26

Gillespie, IL Homes for Sale

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  • /32

    $94,000

    $5K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,895 Sq Ft

    607 Springfield Rd, Gillespie, IL 62033

    Calling all rehab enthusiasts and buyers with vision! This spacious 2-story home offers timeless charm, generous living space, and beautiful original woodwork throughout many rooms. The property includes a large primary bath with jetted tub and separate shower, formal dining room, breakfast area, whole house generator, and a sprawling 1-acre lot with plenty of room to create your dream outdoor

    Agent Photo

    Kimberly Hunt

    360 Prime Realty Group, LLC

    (217) 645-1826

    607 Springfield Rd, Gillespie, IL 62033
  • /14

    $74,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    911 Madison St, Gillespie, IL 62033

    This 2-bedroom, 1-bath home offers comfortable living on a spacious corner lot. The oversized 2-car garage is heated and cooled, providing endless possibilities for projects, entertaining, or extra workspace.

    Agent Photo

    Jenny Wisniewski

    Landmark Realty

    (217) 582-6559

    911 Madison St, Gillespie, IL 62033
  • /2

    $5,000

    • Land
    • 7,501 Sq Ft
    • $29,036 per Acre

    TBD Maple & Clinton, Gillespie, IL 62033

    Great opportunity to build! These two adjoining residential lots include a corner lot plus the neighboring parcel, offering extra space and flexibility for your future plans. Relatively flat and ready for development with plenty of room for a custom home, garage, or additional outdoor space. Convenient location with endless potential!

    Agent Photo

    Kimberly Hunt

    360 Prime Realty Group, LLC

    (217) 863-1884

    TBD Maple & Clinton, Gillespie, IL 62033
  • /12

    $125,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    905 Madison St, Gillespie, IL 62033

    Welcome home to this beautifully maintained newer construction in Gillespie! Built in 2019/2020 on the existing crawl space, this move-in ready 3 bedroom, 1 bath home still shows like new. The open floor plan offers a spacious feel perfect for everyday living and entertaining. Kitchen features cherry-toned cabinetry, quartz countertops, stainless steel appliances, and ample storage. Durable

    Agent Photo

    Kimberly Hunt

    360 Prime Realty Group, LLC

    (217) 759-1458

    905 Madison St, Gillespie, IL 62033
  • /20

    $49,900

    • 2 Beds
    • 1.5 Baths
    • 1,081 Sq Ft

    418 E Elm St, Gillespie, IL 62033

    UNLOCK THIS HOME'S POTENTIAL! This 2-bedroom home in Gillespie offers a great chance to build equity with several key updates already started. Recent improvements include updated electrical work and new PEX water lines, giving you a solid foundation to continue bringing this property to life. Step inside and you’re welcomed by a spacious living room, with a well-sized bedroom just off the main

    Agent Photo

    Matthew Cisler

    Cisler & Associates Real Estate

    (217) 439-4731

    418 E Elm St, Gillespie, IL 62033
  • /19

    $62,900

    • Land
    • 5.17 Acres
    • $12,166 per Acre

    000 Tower Rd, Gillespie, IL 62033

    This is an amazing opportunity to position your investment for future potential with this 5.17 acre vacant farmland in Gillespie, IL. Located within city limits and actively farmed for corn and soybeans, this Macoupin County acreage offers productive ground, dual-road access, and flexibility for agricultural use, long-term investment, or future development. This property features flat topography

    Joe Cebuhar Whitetail Properties Real Estate

    000 Tower Rd, Gillespie, IL 62033
  • /178

    $2,232,036

    • Land
    • 268.92 Acres
    • $8,300 per Acre

    000 Walker Rd, Gillespie, IL 62033

    This amazing Macoupin County property has been cared for greatly by its current owner for over 10 years. This one is keyed up, ready to go and has the history to prove it. The trail system, food plots, ponds, stands, and income have all been established on this property. Pulling down the locked remote lane, you are greeted with an impressive pond full of bluegill, bass and crappie. Next to the

    Joe Cebuhar Whitetail Properties Real Estate

    000 Walker Rd, Gillespie, IL 62033
  • /21

    $399,900

    • Land
    • 2.44 Acres
    • $163,893 per Acre

    2630 Staunton Rd, Gillespie, IL 62033

    2.44 acres of land along St Rt 4 formerly Toni's Family Restaurant. This property has a lot to offer! Large parking area. Seating for approximately 150. Banquet room. 4200 sq feet building. Seller is offering a lease option.

