Chester Homes under $500,000

Welcome to Chester, Indiana, a charming township that perfectly blends small-town warmth with modern conveniences. Nestled in the heart of the Hoosier State, Chester is known for its picturesque landscapes, friendly community, and rich history. With a population that values both tradition and progress, residents enjoy a peaceful lifestyle surrounded by nature, yet remain close to urban amenities.

Chester offers an array of homes under $500,000, making it an ideal destination for first-time buyers, families, and anyone looking to invest in a welcoming community. From cozy single-family homes to spacious modern designs, the real estate options cater to diverse tastes and budgets. Many of these homes feature inviting yards, contemporary interiors, and easy access to local parks and recreational areas, perfect for family gatherings and outdoor activities.

The township is also well-connected, with convenient access to major highways that lead to nearby cities, ensuring that residents can enjoy the tranquility of Chester while still being just a short drive away from bustling urban centers. Local schools are highly regarded, providing quality education and a strong sense of community involvement.

Whether you’re seeking a charming starter home or a spacious abode to accommodate your growing family, Chester, IN, has something for everyone. Discover the warmth of this delightful township and explore the many homes available under $500,000—your dream home awaits in Chester!

Newest Chester Homes under $500,000

$170,000

2 Beds ⋅ 1 Baths ⋅ 202640260 MLS ⋅ 1,084 SqFt. ⋅ Jessica Jordan

Spacious and well-maintained 2 bedroom, 1 bath condo offering comfortable, low-maintenance living in a peaceful setting, all on one-level with an attached garage. The backyard boasts a private patio and is bordered by a creek with access from the main bedroom and living room. Numerous recent updates include new flooring and carpet, HVAC, siding, gutters, water heater, fireplace insert and bathtub/shower.

18 Woodspoint Cir N, North Manchester

Listing courtesy of Jessica Jordan from Rochester Realty, LLC.

$49,900

3 Beds ⋅ 1 Baths ⋅ 202638839 MLS ⋅ 1,102 SqFt. ⋅ Andrea Greer Markham

Fixer-Upper Opportunity Near Downtown with view of the Eel River! Bring your vision and some TLC to this one-story home offering approximately 1,100 square feet, with three bedrooms and one bathroom. The property includes a partial basement with a solid foundation, providing useful storage and potential for additional improvements, and is on city utilities. Situated on nearly one-quarter acre, this property offers several possibilities. Renovate it into a comfortable home, transform it into a rental, take on a flip project, or consider a teardown and expand with a purchase of the neighboring property. Located just steps from Manchester Elementary School and downtown, the property offers convenient access to schools, local businesses, dining, and community amenities. Whether you’re an investor, contractor, or buyer looking for a project, this property presents an opportunity to create value in a convenient location. Selling As-Is.

403 S River Ext Rd, North Manchester

Listing courtesy of Andrea Greer Markham from Manchester Realty.

$215,000

2 Beds ⋅ 1 Baths ⋅ 202637775 MLS ⋅ 936 SqFt. ⋅ Taylor Coratti

Welcome to this two bedroom, one bath home situated on 5.6 acres in southern Wells County. Step inside to the living room featuring a sliding barn-style door, with an adjoining room offering additional usable space. The kitchen provides cabinetry, counter space, and built-in storage. One of the bedrooms features a wood accent wall. The full bathroom also includes the laundry area. Outside, the covered front porch overlooks the property, while the acreage includes open yard space, mature trees, and additional detached structures. With plenty of room to spread out and a peaceful rural setting, this property offers space both inside and out. Schedule your showing today!

2137 W 1000 S Rd, Keystone

Listing courtesy of Taylor Coratti from Uptown Realty Group. Cell: 260-820-1090

$309,900

4 Beds ⋅ 3 Baths ⋅ 202637215 MLS ⋅ 2,408 SqFt. ⋅ Maureen Eastgate

Full of character and timeless charm, this spacious brick home showcases beautiful hardwood floors, original woodwork, built-ins and an eye-catching staircase. The main living areas offer plenty of room to spread out, including a large living room with fireplace, a formal dining, room. Upstairs you'll find generously sized bedrooms with an abundant natural light and continued hardwood flooring. This home also has plenty of storage with a partial basement and walk-up attic. Outside enjoy the mature trees, established landscaping, a private back yard, enclosed porch and attached 2 car garage. Remarkably, this home has had only two owners, adding to its unique history and character. With its timeless details and spacious layout, this home is ready for its next chapter.

