Chester Homes under $250,000

Welcome to Chester, South Carolina – a charming city steeped in history and Southern hospitality. Nestled in the heart of Chester County, this vibrant community offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home. With its picturesque landscapes, friendly neighborhoods, and rich cultural heritage, Chester is a hidden gem waiting to be discovered.

One of the standout features of Chester is its affordability. For those looking to invest in a home without breaking the bank, you’ll be delighted to know that there are numerous options available under $250,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Chester’s real estate market has something for everyone. From cozy bungalows to spacious family homes, you’ll find properties that suit a variety of tastes and lifestyles.

Chester is not just about affordable housing; it’s also about community. The city boasts a variety of parks, recreational facilities, and local events that foster a sense of belonging. Enjoy leisurely strolls along the scenic streets, participate in community festivals, or explore the local dining scene featuring delicious Southern cuisine.

With its blend of affordability, community spirit, and rich history, Chester, SC, offers an inviting atmosphere for those looking to plant their roots. Discover your ideal home in this charming city today and experience all that Chester has to offer!

Newest Chester Homes under $250,000

$200,000

3 Beds ⋅ 1 Baths ⋅ 4427459 MLS ⋅ ACTIVE Status

Welcome to 645 Pine Ridge Road in Chester, SC! This charming full-brick ranch home features 3 bedrooms, 1 full bathroom, and sits on a spacious 0.38-acre lot. Recent updates include a new heat pump installed in 2023, new gutters in 2024, new carpet in all bedrooms in 2025, and new laminate flooring throughout the home in 2025. The concrete driveway, added in 2020, provides convenient off-street parking and excellent curb appeal. Enjoy outdoor living from the covered front porch or back deck, while the fully fenced yard offers privacy and plenty of space for pets, gardening, entertaining, or relaxing. With major updates already completed, this full-brick ranch offers a great combination of comfort, functionality, and value. Schedule your showing today!

645 Pine Ridge Road Unit #54, Chester

Listing courtesy of Mark Spain Real Estate. latashramoorer@markspain.com

$186,900

3 Beds ⋅ 2 Baths ⋅ 4426438 MLS ⋅ ACTIVE Status

Thoughtfully updated, this Chester home pairs inviting character with modern style and convenience. The remodeled kitchen takes center stage with attractive finishes and updated appliances, while renovated bathrooms and updated flooring create a fresh, cohesive feel throughout. Additional improvements include updates to the electrical, plumbing, insulation, and HVAC systems, along with a new roof installed in July 2025. Offering comfort and style with many important improvements already completed, this home is ready for its next chapter. Schedule your private showing to experience 102 Cushman Drive!

102 Cushman Drive, Chester

Listing courtesy of Premier South. leslieblackwood@carolinaheritage.org

$199,900

3 Beds ⋅ 1 Baths ⋅ 4425589 MLS ⋅ ACTIVE Status

Charming All-Brick Home with Updates & Convenient Location! Welcome home to this charming 3-bedroom, 1-bath all-brick home offering comfortable living, thoughtful updates, and a convenient location. Step inside to find fresh interior paint and LVT flooring throughout, creating a clean and inviting atmosphere. The kitchen features a smooth-top range and refrigerator, with the washer and dryer also remaining with the home for added convenience. The home offers an attached carport for covered parking and a covered front porch—the perfect spot to relax and enjoy your morning coffee. Out back, you'll find a nice-sized deck, ideal for grilling, entertaining, or hosting weekend BBQs with family and friends. Enjoy the best of both worlds with a location that is close to town while still benefiting from county taxes. You'll be just minutes from growing downtown Chester and conveniently located for an easy commute to both Charlotte and Columbia.