    Gary Niemeier Legacy Realty & Auction LLC

    2630 Staunton Rd, Gillespie, IL 62033
  • /41

    $169,500

    Open House 6/28 $6K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft

    701 E Chestnut St, Gillespie, IL 62033

    Check out this charming home on a corner lot, fenced in back yard, and an inground pool for relaxing on those hot summer evenings. The owner has devoted a considerable amount of time for improvements, which include a new roof in 2023, remodeled bath, newer flooring and extensive work on the detached garage. This 2 bed, 1 bath home maintains much of the original charm but with modern day

    Steve Mcgartland Tarrant and Harman Real Estate and Auction Co

    701 E Chestnut St, Gillespie, IL 62033
  • /22

    $209,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,002 Sq Ft

    407 E Spruce St, Gillespie, IL 62033

    Beautifully updated 3-bedroom, 2-bath home that is truly move-in ready! This home features many modern updates, including a new roof, new siding, new flooring, and fresh paint throughout the entire home. The fully updated main floor living space offers both comfort and style, along with a separate dining area perfect for entertaining. The remodeled kitchen features newer appliances, all just 1

    Michael Bellovich RE/MAX Alliance

    407 E Spruce St, Gillespie, IL 62033
  • /3

    $15,000

    • Land
    • 8,712 Sq Ft
    • $75,000 per Acre

    305 Shelby St, Gillespie, IL 62033

    Prime corner lot available at 305 Shelby in Gillespie! This well-maintained residential parcel features lush, established grass and a clean layout—making it an ideal setting to build your dream home. Positioned on a desirable corner, located in a quiet neighborhood with a welcoming small-town feel. Utilities available (verify with city), making your building process even smoother. Whether you're

    Melissa Quinones RE/MAX Alliance

    305 Shelby St, Gillespie, IL 62033
  • /21

    $150,000

    • 3 Beds
    • 1 Bath
    • 1,376 Sq Ft

    410 Henry St, Gillespie, IL 62033

    Welcome to this charming 3-bedroom, 1-bath home featuring modern updates and inviting outdoor space. The remodeled kitchen and bathroom offer stylish finishes and a fresh, move-in-ready feel.Step outside to enjoy the covered back patio, perfect for relaxing or entertaining, all within a fenced-in backyard that provides privacy and space for pets or play. The 2-car detached garage adds

    Kylie Dickinson RE/MAX Alliance

    410 Henry 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
  • /35

    $149,999

    Open Sat 11AM - 1PM $9K PRICE DROP
    • 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
  • /37

    $30,000

    $10K PRICE DROP Pending
    • 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
  • /5

    $25,000

    • Land
    • 1.15 Acres
    • $21,739 per Acre

    xxx Tortoise Trail, Gillespie, IL 62033

    Build your dream home on this beautiful 1+ acre lot in a prime location. Nestled just outside of town in the desirable Turtle Creek Estates, this property offers the perfect blend of peaceful surroundings and everyday convenience. This exclusive subdivision consists of only 14 homesites, creating a quiet, quaint setting with a sense of privacy and space. The neighborhood welcomes you with a

    Christina Schmitz RE/MAX Alliance

    xxx Tortoise Trail, Gillespie, IL 62033
  • /15

    $95,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    1005 S MacOupin St, Gillespie, IL 62033

    This two story bungalow on corner lot with some fencing and large yard for gardening. Inside you will find an open living room with big picture window and open to kitchen. The kitchen features a breakfast bar and large counter space that opens up to rest of house. The kitchen has large pantry area and includes all appliances. The lower level bedroom features nice closet and convenient to rest of

    Mark Roberts RE/MAX Alliance

    1005 S MacOupin St, Gillespie, IL 62033
  • /16

    $54,900

    $8K PRICE DROP
    • Land
    • 5.17 Acres
    • $10,619 per Acre

    0 Tower Rd, Gillespie, IL 62033

    Position your investment in the path of future potential with this 5.17-acre vacant farmland opportunity in Gillespie, IL. Located within city limits and actively farmed for corn and soybeans, this Macoupin County acreage offers productive ground, dual-road access, and flexibility for agricultural use, long-term investment, or future development. This property features flat topography and direct

    Joe Cebuhar Whitetail Properties Real Esta

    0 Tower Rd, Gillespie, IL 62033
  • /12

    $50,000

    • 3 Beds
    • 1.5 Baths
    • 1,124 Sq Ft

    603 E Chestnut St, Gillespie, IL 62033

    Investor or Handyman Opportunity!Bring your vision and finishing touches to this promising property. This home is a blank slate and has already seen several major improvements and is ready for completion. The current layout is designed for 3 bedrooms and 1.5 bathrooms, offering plenty of potential for a homeowner or investor.Recent updates include a new roof, black soffit, new windows,

