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:
The Jackson Park Highlands area is seeing explosive growth and revitalization! This isn't just a place to sleep; it's a strategic move into one of the city's most exciting emerging pockets. This recently rehabbed 2-bed, 1-bath condo is move-in ready with modern finishes throughout. Perfect for first-time homebuyers looking for an affordable and stylish home, or investors seeking a solid rental opportunity. Located just minutes from the upcoming Luxury Movie Theater development and the Barack Obama Presidential Library. Enjoy low monthly assessments that include heat, cooking gas, water, and common area maintenance keeping monthly costs affordable. The unit also comes with an assigned parkin

$80,000

2 beds1 bath1,000 sq ft

2044 E 72nd Pl #3, Chicago, IL 60649

$325 HOA • Parking • Built 1946

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Great opportunity to invest in your future! Legal 4 unit apartment building. All units were updated with new flooring, drywall, paint, lighting fixtures and bathroom features. Building possesses newer roof, plumbing and electrical systems. Each unit has its own dedicated electric meter. Heat and electricity can be billed individually by unit. Seller has accrued all the expense to achieve village Certificate of Compliance. Everything will be to code per the village prior to closing and no necessary repairs will be passed along to the buyer. This is a great opportunity so schedule your showing today!

$585,000

5 beds4 baths— sq ft

5122 W 30th Pl, Cicero, IL 60804

New drywall • New flooring • New paint

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Investment opportunity at 4327 W Monroe St in Chicago! This two-flat is fully occupied, making it an ideal income-producing property from day one. The building features two units-a spacious 3-bedroom, 1-bath unit and a comfortable 2-bedroom, 1-bath unit-offering strong rental appeal and steady cash flow. Whether you're expanding your portfolio or looking for a solid investment, this property checks all the boxes with established tenants already in place. Conveniently located with easy access to local amenities, transportation, and more. Don't miss out on this reliable, income-generating asset! Sold AS-IS.

$310,000

5 beds2 baths— sq ft

4327 W Monroe St, Chicago, IL 60624

Steady cash flow • Two units • Fully occupied

$160,000

3 beds1 bath1,120 sq ft

14633 Edbrooke Ave, Dolton, IL 60419

Playset • Electric fireplace • Updated bathroom

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
What a lovely opportunity! With a little TLC you can make this home exactly what you wish! As you enter you will love the layout of this home! The first level has separate Living, Dining and Family Rooms! So much space for entertaining! The spacious family room addition is at the rear of the home boasting beam vaulted ceilings with an oak mantle fireplace. Main level Master bedroom can be converted into a master suite! Both upstairs bedrooms have dormer and ample space. Full unfinished basement can be used for storaged or finished out for more entertainment space. Garage is a spacious 2 Car also has an adjacent paved parking area! A Short walk to metra, pace bus and schools! Property is be

