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

45 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Macoupin County, IL:
Large corner lot with lovely 3 bedroom, 1 bath home. Home includes large living room, 2 main level bedrooms, and 1 upper level bedroom with wood floors. You will love the large kitchen with plenty of cabinets and counterspace, gas stove, new dishwasher and refrigerator, all ready for large family meals! Property includes a large 24x24 pole barn. Easy access to property from Rt 138.

$199,900

3 beds1 bath1,372 sq ft

101 Mor, Wilsonville, IL 62093

0.57 acre lot • Garage • Built 1917

ABOUT THIS HOME
Vintage Home for sale in Macoupin County, IL:
Welcome to this charming 4-bedroom, 1-bath home nestled in the quiet community of Dorchester, Illinois. This property offers a warm residential living space above a versatile lower-level area with commercial potential, making it an excellent opportunity for homeowners and investors alike. An elevator has been added to allow easy access for moving or handicap access. In addition a stair lift on the main stairs makes getting up and down easy. Upstairs, you’ll find a bright and inviting layout featuring a spacious living room, an eat-in kitchen with ample cabinetry, and four comfortable bedrooms. Large windows throughout provide generous natural light, and the home’s simple, functi

$70,000

4 beds1 bath1,800 sq ft

200 W Garrison St, Dorchester, IL 62033

Direct street access • Elevator • 0.44 acre lot

ABOUT THIS HOME
Vintage Home for sale in Macoupin County, IL:
This home has great curb appeal and so many possibilities. It offers 2 bedrooms on the main level, a large living/dining room combo, kitchen and an attic with additional bedroom. The outside features a detached garage, deck and large yard for all your entertaining needs. If you are willing to put in some work, this may be the one for you. Call your favorite realtor today to schedule an appointment. HUD case number 132-340519 UNINSURED. Owned by the US Department of HUD. Seller makes no representations or warranties as to the condition of property. Seller may contribute up to 3% of buyers closing costs upon buyers request. Sold AS-IS. Equal Housing Opportunity.

$65,000

3 beds1 bath1,350 sq ft

607 E Morgan St, Bunker Hill, IL 62014

Attic • Large yard • Deck

ABOUT THIS HOME
Vintage Home for sale in Macoupin County, IL:
Move-In Ready 4-Bedroom Home! Experience comfort and breathe a bit in this spacious 4-bedroom, 2,100 sq. ft. home with plenty of space for the entire family. You'll love relaxing mornings and peaceful evenings on the enclosed front porch, a charming space perfect for sipping coffee, reading a book, or welcoming guests. With protection from the elements, it’s an ideal spot to unwind while taking in the neighborhood views. Step into the spacious living room, where a cozy fireplace becomes the focal point of the space. The generous layout offers plenty of room for comfortable seating, making it the perfect place to gather with family, entertain friends, or unwind after a long day. Large

$179,000

4 beds1.5 baths2,100 sq ft

305 S Hackman St, Staunton, IL 62088

Welcoming patio area • Main floor laundry • Cozy fireplace

ABOUT THIS HOME
Vintage Home for sale in Macoupin County, IL:
Great investment property or first-time home! Partially redone, so you can add your own touches to the home for finishing. Please call or text agent with any questions. Priced to sell quick with repairs and updates in mind. SELLING AS-IS. Seller to make no repairs.

