Gillespie, IL Homes

• 

  

  

  /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
• 

  

  

  /26

  $53,000 Sold Oct 01, 2025

  422 E Elm St, Gillespie, IL 62033

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1915

  Last Sold Summary

  • 29% Below List Price
  • $46/SF
  • 27 Days On Market

  Current Estimated Value $59,923

  Last Listing Agent Kari Vann Century 21 Reid Baugher Realty

  422 E Elm St, Gillespie, IL 62033
• 

  

  

  /36

  Est $129,464 Not Listed For Sale

  10120 Mathis Ln, Gillespie, IL 62033

  • 3 Beds
  • 1.5 Baths
  • 1,810 Sq Ft
  • Built 1960

  10120 Mathis Ln, Gillespie, IL 62033

  Last Sold Summary

  • 81% Above List Price
  • $40/SF
  • 63 Days On Market

  Last Sold Price $71,500

  Last Listing Agent Tom Daugherty Cisler & Associates Real Estate
• 

  

  

  /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
• 

  

  

  /14

  $62,500 Sold Sep 03, 2025

  1103 Madison St, Gillespie, IL 62033

  • 2 Beds
  • 1 Bath
  • 874 Sq Ft

  Last Sold Summary

  • 22% Below List Price
  • $72/SF
  • 326 Days On Market

  Current Estimated Value $69,225

  Last Listing Agent Matthew Cisler Cisler & Associates Real Estate

  1103 Madison St, Gillespie, IL 62033
• 

  

  /33

  Est $233,304 Not Listed For Sale

  304 E Spruce St, Gillespie, IL 62033

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 1940

  304 E Spruce St, Gillespie, IL 62033

  Last Sold Summary

  • 2% Below List Price
  • $133/SF
  • 53 Days On Market

  Last Sold Price $239,000

  Last Listing Agent Michael Bellovich RE/MAX Alliance
• 

  

  /37

  $179,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,830 Sq Ft

  713 N MacOupin St, Gillespie, IL 62033

  Take a look at this beautifully maintained 3-bedroom, 2-bath home situated on a large corner lot on a quiet street — offering space, flexibility, and room to truly spread out. Inside, you’ll immediately notice the gorgeous hardwood floors and multiple living areas designed for both everyday comfort and entertaining. The main living room features a unique sunken layout, creating a cozy, private

  Michael Bellovich RE/MAX Alliance

  713 N MacOupin St, Gillespie, IL 62033
• 

  

  /20

  $148,000 Sold Nov 19, 2025

  708 Madison St, Gillespie, IL 62033

  • 3 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • Built 1950

  Last Sold Summary

  • 18% Below List Price
  • $125/SF
  • 125 Days On Market

  Current Estimated Value $149,986

  Last Listing Agent Mike Mihelcic RE/MAX Alliance

  708 Madison St, Gillespie, IL 62033
• 

  

  /17

  Est $96,248 Not Listed For Sale

  10214 Columbey Dr, Gillespie, IL 62033

  • 2 Beds
  • 1.5 Baths
  • 1,524 Sq Ft
  • Built 1970

  10214 Columbey Dr, Gillespie, IL 62033

  Last Sold Summary

  • 92% Above List Price
  • $33/SF
  • 28 Days On Market

  Last Sold Price $50,000

  Last Listing Agent Marla Zubal Cisler & Associates Real Estate
• 

  

  /17

  $105,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,505 Sq Ft

  212 E Elm St, Gillespie, IL 62033

  Move-in ready with updates throughout! The kitchen has been refreshed with updated cabinetry, countertops, sink, and includes all appliances, plus vinyl plank flooring and space for an eat-in area. Main floor laundry/mudroom conveniently located off the rear sliding door. Separate dining room and a spacious living room, both featuring vinyl plank flooring and wiring for a wall-mounted TV. The

  Mike Mihelcic RE/MAX Alliance

  212 E Elm St, Gillespie, IL 62033
• 

  

  /32

  $194,000 Sold Sep 30, 2025

  715 Clinton St, Gillespie, IL 62033

  • 4 Beds
  • 1.5 Baths
  • 1,555 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $125/SF
  • 3 Days On Market

  Current Estimated Value $178,422

  Last Listing Agent Michael Bellovich RE/MAX Alliance

  715 Clinton St, Gillespie, IL 62033
• 

  

  /37

  Est $154,482 Not Listed For Sale

  1202 Jane Dr, Gillespie, IL 62033

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1975

  1202 Jane Dr, Gillespie, IL 62033

  Last Sold Summary

  • 14% Above List Price
  • $91/SF
  • 33 Days On Market

  Last Sold Price $136,000

  Last Listing Agent Lisa Miller 1st Choice Realty Pros, LLC
• 

  

