Chester Real Estate

Chester Real Estate

Welcome to Chester, Illinois – a hidden gem nestled in the heart of Randolph County! Known for its rich history and vibrant community spirit, Chester offers a unique blend of small-town charm and scenic beauty that is sure to captivate anyone looking for a place to call home.

Chester is famously recognized as the birthplace of Popeye the Sailor Man, and this delightful connection is celebrated throughout the town. Visitors and residents alike can explore the Popeye Park, where life-sized statues of beloved characters bring smiles to faces of all ages. The annual Popeye Picnic is a local highlight, showcasing the town’s lively atmosphere and strong community ties.

Beyond its whimsical charm, Chester is surrounded by stunning natural landscapes, including the picturesque banks of the Mississippi River. Outdoor enthusiasts will appreciate the myriad of recreational activities available, from fishing and boating to hiking along scenic trails. The nearby Shawnee National Forest offers breathtaking views and a chance to immerse oneself in nature’s beauty.

Chester’s tight-knit community is complemented by a range of local amenities, including quaint shops, cozy cafes, and family-owned restaurants that serve up delicious home-cooked meals. The town’s commitment to education is evident in its excellent schools, making it an ideal location for families seeking a nurturing environment for their children.

With a welcoming atmosphere and a strong sense of community, Chester, Illinois, is more than just a place to live – it's a place to thrive. Come discover the warmth and charm of Chester, where every day feels like a new adventure!

Newest Listings in Chester

$105,000
26057651 MLS
Updated office in the middle of town. Several office spaces and a large 30x22 storage space in the rear of the building. Building has a partial basement. Priced below appraisal valuation. Currently leased month to month. Agent owned.

1205 Swanwick St, Chester

Courtesy of Golden Key Realty 618-443-2211

$165,000
4 Beds ⋅ 1 Baths ⋅ 26057284 MLS
This adorable 1941 retro home features 4 bedrooms-1 bath and sits on close to 3/4 of an acre (3 lots total) with a detached one car garage, carport, and two storage sheds. The big backyard is private and shaded with mature trees. Watch the sunrise from the front porch (faces east) and enclosed back porch (check out the knotty pine paneling) gives a great sunset view. The big country kitchen has room to eat-in and the big living room/dining combo give lots of spreading out room to gather. The Moureau family has called this home for many years. The full basement is dry. This one is solid and awaits all the current updates you care to do. Priced to move in this market, so give this one a look before you decide. Sellers are motivated and selling as is.

900 W Holmes St, Chester

Courtesy of Worth Clark Realty 800-991-6092

$179,900
3 Beds ⋅ 1 Baths ⋅ 26056777 MLS
Cute, comfortable, and thoughtfully updated! This well-maintained 3-bed, 1-bath ranch offers just under 1,100 sqft of inviting living space with many of the major updates already taken care of. A BRAND-NEW ROOF adds immediate peace of mind, while newer windows (within the last 2 years), all-new sewer lines (within the last 3 years), updated flooring (within the last 6 years), and a serene water feature in the front landscaping provides even more value! The bathroom was renovated approximately 6 years ago, with the HVAC (2014) and water heater (2016) also having been updated. The third bedroom is currently being used as a cozy family room and features French doors opening to the large composite deck-a fantastic setup for relaxing, entertaining, or enjoying the outdoors. Solar panels, installed approximately 2 years ago (2024), offer the opportunity for added energy savings for the new homeowner! This well cared for, move-in ready home offers an excellent opportunity to enjoy a long list of updates without taking on a long list of projects! Come see everything this charming Chester home has to offer!

328 Van Zant St, Chester

Courtesy of Century 21 Advantage 618-281-7621

$170,000
26056476 MLS
Situated on 2.76 +/- acres along a busy highway, this property offers excellent visibility and easy access. The 17,000 +/- square foot industrial building provides plenty of space and a flexible layout that can accommodate a variety of commercial, industrial, or mixed-use opportunities. Whether you're planning to renovate, repurpose, or develop something new, this property offers a solid foundation with plenty of potential to bring your vision to life.

1260 Lehman Dr, Chester

Courtesy of Property Peddler, Inc 618-473-2500

$525,000
5 Beds ⋅ 4 Baths ⋅ 26055646 MLS
Wow this one checks all boxes! Secluded with lots of trees on the 8.82 acres! Take a deep breath before you enter this amazing home, you're gonna need it! This efficient earth home features 5+ bedrooms (4 on main level, 1 plus bonus room up), 5 bathrooms (3 full-2 half (1 is in the pool house), huge living room with fireplace and open floor plan to the dining room and kitchen. Big 2 car attached garage, in ground concrete swimming pool. This one is move-in ready. So much to tell about this property. Check out the 3-D tour and join us for an open house on Saturday, August 29 from 3 to 4:30 pm.

7 Greenbriar Ln, Chester

Courtesy of Worth Clark Realty 800-991-6092

$1,700,000
4 Beds ⋅ 4 Baths ⋅ 26054683 MLS
Beautiful Custom-built stone/brick home on 20 acres. Whitetail and turkey hunting are 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. Whitetail deer and turkey populate the area these 20 acres that include a wooded area and two fields. A great location for a hunter to place tree stands on his own 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. Additional acreage available.

10631 Wine Hill Rd, Chester

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

$260,000
4 Beds ⋅ 2 Baths ⋅ 26054017 MLS
Welcome to 230 Ridge Dr, a charming split-level tucked away on a quiet street in a peaceful Chester neighborhood. Recently fully renovated, this 4-bedroom, 2-bath home showcases modern updates with plenty of personality, including beautiful wood floors, custom stonework, and updated electrical. Enjoy peaceful forest views from the back of the home and a well-maintained, fully functional hot tub, staying with the property! Conveniently located near Chester’s historic downtown, local shops, restaurants, schools, and major routes. Cute, comfortable, updated, reach out today to take a look!

230 Ridge Dr, Chester

Courtesy of MORE, REALTORS 314-414-6000

$150,000
3 Beds ⋅ 1 Baths ⋅ 26053413 MLS
Full brick, clean as a whistle, and move-in ready are just a few terms to describe this delightful home at 1 Washington Blvd in Chester. New windows were installed by the former owner throughout the home; kitchen has been updated with modern fixtures and countertops. The window seat in the dining room has bookcases on each side and is simply adorable. The big living room has a wood-burning fireplace which the owner hasn't used. But it certainly is a focal point! Two bedrooms and a full bath round out the main level. Upstairs is a great space for a extra sitting room and small bedroom with wall-to-wall bookcases. Lots of storage space upstairs (check out the rounded hobbit door with finished space in the attic). There is a full basement with a walk-out and lots of storage room. A carport is in back of the house. Yard is small but that means less mowing and maintenance. There is alley access. Check out the roses all around the house. Simply beautiful and timeless. Don't let this one slip by you. Close to the high school! Seller is motivated and selling as-is. Information offered is deemed reliable but not guaranteed. Call for a showing today!

1 Washington Blvd, Chester

Courtesy of Worth Clark Realty 800-991-6092

$2,500,000
4 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.

Along Along Wine Hill Rd, Chester

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

$299,000
3 Beds ⋅ 2 Baths ⋅ 26045140 MLS
PRICE REDUCED! SELLER IS MOTIVATED FOR OFFERS! 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

$145,000
3 Beds ⋅ 1 Baths ⋅ 26040465 MLS
BACK ON THE MARKET-No fault of seller. 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

$75,000
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

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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