$36,500

2 beds1 bath1,309 sq ft

622 Francis St, Gillespie, IL 62033

0.32 acre lot • 2 garage spots • Built 1945

Property at 20267 Tall Timber Rd, Staunton, IL 62088, 3 beds, 2 baths

$299,000

3 beds2 baths1,600 sq ft

20267 Tall Timber Rd, Staunton, IL 62088

Property at 123 N Sawyer, Wilsonville, IL 62093, 2 beds, 2 baths

$80,000

2 beds2 baths850 sq ft

123 N Sawyer, Wilsonville, IL 62093

Property at 206 N 7th St, Benld, IL 62009, 2 beds, 1 bath

$39,500

2 beds1 bath1,052 sq ft

206 N 7th St, Benld, IL 62009

Property at 619 E Main St, Staunton, IL 62088, 2 beds, 1 bath

$98,000

2 beds1 bath910 sq ft

619 E Main St, Staunton, IL 62088

Property at 1220 W Henry St, Staunton, IL 62088, 4 beds, 2 baths

$259,000

4 beds2 baths1,800 sq ft

1220 W Henry St, Staunton, IL 62088

Property at 206 N Walnut St, Mount Olive, IL 62069, 3 beds, 1 bath

$64,900

3 beds1 bath1,017 sq ft

206 N Walnut St, Mount Olive, IL 62069

Property at 211 S Lake St, Mount Olive, IL 62069, 3 beds, 1 bath

$159,000

3 beds1 bath1,870 sq ft

211 S Lake St, Mount Olive, IL 62069

Property at 202 E Olive St, Staunton, IL 62088, 3 beds, 1 bath

$167,900

3 beds1 bath1,085 sq ft

202 E Olive St, Staunton, IL 62088

Property at 618 Morgan St, Carlinville, IL 62626, 4 beds, 2 baths

$189,500

4 beds2 baths2,498 sq ft

618 Morgan St, Carlinville, IL 62626

Property at 702 Mayo St, Carlinville, IL 62626, 3 beds, 1 bath

$34,900

3 beds1 bath— sq ft

702 Mayo St, Carlinville, IL 62626

Property at 124 W Prairie St, Staunton, IL 62088, 3 beds, 1 bath

$89,900

3 beds1 bath1,145 sq ft

124 W Prairie St, Staunton, IL 62088

Property at 207 South St, Brighton, IL 62012, 3 beds, 1 bath

$155,000

3 beds1 bath1,680 sq ft

207 South St, Brighton, IL 62012

Property at 311 S Hibbard St, Staunton, IL 62088, 3 beds, 1.5 baths

$205,000

3 beds1.5 baths1,410 sq ft

311 S Hibbard St, Staunton, IL 62088

Property at 207 Brenda Ln, Girard, IL 62640, 2 beds, 1 bath

$99,900

2 beds1 bath1,080 sq ft

207 Brenda Ln, Girard, IL 62640

Property at 1227 W Henry St, Staunton, IL 62088, 3 beds, 1.5 baths

$264,900

3 beds1.5 baths1,317 sq ft

1227 W Henry St, Staunton, IL 62088

Property at 201 N Cherry St, Mount Olive, IL 62069, 2 beds, 1 bath

$69,000

2 beds1 bath1,100 sq ft

201 N Cherry St, Mount Olive, IL 62069

Property at 506 Garfield St, Mount Olive, IL 62069, 4 beds, 1.5 baths

$184,900

4 beds1.5 baths1,538 sq ft

506 Garfield St, Mount Olive, IL 62069

Property at 309 W 3rd South St, Mount Olive, IL 62069, 3 beds, 1 bath

$84,384

3 beds1 bath1,257 sq ft

309 W 3rd South St, Mount Olive, IL 62069

Property at 518 N 2nd St, Girard, IL 62640, 2 beds, 1 bath

$114,000

2 beds1 bath900 sq ft

518 N 2nd St, Girard, IL 62640

Property at 402 S Washington St, Bunker Hill, IL 62014, 2 beds, 1 bath

$99,900

2 beds1 bath950 sq ft

402 S Washington St, Bunker Hill, IL 62014

Property at 709 Mayo, Carlinville, IL 62626, 3 beds, 1.5 baths

$104,000

3 beds1.5 baths1,807 sq ft

709 Mayo, Carlinville, IL 62626

Property at 307 N East St, Carlinville, IL 62626, 3 beds, 2 baths

$187,185

3 beds2 baths1,728 sq ft

307 N East St, Carlinville, IL 62626

Property at 418 E Elm St, Gillespie, IL 62033, 2 beds, 1.5 baths

$47,900

2 beds1.5 baths1,081 sq ft

418 E Elm St, Gillespie, IL 62033

Property at 312 N Main St, Medora, IL 62063, 3 beds, 1 bath

$85,000

3 beds1 bath900 sq ft

312 N Main St, Medora, IL 62063

