 9527 Lowell Ave, Skokie, IL 60076, 4 beds, 2.5 baths

$545,000

4 beds2.5 baths2,800 sq ft

9527 Lowell Ave, Skokie, IL 60076

Property at 3325 N Lincoln Ave #302, Chicago, IL 60657, 2 beds, 2 baths

$645,000

2 beds2 baths— sq ft

3325 N Lincoln Ave #302, Chicago, IL 60657

Property at 1413 S Central Ave, Cicero, IL 60804, 2 beds, 2 baths

$320,000

2 beds2 baths1,269 sq ft

1413 S Central Ave, Cicero, IL 60804

Property at 3709 W Palmer St, Chicago, IL 60647, 4 beds, 3 baths

$450,000

4 beds3 baths— sq ft

3709 W Palmer St, Chicago, IL 60647

Property at 3088 S Lyman St, Chicago, IL 60608, 5 beds, 2 baths

$519,900

5 beds2 baths— sq ft

3088 S Lyman St, Chicago, IL 60608

Property at 2702 Saint James St, Rolling Meadows, IL 60008, 2 beds, 1 bath

$310,000

2 beds1 bath978 sq ft

2702 Saint James St, Rolling Meadows, IL 60008

Property at 2715 Cherrywood Pl, Hazel Crest, IL 60429, 3 beds, 1.5 baths

$189,000

3 beds1.5 baths1,495 sq ft

2715 Cherrywood Pl, Hazel Crest, IL 60429

Property at 8449 N Kedvale Ave, Skokie, IL 60076, 5 beds, 3 baths

$575,000

5 beds3 baths2,100 sq ft

8449 N Kedvale Ave, Skokie, IL 60076

Property at 3806 S Wolcott Ave, Chicago, IL 60609, 3 beds, 2.5 baths

$315,000

3 beds2.5 baths2,000 sq ft

3806 S Wolcott Ave, Chicago, IL 60609

Property at 1534 E Palatine Rd, Palatine, IL 60074, 3 beds, 1.5 baths

$387,900

3 beds1.5 baths1,700 sq ft

1534 E Palatine Rd, Palatine, IL 60074

Property at 1116 Cernan Dr, Bellwood, IL 60104, 3 beds, 1.5 baths

$290,000

3 beds1.5 baths1,050 sq ft

1116 Cernan Dr, Bellwood, IL 60104

Property at 6254 W Barry Ave, Chicago, IL 60634, 5 beds, 3 baths

$529,000

5 beds3 baths2,263 sq ft

6254 W Barry Ave, Chicago, IL 60634

Property at 1212 W 96th St, Chicago, IL 60643, 4 beds, 2 baths

$204,900

4 beds2 baths2,038 sq ft

1212 W 96th St, Chicago, IL 60643

Property at 208 W Washington St #1007, Chicago, IL 60606, 2 beds, 2 baths

$289,900

2 beds2 baths— sq ft

208 W Washington St #1007, Chicago, IL 60606

Property at 2736 W Francis Pl, Chicago, IL 60647, 8 beds, 4 baths

$1,080,000

8 beds4 baths— sq ft

2736 W Francis Pl, Chicago, IL 60647

Property at 2144 Dewey Ave, Evanston, IL 60201, 4 beds, 1 bath

$350,000

4 beds1 bath1,008 sq ft

2144 Dewey Ave, Evanston, IL 60201

Property at 10706 Oak Ave, Chicago Ridge, IL 60415, 3 beds, 1.5 baths

$260,000

3 beds1.5 baths1,120 sq ft

10706 Oak Ave, Chicago Ridge, IL 60415

Property at 10941 Ridgeland Ave, Chicago Ridge, IL 60415, 4 beds, 2 baths

$300,000

4 beds2 baths2,444 sq ft

10941 Ridgeland Ave, Chicago Ridge, IL 60415

Property at 2605 W Division St, Chicago, IL 60622

$465,000

— beds— baths— sq ft

2605 W Division St, Chicago, IL 60622

Property at 5401 S Maryland Ave, Chicago, IL 60615, 4 beds, 2.5 baths

$695,000

4 beds2.5 baths2,400 sq ft

5401 S Maryland Ave, Chicago, IL 60615

Property at 4541 S Laporte Ave, Chicago, IL 60638, 3 beds, 1 bath

$259,000

3 beds1 bath912 sq ft

4541 S Laporte Ave, Chicago, IL 60638

Property at 4015 W Potomac Ave, Chicago, IL 60651, 6 beds, 2 baths

$419,900

6 beds2 baths— sq ft

4015 W Potomac Ave, Chicago, IL 60651

Property at 470 Sheridan Rd #2, Evanston, IL 60202, 2 beds, 2 baths

$545,000

2 beds2 baths1,560 sq ft

470 Sheridan Rd #2, Evanston, IL 60202

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Based on information submitted to the MLS GRID as of Sun Aug 30 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 4896 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, 5258 homes have been sold in Cook County. In addition to houses in Cook County, there were also 7081 condos, 1441 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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