Chester Homes under $150,000

Welcome to Chester, Illinois, a charming city nestled in the heart of Randolph County. Known for its rich history and picturesque landscapes, Chester offers a unique blend of small-town charm and modern amenities. With a population of just over 8,000 residents, this vibrant community boasts a friendly atmosphere, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

One of Chester's standout features is its stunning natural beauty. The city is situated along the banks of the Mississippi River, providing residents with breathtaking views and ample opportunities for outdoor activities. Enjoy leisurely strolls along the riverfront, explore the scenic trails at nearby parks, or indulge in fishing and boating adventures. The city's historic downtown area is filled with quaint shops, delightful eateries, and local events that foster a strong sense of community.

For those looking to call Chester home, the housing market offers an array of options, including an impressive selection of homes priced under $150,000. Whether you're a first-time buyer or an investor seeking a rental property, Chester has something to fit your needs. From cozy bungalows to charming ranch-style homes, you can find affordable housing that doesn't compromise on character or comfort.

Chester's affordable real estate, combined with its welcoming community and beautiful surroundings, makes it an exceptional choice for anyone looking to settle down in a serene yet vibrant environment. Come discover the charm of Chester, where your dream home awaits!

Newest Chester Homes under $150,000

$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

$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