Chester Homes for Sale

Welcome to Chester, Illinois—a hidden gem nestled in the heart of Randolph County. Known for its rich history and vibrant community, Chester offers a unique blend of small-town charm and modern conveniences. With its picturesque landscapes along the banks of the Mississippi River, Chester is a haven for nature lovers and outdoor enthusiasts alike. The city is home to several parks, walking trails, and recreational facilities, making it an ideal spot for families and individuals seeking an active lifestyle.

Chester boasts a welcoming atmosphere, where neighbors become friends and community events bring everyone together. The local dining scene features delightful eateries that showcase the region’s culinary flair, while charming boutiques and shops provide a perfect backdrop for leisurely afternoons. History buffs will appreciate Chester’s historical significance, with landmarks and museums that tell the story of its past, including its connection to the famous cartoonist, Popeye.

For those considering a move, Chester offers an array of homes for sale that cater to diverse tastes and budgets. Whether you're searching for a cozy single-family home, a spacious property with land, or a charming historic residence, Chester has something for everyone. The real estate market here is thriving, with opportunities for first-time buyers and seasoned investors alike.

Experience the warmth and hospitality of Chester, IL, where community spirit thrives and every day feels like home. Discover your dream home in this delightful city—your new beginning awaits!

Newest Chester Homes for Sale

$2,500,000

3 Beds ⋅ 4 Baths ⋅ 26045158 MLS

Seldom does a property of this quality come onto the market ! A rare opportunity to own a custom-built home on 113 acres. This property offers many features that make it ideal for a farming operation and homestead, whether you're looking to run cattle, horses, or any other livestock. The land has been utilized as a cow-calf operation, but could offer some cropland or whatever it is that you have in mind. Whitetail and turkey hunting are very good! This 4 bed/3.5 bath stone and brick residence offers about 4,000 square feet of beautifully finished space. The home overlooks a 3 acre stocked pond. All custom cherry trim, cabinetry and solid cherry doors. The great room features a Fondulac stone gas log fireplace to add warmth and charm as well as a great view outdoors. Kitchen includes Italian quartzite countertops, cherry cabinets, center island, pantry, breakfast bar, and a casual dining space. The primary suite on the main level includes double sinks, bathtub/shower and large walk-in closet. Upstairs are 3 bedrooms, one ensuite and two share a Jack & Jill bath. Bonus room for hobbies or another bedroom. The main level laundry room has quartzite custom finish countertop and utility sink. Attached 2 car garage. A full unfinished basement includes stubbed in plumping for a bathroom. Geothermal heating and cooling, along with an outside wood burner and an electric heat back up insure comfort. Outdoor living is welcoming with a brick covered back porch that overlooks the pond and scenic acreage, making it the perfect spot to enjoy morning coffee, evening relaxation, or watch wildlife roam. There is also a covered 20X15 pavilion overlooking the pond. For those who need space beyond the home, the 30X60 detached shop near the residence offers endless possibilities—from a dream workshop to additional storage or hobby space—complete with loft, heat and AC and hot water floor heat. At the farm, a 60X40 machine shop with hot water floor heat also adds work space and storage. A 60X60 barn with a 24x48 lean-to with concrete corral, two older sheds and a chicken coop complete the farm buildings. There is an old artesian well behind the barn! The property is a mix of pasture, tillable acreage, and established woods that have not been logged in many years. Whitetail deer and turkey populate the area. There are prime locations for a hunter to place tree stands on this unrestricted property. Whether you are looking for a private country estate, hobby farm, hunting retreat, or weekend getaway, this versatile property offers space, quality construction, natural beauty, and long-term value. By appointment only. No drive-bys.

10631 Wine Hill Rd, Chester

Courtesy of Buy A Farm Land & Auction Co 618-713-7677

$349,900

3 Beds ⋅ 2 Baths ⋅ 26045140 MLS

So much to take in, and you don't find a property like this in the city limits often. Features 1.75 acres of seclusion with woods but so close to the downtown part of Chester. Three buildings: Lovely home built in 1990, former beauty shop and tanning salon (built in 2003) and oversized garage/workshop building all sits at the top of a hill in a very private location close to Cole Memorial Park in Chester. The split level home has 3 bedrooms, 2 full bathrooms, an above-ground pool (needs work) with a large fenced deck, wrap around porch and a big family room with fireplace on the lower level. You must see this one to take it all in. If you are looking for a fine home and a place to have a business or convert it to a mother-in-law residence, look no further than this one. The solar panels are installed but they aren't functioning presently. Call for a viewing of this one today. Seller prefers well-qualified preapproved buyers please. This is a very special home; come and see for yourself.

