Chester Homes under $350,000

Welcome to Chester, Illinois, a charming city nestled in the heart of Randolph County. Known for its picturesque landscapes and rich history, Chester offers a unique blend of small-town charm and modern conveniences. With a population of just over 8,000 residents, this welcoming community is perfect for families, retirees, and anyone looking to enjoy a peaceful lifestyle.

Chester is steeped in history, famously recognized as the birthplace of the beloved comic strip character Popeye. The city celebrates its heritage with various events and attractions, including the Popeye Picnic held annually in September, drawing visitors from all over. Nature enthusiasts will appreciate the scenic beauty of the nearby Mississippi River, along with numerous parks and recreational areas that provide ample opportunities for hiking, fishing, and picnicking.

For those seeking a new home, Chester is an ideal destination, especially with a variety of charming properties available under $350,000. Whether you're looking for a cozy bungalow, a spacious family home, or a quaint cottage, Chester offers a diverse selection of real estate options to suit every taste and budget. The affordability of homes in this area makes it an attractive choice for first-time buyers and those looking to downsize.

With excellent schools, friendly neighbors, and a strong sense of community, Chester is more than just a place to live; it’s a place to call home. Explore the possibilities of life in Chester, where your dream home awaits!

Newest Chester Homes under $350,000

$310,000

4 Beds ⋅ 4 Baths ⋅ 26061963 MLS

Discover this beautiful home in the heart of Chester, conveniently located just minutes from local schools, downtown shopping, and everyday amenities. Enter through the double front doors into an inviting foyer. The main level offers a spacious kitchen with ample cabinet storage, a separate dining room, a den or office with a fireplace, a convenient half bath, and a comfortable family room featuring another fireplace. A beautiful spiral staircase leads to the upper level, where you’ll find four bedrooms and two full bathrooms. The spacious primary suite includes a large, master bathroom. The finished walkout basement provides additional living and entertaining space, complete with an entertainment area, fireplace, and full bathroom. The unfinished portion of the basement includes the laundry room and offers plenty of storage. Kitchen appliances and the pool table are included. Set on a total of 3.4 acres, this property offers space, character, and convenience in a desirable location.

900 Park Ave, Chester

Courtesy of eXp Realty 888-574-9405

$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

$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

$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

$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

$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

$280,000

4 Beds ⋅ 2 Baths ⋅ 26036541 MLS

Enjoy the perfect balance of country living and everyday convenience with this rare 5-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! A neighboring property is also for sale, and the owner is willing to negotiate the price on a package deal!

1924 High St, Chester

Courtesy of MORE, REALTORS 314-414-6000

$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

$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