11

Gillespie, IL Homes for Sale

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  • 1103 Madison St, Gillespie, IL 62033
    1103 Madison St, Gillespie, IL 62033
    1103 Madison St, Gillespie, IL 62033
    /14

    $74,900

    • 2 Beds
    • 1 Bath
    • 874 Sq Ft

    1103 Madison St, Gillespie, IL 62033

    Welcome Home! Recently updated and move-in ready, this charming 2-bedroom, 1-bath home has been thoughtfully upgraded for your convenience. Major improvements, including a new roof, siding, furnace, air conditioner, and more, have been completed in the past 2 years, giving you peace of mind. Step outside to enjoy the low-maintenance yard, complete with a storage shed for tools and lawn equipment,

    Agent Photo

    Matthew Cisler

    Cisler & Associates Real Estate

    (217) 952-1799

    1103 Madison St, Gillespie, IL 62033
  • 0 Maple & Clinton St Unit MAR24065949, Gillespie, IL 62033
    0 Maple & Clinton St Unit MAR24065949, Gillespie, IL 62033
    /2

    $10,000

    • Land
    • 0.40 Acre
    • $25,000 per Acre

    0 Maple & Clinton St Unit MAR24065949, Gillespie, IL 62033

    Build your own home on this corner lot in Gillespie.

    Agent Photo

    Kimberly Hunt

    360 Prime Realty Group, LLC

    (217) 833-8850

    0 Maple & Clinton St Unit MAR24065949, Gillespie, IL 62033
  • 14502 Deerfield Dr, Gillespie, IL 62033
    14502 Deerfield Dr, Gillespie, IL 62033
    14502 Deerfield Dr, Gillespie, IL 62033
    /32

    $409,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    14502 Deerfield Dr, Gillespie, IL 62033

    Charming Ranch-Style Retreat on 10 Acres with Private Pond. Discover peace, privacy, and modern comfort in this beautifully maintained 3-bedroom, 2-bath ranch-style home nestled on a picturesque 10-acre wooded lot. Perfectly blending rustic charm with contemporary living, this open-concept home offers everything you need for everyday comfort and year-round relaxation. Step inside to a spacious

    Mark Roberts RE/MAX Alliance

    14502 Deerfield Dr, Gillespie, IL 62033
  • 209 Charles St, Gillespie, IL 62033
    209 Charles St, Gillespie, IL 62033
    209 Charles St, Gillespie, IL 62033
    /30

    $224,999

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    209 Charles St, Gillespie, IL 62033

    Fully Remodeled 3-Bed, 2.5-Bath Home with Oversized Garage & Loft!This stunning home has been completely renovated from top to bottom—featuring a new roof, AC, siding, fascia, soffit, garage door, privacy fence, lighting, cabinets, flooring, and appliances. The spacious living room includes a fireplace and large windows overlooking a private, fenced yard. The open-concept dining/living space

    Mark Roberts RE/MAX Alliance

    209 Charles St, Gillespie, IL 62033
  • 900 Montana St, Gillespie, IL 62033
    900 Montana St, Gillespie, IL 62033
    900 Montana 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
  • 300 W Baker St, Gillespie, IL 62033
    300 W Baker St, Gillespie, IL 62033
    300 W Baker St, Gillespie, IL 62033
    /20

    $99,500 Open Wed 5PM - 7PM

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    300 W Baker St, Gillespie, IL 62033

    Very nice remodeled and fully updated 2 bedroom and 1 bath home on large corner lot. Home features all new floors, windows, HVAC system, fresh paint new dry wall and new appliances. Enter into a nice living room with nice windows and plenty of space for multiple layouts. The large eat in kitchen features new white cabinets and countertops. This has main level laundry and room for tables and

    Mark Roberts RE/MAX Alliance

    300 W Baker St, Gillespie, IL 62033
  • 418 E Maple St, Gillespie, IL 62033
    418 E Maple St, Gillespie, IL 62033
    418 E Maple St, Gillespie, IL 62033
    /30

    $184,900

    • 3 Beds
    • 2 Baths
    • 1,550 Sq Ft

    418 E Maple St, Gillespie, IL 62033

    Back on market at no fault of seller! Welcome home to 418 Maple St! This beautifully maintained 3-bedroom, 2-bath ranch home is perfectly situated on a large corner lot in a quiet, friendly neighborhood. Offering seamless open flow between kitchen, dining, and living spaces, this home combines comfort, functionality, and space for future growth. Primary bedroom offers a large walk in closet and