410 E 3rd St, North Manchester

Listing courtesy of Maureen Eastgate from M&M Rental Property Mgmt & Realty. MEastgate@hotmail.com

$144,000

2 Beds ⋅ 2 Baths ⋅ 202637202 MLS ⋅ 1,254 SqFt. ⋅ Keli Cordill

Bring your ideas to this 2 bedroom and 1.5 bath home with an original 30x40 barn. All on one level, laundry room just off the kitchen. The large kitchen has room for a table and chairs. No appliances included. Spacious 12x15 living room has a large picture window with original stained glass. Formal dining room 13x15 could also be used as a family room. Full bath has a stand-up shower; there is also a half bath. The covered front porch is very charming and will look great decorated for the seasons. Some recent updates include: Roof, Water Heater & Electrical. Great starter home or for those seeking to downsize at 1254 sq ft of living finished living space. Sold AS IS

709 N Sycamore St, North Manchester

Listing courtesy of Keli Cordill from Tri Oaks Realty.

$230,000

4 Beds ⋅ 1 Baths ⋅ 202636038 MLS ⋅ 2,162 SqFt. ⋅ Jody Holloway

Private Country Setting on 1.57 Acres! This 4-bedroom, 1-bath home offers over 2,100 sq. ft. of living space with two separate living areas and several rooms featuring hardwood floors. Three bedrooms are located upstairs, including one semi-private landing room that would make a great bedroom, office, or hobby space. The kitchen offers plenty of cabinet and counter space, with the kitchen appliances plus washer and dryer staying with the home (pre-owned appliances are not warranted). Enjoy the peaceful outdoor setting with a private pond, wooden deck, and a large firepit area. The 92' x 8' wrap-around covered porch extends along two sides of the home and provides plenty of space to relax and enjoy the privacy. Additional amenities include a Lennox LP gas furnace and central air on the first floor, a carport, storage container, and 1-car detached garage. Conveniently located less than 3 miles from Southern Wells Schools. The middle raised garden bed does not stay.

10677 S 200, Keystone

Listing courtesy of Jody Holloway from Coldwell Banker Holloway. Cell: 260-273-0999

$272,000

2 Beds ⋅ 2 Baths ⋅ 202635853 MLS ⋅ 1,201 SqFt. ⋅ Brenda Williams

Just like new and move-in ready! This beautifully maintained 2-bedroom, 2-bath villa offers quality finishes, thoughtful upgrades, and easy, low-maintenance living. The entire home is handicap accessible, and both spacious bedrooms feature walk-in closets. The primary suite includes a walk-in shower, marble vanity top, and upgraded carpet. You’ll love the hickory cabinetry, composite kitchen sink, pantry, plank flooring, high baseboard trim, and Andersen windows with faux blinds. Additional features include a finished 2-car attached garage, covered porch, and a mature yard with established landscaping. Enjoy neighborhood walking trails and affordable average monthly utilities—approximately $71 electric, $58 gas, and $92 water. With its beautiful condition, accessibility features, and upgraded finishes, this villa truly feels just like new!

1105 Marshall Way, North Manchester

Listing courtesy of Brenda Williams from CENTURY 21 Bradley Realty, Inc. Cell: 260-358-6412

$130,000

4 Beds ⋅ 2 Baths ⋅ 202635262 MLS ⋅ 2,422 SqFt. ⋅ Nathan Smith

Buyer Funding Fell thru, now Back on market for you! Bring your home remodeling ideas to this large turn of the Century home on a great street near the College! Nice and roomy with open spaces, needs some updating but worth the investment, as it is listed under assessed value!. 4 bedrooms and 1.5 baths, Main level Owners Suite, Covered Porch and a detached Garage on a Quarter Acre lot. Take advantage of this great opportunity today! Taxes Reflect no current Exemption