Property at 802 E Pleasant St, Bunker Hill, IL 62014, 3 beds, 1.5 baths

$129,900

3 beds1.5 baths1,678 sq ft

802 E Pleasant St, Bunker Hill, IL 62014

Property at 709 1st St, Gillespie, IL 62033, 2 beds, 2 baths

$50,000

2 beds2 baths1,119 sq ft

709 1st St, Gillespie, IL 62033

Property at 207 W Vine St, Brighton, IL 62012, 2 beds, 2 baths

$238,000

2 beds2 baths1,200 sq ft

207 W Vine St, Brighton, IL 62012

Property at 619 E Main St, Carlinville, IL 62626, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths3,000 sq ft

619 E Main St, Carlinville, IL 62626

Property at 418 E Maple St, Gillespie, IL 62033, 3 beds, 2 baths

$184,900

3 beds2 baths1,550 sq ft

418 E Maple St, Gillespie, IL 62033

Property at 114 W 2nd South St, Mount Olive, IL 62069, 1 bed, 1 bath

$55,000

1 bed1 bath1,200 sq ft

114 W 2nd South St, Mount Olive, IL 62069

Property at 525 Denby St, Carlinville, IL 62626, 2 beds, 1 bath

$49,500

2 beds1 bath728 sq ft

525 Denby St, Carlinville, IL 62626

Property at 841 N Franklin St, Staunton, IL 62088, 3 beds, 2 baths

$190,000

3 beds2 baths1,400 sq ft

841 N Franklin St, Staunton, IL 62088

Property at 209 Charles St, Gillespie, IL 62033, 3 beds, 2.5 baths

$160,000

3 beds2.5 baths1,500 sq ft

209 Charles St, Gillespie, IL 62033

Property at 107 Richard St, Gillespie, IL 62033, 3 beds, 1.5 baths

$71,900

3 beds1.5 baths1,286 sq ft

107 Richard St, Gillespie, IL 62033

Property at 212 E Main St, Carlinville, IL 62626, 3 beds, 1.5 baths

$250,000

3 beds1.5 baths3,784 sq ft

212 E Main St, Carlinville, IL 62626

Property at 619 S Wood St, Staunton, IL 62088, 4 beds, 2 baths

$226,500

4 beds2 baths1,850 sq ft

619 S Wood St, Staunton, IL 62088

Viewing page 1 of 2

Based on information submitted to the MLS GRID as of Thu Dec 04 2025. 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 Macoupin County

There are currently 45 vintage homes for sale in Macoupin County at a median listing price of $175K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Macoupin County stay on the market for 59 days. This map is refreshed with the newest listings in Macoupin County every 15 minutes.

In the past month, 19 homes have been sold in Macoupin County. In addition to houses in Macoupin County, there was also 1 condo, 1 townhouse, and 1 multi-family unit for sale in Macoupin County last month. Find your dream home in Macoupin 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 Macoupin County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Macoupin County. If you're looking to sell your home in the Macoupin County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Macoupin County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Macoupin County, IL

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Macoupin County, IL

How to buy a house in Macoupin County, IL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Illinois

Chicago homes for sale
$345,000
Naperville homes for sale
$644,500
Schaumburg homes for sale
$299,900
Arlington Heights homes for sale
$430,000
Glenview homes for sale
$754,500
Oak Park homes for sale
$350,000
Evanston homes for sale
$425,000
Des Plaines homes for sale
$387,000
Orland Park homes for sale
$379,900
Downers Grove homes for sale
$495,000
Mount Prospect homes for sale
$434,500
St. Charles homes for sale
$460,000
Skokie homes for sale
$439,000
Glen Ellyn homes for sale
$565,000
Northbrook homes for sale
$619,900

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.