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

4,702 homes + 196 early access

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ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Calling ALL INVESTORS! Tenant occupied with a 2 years lease paying full market rent. Beautiful Brick Bungalow that has been completely renovated includes 5 bedrooms 3 baths. All new updated plumbing and electric. New Windows throughout. High End finishes in bathrooms. Full finished basement with epoxy floors including a family room. High End stainless steel appliances, newly updated HVAC. Gated entry on property. This is a Must See!!!

$330,000

5 beds3 baths1,396 sq ft

8640 S Blackstone Ave, Chicago, IL 60619

Completely renovated • Gated entry • New updated plumbing

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Turnkey 6-unit greystone. - all six units leased. Fixed-term leases in place into 2027 for stability, with near-term rent upside on the month-to-month units. This property has 15 bedrooms and 6 bathrooms. New roof, rebuilt rear porch, two water heaters, tuckpointing, rear concrete parking pad, and refreshed units with refinished hardwood. CHA/Section 8 approved building-wide - dependable, government-backed rent. The 2024 Cook County reassessment is already appealed and resolved, with taxes documented through the current cycle. Finances cleanly via DSCR/commercial and covers debt service with room to spare. Full rent roll and P & L available to qualified buyers.

$739,000

15 beds6 baths5,900 sq ft

1264 S Saint Louis Ave, Chicago, IL 60623

Tuckpointing • 6 unit greystone • Rebuilt rear porch

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Excellent investment opportunity in Chicago's Chatham neighborhood. This solid brick 2-Flat multifamily property offers strong income potential and value-add upside. The building features spacious residential units, a full basement unit, and sits on a generous city lot. Conveniently located near public transportation, major thoroughfares, shopping, schools, and neighborhood amenities. Ideal for investors seeking to expand their portfolio or owner-occupants looking to offset housing costs with rental income. Property is being sold as-is. Schedule your private tour and explore the potential this South Side asset has to offer.

$371,900

8 beds3 baths— sq ft

8052 S Langley Ave, Chicago, IL 60619

Solid brick 2-flat • Value-add upside • Chatham neighborhood

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
Welcome home to this bright and inviting 2-bedroom, 2-bathroom condominium featuring an open-concept layout, soaring ceilings, and contemporary finishes throughout. Designed for comfortable everyday living, this home offers generous living spaces, abundant storage, and a functional floor plan perfect for both relaxing and entertaining. The spacious kitchen is the heart of the home, showcasing granite countertops, abundant maple cabinetry, black appliances, a breakfast bar, and plenty of prep space. It flows seamlessly into the expansive living and dining area, creating an ideal setting for hosting friends or enjoying a quiet evening at home. The primary suite features a private en-suite bat

$309,000

2 beds2 baths1,065 sq ft

8 W Monroe St #808, Chicago, IL 60603

Large walk-in closet • Granite countertops • Breakfast bar

ABOUT THIS HOME
Vintage Home for sale in Cook County, IL:
INVESTORS a fantastic opportunity for extra income with long term tenants, separate utilities ( except water). This 2 unit with a side lot is the perfect to expand or start your real estate portfolio. Each unit is 2 bedroom, 1 full bathroom, living room, located near schools, expressway access call for your appointment today.