554 Gardendale Circle, Chester

Listing courtesy of New Chester Realty LLC. baustin@comporium.net

$187,500

5 Beds ⋅ 3 Baths ⋅ 4426101 MLS ⋅ ACTIVE Status

This charming turn-of-the-century home features a wraparound rocking chair porch, a detached one-car garage, and a fenced backyard. Inside, it offers an impressive five bedrooms and three full bathrooms, with the master suite on the main level. Enjoy formal dining and living rooms, plus a spacious kitchen with a granite island. A downstairs den with a laundry area completes the space. The property is just waiting for some finishing touches. Home Sold As-Is

123 York Street, Chester

Listing courtesy of Gibbs Realty & Auction Co Inc.. cyeparker3@gmail.com

$239,000

3 Beds ⋅ 1 Baths ⋅ 4425939 MLS ⋅ ACTIVE Status

Welcome to country living on over 2 acres! This move-in ready home has plenty of charm along with several recent updates. Inside, you’ll find LVP flooring, fresh paint, a spacious living room with a brick fireplace, and an updated kitchen with new countertops, backsplash, sink, and stainless steel appliances. The bathroom has also been refreshed with a new tub/shower. 2025 improvements include a new cooling system, electric water heater, reinforced flooring, and a leveled backyard. Outside, there’s a large back deck, fenced yard area, and wooded acreage for added privacy! No HOA and conveniently located with easy access to Chester, Rock Hill, shopping, and I-77.

823 Great Falls Highway, Chester

Listing courtesy of Bloom Realty. ari@arisimpson.com

$249,000

3 Baths ⋅ 4424358 MLS ⋅ ACTIVE Status

Discover the possibilities at 717 Celsey Road! Situated on approximately 2.07 acres just a few miles outside the City of Chester, this well-maintained, site-built property offers a spacious and versatile layout with potential for both commercial and residential use. Currently utilized as a commercial/religious assembly building, the property is well-suited for a variety of uses. For those seeking a residential opportunity, the property is zoned RG-1 and has the potential for conversion to a single-family home or multi-family residence. The existing structure would require upfitting to add typical residential features such as a kitchen, bedrooms, and full bathrooms. The building features a large open meeting area with a stage, two adjoining storage closets, a separate classroom/meeting room, and three restrooms, including one designated accessible restroom. The maximum building capacity is 250. The property offers three points of access, including a ramped accessible entrance, accessible parking, wide interior passageways, and no interior steps. The brick and vinyl exterior has been well maintained, and improvements made in 2019 include a new roof and fresh interior paint. Outside, you'll find a large rear parking area, storage shed, and a covered drive-through awning providing convenient sheltered access to the building. Public water and sewer serve the property. With its generous acreage, established parking, accessibility features, flexible interior space, and convenient location on the west Chester side of the area, this property presents an exciting opportunity for its next owner. Other uses including religious, educational, civic or social organizations, daycare, office, or community gathering space. Whether you are looking for a commercial facility, a place to serve your organization, or a property with potential to convert into a unique residential home, 717 Celsey Road offers endless possibilities. This location is close to the Chester State Park, just a few miles outside of the city and close to public softball and baseball complexes. Schedule your private tour today and discover all that 717 Celsey Road has to offer!

717 Celsey Road, Chester

Listing courtesy of Darby Real Estate and Appraisals, LLC. beth.darbySC@gmail.com

$214,900

3 Beds ⋅ 2 Baths ⋅ 4424061 MLS ⋅ ACTIVE Status

This fully renovated 3-bedroom, 2-bathroom home checks every box for move-in ready living! Built in 2011 and thoughtfully updated throughout, this 1,427 sq ft home sits on a .19-acre lot just minutes from downtown Chester. Step inside to find luxury vinyl plank flooring flowing throughout the home, complemented by appealing light fixtures and ceiling fans. The kitchen has stainless steel appliances, granite countertops, white shaker cabinets, and updated hardware, faucet, and sink. Both bathrooms were recently remodeled with new cabinetry, tile, fixtures, and lighting. The primary suite features a vaulted ceiling and two closets for ample storage. Outside, enjoy the large covered front porch — ideal for rocking chairs and relaxing afternoons — plus a covered side patio perfect for entertaining. The partially fenced, flat backyard includes a spacious shed and a lovely pear tree. A new concrete pad accommodates two vehicles, with additional street parking available.