    Anna Schweppe RE/MAX Alliance

    603 E Chestnut St, Gillespie, IL 62033
  • /41

    $215,000

    Open Sun 12PM - 1:30PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    503 W Chestnut St, Gillespie, IL 62033

    Checkout this amazing restoration, this 3 bed, 2 full bath home has all the bells and whistles on a quiet street. Home features, new everything, from roof, siding, windows, kitchen cabinets, solid surface countertops, new appliances, trim doors, both bathrooms are new including all fixtures and custom items, new HVAC, wiring, plumbing, water heater, flooring, lighting, outside has all been

    Jared Childress Market Pro Realty, Inc

    503 W Chestnut St, Gillespie, IL 62033
  • /2

    $7,000

    • Land
    • 6,534 Sq Ft
    • $46,667 per Acre

    302 E Elm St, Gillespie, IL 62033

    Nice corner lot on main route in Gillespie. Easy access to shopping, downtown and schools. Lot is ready for construction.

    Mark Roberts RE/MAX Alliance

    302 E Elm St, Gillespie, IL 62033
  • /29

    $129,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,375 Sq Ft

    208 E Elm St, Gillespie, IL 62033

    Welcome home to this solid and nicely maintained 1.5-story charmer offering 3 bedrooms and a full bath! Step inside to find a spacious living room with plenty of room for a small dining area, plus an inviting kitchen featuring attractive cabinetry and stainless steel appliances—the refrigerator, stove, dishwasher, washer & dryer all stay. You'll love the tastefully updated full bathroom! Two

    Mike Mihelcic RE/MAX Alliance

    208 E Elm St, Gillespie, IL 62033
  • /26

    $115,000

    $4K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    506 W Walnut St, Gillespie, IL 62033

    We are back!!! The basement has been professionally stabilized, providing a solid foundation, and peace of mind for years to come. Welcome to this charming two bedroom, one bath home in Gillespie, IL on an oversized lot. 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,

    Matt Garrison The Real Estate Group, Inc.

    506 W Walnut St, Gillespie, IL 62033
  • /2

    $12,500

    • Land
    • 13,063 Sq Ft
    • $41,681 per Acre

    201 Southern St, Gillespie, IL 62033

    Cleared ready to build on residential lot in Gillespie off Route 4. Land is flat and cleared and on large corner lot.

    Mark Roberts RE/MAX Alliance

    201 Southern St, Gillespie, IL 62033
  • /38

    $112,000

    • 2 Beds
    • 1 Bath
    • 1,135 Sq Ft

    1001 S MacOupin St, Gillespie, IL 62033

    Very well maintained 2 bedroom, 1 bath home has had extensive renovations in 2021. Home has lots of windows providing an abundance of natural light. Kitchen includes center island and a door leading to nice fenced backyard. Detached garage with newly rocked driveway that offers additional parking for two more vehicles. Situated on nice corner lot.

    Jackie Sumpter Landmark Realty

    1001 S MacOupin St, Gillespie, IL 62033
  • /32

    $360,000

    $10K PRICE DROP
    • 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

Frequently Asked Questions

What is the average home price in Gillespie, IL?
Homes for sale in Gillespie, IL have an average home price of $144,320.
Are home prices dropping in Gillespie?
Yes, home prices in Gillespie are down 1% in the last 12 months.
How many homes have sold over the last 12 months in Gillespie, IL?
22 homes have sold in Gillespie, IL over the last 12 months.
What is the average household income in Gillespie, IL?
The average household income in Gillespie, IL is $64K.
What are the most popular zip codes in Gillespie, IL?
The most popular zip codes in Gillespie, IL include 62033, 62009, 62069, 62685 and 62088.
How much do you need to make to afford a house in Gillespie?
The median home price in Gillespie is $135,700. If you put a 20% down payment of $27,100 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $690 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $30K a year to afford the median home price in Gillespie. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Gillespie is $64K.
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.

Home Prices in Gillespie, IL

Home Price Trends

Median Sale Price
$129,500
Median Single Family Sale Price
$115,000
Median 2 Bedroom Sale Price
$107,500
Average Price Per Sq Ft
$94
Number of Homes for Sale
12
Last 12 months Home Sales
22
Months of Supply
6.50
Median List Price
$135,700
Median Change From 1st List Price
11%
Median Home Sale Price YoY Change
4%
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