20

Gillespie, IL Houses for Sale

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  • /12

    $119,000

    $6K PRICE DROP 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

    905 Madison St, Gillespie, IL 62033
  • /20

    $41,900

    $8K PRICE DROP Under Contract
    • 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

    Agent Photo

    Matthew Cisler

    Cisler & Associates Real Estate

    418 E Elm St, 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

    911 Madison St, Gillespie, IL 62033
  • /26

    $79,999

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    390 Dorsey Rd, Gillespie, IL 62033

    This partially renovated 2-bedroom, 2-bathroom ranch-style home was built in 1990 and sits on a 0.1722-acre lot. Exterior features include vinyl siding, a metal roof installed in 2023, and a private backyard with a rear deck installed in 2023 and distinctive metal fencing installed in 2024. A long covered front porch welcomes you into a bright, open main living area. Large front windows bring in

    Amy Quarton Tarrant and Harman Real Estate and Auction Co

    390 Dorsey Rd, Gillespie, IL 62033
  • /45

    $167,500

    $8K 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
  • /15

    $95,000

    • 3 Beds
    • 1 Bath
    • 1,456 Sq Ft

    504 E Walnut St, Gillespie, IL 62033

    Welcome to this charming 3-bedroom, 1-bath home offering comfortable living space in the heart of Gillespie. The functional floor plan provides inviting living areas with abundant natural light and a layout designed for everyday living and entertaining. The kitchen offers ample cabinet and workspace, while the bedrooms provide flexibility for a variety of needs, including guest accommodations, a

    John Blasingame Keller Williams Marquee

    504 E Walnut St, Gillespie, IL 62033
  • /30

    $249,000

    Open Fri 5PM - 7PM
    • 4 Beds
    • 2 Baths
    • 1,650 Sq Ft

    106 Henry St, Gillespie, IL 62033

    Welcome to this beautifully renovated 4-bedroom, 2-bathroom home, where modern design meets functionality. As you enter, you're greeted by a spacious living room and dining room combo, offering an open and airy feel—ideal for both relaxing and entertaining. The large, flexible layout provides ample space for family gatherings and hosting guests. The expansive master bedroom features a private,

    Mark Roberts RE/MAX Alliance

    106 Henry 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
  • /38

    $325,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,236 Sq Ft

    411 W Burton St, Gillespie, IL 62033

    NEWER CONSTRUCTION BEAUTY! Welcome to this 4-bedroom, 3-bathroom home built in 2018. It offers the perfect blend of modern comfort, thoughtful design, and generous living space. From the inviting covered front porch to the bright, open-concept interior, every detail has been designed for comfortable everyday living and effortless entertaining. Step inside to discover soaring vaulted ceilings,

    Kassidy Paine Century 21 Reid Baugher Realty

    411 W Burton St, Gillespie, IL 62033
  • /35

    $138,900

    $20K 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
  • /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
  • /20

    $215,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,890 Sq Ft

    105 E Elm St, Gillespie, IL 62033

    Welcome home to a place where comfort, functionality, and outdoor living come together beautifully. From the moment you arrive, you’ll appreciate the inviting front porch—the perfect spot to begin your day with a cup of coffee or unwind in the evening with a glass of iced tea while watching the neighborhood pass by. Step inside to a thoughtfully designed floor plan featuring a spacious galley

    Dana Allen Key Estates Realty and Property Management

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

    $110,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    411 E Chestnut St, Gillespie, IL 62033

    Welcome to 411 E. Chestnut Street in Gillespie, Illinois—a place where you’ll have room to spread out, relax, and truly enjoy home. Imagine sipping your morning coffee while overlooking your expansive backyard, watching children play, dogs run, or planning the garden you’ve always wanted. This property includes two lots totaling approximately 0.61 acre, giving you over half an acre of outdoor

    Dana Allen Key Estates Realty and Property Management

    411 E Chestnut St, Gillespie, IL 62033
  • /12

    $40,000

    $10K PRICE DROP
    • 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

    Pending
    • 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
  • /35

    $139,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,275 Sq Ft

    908 Staunton Rd, Gillespie, IL 62033

    Welcome home to this 3 bed 1 bath ranch situated on a beautifully landscaped double lot! From the moment you arrive, you'll appreciate the attractive curb appeal, asphalt driveway, covered carport, 1 car garage, and charming front entry featuring vinyl railings that welcome you into a warm and inviting foyer. Inside, you'll find an open, functional floor plan with a spacious 19' x 13' living room

    Lisa Miller 1st Choice Realty Pros, LLC

    908 Staunton Rd, Gillespie, IL 62033
  • /33

    $219,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,971 Sq Ft

    716 Springfield Rd, Gillespie, IL 62033

    Don't miss this well-maintained ranch home offering the perfect blend of comfort, convenience, and space! Situated on a corner lot just over a half acre, this 3-bedroom, 2-bath home features desirable one-level living and a spacious floor plan. The large master suite offers a private retreat, while the additional bedrooms provide plenty of room for family, guests, or a home office. The heart of

    Michael Bellovich RE/MAX Alliance

    716 Springfield Rd, Gillespie, IL 62033
  • /26

    $99,900

    $19K PRICE DROP Pending
    • 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
  • /38

    $112,000

    Under Contract
    • 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. The home's foundation was stabilized on 6/9/26.

    Jackie Sumpter Landmark Realty

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

    $360,000

    $10K PRICE DROP Pending
    • 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

Single Family Home Price Trends

Median Home Price
$113,500
Median 3-Bedroom Home Price
$129,500
Median 4-Bedroom Home Price
$221,500
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