Courtesy: RE/MAX Alliance
618-635-2900
Private Acreage Living in the Heart of the City Discover the best of both worlds with this 3-bedroom, 2-full-bath home situated on 1.2 pristine acres within city limits. Enjoy the convenience of city living while surrounded by the privacy, peacefulness, and natural beauty of a country setting. The lower level welcomes you from the parking area with a spacious living room that flows into the modernized eat-in kitchen. The generous living space offers plenty of flexibility for a variety of furniture layouts and could easily accommodate a dedicated dining area. The updated kitchen features refreshed cabinetry and countertops, ample counter space, updated appliances, and room for a comfortable kitchen table and chairs. On the main level, you'll find a large renovated family room filled with beautiful windows, creating a bright and inviting space that could also serve as a separate entertaining area. The spacious primary suite offers a large walk-in closet and a charming built-in electric fireplace, with plenty of room for both a bedroom and sitting area. Two additional nicely sized bedrooms complete the main living area. Step outside onto the large walk-out patio and take in the expansive, rolling, meticulously manicured lawn. The property offers a wonderful combination of open yard and wooded areas, creating a private backdrop for relaxing, entertaining, or enjoying the outdoors. The grounds gently meander toward a small creek, providing a unique opportunity to explore and enjoy nature right in your own backyard. A standout feature of this property is the large detached 3-car garage, located off a private drive and offering generous parking, storage, and workshop space. The garage is heated by a wood-burning stove, which can also provide heat to the main residence as an option. With its spacious interior, extensive updates, oversized garage, private acreage, wooded setting, and creek—all while remaining within city limits—this property offers a rare opportunity to enjoy privacy and nature without giving up the conveniences of town.
Courtesy: Tarrant and Harman Real Estate and Auction Co
618-433-9436
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 natural light, while neutral finishes, recessed lighting, ceiling fans, and continuous vinyl plank flooring create a clean, cohesive look. The kitchen features brand-new cabinetry and flows into the dining and living spaces, creating a flexible setting that can be completed and arranged to suit the buyer’s needs. Two bedrooms feature neutral carpeting. Both bathrooms have ceramic tile flooring, with portions of the renovation work remaining to be completed. A convenient combination mudroom and laundry area provides a main-floor laundry hookup. Convenient alley access leads to concrete and asphalt parking. Electric service is connected, with public water and sewer readily available. Several interior projects remain to be completed. All building materials currently at the property will remain, giving the buyer a head start on completing the improvements and selecting finishing touches that suit their style. Property is being sold as-is. Schedule your showing today to explore everything this home has to offer.
Courtesy: RE/MAX Alliance
618-635-2900
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, en-suite full bath, and includes a versatile office or dressing room area. The brand-new kitchen is a chef’s dream, showcasing stainless steel appliances, sleek countertops, and plenty of cabinet space, making cooking and meal prep a delight. Each of the generously sized bedrooms boasts walk-in closets, offering great storage and organization. The main floor laundry room adds extra convenience to your daily routine. This home is also equipped with a brand-new HVAC. Step outside to find a large, detached 4-car garage with alley access, providing ample space for many vehicles and a nice workshop. A large gazebo in a patio area is there for entertainment.
Courtesy: Keller Williams Marquee
618-876-0024
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 home office, or hobby space. Outside, enjoy a spacious yard with room for gardening, outdoor activities, or future enhancements. Conveniently located near local parks, schools, shopping, dining, and community amenities, this property also offers easy access to major roadways for commuting throughout Macoupin County and surrounding areas. Schedule your private showing today and discover all that 504 E. Walnut Street has to offer! This property may qualify for Seller Financing (Vendee). If Property was built prior to 1978, Lead Based Paint Potentially Exists Buyer and/or buyer agent to verify all MLS data. ALL information is deemed reliable but is not guaranteed and should be verified by the buyer and/or buyers agent before making an offer.