$179,500

3 beds2 baths1,723 sq ft

3615 214th St, Matteson, IL 60443

Oak mantle fireplace • 6,600 sq ft lot • 2 garage spots

Property at Sign in for address, Sauk Village, IL 60411, 3 beds, 2 baths

$164,900

3 beds2 baths1,260 sq ft

Property at 335 Oakwood St, Park Forest, IL 60466, 4 beds, 2 baths

$145,000

4 beds2 baths1,691 sq ft

335 Oakwood St, Park Forest, IL 60466

Property at 1430 S 14th Ave, Maywood, IL 60153, 3 beds, 1 bath

$280,000

3 beds1 bath2,065 sq ft

1430 S 14th Ave, Maywood, IL 60153

Property at 1473 W 77th St, Chicago, IL 60620, 7 beds, 5 baths

$285,000

7 beds5 baths— sq ft

1473 W 77th St, Chicago, IL 60620

Property at 2201 Thornton Lansing Rd, Lansing, IL 60438, 3 beds, 1 bath

$199,000

3 beds1 bath1,734 sq ft

2201 Thornton Lansing Rd, Lansing, IL 60438

Property at 6206 S Knox Ave, Chicago, IL 60629, 2 beds, 1.5 baths

$420,000

2 beds1.5 baths3,528 sq ft

6206 S Knox Ave, Chicago, IL 60629

Property at 7214 S Saint Lawrence Ave, Chicago, IL 60619, 6 beds, 2 baths

$350,000

6 beds2 baths— sq ft

7214 S Saint Lawrence Ave, Chicago, IL 60619

Property at Sign in for address, Maywood, IL 60153, 2 beds, 1 bath

$235,000

2 beds1 bath880 sq ft

Property at 7026 S Saint Lawrence Ave, Chicago, IL 60637, 7 beds, 4 baths

$299,000

7 beds4 baths— sq ft

7026 S Saint Lawrence Ave, Chicago, IL 60637

Property at 3804 W North Ave, Chicago, IL 60647

$290,000

— beds— baths2,200 sq ft

3804 W North Ave, Chicago, IL 60647

Property at 850 N Lake Shore Dr #405, Chicago, IL 60611, 2 beds, 3 baths

$1,550,000

2 beds3 baths2,193 sq ft

850 N Lake Shore Dr #405, Chicago, IL 60611

Property at 351 - 355 S Cicero Ave, Chicago, IL 60644

$499,900

— beds— baths5,737 sq ft

351 - 355 S Cicero Ave, Chicago, IL 60644

Property at 7227 S Michigan Ave, Chicago, IL 60619, 6 beds, 2 baths

$400,000

6 beds2 baths— sq ft

7227 S Michigan Ave, Chicago, IL 60619

Property at 354 E 115th St, Chicago, IL 60628

$96,750

— beds— baths2,100 sq ft

354 E 115th St, Chicago, IL 60628

Property at Sign in for address, Chicago, IL 60621, 3 beds, 1.5 baths

$150,000

3 beds1.5 baths1,050 sq ft

Property at 4535 S Honore St, Chicago, IL 60609, 10 beds, 4 baths

$389,000

10 beds4 baths— sq ft

4535 S Honore St, Chicago, IL 60609

Property at 17831 Community St, Lansing, IL 60438, 4 beds, 2 baths

$190,000

4 beds2 baths1,272 sq ft

17831 Community St, Lansing, IL 60438

Property at 12409 S Green St, Calumet Park, IL 60827, 6 beds, 2 baths

$175,000

6 beds2 baths— sq ft

12409 S Green St, Calumet Park, IL 60827

Property at 557 Forsythe Ave, Calumet City, IL 60409, 5 beds, 2 baths

$128,000

5 beds2 baths920 sq ft

557 Forsythe Ave, Calumet City, IL 60409

Property at 11720 S Wentworth Ave, Chicago, IL 60628, 4 beds, 2 baths

$119,999

4 beds2 baths— sq ft

11720 S Wentworth Ave, Chicago, IL 60628

Property at 124 Wilson St, Park Forest, IL 60466, 3 beds, 2 baths

$230,000

3 beds2 baths1,088 sq ft

124 Wilson St, Park Forest, IL 60466

Property at 850 N Lake Shore Dr #807, Chicago, IL 60611, 2 beds, 2 baths

$889,000

2 beds2 baths1,402 sq ft

850 N Lake Shore Dr #807, Chicago, IL 60611

Property at 5027-29 W Washington Blvd, Chicago, IL 60644, 21 beds, 8 baths

$1,425,000

21 beds8 baths— sq ft

5027-29 W Washington Blvd, Chicago, IL 60644

Property at 8623 S Manistee Ave, Chicago, IL 60617, 4 beds, 2 baths

$79,500

4 beds2 baths— sq ft

8623 S Manistee Ave, Chicago, IL 60617

Property at 3829 W Maypole Ave, Chicago, IL 60624, 9 beds, 3 baths

$485,000

9 beds3 baths— sq ft

3829 W Maypole Ave, Chicago, IL 60624

Property at 118 Warwick St, Park Forest, IL 60466, 4 beds, 2.5 baths

$235,000

4 beds2.5 baths1,265 sq ft

118 Warwick St, Park Forest, IL 60466

Property at 3643 W 55th St, Chicago, IL 60632

$899,999

— beds— baths— sq ft

3643 W 55th St, Chicago, IL 60632

Property at 215 W 146th St, Riverdale, IL 60827, 3 beds, 1.5 baths

$147,700

3 beds1.5 baths940 sq ft

215 W 146th St, Riverdale, IL 60827

Property at 2712 W North Ave, Chicago, IL 60647

$1,600,000

— beds— baths8,600 sq ft

2712 W North Ave, Chicago, IL 60647

Property at 8406 S Oglesby Ave, Chicago, IL 60617, 4 beds, 2 baths

$299,999

4 beds2 baths1,800 sq ft

8406 S Oglesby Ave, Chicago, IL 60617

Property at 2817 Flossmoor Rd, Flossmoor, IL 60422, 3 beds, 2.5 baths

$246,900

3 beds2.5 baths3,472 sq ft

2817 Flossmoor Rd, Flossmoor, IL 60422

Property at 4606 S Ashland Ave, Chicago, IL 60609

$475,000

— beds— baths— sq ft

4606 S Ashland Ave, Chicago, IL 60609

Property at 7436 S Langley Ave, Chicago, IL 60619, 6 beds, 2 baths

$339,900

6 beds2 baths— sq ft

7436 S Langley Ave, Chicago, IL 60619

Property at 7042 S Eberhart Ave, Chicago, IL 60637, 6 beds, 2.5 baths

$342,000

6 beds2.5 baths2,500 sq ft

7042 S Eberhart Ave, Chicago, IL 60637

Property at 11327 S King Dr, Chicago, IL 60628, 12 beds, 10 baths

$679,000

12 beds10 baths6,627 sq ft

11327 S King Dr, Chicago, IL 60628

Property at 16145 Hermitage Ave, Markham, IL 60428, 3 beds, 1 bath

$159,000

3 beds1 bath1,032 sq ft

16145 Hermitage Ave, Markham, IL 60428

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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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