    Andrew Milkovich RE/MAX Alliance

    418 E Maple St, Gillespie, IL 62033
  • 506 W Walnut St, Gillespie, IL 62033
    506 W Walnut St, Gillespie, IL 62033
    506 W Walnut St, Gillespie, IL 62033
    /25

    $119,000

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    506 W Walnut St, Gillespie, IL 62033

    Welcome to this charming 2-bedroom, 1-bath home. From the moment you step inside, you'll fall in love with the character and warmth this home offers. The spacious living room and bedrooms boast beautiful original wood floors, an eye-catching exposed brick column, and tall ceilings that create an open feeling throughout. The front bay window floods the living space with natural light, making it

    Matt Garrison The Real Estate Group, Inc.

    506 W Walnut St, Gillespie, IL 62033
  • 525 Park Ave, Gillespie, IL 62033
    525 Park Ave, Gillespie, IL 62033
    /2

    $13,500

    • Land
    • 0.47 Acre
    • $28,908 per Acre

    525 Park Ave, Gillespie, IL 62033

    Are you looking for a lot that you could build a new house or garage on? Then this may be the opportunity for you. This lot boasts slightly under half an acre of space that can be used. It is also located in a convenient spot only 15 minutes from Staunton, Litchfield, and Carlinville. Do not let this opportunity pass by you, reach out to an agent today and take a tour of this lot.

    Jon Daugherty Cisler & Associates Real Estate

    525 Park Ave, Gillespie, IL 62033
  • 201 Southern St, Gillespie, IL 62033
    201 Southern St, Gillespie, IL 62033
    /2

    $7,500

    • Land
    • 0.30 Acre
    • $25,008 per Acre

    201 Southern St, Gillespie, IL 62033

    Mark Roberts RE/MAX Alliance

    201 Southern St, Gillespie, IL 62033
  • 16 State Route, Gillespie, IL 62033
    16 State Route, Gillespie, IL 62033
    16 State Route, Gillespie, IL 62033
    /6

    $10,000

    • Land
    • 1.50 Acres
    • $6,667 per Acre

    16 State Route, Gillespie, IL 62033

    Price listed is Starting Bid Only. Bidding starts closing Thurs., Aug. 28, 2025 at 6:30PM. Opportunity knocks with this 1.5± acre commercial lot located in Gillespie, IL! The property is located directly off the intersection of IL Route 16 and Springfield Road with a combined AADT of approximately 12,700+/- vehicles per day. This mostly level corner parcel offers exceptional visibility and

    Adam Jokisch Adams Auction & Real Estate Services Inc.

    16 State Route, Gillespie, IL 62033
Illinois Macoupin County Gillespie

Real Estate & Homes for Sale in Gillespie, IL

Frequently Asked Questions Why Live in Gillespie

What is the average home price in Gillespie, IL?
Homes for sale in Gillespie, IL have an average home price of $141,313.
How many homes have sold over the last 12 months in Gillespie, IL?
15 homes have sold in Gillespie, IL over the last 12 months.
What are the most popular zip codes in Gillespie, IL?
The most popular zip codes in Gillespie, IL include 62033, 62009, 62069, 62056 and 62088.
How much do you need to make to afford a house in Gillespie?
The median home price in Gillespie is $189,900. If you put a 20% down payment of $38,000 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $970 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $42K a year to afford the median home price in Gillespie.
How are the schools in Gillespie, IL?
Gillespie, IL has highly rated public and private schools. Some of the best schools in Gillespie based on Niche Grades are Ben-Gil Elementary School, Gillespie High School and Gillespie Middle School. Browse all the schools in Gillespie, IL to learn more.
Learn more about living in Gillespie

Home Trends in Gillespie, IL

On average, homes in Gillespie, IL sell after 87 days on the market compared to the national average of 70 days. The median sale price for homes in Gillespie, IL over the last 12 months is $132,000, up 50% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$132,000
Median Single Family Sale Price
$132,000
Average Price Per Sq Ft
$51
Number of Homes for Sale
0
Last 12 months Home Sales
15
Months of Supply
0.00
Median List Price
$189,900
Median Change From 1st List Price
30%
Median Home Sale Price YoY Change
50%
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