Courtesy: Century 21 Reid Baugher Realty
217-324-5286
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, abundant natural light, and a spacious living room centered around a cozy fireplace. The open dining area flows seamlessly into the stunning kitchen, featuring crisp white cabinetry, stainless steel appliances, a center island, ample counter space, and plenty of storage for the home chef. The spacious primary suite provides a peaceful retreat with a private en-suite bath complete with dual vanities, a soaking tub, and a separate shower. Three additional bedrooms and two more full bathrooms offer flexibility for family, guests, or a home office. Downstairs, you'll find an expansive finished basement with a huge family room, an additional bedroom and full bath, plus endless possibilities for a game room, home theater, gym, or play area. Outside, enjoy relaxing on the covered front porch or spending time in the backyard, while the oversized attached garage provides plenty of room for vehicles, tools, and storage. This move-in ready home checks all the boxes with spacious living areas, modern finishes, and room for everyone. Did I mention it also has a large, fenced backyard? Don't miss your opportunity to make this beautiful property your next home—schedule your private showing today!
Courtesy: Key Estates Realty and Property Management
618-407-1234
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 kitchen with everything within easy reach, making meal preparation both efficient and enjoyable. The adjoining dining area is filled with natural light and opens directly onto the backyard deck, creating a seamless transition for entertaining family and friends. Outside, your own backyard retreat awaits. The deck overlooks the sparkling pool, creating the perfect setting for summer barbecues, lazy afternoons in the sun, or evenings spent making memories with those you love. The fenced backyard offers privacy, room for pets and play, and plenty of space to enjoy the outdoors. This home features a desirable split-bedroom floor plan. The main level offers two bedrooms, including a spacious primary suite with its own private full bathroom. Upstairs, you’ll find two additional bedrooms and a generously sized full bath complete with an oversized storage closet—perfect for linens, seasonal clothing, holiday décor, or extra household storage. Need even more space? The full poured concrete basement offers endless possibilities. With tall ceilings, a plumbing rough-in already in place for a future third bathroom, and ample square footage, it’s ready to become the family room, recreation area, home office, guest suite, or additional living space you’ve always wanted. The home also includes a radon mitigation system that’s already installed for added peace of mind, along with a sump pump. A spacious attached two-car garage provides plenty of room for vehicles, tools, hobbies, and additional storage. Whether you’re enjoying quiet mornings on the front porch, hosting friends around the pool, or envisioning the possibilities of the unfinished basement, this home offers the space, comfort, and flexibility to fit your lifestyle today—and room to grow tomorrow. Schedule your private showing and experience everything this beautiful home has to offer.
Courtesy: Key Estates Realty and Property Management
618-407-1234
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 space that’s becoming increasingly difficult to find. Inside, you’ll find a warm and inviting 2-bedroom, 1-bath home filled with natural light and comfortable living spaces. Whether you’re hosting family, enjoying a quiet evening, or simply settling in after a long day, this home offers a cozy atmosphere you’ll appreciate. The kitchen comes complete with a stove, refrigerator, and portable dishwasher, making move-in simple and convenient. The full basement provides even more possibilities. While unfinished, it offers excellent additional living space for a recreation room, hobby area, workshop, or home gym, along with abundant storage. An additional toilet is located in the basement, and washer and dryer hookups are already in place. Step outside to enjoy the fully fenced backyard, perfect for entertaining, pets, gardening, or simply unwinding at the end of the day. The oversized detached garage offers plenty of room for vehicles, lawn equipment, tools, and weekend projects. Located in the welcoming community of Gillespie, you’ll enjoy small-town charm while being conveniently situated between St. Louis, Missouri, and Springfield, Illinois, with quick access to Interstate 55 for an easy commute. If you’ve been looking for an affordable home with elbow room, a spacious yard, and endless possibilities both inside and out, 411 E. Chestnut Street is ready to welcome you home. Property Features: • Fenced backyard • Two lots totaling approximately 0.61 acre • Oversized detached garage with electricity • 2 Bedrooms • 1 Full Bathroom • Additional bathroom toilet in the basement • Full basement with bonus living space and abundant storage • Washer & dryer hookups • Stove, refrigerator & portable dishwasher included • Convenient access to Interstate 55, St. Louis, and Springfield
Courtesy: 1st Choice Realty Pros, LLC
217-825-3999
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 that flows into the 15' x 14' kitchen, creating an ideal space for everyday living and entertaining. The generous 17' x 11' primary bedroom includes a walk-in closet, and the convenience of main-floor laundry makes one-level living even more appealing. Step outside to enjoy the 23' x 14' screened-in porch, a wonderful place to relax, entertain guests, or enjoy the outdoors in comfort. The beautifully landscaped double lot approx. 88 x 137 provides plenty of room to garden, play, or simply unwind. Recent updates include a roof (2016), Lennox boiler (2013), Lennox central air (2013) with a new A/C coil (2025), water heater (2025), cooktop (2025), and microwave (2021). It's easy to see the pride of ownership throughout this home—every detail reflects the excellent care it has received over the years. This is a property you'll be proud to call home. Selling AS IS, Inspections welcome but no repairs will be made by seller.
