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

$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

$183,000

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

$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

$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

$379,000

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

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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