$179,000

4 beds2 baths— sq ft

13228 S Houston Ave, Chicago, IL 60633

Extra income • Near schools • Expressway access

Property at 4355 W Le Moyne St, Chicago, IL 60651, 3 beds, 2 baths

$549,000

3 beds2 baths— sq ft

4355 W Le Moyne St, Chicago, IL 60651

Property at 227 W 146th St, Dolton, IL 60419, 3 beds, 1 bath

$140,000

3 beds1 bath1,170 sq ft

227 W 146th St, Dolton, IL 60419

Property at 4200 W Hirsch St, Chicago, IL 60651, 18 beds, 41 baths

$1,200,000

18 beds41 baths— sq ft

4200 W Hirsch St, Chicago, IL 60651

Property at 16454 Winchester Ave, Markham, IL 60428, 3 beds, 1 bath

$180,000

3 beds1 bath1,050 sq ft

16454 Winchester Ave, Markham, IL 60428

Property at 16905 S Crane Ave, Hazel Crest, IL 60429, 5 beds, 1.5 baths

$255,000

5 beds1.5 baths1,740 sq ft

16905 S Crane Ave, Hazel Crest, IL 60429

Property at 8659 S Kingston Ave, Chicago, IL 60617

$225,000

— beds— baths— sq ft

8659 S Kingston Ave, Chicago, IL 60617

Property at 6816 S Cornell Ave, Chicago, IL 60649, 19 beds, 7 baths

$1,200,000

19 beds7 baths— sq ft

6816 S Cornell Ave, Chicago, IL 60649

Property at 2646 E 77th St, Chicago, IL 60649, 3 beds, 3.5 baths

$299,000

3 beds3.5 baths1,789 sq ft

2646 E 77th St, Chicago, IL 60649

Property at 14221 S Edbrooke Ave, Riverdale, IL 60827, 3 beds, 1.5 baths

$72,725

3 beds1.5 baths1,300 sq ft

14221 S Edbrooke Ave, Riverdale, IL 60827

Property at 18032 Commercial Ave, Lansing, IL 60438, 2 beds, 1 bath

$180,000

2 beds1 bath1,062 sq ft

18032 Commercial Ave, Lansing, IL 60438

Property at 1513 W 87th St, Chicago, IL 60620, 8 beds, 11 baths

$950,000

8 beds11 baths— sq ft

1513 W 87th St, Chicago, IL 60620

Property at 7914 S Dobson Ave, Chicago, IL 60619, 16 beds, 13 baths

$1,100,000

16 beds13 baths— sq ft

7914 S Dobson Ave, Chicago, IL 60619

Property at 91 Winslow St, Park Forest, IL 60466, 3 beds, 2 baths

$199,900

3 beds2 baths1,505 sq ft

91 Winslow St, Park Forest, IL 60466

Property at 8017 S Hermitage Ave, Chicago, IL 60620, 4 beds, 2 baths

$407,900

4 beds2 baths— sq ft

8017 S Hermitage Ave, Chicago, IL 60620

Property at 8935 S Cregier Ave, Chicago, IL 60617, 2 beds, 2 baths

$228,850

2 beds2 baths1,060 sq ft

8935 S Cregier Ave, Chicago, IL 60617

Property at 140 W 66th St Unit G, Chicago, IL 60621, 3 beds, 1 bath

$200,000

3 beds1 bath1,000 sq ft

140 W 66th St Unit G, Chicago, IL 60621

Property at 6219 S Rhodes Ave, Chicago, IL 60637, 22 beds, 12 baths

$1,100,000

22 beds12 baths— sq ft

6219 S Rhodes Ave, Chicago, IL 60637

Property at 1700 Euclid Ave, Chicago Heights, IL 60411, 3 beds, 2 baths

$235,000

3 beds2 baths— sq ft

1700 Euclid Ave, Chicago Heights, IL 60411

Property at 6743 S Carpenter St, Chicago, IL 60621, 4 beds, 2 baths

$180,000

4 beds2 baths998 sq ft

6743 S Carpenter St, Chicago, IL 60621

Property at 140 W 66th St Unit 1R, Chicago, IL 60621, 3 beds, 1 bath

$250,000

3 beds1 bath969 sq ft

140 W 66th St Unit 1R, Chicago, IL 60621

Property at 140 W 66th St Unit 2R, Chicago, IL 60621, 3 beds, 1 bath

$250,000

3 beds1 bath969 sq ft

140 W 66th St Unit 2R, Chicago, IL 60621

Property at 140 W 66th St Unit 2F, Chicago, IL 60621, 3 beds, 1 bath

$225,000

3 beds1 bath1,000 sq ft

140 W 66th St Unit 2F, Chicago, IL 60621

Property at 1721 S Cumberland Ave, Park Ridge, IL 60068, 4 beds, 3 baths

$725,000

4 beds3 baths3,266 sq ft

1721 S Cumberland Ave, Park Ridge, IL 60068

Property at 747 N Sedgwick St Unit 4RS, Chicago, IL 60654, 2 beds, 2 baths

$485,000

2 beds2 baths1,500 sq ft

747 N Sedgwick St Unit 4RS, Chicago, IL 60654

Property at 867 W Cornelia Ave #1, Chicago, IL 60657, 3 beds, 2 baths

$575,000

3 beds2 baths1,400 sq ft

867 W Cornelia Ave #1, Chicago, IL 60657

Property at 20 N State St #1013, Chicago, IL 60602, 1 bed, 1 bath

$275,000

1 bed1 bath— sq ft

20 N State St #1013, Chicago, IL 60602

Property at 6030 N Sheridan Rd #803, Chicago, IL 60660, 1 bed, 1 bath

$164,000

1 bed1 bath750 sq ft

6030 N Sheridan Rd #803, Chicago, IL 60660

Property at 1750 N Wolcott Ave #304, Chicago, IL 60622, 2 beds, 2 baths

$1,150,000

2 beds2 baths2,200 sq ft

1750 N Wolcott Ave #304, Chicago, IL 60622

Property at 5052 S Blackstone Ave #2, Chicago, IL 60615, 3 beds, 1 bath

$249,000

3 beds1 bath1,000 sq ft

5052 S Blackstone Ave #2, Chicago, IL 60615

Property at 633 S Plymouth Ct #702, Chicago, IL 60605, 1 bed, 1.5 baths

$299,990

1 bed1.5 baths1,505 sq ft

633 S Plymouth Ct #702, Chicago, IL 60605

Property at 1640 Butler St, Chicago Heights, IL 60411, 3 beds, 1 bath

$95,000

3 beds1 bath700 sq ft

1640 Butler St, Chicago Heights, IL 60411

Property at 389 W 12th St, Chicago Heights, IL 60411, 3 beds, 1 bath

$150,000

3 beds1 bath1,029 sq ft

389 W 12th St, Chicago Heights, IL 60411

Property at 55 Apple Ln, Park Forest, IL 60466, 3 beds, 1 bath

$145,000

3 beds1 bath1,374 sq ft

55 Apple Ln, Park Forest, IL 60466

Property at 317 Mohawk St, Park Forest, IL 60466, 2 beds, 1 bath

$143,000

2 beds1 bath1,000 sq ft

317 Mohawk St, Park Forest, IL 60466

Property at 2612 Central Dr Unit 1N, Flossmoor, IL 60422, 2 beds, 2 baths

$115,000

2 beds2 baths1,200 sq ft

2612 Central Dr Unit 1N, Flossmoor, IL 60422

Property at 2634 Central Dr Unit 2E, Flossmoor, IL 60422, 2 beds, 2 baths

$165,000

2 beds2 baths1,000 sq ft

2634 Central Dr Unit 2E, Flossmoor, IL 60422

Viewing page 78 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 4898 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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