Macoupin, IL Homes

• 

  

  /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.

  

  Kimberly Hunt

  360 Prime Realty Group, LLC

  (217) 833-8850

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

  

  

  /32

  $132,000 Sold Jul 31, 2025

  • 5,032 Sq Ft
  • $26/SF
  • 126 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1910

  209 South St, Gillespie, IL 62033

  Unique Corner Lot Property with Endless Potential!This recently zoned residential property, situated on a spacious corner lot, offers over 5,000 square feet of living space! The building features a solid brick structure with a brand-new roof, ensuring both durability and peace of mind. The upstairs apartment has been completely remodeled and includes 3 generously-sized bedrooms, making it

  Michael Bellovich RE/MAX Alliance

  209 South St, Gillespie, IL 62033
• 

  

  

  /45

  Est $228,213 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,919 Sq Ft

  800 1st St, Gillespie, IL 62033

  800 1st 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,

  Matthew Cisler Cisler & Associates Real Estate

  1103 Madison St, Gillespie, IL 62033
• 

  

  

  /36

  $192,400 Sold Jul 25, 2025

  • 1,800 Sq Ft
  • $107/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1947

  701 Olive St, Gillespie, IL 62033

  Completely updated 3 bed, 2 bath home on a spacious corner lot! Step into a formal living area with an open feel—perfect for entertaining. Living room is open to all types of furniture and layouts. The bright dining room features large windows, ideal for natural light and plant lovers. Dining area has plenty of space for a full size table and chairs. A second family room in the back offers

  Mark Roberts RE/MAX Alliance

  701 Olive St, Gillespie, IL 62033
• 

  

  /36

  Est $79,999 Not Listed For Sale

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

  10120 Mathis Ln, Gillespie, IL 62033

  10120 Mathis Ln, 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
• 

  

  /10

  $45,000 Sold Jul 22, 2025

  • 1,100 Sq Ft
  • $41/SF
  • 3 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1940

  215 Berry St, Gillespie, IL 62033

  Cute two bedroom house lots of kitchen cabinets for plenty of storage one and a half baths on a large corner lot

  Sue Pirok Cisler & Associates Real Estate

  215 Berry St, Gillespie, IL 62033
• 

  

  /33

  Est $230,111 Not Listed For Sale

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

  304 E Spruce St, Gillespie, IL 62033

  304 E Spruce St, Gillespie, IL 62033
• 

  

  /43

  $159,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,356 Sq Ft

  908 Abba St, Gillespie, IL 62033

  HUGE 40 x 70 Stran Steel Building on .35 acre corner lot! AND it also includes a 2 bedroom, 1 bath brick home with a nice covered patio connecting the home & garage. The home features good size rooms and spacious closets. There is also a bonus room currently used as an office. The garage/steel building is heated & insulated. It includes workshop space as well as two overhead doors (18x12 &

  Annita Jackson Century 21 Reid Baugher Realty

  908 Abba St, Gillespie, IL 62033
• 

  

  /15

  $110,000 Sold Jul 14, 2025

  • 1,047 Sq Ft
  • $105/SF
  • 67 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  504 Henrietta St, Gillespie, IL 62033

  Back on the market for the right buyer. House is 75 years old and aging gracefully, think Dolly Parton, had a little work done, might need more as time goes by. Great bones and numerous updates. Whole house inspection report is available through your realtor for your review. At 105,000, the seller will not be installing a new furnace; it has been inspected and serviced. Works like a champ. Clean

  Marge Haworth Market Pro Realty, Inc

  504 Henrietta St, Gillespie, IL 62033
• 

  

  /14

  Est $61,784 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  224 W Oak St, Gillespie, IL 62033

  224 W Oak St, Gillespie, IL 62033
• 

  

  /10

  $149,900 Under Contract

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

  211 Edgar St, Gillespie, IL 62033

  Welcome to your new home!! This spacious 1384 Square Foot, 3 Bed, 3 bath home, built in 1975 is calling your name!! An attached 3 car garage offers all the parking space and workshop area you need!! Walk in from the garage to an extra large entry foyer! Stained glass in the stairwell going to the second floor, adds elegance and beauty! Separate living and dining rooms gives all the comforts of

  Scott Schardan Cisler & Associates Real Estate

  211 Edgar St, Gillespie, IL 62033
• 

  

  /33

  $117,000 Sold Jul 08, 2025

  • 1,810 Sq Ft
  • $65/SF
  • 32 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  15222 Circle Dr, Gillespie, IL 62033

  You do not want to miss this lakefront cabin retreat on Gillespie Lake! This beautiful 3-bedroom cabin sits right on Gillespie Lake, with direct access to both the old Lake boat ramp and the new lake just steps away from your door. Step inside to a bright main level, featuring two bedrooms, full bath, and a stunning open living room that flows onto a newer deck. The enclosed front room offers