  /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
• 

  /2

  $5,500 Sold Mar 17, 2026

  365 Dorsey Rd, Gillespie, IL 62033

  • Land
  • 0.55 Acre
  • $10,064 per Acre

  Last Sold Summary

  • 42% Below List Price
  • 48 Days On Market

  Current Estimated Value $82,529

  Last Listing Agent Henry Torn ListWithFreedom.com

  365 Dorsey Rd, Gillespie, IL 62033
• 

  

  /23

  Est $207,873 Not Listed For Sale

  200 Lorraine Dr, Gillespie, IL 62033

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1987

  200 Lorraine Dr, Gillespie, IL 62033

  Last Sold Summary

  • 14% Above List Price
  • $76/SF
  • 67 Days On Market

  Last Sold Price $183,000

  Last Listing Agent Kylie Dickinson RE/MAX Alliance
• 

  

  /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
• 

  

  /10

  $130,000 Sold Jan 09, 2026

  211 Edgar St, Gillespie, IL 62033

  • 3 Beds
  • 3 Baths
  • 1,384 Sq Ft
  • Built 1975

  Last Sold Summary

  • 13% Below List Price
  • $94/SF
  • 133 Days On Market

  Current Estimated Value $115,908

  Last Listing Agent Scott Schardan Cisler & Associates Real Estate

  211 Edgar St, Gillespie, IL 62033
• 

  

  /40

  Est $284,906 Not Listed For Sale

  1310 Jane Dr, Gillespie, IL 62033

  • 3 Beds
  • 4 Baths
  • 3,015 Sq Ft
  • Built 1978

  1310 Jane Dr, Gillespie, IL 62033

  Last Sold Summary

  • 16% Above List Price
  • $81/SF
  • 38 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Kassidy Paine Century 21 Reid Baugher Realty
• 

  

  /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
• 

  

  /6

  $33,500 Sold Sep 29, 2025

  16 State Route, Gillespie, IL 62033

  • Land
  • 1.5 Acres
  • $22,333 per Acre

  Last Sold Summary

  • 235% Above List Price
  • 17 Days On Market

  Last Listing Agent Adam Jokisch Adams Auction & Real Estate Services Inc.

  16 State Route, Gillespie, IL 62033
• 

  

  /25

  Est $124,818 Not Listed For Sale

  1200 Jane Dr, Gillespie, IL 62033

  • 3 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • Built 1970

  1200 Jane Dr, Gillespie, IL 62033

  Last Sold Summary

  • 39% Above List Price
  • $78/SF
  • 225 Days On Market

  Last Sold Price $90,000

  Last Listing Agent David Cisler Cisler & Associates Real Estate
• 

  

  /24

  $115,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  811 Adams St, Gillespie, IL 62033

  Welcome home to this beautifully updated craftsman-style bungalow in the heart of Gillespie. This charming 2-bedroom, 1-bath home blends classic character with modern updates, offering a bright and welcoming layout filled with natural light and beautiful original woodwork throughout. The updated kitchen features new cabinetry and countertops, with appliances included, and flows easily into the

  Michael Bellovich RE/MAX Alliance

  811 Adams St, Gillespie, IL 62033
• 

  

  /33

  $117,000 Sold Jul 08, 2025

  15222 Circle Dr, Gillespie, IL 62033

  • 3 Beds
  • 1.5 Baths
  • 1,810 Sq Ft
  • Built 1950

  Last Sold Summary

  • 33% Below List Price
  • $65/SF
  • 32 Days On Market

  Last Listing Agent Barry Schulhofer Strano & Associates

  15222 Circle Dr, Gillespie, IL 62033
• 

  

  /28

  Est $167,773 Not Listed For Sale

  200 E Burton St, Gillespie, IL 62033

  • 3 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  200 E Burton St, Gillespie, IL 62033

  Last Sold Summary

  • 5% Above List Price
  • $118/SF
  • 53 Days On Market

  Last Sold Price $159,900

  Last Listing Agent Mark Roberts RE/MAX Alliance
• 

  

  /29

  $110,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 850 Sq Ft

  304 Francis St, Gillespie, IL 62033

  Renovated 3-bedroom, 2-bath bungalow located in-town in Gillespie offering modern updates with small town convenience. A covered front porch welcomes you into a spacious open living room and kitchen combination featuring new flooring and all new appliances. The main floor also includes two comfortable bedrooms, an updated bathroom with step-in shower, and a convenient mudroom with main floor

  Susan Slemmer Tarrant and Harman Real Estate and Auction Co

  304 Francis St, Gillespie, IL 62033
• 

  

  /32

  $129,000 Sold Dec 16, 2025

  301 Park Ave, Gillespie, IL 62033

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1945

  Last Sold Summary

  • 17% Below List Price
  • $78/SF
  • 32 Days On Market

  Current Estimated Value $132,770

  Last Listing Agent Michael Bellovich RE/MAX Alliance

  301 Park Ave, Gillespie, IL 62033
• 

  