Courtesy: RE/MAX Alliance
618-635-2900
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 the home is the inviting eat-in kitchen, complete with modern custom cabinetry, abundant cabinet space, and a breakfast/coffee bar that's perfect for busy mornings or casual entertaining. Designed with gathering in mind, the home's open living spaces flow effortlessly to the back patio, creating the perfect setting for cookouts, relaxing evenings, or family get-togethers. The partially fenced backyard offers room to play, garden, or simply enjoy the outdoors. The oversized attached 2-car garage provides ample storage and includes a versatile bonus room that can be transformed into a rec room, man cave, she shed, home gym, office, or additional living space to fit your needs. Conveniently located on Route 4, this move-in-ready home is ideal for first-time buyers, growing families, or anyone looking to enjoy the ease of single-level living with plenty of space inside and out.
Courtesy: Landmark Realty
618-466-1513
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. Foundation recovery system has a transferable warranty of 25 years.
Courtesy: Landmark Realty
618-4661513
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.
Courtesy: RE/MAX Alliance
618-656-2111
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, and the start of electrical upgrades. New siding has been installed and only requires finishing work. Situated on two lots, the property features a spacious yard with room to enjoy or expand. As an added bonus, many of the building materials already purchased for the renovation will be included with the sale, helping you save both time and money as you complete the project. Don't miss this chance to customize a home with much of the heavy lifting already started! This home is to be sold "AS-IS"
Courtesy: RE/MAX Alliance
618-635-2900
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 house. Upstairs and open loft for bedrooms and can feature multiple beds or make nice suite. An office is also located off the mud room and can be converted to small bedroom. Garage has been converted into a great workshop with an additional office and plenty of floor space for woodworking or hobbies. Garage would need converted back with garage doors but could possibly converted back to hold multiple vehicles. This house is located in a very convenient main location in Gillespie close to downtown and gas stations.
Courtesy: Tarrant and Harman Real Estate and Auction Co
618-433-9436
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 conveniences. The living room is spacious enough for social gatherings but still maintains a cozy feeling. The pool has a new pump, cover, and storage shed for supplies. An eat-in kitchen provides a comfortable dining area for intimate dinners or for family and friends. A complete remodel of the bathroom adds convenience and charm. The laundry room is tucked away in the walk-in closet in the primary bedroom. A full, unfinished basement is a haven for storage and possibly a workshop area. An extremely spacious detached garage (app. 1,216 s/f) will accommodate two vehicles; has a mini split for heating and AC; roughed in plumbing for a bath, is drywalled, and still provides ample room for equipment storage and a workshop. Contact your favorite realtor to schedule a viewing.
Courtesy: RE/MAX Alliance
618-635-2900
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 convenience and extra storage. Home is being sold as-is, offering a great opportunity for buyers looking to add their personal touch. Schedule your showing today!!
Courtesy: Cisler & Associates Real Estate
618-635-2244
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 area. Both bedrooms offer comfortable space and flexibility. The kitchen features a functional layout with ample storage, making it practical for everyday use. A nearby closet presents an excellent opportunity to be converted into a laundry area and potential half bath. The basement provides convenient access to the home’s mechanical systems along with additional space for storage. Step outside and enjoy one of this property’s true highlights—a large, shaded backyard offering the perfect setting for relaxing, entertaining, or future expansion. The home also features convenient front yard parking with turnaround space, a rare and practical bonus. A covered back porch provides a comfortable spot to unwind, while the outdoor water spigot and electrical outlet add everyday functionality and versatility to the space. Whether you're searching for your next investment, a flip, or a place to truly make your own, this property offers the perfect opportunity to build equity and bring your vision to life. Don’t miss your chance—schedule your showing today and see the potential for yourself!
