Gillespie, IL Houses for Sale

/23
$120,000
- 2 Beds
- 1.5 Baths
- 1,320 Sq Ft
307 South St, Gillespie, IL 62033

Back on Market - No Fault to Seller - this charming home is move-in ready with 2-bedrooms & 1-bathroom —perfect for first-time buyers or those looking to comfortably downsize. Nestled in a welcoming community with many amenities, this home offers the ideal blend of convenience, character, and functionality.Inside, you’ll find original hardwood floors in many of the rooms, adding warmth and

Becky Leach

Cisler & Associates Real Estate

(217) 920-0496

307 South St, Gillespie, IL 62033
/37
$39,900
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
709 1st St, Gillespie, IL 62033

Opportunity is knocking with this 2 bed, 2 bath two story home sitting on a spacious lot with a large privacy fenced backyard all just minutes from local baseball fields and the park. Priced at just $39,900, this property offers strong potential for investors or buyers looking to build equity. Inside, you’ll find a surprisingly spacious layout featuring original woodwork, custom wood ceilings,

Curtis Schalk Cisler & Associates Real Estate

709 1st St, Gillespie, IL 62033
/28
$99,900
- 3 Beds
- 1 Bath
- 1,333 Sq Ft
715 Springfield Rd, Gillespie, IL 62033

This charming 2-3 bedroom home presents a wonderful canvas for your imagination, inviting you to dream up a world of comfort and personal style within its walls. The seller has already completed the big tasks for you! There's new plumbing throughout, a new heat exchanger, a new front storm door, water heater, newer appliances, and the roof is approx 10 years old. There's newer vinyl replacement

Melissa Smith MCR Realty Professionals, Inc

715 Springfield Rd, Gillespie, IL 62033
/37
$159,000
- 3 Beds
- 1 Bath
- 1,400 Sq Ft
705 N MacOupin St, Gillespie, IL 62033

Move-in ready and full of charm, this beautifully redone 3-bedroom home offers space, style, and comfort on a desirable oversized corner lot. Step inside to find pristine original wood work as well as hardwood floors that add warmth and character, complemented by fresh updates throughout, including new carpet, a new roof, newer AC unit, and furnace for peace of mind. The spacious layout features

Michael Bellovich RE/MAX Alliance

705 N MacOupin St, Gillespie, IL 62033
/11
$121,500
- 2 Beds
- 1 Bath
- 1,134 Sq Ft
208 Henrietta St, Gillespie, IL 62033

Welcome to your new home!!! This beautifully maintained 2 bedroom, 1 bath 1134 square foot brick home has been waiting for you!! A fenced in backyard with patio space for that outdoor comfort!! A large detached 2 car garage offers great parking out of the elements as well as great space for hobbies! Plenty of storage in the garage to make the most of your space in the home!! Main floor laundry

Scott Schardan Cisler & Associates Real Estate

208 Henrietta St, Gillespie, IL 62033
/24
$179,000
- 3 Beds
- 2 Baths
- 2,759 Sq Ft
301 Montgomery St, Gillespie, IL 62033

Very motivated seller that has made many recent updates and repairs! Check out this corner lot home in Gillespie that has space galore for the growing family including 3 beds on the main level and three large bonus rooms on the second level for a potential for 3 more bedrooms! Also offers 2 full baths, a large family room with fireplace, a full partially finished basement, a large, covered deck

Amy Kline GOODMAN AGENCY INC

301 Montgomery St, Gillespie, IL 62033
/32
$360,000
- 3 Beds
- 2 Baths
- 1,840 Sq Ft
900 Montana St, Gillespie, IL 62033

Welcome to your own slice of quiet on the edge of town! This 3 bed, 2 bath home sits on a beautifully landscaped 2.4-acre corner lot in Gillespie—within city limits but with a peaceful, country feel. Out back, enjoy your heated, ionized inground pool with black steel fencing, a pergola, pool house, and plenty of space to entertain. Inside, the open layout connects the kitchen, dining, and living

Mike Mihelcic RE/MAX Alliance

900 Montana St, Gillespie, IL 62033

Illinois Macoupin County Gillespie

Why Live in Gillespie

Gillespie, located in Macoupin County, Illinois, is a small rural city with a lower cost of living and a commuter lifestyle. Originally established in the 1850s with a strong coal mining presence, Gillespie has evolved into a bedroom community where many residents commute to nearby cities such as Litchfield, 10 miles east, and Springfield, approximately 53 miles north. The city features cost-effective single-family homes along gridded residential streets with gravel alleyways and grassy lawns. Housing styles include minimal traditional single-story homes, bungalows, ranch-style homes from the 1950s to 1970s, split levels, and American Foursquares from the 1920s to 1940s. Gillespie Community Unit School District serves the area, with Gillespie High School offering Career and Technical Education pathways and dual enrollment credits at Lewis and Clark Community College. Recreational features include Big Brick Park with a playground and tennis courts, Welfare Park with baseball fields, and a sports complex with soccer fields. Gillespie Lakes, located 4 miles northwest, provide fishing, boating, swimming, and camping amenities. Downtown Gillespie hosts small businesses and restaurants along Macoupin Street, with additional dining options along Illinois state Route 4. For groceries, residents travel to nearby Benld or Litchfield. Commuting is facilitated by Illinois state Routes 16 and 4, with the St. Louis Lambert International Airport about 62 miles away.

Learn more about living in Gillespie

Home Trends in Gillespie, IL

On average, homes in Gillespie, IL sell after 72 days on the market compared to the national average of 55 days. The median sale price for homes in Gillespie, IL over the last 12 months is $131,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$131,000

Median Single Family Sale Price

$130,000

Average Price Per Sq Ft

$90

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.30

Median List Price

$151,900

Median Change From 1st List Price

Median Home Sale Price YoY Change

11%

How to Buy a Home How to Finance a Home How to Sell a Home

In Gillespie, there are currently 7 houses for sale, offering an array of options for potential buyers. With houses priced between $39,900 to $360,000, there's a range to accomodate every budget. As of April, 2026 the median home price in Gillespie is $151,900, while the average sale price is $122,333, offering insights into the local housing market. On average, houses spend 72 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Gillespie, IL and find the perfect place to call home.

Gillespie Types of Homes for Sale

Gillespie Land for Sale

More About Living in Gillespie

Single-family Homes for Sale in Nearby Cities

Single-family Homes for Sale in Nearby Counties

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