  /35

  Est $216,839 Not Listed For Sale

  713 Plum St, Gillespie, IL 62033

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft
  • Built 1970

  713 Plum St, Gillespie, IL 62033

  Last Sold Summary

  • 33% Above List Price
  • $73/SF
  • 34 Days On Market

  Last Sold Price $162,500

  Last Listing Agent Wendi Rensing CCDC Property Management & Real Estate
• 

  

  /3

  $15,000

  • Land
  • 0.2 Acre
  • $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
• 

  

  /28

  $146,040 Sold Oct 10, 2025

  309 W Chestnut St, Gillespie, IL 62033

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Below List Price
  • $97/SF
  • 1 Day On Market

  Current Estimated Value $151,101

  Last Listing Agent Shelly Niemeier Legacy Realty & Auction, Llc

  309 W Chestnut St, Gillespie, IL 62033
• 

  

  /19

  Est $122,094 Not Listed For Sale

  701 W Oak St, Gillespie, IL 62033

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1970

  

  701 W Oak St, Gillespie, IL 62033

  Last Sold Summary

  • 230% Above List Price
  • $23/SF
  • 2 Days On Market

  Last Sold Price $37,000

  Last Listing Agent Mary Jo Welch RE/MAX Professionals
• 

  

  /21

  $39,900 Pending

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  398 Dorsey Rd, Gillespie, IL 62033

  INVESTOR SPECIAL: This 3 bed 1 bath home located on a corner lot hosts good sq ft and lots of potential, 3 car detached garage. Set your appointment today! Seller to make no repairs or provide occupancy.

  Jared Childress Market Pro Realty, Inc

  398 Dorsey Rd, Gillespie, IL 62033
• 

  

  /20

  $140,000 Sold Oct 07, 2025

  14836 Route 138, Gillespie, IL 62033

  • Land
  • 13.75 Acres
  • $10,182 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 6 Days On Market

  Last Listing Agent Jared Childress Market Pro Realty, Inc

  14836 Route 138, Gillespie, IL 62033
• 

  

  /24

  Est $116,570 Not Listed For Sale

  614 W Maple St, Gillespie, IL 62033

  • 3 Beds
  • 1.5 Baths
  • 1,311 Sq Ft

  614 W Maple St, Gillespie, IL 62033

  Last Sold Summary

  • 64% Above List Price
  • $54/SF
  • 105 Days On Market

  Last Sold Price $71,000

  Last Listing Agent Kassidy Paine Century 21 Reid Baugher Realty
• 

  

  /4

  $12,000

  • Land
  • 0.15 Acre
  • $78,329 per Acre

  302 E Elm St, Gillespie, IL 62033

  Ready to build your dream?? This 44.5 x 150 vacant lot is your canvas! With utilities available on site, now is the perfect opportunity to start planning your dream property!! Call your favorite agent today to schedule a showing before it’s too late!!

  Scott Schardan Cisler & Associates Real Estate

  302 E Elm St, Gillespie, IL 62033
• 

  

  /41

  $183,000 Sold May 23, 2025

  208 Park Ave, Gillespie, IL 62033

  • 4 Beds
  • 2 Baths
  • 1,891 Sq Ft
  • Built 1942

  Last Sold Summary

  • 1% Below List Price
  • $97/SF
  • 64 Days On Market

  Current Estimated Value $209,554

  Last Listing Agent Kelly May-Bramlet Coldwell Banker Brown Realtors

  208 Park Ave, Gillespie, IL 62033
• 

  

  /30

  Est $160,141 Not Listed For Sale

  708 Springfield Rd, Gillespie, IL 62033

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1940

  708 Springfield Rd, Gillespie, IL 62033

  Last Sold Summary

  • 7% Above List Price
  • $125/SF
  • 31 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Mark Roberts RE/MAX Alliance
• 

  

  /13

  $10,000 Pending

  • Land
  • 0.51 Acre
  • $19,429 per Acre

  509 E Wilson Ave, Gillespie, IL 62033

  Wooded lots total of 1.189 acres to build or hobbies. There is a small creek and lots of trees! Lots of possibilities for this! Check it out!

  Amy Sujanani RE/MAX Alliance

  509 E Wilson Ave, Gillespie, IL 62033
• 

  

  /27

  $148,000 Sold Oct 21, 2025

  118 Park Ave, Gillespie, IL 62033

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1945

  Last Sold Summary

  • 4% Below List Price
  • $106/SF
  • 16 Days On Market

  Current Estimated Value $152,994

  Last Listing Agent Michael Bellovich RE/MAX Alliance

  118 Park Ave, Gillespie, IL 62033
• 

  

  /18

  Est $113,930 Not Listed For Sale

  714 Springfield Rd, Gillespie, IL 62033

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1940

  714 Springfield Rd, Gillespie, IL 62033

  Last Sold Summary

  • 107% Above List Price
  • $48/SF
  • 121 Days On Market

  Last Sold Price $55,000

  Last Listing Agent Kassidy Paine Century 21 Reid Baugher Realty
• 

  

  /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

Showing Results 1 - 40, Page 1 of 18