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:
Unlock an incredible opportunity with this unique AS-IS property featuring a storefront space. Upstairs, you'll find a spacious 3-bedroom unit complete with a finished attic that adds a 4th bedroom and a cozy sitting area-ideal for a home office, guest suite. The possibilities here are endless. Whether you're looking to create a daycare center, beauty salon, barber shop, this versatile building is ready to bring your vision to life. Currently No Property Taxes! This property benefits from a church exemption. Perfect for investors, business owners, or creative renovators-don't miss this rare chance to own a property with built-in flexibility.

$199,999

— beds— baths— sq ft

1638 S Pulaski Rd, Chicago, IL 60623

Finished attic • Built-in flexibility • Guest suite

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Attention investors, rehabbers, and visionaries! This 4 bed 2 bath 2 story home in Chicago's West Pullman neighborhood is an opportunity to unlock serious potential. The property requires a full renovation, making it a canvas for a profitable fix-and-flip or a custom renovation for an owner-occupant ready to build instant equity. With its generous footprint and classic two-story layout, the possibilities are wide open to create a modern, high-value home. Whether you're looking to transform it into a stylish residence or maximize resale value, this property offers the kind of upside savvy buyers search for. Bring your contractor, your creativity, and your vision; this is your chance to turn

$45,000

4 beds2 baths1,586 sq ft

11931 S Wallace St, Chicago, IL 60628

Built 1898 • Listed 175 days

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome to this beautifully gut-rehabbed mixed-use property in the heart of Irving Park. An excellent turnkey investment opportunity, this fully-occupied building features stable tenants in place and strong cash flow. Completely updated from top to bottom, the property offers a low-maintenance ownership experience with no upcoming capital expenses and is income-producing from Day One. Located on Irving Park Road at the gateway to I-90/I-94, the property benefits from nearly 30,000 vehicles per day (VPD), providing outstanding visibility and advertising exposure. Zoned B3-1, it is conveniently served by a bus stop at the corner and offers easy access to both the Metra and the Blue Line. Surr

$699,000

— beds— baths— sq ft

3044 W Irving Park Rd, Chicago, IL 60618

Zoned b3-1 • Near horner park • Ample gated parking

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome to 332 Gentry St, a charming split-level home ideally situated on a beautiful corner lot in Park Forest! This 3-bedroom, 2-bath residence offers comfortable living with thoughtful features. Step inside to a spacious living room perfect for relaxation, leading to a functional kitchen equipped with a fridge/freezer, oven with hood, and dishwasher. The adjacent dining room is ideal for everyday meals. The upper level hosts three comfortable bedrooms that share a full bath. The lower level expands your living space with a versatile family room/office space, an additional lower bedroom, and another convenient full bath. You'll also find a spacious laundry room/utilities area and a sump p