  Barry Schulhofer Strano & Associates

  15222 Circle Dr, Gillespie, IL 62033
• 

  

  /17

  Est $79,146 Not Listed For Sale

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

  10214 Columbey Dr, Gillespie, IL 62033

  10214 Columbey Dr, Gillespie, IL 62033
• 

  

  /20

  $165,000 Under Contract

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

  708 Madison St, Gillespie, IL 62033

  Freshly remodeled 3 bed, 2 bath home on a large corner lot! Inside, you’ll find an open living and kitchen area with luxury vinyl plank flooring throughout. The primary bedroom includes its own full bath with a tub/shower combo, and two more good-sized bedrooms share a second full bath—also with a tub/shower. Full unfinished basement with laundry area offers extra space and storage. Outside,

  Mike Mihelcic RE/MAX Alliance

  708 Madison St, Gillespie, IL 62033
• 

  

  /4

  $10,000 Sold Jun 06, 2025

  • 1,200 Sq Ft
  • $8/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath

  803 Madison St, Gillespie, IL 62033

  Nice property with super clean garage located in downtown area. House itself is not livable in its current state and needs complete rehab or tear down. This is great investment opportunity for someone to locate to or use the garage specifically. We will not allow tour of house for at this time unless waiver is signed. We can give access to garage and outside premises upon booking appointment

  Mark Roberts RE/MAX Alliance

  803 Madison St, Gillespie, IL 62033
• 

  

  /40

  Est $268,389 Not Listed For Sale

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

  1310 Jane Dr, Gillespie, IL 62033

  1310 Jane Dr, Gillespie, IL 62033
• 

  

  /30

  $229,999 Open Sun 11AM - 1PM

  • 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
• 

  

  /32

  $115,000 Sold May 23, 2025

  • 988 Sq Ft
  • $116/SF
  • 32 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  400 Broadway St, Gillespie, IL 62033

  Charming & Move-In Ready 2-Bedroom Home in Gillespie, IL!This nicely maintained and move-in ready 2-bedroom home is full of charm and convenience. Inside, you'll find an updated bathroom, a spacious living room and dining room combo, and a bright eat-in kitchen perfect for home-cooked meals. The full basement offers plenty of storage space, while the detached garage provides covered parking and

  David Cisler Cisler & Associates Real Estate

  400 Broadway St, Gillespie, IL 62033
• 

  

  /25

  Est $124,228 Not Listed For Sale

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

  1200 Jane Dr, Gillespie, IL 62033

  1200 Jane Dr, Gillespie, IL 62033
• 

  

  /23

  $129,900

  • 4 Beds
  • 2 Baths
  • 1,659 Sq Ft

  810 Harding Ave, Gillespie, IL 62033

  Rural retreat on 2.5 acres with a private pond! This home features a comfortable hardwood and carpet combination. The kitchen boasts classic wood cabinets. Bathrooms are in good condition, including a master bath with a walk-in shower and double sinks/pantry. A large unfinished basement offers potential, with a sump pump and backup. Enjoy city water/sewer, 200 amp service, a 2015/2016 roof, and a

  Kathleen Bak Gates and Gables Realty

  810 Harding Ave, Gillespie, IL 62033
• 

  

  /41

  $183,000 Sold May 23, 2025

  • 1,891 Sq Ft
  • $97/SF
  • 64 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1942

  208 Park Ave, Gillespie, IL 62033

  MOVE IN READY home with tons of space and so many updates! Check out this 4-5 bedroom, 2 bathroom home filled with character and charm and very spacious rooms. Bright living/dining room has a beautiful staircase that leads to the second floor. Kitchen has been updated with newer cabinets, all appliances stay! Home features a main level laundry room, a main level bedroom, and a beautifully

  Kelly May Coldwell Banker Brown Realtors

  208 Park Ave, Gillespie, IL 62033
• 

  

  /35

  Est $209,085 Not Listed For Sale

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

  713 Plum St, Gillespie, IL 62033

  713 Plum St, Gillespie, IL 62033
• 

  

  /32

  $350,000

  • 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
• 

  

  /22

  $143,500 Sold May 21, 2025

  • 1,421 Sq Ft
  • $101/SF
  • 78 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  308 Shelby St, Gillespie, IL 62033

  Looking for a move-in ready home with all the updates including furnace, AC, water heater, windows, dishwasher, gas cook top, wall oven, sink and more! This 3-bedroom, 2-bath home has it all! The main floor features a cozy living room, a nice-sized dining room, and an updated kitchen. With 3 good-sized bedrooms, including a main floor primary suite, there’s plenty of space for everyone and plenty

  Mike Mihelcic RE/MAX Alliance

  308 Shelby St, Gillespie, IL 62033
• 

  

