Chester Homes under $500,000

Chester Homes under $500,000

Welcome to Chester, South Carolina, a charming city that beautifully blends small-town warmth with modern conveniences. Nestled in Chester County, this vibrant community is known for its rich history, friendly atmosphere, and picturesque landscapes. With a population that cherishes its heritage and community spirit, Chester offers a unique lifestyle that appeals to families, retirees, and everyone in between.

The city boasts an array of recreational opportunities, from scenic parks to local festivals that celebrate the region's culture. Outdoor enthusiasts will enjoy the nearby fishing and hiking spots, while history buffs can explore the historic downtown area, featuring stunning architecture and quaint shops. Chester also offers a variety of dining options, ensuring that you can savor delicious meals without venturing far from home.

For those seeking a place to call home, Chester has an impressive selection of properties available for under $500,000. Whether you're looking for a cozy cottage, a spacious family home, or a charming ranch-style house, you'll find diverse options that cater to various lifestyles and preferences. The real estate market in Chester is thriving, making it an ideal time to invest in your dream home without breaking the bank.

With its affordable housing, welcoming community, and abundance of local amenities, Chester, SC, is more than just a place to live—it's a place to thrive. Discover your perfect home in this delightful city and experience the warmth and charm that Chester has to offer!

Newest Chester Homes under $500,000

511 Birdie Haven Drive, Chester
$339,900
3 Beds ⋅ 2 Baths ⋅ 4435345 MLS

511 Birdie Haven Drive, Chester
1172 Deer Run Road, Chester
$379,900
3 Beds ⋅ 3 Baths ⋅ 4434930 MLS
Room to breathe, space to play and a backyard made for summer! Set on a generous 1.26-acre lot in the Peden Oaks community of Chester, this two-story home pairs everyday comfort with true outdoor living. Gather by the gas fireplace in the inviting living room, host dinners in the separate dining room, and cook in a kitchen equipped with a gas range. A main-level office makes working from home easy. Upstairs, three bedrooms and two full baths are joined by a flexible bonus room, ideal for a playroom, media room or guest space. Step outside and the fun begins: the back deck overlooks your own private pool, while the pool cabana and shed, both with electricity, are ready for a home gym, workshop or poolside hangout. Sip your morning coffee on the front porch and enjoy the quiet, wide-open feel of country living. Schedule your showing today!

1172 Deer Run Road, Chester
914 S Naughton Street, Chester
$239,000
3 Beds ⋅ 2 Baths ⋅ 4434176 MLS
Come see 914 S Naughton Street located in Chester, South Carolina! The Sanford is one of our ranch plans featured at Woodhaven at Chester in Chester, SC. This home features three bedrooms, two bathrooms, and one-car garage. As you enter the home you will see the two secondary bedrooms and shared bathroom. The home then opens up to the kitchen and living area. The kitchen is equipped with a pantry, stainless steel appliances, and ample counter space, making it perfect for both dining and entertaining. The home also features a luxurious primary suite, complete with a large walk-in closet and a primary bathroom. This bright and sunny home has 3 bedrooms, 2 baths and a beautiful open floor plan. Spacious kitchen with quartz counters, stainless steel electric range/microwave/dishwasher and pantry. The kitchen opens into family room w/ elegant and durable vinyl plank floors throughout main living space. Primary bedroom features a walk-in closet, luxurious bathroom with large shower, and raised height vanity with quartz top. Walk in Laundry. Fully sodded yard, garage door opener with remote and 8' x 10 rear patio all included! BRAND NEW HOME WITH COMPLETE BUILDERS WARRANTY! MOVE IN PACKAGE (REFRIGERATOR, WASHER-DRYER, AND BLINDS)

914 S Naughton Street, Chester
114 Hampton Street, Chester
$189,900
3 Beds ⋅ 2 Baths ⋅ 4433726 MLS
Nice home with so much potential, owned by the same family for over 60 years. The home features a very large living room, spacious dining room, a flex space or office, high ceilings, and more. Enjoy the large, relaxing rocking-chair front porch and the beautiful yard. Dining room furniture and piano are available if desired. Add your own touch and make this home something special!

