Chester, SC Homes for Sale under $300,000

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  /24

  $199,900

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  805 Yarborough Rd, Chester, SC 29706

  Looking for room to breathe? Welcome to peaceful country living on approximately one acre in Chester, SC. Surrounded by mature trees and open green space, this charming home that offers the privacy and freedom that’s becoming harder to find. With no HOA, you’ll have the flexibility to create the lifestyle you want whether that means gardening, keeping pets, parking your RV or boat, enjoying

  

  Saige Maxwell

  Saige Real Estate

  

  805 Yarborough Rd, Chester, SC 29706
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  /12

  $115,000

  $35K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,554 Sq Ft

  111 Dye St, Chester, SC 29706

  Charming brick home situated on a spacious 0.50-acre lot in the heart of Chester! This 4-bedroom, 2-bath property offers plenty of space both inside and out, along with classic curb appeal featuring a welcoming covered front porch perfect for relaxing and enjoying the peaceful surroundings.Inside, you’ll find generously sized rooms, and abundant natural light throughout. The spacious kitchen

  

  Nancy Braun

  Showcase Realty LLC

  

  111 Dye St, Chester, SC 29706
• 

  

  

  /17

  $131,000

  $14K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,143 Sq Ft

  530 Pinckney Rd, Chester, SC 29706

  Welcome to this charming one-story home featuring new carpet and fresh paint throughout. The bright, inviting interior offers a spacious kitchen with a breakfast bar and separate dining area, perfect for everyday living and entertaining. Step outside to enjoy the mostly fenced backyard—ideal for pets, play, or relaxing. Move-in ready, this home presents an excellent opportunity for homeowners and

  

  Vivian Knight

  RE/MAX Executive

  

  530 Pinckney Rd, Chester, SC 29706
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  /9

  $16,995

  $2K PRICE DROP

  • Land
  • 10,105 Sq Ft
  • $73,254 per Acre

  767 Pinckney Rd, Chester, SC 29706

  Build your dream home on this spacious corner lot in a great Chester location! The property is already equipped with public water and sewer, making it ready for your new build. It also includes 30-amp and 50-amp plugs, offering a versatile power setup perfect for charging an electric vehicle or meeting additional power needs. Conveniently located near downtown Chester, schools, and shopping.

  

  Mike Morrell

  Keller Williams Connected

  

  767 Pinckney Rd, Chester, SC 29706
• 

  

  

  /25

  $130,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,021 Sq Ft

  596 Armory Rd, Chester, SC 29706

  Back on the market—no fault of the seller! A second chance to secure this excellent investment opportunity on 3.26 acres. The property includes a separate living space/Tiny house featuring a full bathroom, kitchen, and a spacious living area. The interior has been recently updated and is ready for occupancy. The main brick home is currently uninhabitable and requires a complete renovation. Do not

  

  Mike Morrell

  Keller Williams Connected

  

  596 Armory Rd, Chester, SC 29706
• 

  

  /21

  $265,000

  New Construction $36K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,749 Sq Ft

  1016 Horizon Ln, Chester, SC 29706

  Come see 1016 Horizon Lane in Woodhaven located in Chester, SC. The Darwin is one of our two-story plans featured at Woodhaven at Chester in Chester, SC. The Darwin is a spacious and modern two-story home that boasts an impressive level of comfort, luxury, and style. This home offers three bedrooms, two and a half bathrooms and a two-car garage. The moment you step inside this home you will be

  

  D.R. Horton

  Builder

  1016 Horizon Ln, Chester, SC 29706
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  /24

  $275,615

  New Construction $32K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,927 Sq Ft

  548 N Sparkleberry St, Chester, SC 29706

  Come see 548 N. Sparkleberry Street located in Chester, South Carolina! The Aisle is one of our two-story plans at Woodhaven at Chester in Chester, SC. The Aisle is a spacious and modern two-story home designed with open concept living in mind. This home features four bedrooms, two and a half bathrooms and a two-car garage, making it perfect for your new home. Upon entering the home, you'll be

  

  D.R. Horton

  Builder

  548 N Sparkleberry St, Chester, SC 29706
• 

  

  /21

  $265,000

  New Construction $38K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,749 Sq Ft