719 N Sycamore St, North Manchester

Listing courtesy of Nathan Smith from Coldwell Banker Real Estate Gr. Cell: 260-248-6700

$239,000

3 Beds ⋅ 2 Baths ⋅ 202633041 MLS ⋅ 1,846 SqFt. ⋅ Julie Mobley

Don't miss this 3 bedroom 2 bath home with a beautiful in ground pool. Sit in the 4 seasons room and enjoy the the comforts of the AC viewing the pool or be outside on the deck or the patio enjoying the sun and the pool. The large entry when coming in from the garage would be great for an extra refrigerator or freezer and all your coats and shoes. 2nd bath with laundry are just off the garage entry for easy access. Family room has a gas fire place. A utility shed for lawn mower and yard tools sit outside the privacy fence and a 2nd one for pool supplies is by the pool. the pool is on it own electrical box.

1401 Westchester Dr, North Manchester

Listing courtesy of Julie Mobley from Wander Home Realty, LLC. Cell: 260-415-6296

$274,500

4 Beds ⋅ 2 Baths ⋅ 202633773 MLS ⋅ 1,469 SqFt. ⋅ Keli Cordill

This stunning home was fully renovated, everything replaced floor to ceiling with exceptional attention to detail using quality materials. The kitchen boasts new stainless steel Frigidaire appliances and beautiful custom cabinetry plus a pantry providing abundant storage. This kitchen could be in a magazine! The living room (24x11) is spacious and feels bright & clean! Two bedroom on the main level, The main bedroom with an en suite bath has a tub/shower combination, plus another full bath with a stand up shower. The laundry room provides a new Maytag washer & dryer with ample room for a table or clothes rack. Upstairs you will find 2 bedrooms with plush carpet. This house is new, inside & out. The quality is exceptional and tastefully designed. Home has an attached 1 car garage and sets on a corner lot.

607 N Mill St, North Manchester

Listing courtesy of Keli Cordill from Tri Oaks Realty.

14589 State Road 13th Rd, North Manchester

$249,900

3 Beds ⋅ 2 Baths ⋅ 202634153 MLS ⋅ 1,456 SqFt. ⋅ Deedra Mauricio

Enjoy peaceful country living in this this beautiful remodeled 3-bedroom, 2-full-bath home offers approximately 1,456 square feet and is surrounded by mature trees, established landscaping, and plenty of open yard space. Inside, you’ll find new flooring throughout, including attractive luxury vinyl plank and fresh carpeting, along with updated lighting and ceiling fans. The refreshed kitchen features new countertops, newer appliances, and a brand-new dishwasher. The spacious owner’s suite includes a walk-in closet and private bathroom featuring a double vanity, walk-in shower, and relaxing jetted tub. Step through the sliding glass doors onto the large rear deck overlooking the private, tree-lined property—an ideal setting for relaxing or entertaining. Additional outdoor highlights include a covered front porch, gazebo, garden areas, and a large outbuilding offering abundant space for storage, equipment, hobbies, or a workshop. Enjoy peaceful country living while remaining conveniently close to North Manchester.

14589 State Road 13th Rd, North Manchester

Listing courtesy of Deedra Mauricio from BND Property Management.

$169,995

4 Beds ⋅ 3 Baths ⋅ 202633663 MLS ⋅ 2,131 SqFt. ⋅ Atalie Honaker

Freshly remodeled and move-in ready! This spacious 2,132 sq. ft. home offers 4 bedrooms, 2.5 bathrooms, and plenty of room to spread out. Updates throughout include new flooring, fresh paint, new lighting, beautifully updated bathrooms, and a refreshed kitchen featuring new cabinetry and included kitchen appliances. Outside, enjoy a fantastic .31-acre lot with plenty of room to play, entertain, or simply relax. A charming covered front porch welcomes you home, while the open back deck provides the perfect spot for grilling and enjoying the outdoors. With generous living space, modern updates, and a great-sized lot, this home is ready for its next owners to move right in and enjoy! Schedule your showing today!

10088 S Ohio St, Keystone

Listing courtesy of Atalie Honaker from The LT Group Real Estate.

Start Your Search

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.