114 Hampton Street, Chester
218 Center Street, Chester
$149,900
2 Beds ⋅ 1 Baths ⋅ 4432536 MLS
Welcome to this charming 2-bedroom cottage in historic Chester, SC - an inviting opportunity for a first-time homebuyer or anyone looking for a home with comfort and convenience. Step inside to a bright, open floor plan featuring a spacious great room that flows easily into the cozy eat-in kitchen. Abundant natural light creates a warm and welcoming feel throughout the home. Enjoy your morning coffee or afternoon tea on the front porch. Conveniently located within walking distance of shopping, dining, and entertainment, this cottage offers small-town charm with everyday conveniences close by. Whether you're ready to make the move to homeownership or add to your investment portfolio, this Chester cottage is worth a look!

218 Center Street, Chester
102 Mlk Memorial Drive, Chester
$215,000
3 Beds ⋅ 1 Baths ⋅ 4353186 MLS
Lots of updates to this charming all brick ranch home. Newly added wooden front porch railing. Original hardwood floors restored. Kitchen, bathroom, and first bedroom updated with Luxury vinyl plank. New vanity in bathroom, Fresh new paint interior and exterior. Brand new mailbox. New window blinds.

102 Mlk Memorial Drive, Chester
530 Pinckney Road, Chester
$118,000
2 Beds ⋅ 1 Baths ⋅ 4431958 MLS
Welcome home to this charming, move-in-ready one-story home featuring fresh interior paint and new carpet throughout. The bright and inviting floor plan offers comfortable living spaces, including a spacious kitchen with a breakfast bar and separate dining area—perfect for gatherings. Step outside to enjoy the mostly fenced backyard, offering plenty of space for pets, play, gardening, or simply relaxing outdoors. Whether you’re searching for a primary residence or an investment opportunity, this home offers flexibility and value. The seller is offering up to $3,000 in concessions with an acceptable offer, which may be applied toward closing costs, an interest rate buy-down, or other eligible buyer expenses. Take advantage of this opportunity to make your move with less upfront expense!

530 Pinckney Road, Chester
121 York Street, Chester
$169,900
5 Beds ⋅ 4 Baths ⋅ 4430920 MLS
Check out this beautiful Victorian home located in the historic district of Chester, SC. The home is priced to sell and well below the appraised value. The owner has done may updates during her residency. With some extra TLC, this home could be another bright spot on historic York St. The home is being sold as is where is. The seller will not make any repairs.

121 York Street, Chester
622 Fernwood Drive, Chester
$275,000
3 Beds ⋅ 2 Baths ⋅ 4431467 MLS
Enjoy the ease of new construction in Chester, SC with a thoughtfully designed 3-bedroom, 2-bath home offering modern finishes, an open floor plan, and plenty of room to enjoy both indoors and out. The heart of the home brings the living room, kitchen, and dining area together in one bright, open space, making everyday living and entertaining feel effortless. An abundance of windows fills the home with natural light, while LVP flooring throughout provides a clean, cohesive look that's also easy to maintain. The kitchen is designed for both function and gathering, featuring granite countertops, a center island, pantry, and a full appliance package. The open layout keeps the kitchen connected to the main living and dining areas while providing plenty of workspace and storage. Three bedrooms and two full baths offer a practical layout for a variety of needs. Whether you're purchasing your first home, looking for something brand new with less maintenance, or simply ready for a home with a little more breathing room, this floor plan makes great use of the space. Outside, enjoy a large lot and back patio with room for grilling, outdoor dining, gardening, or creating the backyard you've been picturing. A two-car garage adds valuable parking and storage. If you've been searching for a new construction home in Chester, South Carolina with modern finishes, an open-concept layout, a two-car garage, and a spacious lot, this home delivers a fresh, functional space ready for its first owner.