153 Loomis Street, Chester

Listing courtesy of Ouzts Realty Company, LLC. robert@ouztsrealty.com

$225,000

3 Beds ⋅ 1 Baths ⋅ 4422504 MLS ⋅ ACTIVE Status

Some homes just feel like they’ve been loved, and this sweet Stringfellow Road home has more than thirty years of memories within its walls. Now it’s ready for a new owner, a little fresh vision, and its next chapter. Offering three bedrooms, one bath, and just over 1,000 square feet, this home is comfortable, manageable, and fully move-in ready. Fresh paint has already brightened things up, and a brand-new back deck gives you a great spot for morning coffee, evening conversations, or a backyard cookout. The washer and dryer are included, too. There’s still room here to add your own style and make updates along the way, without needing to tackle everything before moving in. Whether you’re buying your first home, ready to downsize, or simply looking for a place you can make your own, this one offers plenty of possibility. And then there’s the location. Tucked away in a highly sought-after area in Chester, where homes don’t come available often, this is your chance to put down roots in an established area and turn a well-loved house into a home that feels completely yours.

1242 Stringfellow Road, Chester

Listing courtesy of EXP Realty LLC Ballantyne. 803-804-7097

$234,900

4 Beds ⋅ 2 Baths ⋅ 4422793 MLS ⋅ ACTIVE Status

Peaceful country living on 1 acre in Chester, SC! This 4BR/2BA manufactured home offers privacy, space, and plenty of potential. Recent updates include new flooring in the kitchen, dining area, and laundry room, with the owner offering a $3,000 credit toward replacement of the remaining flooring—an excellent opportunity to personalize the home to your taste. The spacious primary suite features a bonus room ideal for a home office, nursery, or flex space. Relax and enjoy the outdoors from either of the two screened porches. A 30x40 wired detached garage/workshop provides abundant space for storage, hobbies, projects, or additional workspace. The generous workshop is especially appealing to self-employed landscapers, mechanics, contractors, hobbyists, or anyone needing space for a home-based business. Whether you're an investor looking for your next project or a buyer seeking a private rural retreat with room to customize, this property offers endless possibilities!

1409 Clayton Drive, Chester

Listing courtesy of Coldwell Banker Realty. Lisa.Parker@CBRealty.com

$240,000

3 Beds ⋅ 2 Baths ⋅ 4421647 MLS ⋅ ACTIVE UNDER CONTRACT Status

If there was ever a LIVE-LOVE-LAUGH home, then this just might be it! Comfortable brick ranch home located just outside of Chester city limits in the ideally-located neighborhood of Pinegrove (no HOA). Three bedrooms, two bathrooms, 1626 HSF, 0.37 acres. The lovely shaded front yard plus a deep fenced-in backyard provides curb appeal along with privacy and security. Close proximity to shopping, restaurants, banking and commonly desired amenities without being subjected to city taxes. Invest in a well-loved comfortable home with established trees, neighbors and conveniences.

517 Mcdowell Drive, Chester

Listing courtesy of Liz Odum Realty LLC. liz@lizodumrealty.com

$180,000

3 Beds ⋅ 2 Baths ⋅ 4418736 MLS ⋅ ACTIVE Status

213 Jewel street is back on the market ready for its next owner. Home has been renovated, and with finishing touches will be a fantastic home to its next occupants. Perfect for investors or first time homebuyers. Please reach out to listing agent, or your buyers agent with any inquiries you may have regarding the history of the home. For clarification of the "title defect" / SCDOT Easement that is currently being addressed, please don't hesitate to reach out.

213 Jewel Street, Chester

Listing courtesy of Worthy & Associates Real Estate LLC. worthy.jeremy1@gmail.com

$225,000

2 Beds ⋅ 1 Baths ⋅ 4418475 MLS ⋅ ACTIVE UNDER CONTRACT Status

Escape to your own private retreat on 6.3 wooded acres! This charming 2-bedroom, 1-bathroom home offers 1,228 square feet of comfortable living space, tucked at the end of a long driveway for maximum privacy and seclusion. The kitchen features stainless steel appliances, ready for everyday living or weekend entertaining. Enjoy the peace and quiet of country living while staying just 10 minutes from I-77 for an easy commute. Whether you're looking for a homestead, hobby farm, or simply room to breathe, this property delivers space, privacy, and convenience all in one. Don't miss this rare opportunity to own acreage close to town!

1646 Joe Caldwell Road, Chester

Listing courtesy of Keller Williams Connected. ryanbigger@kw.com

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 or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Some IDX listings have been excluded from this website. Properties may or may not be listed by the office/agent presenting the information © 2026 Canopy MLS as distributed by MLS GRID”

Last Updated: