Chester Homes under $250,000

Welcome to Chester, Illinois, a hidden gem nestled in the heart of Randolph County. Known for its picturesque landscapes and small-town charm, Chester offers a unique blend of history, community spirit, and modern conveniences. With a population of just over 8,000 residents, this welcoming city provides a peaceful retreat while still offering access to essential amenities and recreational activities.

Chester is steeped in rich history, famously recognized as the birthplace of the beloved cartoon character Popeye. The city's vibrant arts scene, highlighted by the annual Popeye Picnic, brings residents together to celebrate local culture and community pride. Nestled along the banks of the Mississippi River, Chester is also a haven for outdoor enthusiasts. Enjoy scenic walks along the riverfront, explore the nearby Shawnee National Forest, or take advantage of the city’s parks and recreational facilities.

For those looking to make Chester their home, you’ll be pleased to discover a variety of charming residences available for under $250,000. Whether you’re searching for a cozy single-family home, a quaint bungalow, or a spacious ranch-style property, Chester offers an array of options that cater to diverse tastes and budgets. With its affordable housing market, Chester is an ideal choice for first-time homebuyers, families, and retirees alike.

Experience the warmth of a close-knit community, the beauty of nature, and the comfort of affordable living in Chester, Illinois. Your dream home awaits in this delightful city, where every day feels like a warm embrace. Come explore the possibilities today!

Newest Chester Homes under $250,000

$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! Seller is ready to move quickly for the right offer.

328 Van Zant St, Chester

Courtesy of Century 21 Advantage 618-281-7621

$140,000

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

$138,500

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

$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

$75,000

3 Beds ⋅ 1 Baths ⋅ 26009893 MLS

Charming 3 bedroom family home - A wonderful opportunity! This cozy three-bedroom home is perfect for your growing family! Enjoy a bright, sunny kitchen, a comfortable living room that opens to a formal dining area, ideal for family meals or gatherings. The spacious bathroom is also conveniently located on the main floor. Upstairs you will find three spacious bedrooms giving everyone their own space. The full basement offers endless possibilities for a future bedroom, bathroom, gaming area and is great for extra storage. You'll have peace of mind knowing the roof, and HVAC was replaced in 2016. The hot water heater in 2024 and the electric has been updated, as well. There is also a 2 car-carport with garage and a large back deck off the kitchen.

1120 George 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