622 Fernwood Drive, Chester
624 Fernwood Drive, Chester
$275,000
3 Beds ⋅ 2 Baths ⋅ 4431445 MLS
Enjoy the ease of new construction in Chester, SC with a thoughtfully designed 3-bedroom, 2-bath home offering modern finishes, an open floor plan, and plenty of room to enjoy both indoors and out. The heart of the home brings the living room, kitchen, and dining area together in one bright, open space, making everyday living and entertaining feel effortless. An abundance of windows fills the home with natural light, while LVP flooring throughout provides a clean, cohesive look that's also easy to maintain. The kitchen is designed for both function and gathering, featuring granite countertops, a center island, pantry, and a full appliance package. The open layout keeps the kitchen connected to the main living and dining areas while providing plenty of workspace and storage. Three bedrooms and two full baths offer a practical layout for a variety of needs. Whether you're purchasing your first home, looking for something brand new with less maintenance, or simply ready for a home with a little more breathing room, this floor plan makes great use of the space. Outside, enjoy a large lot and back patio with room for grilling, outdoor dining, gardening, or creating the backyard you've been picturing. A two-car garage adds valuable parking and storage. If you've been searching for a new construction home in Chester, South Carolina with modern finishes, an open-concept layout, a two-car garage, and a spacious lot, this home delivers a fresh, functional space ready for its first owner.

624 Fernwood Drive, Chester
528 6th Street Unit #24, Chester
$160,000
2 Beds ⋅ 2 Baths ⋅ 4430778 MLS
*** PRICE IMPROVEMENT **** HOME HAS BEEN APPRAISED WELL ABOVE ASKING PRICE! INSTANT EQUITY Seller is offering $5,000 toward closing costs or a rate buy-down with a competitive offer! Welcome to this remodeled and beautifully reimagined home in Chester Every inch of this property has been thoughtfully designed and constructed from the ground up, creating a move-in-ready home that stands apart from anything else on the market. Step inside to discover over 1,000 square feet of well-appointed living space featuring 2 spacious bedrooms and 2 full bathrooms. The layout features a new kitchen with brand-new countertops, sleek cabinetry, and modern flooring, perfect for both everyday living and entertaining. Both bathrooms have been stylishly renovated, while the entire home features New drywall, electrical, plumbing, energy-efficient windows, and a rebuilt foundation complete with insulation and a moisture barrier for lasting durability and energy efficiency.. Enjoy the comfort of new LVP and carpet flooring, along with a newer gas pack system that keeps the home efficient year-round. The R-30 insulated attic and crawlspace further enhance the home’s energy performance. Outside, the property sits on a generous .27 acre fenced lot, offering plenty of space for outdoor enjoyment. A 15’x15’ workshop, built just three years ago and equipped with electricity, provides endless possibilities for hobbies, storage, or a home business. The durable hardboard fiber cement siding ensures low maintenance and long-lasting curb appeal. All renovations were fully permitted and approved by Chester County, giving buyers peace of mind in the quality of construction. Located in a USDA-eligible area, this home may qualify for 100% financing for eligible buyers. Some photos have been virtually staged

528 6th Street Unit #24, Chester
633 Ashford Street, Chester
$255,000
3 Beds ⋅ 2 Baths ⋅ 4430424 MLS
Welcome home to this charming 3-bedroom 2-bathroom, well-maintained home featuring a bright, open layout with vaulted ceilings and comfortable living spaces throughout. The kitchen offers white cabinetry, generous counter space, stainless steel appliances, that flow into the dining and living areas. Enjoy a spacious yard surrounded by mature trees, a one-car garage, and plenty of room to relax or entertain. With neutral finishes and a functional floor plan, this home is move-in ready and waiting for its next owner!

633 Ashford Street, Chester
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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .

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