  /19

  Est $144,205 Not Listed For Sale

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

  701 W Oak St, Gillespie, IL 62033

  

  701 W Oak St, Gillespie, IL 62033
• 

  

  /32

  $115,000

  • 3 Beds
  • 1.5 Baths
  • 1,465 Sq Ft

  410 W Easton St, Gillespie, IL 62033

  Looking for the perfect home in the perfect location? You just found it! Move in ready 2 bedroom, 2 bathroom home with a potential extra bedroom in the basement. Large, open concept living and dining room with lots of natural light. Additional entry room would be a great mudroom or an office! Newer windows, flooring and freshly painted. New water and sewer lines in 2016. Plumbing and Electric

  Kassidy Paine Century 21 Reid Baugher Realty

  410 W Easton St, Gillespie, IL 62033
• 

  

  /58

  $99,900 Sold May 16, 2025

  • 1,500 Sq Ft
  • $67/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2000

  392 N Salisbury St, Gillespie, IL 62033

  Charming Country Home with Pole Barn Garage on an ACRE of land! Discover privacy and community charm in this lovely property. Situated near a small town park known for its annual homecoming and famous fish fry, this home offers a unique lifestyle experience.Property Features:- Spacious Pole Barn Garage: 30 x 46 garage with a lean-to shed for ample storage.- Park Views: Bordered by a park,

  Dana Allen Key Estates Realty and Property Management

  392 N Salisbury St, Gillespie, IL 62033
• 

  

  /24

  Est $99,877 Not Listed For Sale

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

  614 W Maple St, Gillespie, IL 62033

  614 W Maple St, Gillespie, IL 62033
• 

  

  /19

  $102,000

  • 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
• 

  

  /41

  $166,900 Sold Apr 25, 2025

  • 1,300 Sq Ft
  • $128/SF
  • 181 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  208 L J Ave, Gillespie, IL 62033

  Beautifully redone brick ranch within walking distance of the schools! Check out this 3-bedroom 1.5 bath gem that boasts a breakfast bar, separate dining, main floor laundry and a one car attached garage. This move in ready home has tons of natural light with many modern upgrades. Your large kitchen offers plenty of cabinet space, new appliances and lots of counter space, plus a bonus area near

  Michael Bellovich RE/MAX Alliance

  208 L J Ave, Gillespie, IL 62033
• 

  

  /23

  Est $251,730 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  708 Clay St, Gillespie, IL 62033

  708 Clay 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
• 

  

  /8

  $68,000 Sold Apr 18, 2025

  • 880 Sq Ft
  • $77/SF
  • 56 Days On Market

  • 2 Beds
  • 1 Bath

  416 Park Ave, Gillespie, IL 62033

  Just pack your bags and be ready to move in.Very cute 2 Bedroom home. All new vinyl Plank flooring throughout and new paint. Sliding door off back entry way to a large deck. Yard is fenced with chain link.To minimize any concerns for near future expenses a new roof is 6 months old and new HVAC and windows installed in 2023.

  Sue Pirok Cisler & Associates Real Estate

  416 Park Ave, Gillespie, IL 62033
• 

  

  /18

  Est $105,618 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  714 Springfield Rd, Gillespie, IL 62033

  714 Springfield Rd, 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
• 

  

  /37

  $139,000 Sold Mar 14, 2025

  • 2,106 Sq Ft
  • $66/SF
  • 168 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1920

  210 E Elm St, Gillespie, IL 62033

  Welcome home to 210 E Elm St! This delightful 2-bedroom, 2-bathroom residence offers a perfect blend of comfort and style. An inviting design flows through the living areas, creating a cozy atmosphere. Enjoy a large master bedroom with ample closet space and an ensuite bathroom for your convenience. The upstairs bonus room is perfect for a home office, playroom, or another living space, offering

  Andrew Milkovich RE/MAX Alliance

  210 E Elm St, Gillespie, IL 62033
• 

  

  /27

  Est $181,047 Not Listed For Sale

  • 6 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  110 Berry St, Gillespie, IL 62033

  110 Berry St, Gillespie, IL 62033
• 

  

  /19

  $119,500 Pending

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  210 Francis St, Gillespie, IL 62033

  Charming 2-Bedroom Brick Home on a Corner Lot! Welcome to this adorable 2-bedroom, 1-bath brick home, perfectly situated on a spacious corner lot. With its open and airy layout, this property offers a warm and inviting atmosphere ideal for first-time buyers or those looking to downsize. Step outside to enjoy a large, fenced-in backyard—perfect for pets, play, or outdoor gatherings—plus a cozy

  Michael Bellovich RE/MAX Alliance

  210 Francis St, Gillespie, IL 62033

Showing Results 1 - 40, Page 1 of 18