Courtesy: RE/MAX Alliance
618-635-2900
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 large bedrooms and a versatile loft area—perfect for a home office, playroom, or additional living space or your 4th bedroom. Enjoy relaxing in the sunroom/sitting room filled with natural light and ideal for morning coffee or quiet evenings. Outside, the large yard provides plenty of room to entertain, garden, or simply unwind. Your fur babies will love the room to run! This home blends classic character with modern updates—ready for you to move right in and make it your own. Priced to sell, this gem won't won't last long, so make your appointment today.
Courtesy: Market Pro Realty, Inc
618-251-9121
Don't miss this 100% move-in ready, fresh, and tastefully updated home. All on one level. The newly remodeled kitchen has new cabinetry, countertops, flooring, and tile backsplash. All appliances stay. Two generously sized bedrooms and the third is the sweetest little nursery off the primary. Front porch rebuilt 2025, Roof new in 2024; siding & windows in 2010; water heater 2025 Great flat backyard waiting for your garden! One car detached garage with a workbench. Additional Rooms: Mud Room
Courtesy: Cisler & Associates Real Estate
618-635-2244
Cute two bedroom house lots of kitchen cabinets for plenty of storage one and a half baths on a large corner lot
Courtesy: Re/max Alliance
618-635-2900
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, there’s a detached 2-car garage and a shed for even more storage.
Courtesy: Strano & Associates
618-277-7653
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 views of the old Lake, the perfect spot for morning coffee or evening relaxation. The renovated lower level includes a large family room and a third bedroom, both with walkout access to a patio. A half bath and ample storage for all your lake gear round out this space. Home comes furnished - everything you see is included! Bring your toothbrush and start enjoying lake life! Additional highlights include a tankless water heater, private well water system, and plenty of room to entertain or unwind. This is a cash -only sale and house sold as-is. Contact your favorite agent today for a private tour and more details!
Courtesy: Century 21 Reid Baugher Realty
217-324-5286
Dreaming of Cul-de-sac living? This 4-bedroom, 2-bathroom cutie is the total package — stylish, spacious, and tucked away where life is a little quieter but still close to everything you need. Renovated and move in ready, this property features a main level primary bedroom with an ensuite bathroom, main level laundry, and an attached two car garage. Beautiful kitchen with new appliances. The partially finished basement comes with a family room and a fourth bedroom — perfect for guests, moody teenagers, or that drum set you swore you’d learn during quarantine. (You didn’t. It’s fine. There's still time.) Outside, you’re tucked into a quiet cul-de-sac where the biggest traffic problem is kids on scooters and neighbors who will probably wave at you. Great curb appeal and a covered front porch that's just waiting for amazon packages. Come check it out before someone else realizes they, too, deserve a house this fabulous.
Courtesy: Re/max Alliance
618-635-2900
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 perfect for family living or rental opportunities. With three levels of versatile space, this property provides a range of possibilities—from creating large entertainment areas to accommodating extended family or guests (even those you don't particularly enjoy). With an open slate to make it your own, the potential for customization is limitless. Whether you're looking for a personal residence or an investment property, this is a rare opportunity to own a property that blends charm, modern updates, and a prime location.
Courtesy: Re/max Alliance
618-635-2900
3 Bed, 1 Bath investment property! Home is in need of repair and being sold as-is. Large living room, separate full dining room with kitchen in the back of the home. Full basement. Utilities will not be turned on for inspections. Cash or Conventional in house loan only.
Courtesy: Cisler & Associates Real Estate
618-635-2244
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, plus space for outdoor entertaining. Inside, the spacious living room offers flexibility for any layout, perfect for relaxing or hosting guests. The separate dining room is ideal for gatherings, a home office, or extra living space. The large kitchen features plenty of counter and cabinet space, making meal prep a breeze. The full, unfinished basement provides abundant storage and potential for customization. Don’t miss your chance to own this beautifully updated home. Schedule a tour today and make it yours!
Gillespie is located in Illinois. Gillespie, Illinois has a population of 2,945. Gillespie is less family-centric than the surrounding county with 22.62% of the households containing married families with children. The county average for households married with children is 25.51%.
The median household income in Gillespie, Illinois is $45,817. The median household income for the surrounding county is $58,227 compared to the national median of $69,021. The median age of people living in Gillespie is 45.7 years.
The average high temperature in July is 87.5 degrees, with an average low temperature in January of 20.3 degrees. The average rainfall is approximately 39.9 inches per year, with 16 inches of snow per year.