601 Erskine St, Chester

Courtesy of Worth Clark Realty 800-991-6092

$130,000

4 Beds ⋅ 1 Baths ⋅ 26044428 MLS

Well maintained 4-bed, 1 bath home with full finished dry basement (extra kitchen), detached garage, and a long backyard! Classic home built in 1949; perhaps could use some modern touches, but if you like the retro feel, this one checks the box! Water heater is 3 years old. The roof and furnace/ac are older but in good condition. If you want a reasonably priced, well-built and cared for home, check this one out!

2432 State St, Chester

Courtesy of Worth Clark Realty 800-991-6092

$145,000

3 Beds ⋅ 1 Baths ⋅ 26040465 MLS

This 1930-built classic awaits a new owner to love it! So much to love here! The arched front door and foyer with classic windows welcome you into this well-built and sturdy home. The huge living room has a fireplace and access to the enclosed front porch. What a beautiful room to sit and watch the sun come up! The big formal dining room and breakfast nook give lots of room for entertaining and the kitchen has classic cabinetry and fun built ins. It is believed that there are classic hardwoods under that carpet! Down the hall are (3) big bedrooms and an updated bathroom with low step in shower. Why there's even a laundry chute! Take a moment to look at the built-ins along the hallway wall and check out those classic glass door knobs! The big basement downstairs has a half-bath which can be reconnected and updated as you wish. The laundry hookups are along the west wall. The home has had some weatherization done by Western Egyptian which included new tilt-in windows, insulation and updated electric. Plumbing is mostly PVC. The roof and hvac system are around 16 years old, and the cedar shake siding could use an update. If you are looking for a sturdy home to add a few cosmetic touches to make it your own style, look no further. The big back yard has a one car garage and has alley entrance for off street parking. Give this one a look before it's gone!

1027 William St, Chester

Courtesy of Worth Clark Realty 800-991-6092

$149,000

3 Beds ⋅ 2 Baths ⋅ 26039071 MLS

Welcome to 1040 William Street! An adorable 3 bed-2 bath home on a quiet side street just off the main business area of Chester. Open kitchen/dining/living room area nicely updated with new flooring and modern paint colors. Two bedrooms and full bath on the main level. Upstairs there's another large bedroom, full bathroom, and a bonus room. Full unfinished basement with walkout to the big backyard. In the evening sit on the front porch (nice composite flooring, no maintenance) and watch the sun go down, and enjoy the sunrise with your morning coffee off the big deck off the kitchen in back. Long backyard opens to woods and the whitetail deer frequently come through. Very well maintained and had been a rental property with a long-term tenant for quite a while. Seller is ready to retire from being a landlord. This home would make a great investment property or it's roomy enough for a growing family. Make this one on your must-see list if you are looking for a nice home reasonably priced.

1040 William St, Chester

Courtesy of Worth Clark Realty 800-991-6092

$79,000

3 Beds ⋅ 1 Baths ⋅ 26036926 MLS

Are you looking for an affordable and comfy home close to the high school and walking distance to the business section of Chester? Here you go! Needs some cosmetic touches, and furnace & Roof are aged, but the A/C is only 6 years old. Features a big living room and kitchen, main-floor master and washer-dryer hookups in the kitchen. Front porch makes a great place to watch the Chester parades, and the back deck is convenient to parking area. 2-3 bedrooms upstairs and a full basement (cellar type) gives some spreading out room. Would make an ideal rental property as well. Yard is small so less mowing, and the corner lot allows for off street parking. Seller is motivated! Come and see for yourself.

1527 Swanwick St, Chester

Courtesy of Worth Clark Realty 800-991-6092

$300,000

4 Beds ⋅ 2 Baths ⋅ 26036541 MLS

Experience the perfect balance of country living and everyday convenience with this rare 11.52-acre property offering room to roam and zoning that welcomes horses! This well-maintained 4-bedroom, 2-bath home has been thoughtfully updated with modern touches throughout. Outside, enjoy a wraparound front porch, rear deck, and a beautifully renovated detached building that offers endless possibilities as a home office, gym, studio, or whatever hobby you enjoy. Additional covered parking and storage provide even more flexibility. Equestrian enthusiasts will appreciate the well-equipped barn, fenced pastures, and ample space for horses and livestock. With productive hay ground and plenty of room to enjoy the outdoors, this property offers a unique opportunity to embrace a rural lifestyle without giving up the convenience of being close to town. Properties with this much acreage and versatility are hard to find. Come see everything this exceptional property has to offer!