$179,000

4 beds2 baths1,188 sq ft

332 Gentry St, Park Forest, IL 60466

Functional kitchen • Two-car garage • Corner lot

$449,999

5 beds3 baths— sq ft

5037 W West End Ave, Chicago, IL 60644

Large backyard • Finished basement • Two car garage

Property at 3024 W Fargo Ave, Chicago, IL 60645, 5 beds, 2.5 baths

$745,000

5 beds2.5 baths— sq ft

3024 W Fargo Ave, Chicago, IL 60645

Property at 18145 Harlem Ave, Tinley Park, IL 60477, 3 beds, 1.5 baths

$439,000

3 beds1.5 baths1,488 sq ft

18145 Harlem Ave, Tinley Park, IL 60477

Property at 7804 S Paxton Ave, Chicago, IL 60649, 4 beds, 3 baths

$400,000

4 beds3 baths2,700 sq ft

7804 S Paxton Ave, Chicago, IL 60649

Property at 4601 184th St, Country Club Hills, IL 60478, 4 beds, 2 baths

$275,000

4 beds2 baths1,806 sq ft

4601 184th St, Country Club Hills, IL 60478

Property at 4523.5 S Drexel Blvd Unit 3W, Chicago, IL 60653, 2 beds, 1 bath

$154,900

2 beds1 bath— sq ft

4523.5 S Drexel Blvd Unit 3W, Chicago, IL 60653

Property at 4763 S Princeton Ave, Chicago, IL 60609, 2 beds, 1 bath

$68,250

2 beds1 bath780 sq ft

4763 S Princeton Ave, Chicago, IL 60609

Property at 5932 S Parnell Ave, Chicago, IL 60621, 5 beds, 2 baths

$259,900

5 beds2 baths— sq ft

5932 S Parnell Ave, Chicago, IL 60621

Property at 531 Wildwood Dr, Park Forest, IL 60466, 3 beds, 1.5 baths

$200,000

3 beds1.5 baths1,472 sq ft

531 Wildwood Dr, Park Forest, IL 60466

Property at 6918 Garden Ln, Bridgeview, IL 60455, 4 beds, 1 bath

$288,000

4 beds1 bath1,126 sq ft

6918 Garden Ln, Bridgeview, IL 60455

Property at 200 E 141st St, Dolton, IL 60419, 3 beds, 1 bath

$65,000

3 beds1 bath1,141 sq ft

200 E 141st St, Dolton, IL 60419

Property at 2717 W Lexington St, Chicago, IL 60612, 5 beds, 3 baths

$237,700

5 beds3 baths— sq ft

2717 W Lexington St, Chicago, IL 60612

Property at 2455 Rhodes Ave, River Grove, IL 60171, 3 beds, 2 baths

$550,000

3 beds2 baths1,719 sq ft

2455 Rhodes Ave, River Grove, IL 60171

Property at 14510 S Emerald Ave, Riverdale, IL 60827, 3 beds, 2 baths

$199,900

3 beds2 baths1,520 sq ft

14510 S Emerald Ave, Riverdale, IL 60827

Property at 17333 Roy St, Lansing, IL 60438, 3 beds, 1 bath

$159,000

3 beds1 bath960 sq ft

17333 Roy St, Lansing, IL 60438

Property at 5738 S Ada St, Chicago, IL 60636, 4 beds, 1 bath

$135,000

4 beds1 bath995 sq ft

5738 S Ada St, Chicago, IL 60636

Property at 6930 S Laflin St, Chicago, IL 60636, 4 beds, 2 baths

$243,000

4 beds2 baths1,392 sq ft

6930 S Laflin St, Chicago, IL 60636

Property at 7601 S Essex Ave #2, Chicago, IL 60649, 2 beds, 1 bath

$85,000

2 beds1 bath1,100 sq ft

7601 S Essex Ave #2, Chicago, IL 60649

Property at 13513 S Baltimore Ave, Chicago, IL 60633, 10 beds, 4 baths

$199,900

10 beds4 baths— sq ft

13513 S Baltimore Ave, Chicago, IL 60633

Property at 8731 S Clyde Ave, Chicago, IL 60617, 4 beds, 3 baths

$229,000

4 beds3 baths1,448 sq ft

8731 S Clyde Ave, Chicago, IL 60617

Property at 6402 S Greenwood Ave, Chicago, IL 60637, 10 beds, 4 baths

$759,000

10 beds4 baths— sq ft

6402 S Greenwood Ave, Chicago, IL 60637

Property at 1773 E 158th St, South Holland, IL 60473, 5 beds, 2 baths

$225,000

5 beds2 baths1,800 sq ft

1773 E 158th St, South Holland, IL 60473

Property at 5105 S Lamon Ave, Chicago, IL 60638, 4 beds, 2 baths

$345,000

4 beds2 baths1,789 sq ft

5105 S Lamon Ave, Chicago, IL 60638

Property at 3553 W 77th St, Chicago, IL 60652, 3 beds, 1 bath

$251,200

3 beds1 bath1,121 sq ft

3553 W 77th St, Chicago, IL 60652

Property at 1463 Speechley Blvd, Berkeley, IL 60163, 4 beds, 1.5 baths

$349,900

4 beds1.5 baths1,628 sq ft

1463 Speechley Blvd, Berkeley, IL 60163

Property at 5638 N Western Ave, Chicago, IL 60659

$599,000

— beds— baths— sq ft

5638 N Western Ave, Chicago, IL 60659

Property at 3704 W 58th St, Chicago, IL 60629, 5 beds, 2 baths

$399,997

5 beds2 baths— sq ft

3704 W 58th St, Chicago, IL 60629

Property at 17246 Burnham Ave, Lansing, IL 60438, 2 beds, 1 bath

$118,000

2 beds1 bath945 sq ft

17246 Burnham Ave, Lansing, IL 60438

Property at 142 Marquette St, Park Forest, IL 60466, 3 beds, 1 bath

$119,000

3 beds1 bath1,000 sq ft

142 Marquette St, Park Forest, IL 60466

Property at 402 S 12th Ave, Maywood, IL 60153, 8 beds, 4 baths

$449,000

8 beds4 baths— sq ft

402 S 12th Ave, Maywood, IL 60153

Property at 15316 Parkside Dr, Markham, IL 60428, 3 beds, 1 bath

$189,900

3 beds1 bath1,113 sq ft

15316 Parkside Dr, Markham, IL 60428

Property at 8740 S Fairfield Ave, Evergreen Park, IL 60805, 3 beds, 1 bath

$160,600

3 beds1 bath640 sq ft

8740 S Fairfield Ave, Evergreen Park, IL 60805

Property at 1527 Wentworth Ave, Calumet City, IL 60409, 4 beds, 1 bath

$119,950

4 beds1 bath1,123 sq ft

1527 Wentworth Ave, Calumet City, IL 60409

Property at 6315 S Eberhart Ave, Chicago, IL 60637, 8 beds, 3 baths

$389,900

8 beds3 baths— sq ft

6315 S Eberhart Ave, Chicago, IL 60637

Property at 5108 S Woodlawn Ave Unit 3G, Chicago, IL 60615, 2 beds, 1 bath

$285,000

2 beds1 bath— sq ft

5108 S Woodlawn Ave Unit 3G, Chicago, IL 60615

Property at 1450 E 55th Pl Unit 720S, Chicago, IL 60637, 2 beds, 2 baths

$170,000

2 beds2 baths1,050 sq ft

1450 E 55th Pl Unit 720S, Chicago, IL 60637

Property at 7751 S Phillips Ave, Chicago, IL 60649, 7 beds, 3.5 baths

$400,000

7 beds3.5 baths— sq ft

7751 S Phillips Ave, Chicago, IL 60649

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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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