1924 High St, Chester

Courtesy of MORE, REALTORS 314-414-6000

$385,000

3 Beds ⋅ 3 Baths ⋅ 26030341 MLS

This one will take your breath away folks. Fully updated and move-in ready. You'll love the fireplaces (propane), tall cathedral ceilings and spacious open floor plan -(notice three huge picture windows facing the trees from the living room) and the entertainment center in the lower level with walk-out to the patio and fire pit; 3 bathrooms and the master suite has a huge walk-in closet. This one comes with 3 lots and covers almost 2 acres. Big two-car garage and concrete driveway. If you are looking for luxury living, look no further! More pics, drone and floor plan will be uploaded this weekend. Allow 24 hour notice for showing requests as home is occupied. Don't let this one pass you by!

201 Estate Dr, Chester

Courtesy of Worth Clark Realty 800-991-6092

$275,000

4 Beds ⋅ 3 Baths ⋅ 26030307 MLS

Put this one on your "checks a lot of boxes" and "must see" list! To name just a few of the exceptional things this home offers: Big family room with two walk-outs to the fenced side yard, deck and swimming pool. The Cabana/Tiki Bar for the pool is a great place to party! Huge master bedroom suite with walk-in closet (it's the size of small bedroom itself). Lots of updates to this beautiful home. Main floor laundry and there's another bedroom and 2 bathrooms on the main level; upstairs there are 2 more bedrooms and half bath upstairs. The big basement has tons of storage. 2 garages on the lots with the house. You can sit on the cute front porch, but you'll want to spend all your time at the Tiki-bar in the back! Come and see this one for yourself!

209 Knapp Ave, Chester

Courtesy of Worth Clark Realty 800-991-6092

$299,000

3 Beds ⋅ 3 Baths ⋅ 26027859 MLS

Put this one on your must-see list! A whopping 2,787 square feet with a total of 3 bedrooms and 3 1/2 baths. Features finished lower level with family room and fireplace, has a walk-out to the large patio area in the backyard, huge primary bedroom and bathroom upstairs, and 2 more bedrooms and laundry room with half-bath on the main level! Seller loves the home but needs to downsize a bit. If you need lots of spreading out room, this one has it. Call to set up a showing today.

103 Estate Dr, Chester

Courtesy of Worth Clark Realty 800-991-6092

$185,000

5 Beds ⋅ 2 Baths ⋅ 26016790 MLS

A brick antique house that has much remodeling done. It is located near the heart of Chester giving easy access to to all directions. The 3rd. floor storage room has a skylight giving it plenty of natural light. It could easily be made in to a bed and breakfast or a multi family residence with some additional changes. The garage has a upstairs floor for additional storage or could possibly be made into a small apartment. The house has many of the original features preserved such as window transits, decorative doors, the trim around the gables and front porch. There is a tunnel from the basement out to the street, it has a skylight. A very spacious house with a lot of room.

1009 Swanwick St, Chester

Courtesy of Golden Key Realty 618-443-2211

$188,000

3 Beds ⋅ 1 Baths ⋅ 26018226 MLS

BACK ON MARKET - No fault of seller. If you are looking for a fully updated 3-bed 1 bath home on a corner lot with an attached garage and full dry basement, stop and have a look at this one! All new flooring throughout the entire home in the last 5 years. New windows, updated kitchen, 15x24 composite deck (only 2 years old) on the west side of the house. HVAC is 6 years old, water heater 4 years old. Roof is 9 years old and solar panel system was installed in 2024. The electric bill went from $300-400 a month to less than $39 even in the coldest winter in years. WOW! Solar purchase agreement is $162 per month and is transferable to new owner. Copy of agreement available to serious buyers. There is a new water feature installed in the front yard and the home is the cleanest one I think I've ever seen. This one is truly move-in ready, and the sellers are ready to relocate to another state. They are ready to make a deal. Call for a showing soon before this one gets away!

328 Van Zant St, Chester

Courtesy of Worth Clark Realty 800-991-6092

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Listing information is provided courtesy of the Broker Reciprocity/IDX of Bagnell Dam Association of REALTORS® and Lake of the Ozarks Board of REALTORS®, Inc. Multiple Listing Services. Copyright 2026 Multiple Listing Service, Inc. of Bagnell Dam Association of REALTORS® MLS, Inc. and Lake of the Ozarks Board of REALTORS® MLS, Inc. Information is being provided for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information herein is believed to be accurate and timely, but no warranty as such is expressed or implied. 2026 Century 21 Community