  1027 Horizon Ln, Chester, SC 29706

  Come see 1027 Horizon Lane in Woodhaven located in Chester, SC. The Darwin is one of our two-story plans featured at Woodhaven at Chester in Chester, SC. The Darwin is a spacious and modern two-story home that boasts an impressive level of comfort, luxury, and style. This home offers three bedrooms, two and a half bathrooms and a two-car garage. The moment you step inside this home you will be

  

  D.R. Horton

  Builder

  1027 Horizon Ln, Chester, SC 29706
• 

  

  /21

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  191 W End St, Chester, SC 29706

  Motivated Sellers and closing costs assistance with this spacious 3-bedroom, 2-bath ranch home on a beautiful 1-acre lot featuring a detached 2-car garage, wired outbuilding, fenced backyard, above-ground pool, and covered back porch—everything you need for relaxing, entertaining, or enjoying extra space. With generous square footage, charming original built-in bookcases, shelving, and a built-in

  

  Michelle Jackson

  ERA Live Moore

  

  191 W End St, Chester, SC 29706
• 

  

  /48

  $187,500

  • Land
  • 13.6 Acres
  • $13,787 per Acre

  1413 Old Columbia Rd, Chester, SC 29706

  Opportunity awaits on this nearly 14-acre tract located just 3 miles from the City of Chester at the corner of Highway 321 (Columbia Highway) and Old Columbia Highway. Being separated from a larger parcel, this property offers over 1,050 feet of road frontage, creating exceptional access and flexibility for future use. One of the property's standout features is a picturesque pond that provides a

  

  Lee Whitley

  Mossy Oak Properties Land and Luxury

  

  1413 Old Columbia Rd, Chester, SC 29706
• 

  

  /18

  $57,000

  • Land
  • 2.51 Acres
  • $22,709 per Acre

  1802 Goings Rd, Chester, SC 29706

  Welcome to Mountain Lakes in Chester, where Lot 7 offers a rare opportunity to own a wooded homesite in a quiet, natural setting. The waterline is especially interesting, the shoreline is untouched, and birds and wildlife add to the peaceful character of the area. Lot 7 is dockable with county permission, and non-gasoline-powered watercraft are allowed on the water. The lake lots on either side

  

  Melissa Vess

  ALBRICK

  

  1802 Goings Rd, Chester, SC 29706
• 

  

  /3

  $273,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  110 Gaston St, Chester, SC 29706

  Be among the first to own this thoughtfully designed new construction home in an established residential neighborhood in the City of Chester. Blending contemporary farmhouse architecture with modern functionality, this to-be-built home offers 3 bedrooms, 2 full bathrooms, 1 half bath, and an attached one-car garage, creating a comfortable layout for everyday living. The open-concept main level is

  

  Brenda Hayden

  Keller Williams Unlimited

  

  110 Gaston St, Chester, SC 29706
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  /34

  $283,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,368 Sq Ft

  Robie Plan at Woodhaven at Chester, Chester, SC 29706

  The Robie is one of our two-story plans featured at Woodhaven at Chester in Chester, SC, offering three modern elevations. This home offers a guest bedroom on the main floor, five bedrooms, three bathrooms, and a two-car garage. Upon entering, you’ll be greeted by a foyer inviting you to the center of the home. At its heart, you’ll find a spacious family room and dining room that blend with the

  D.R. Horton Builder

  804 N Naughton St Unit 36208953, Chester, SC 29706
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  /27

  $253,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,613 Sq Ft

  Taylor Plan at Woodhaven at Chester, Chester, SC 29706

  The Taylor is one of our two-story plans featured at Woodhaven at Chester in Chester, SC offering 3 modern elevations. The home offers four bedrooms, two and a half bathrooms and two-car garage. The moment you step inside the home, you’ll be greeted by a foyer which invites into the center of the home. At the heart of the home is a spacious family and dining room that blends together with the

  D.R. Horton Builder

  804 N Naughton St Unit 36208947, Chester, SC 29706
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  /31

  $267,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,927 Sq Ft

  Aisle Plan at Woodhaven at Chester, Chester, SC 29706

  The Aisle is one of our two-story plans at Woodhaven at Chester in Chester, SC offering 5 elevations. The Aisle is a spacious and modern two-story home designed with open concept living in mind. This home features four bedrooms, two and a half bathrooms and a two-car garage, making it perfect for your new home. Upon entering the home, you'll be greeted by an inviting foyer that leads directly

  D.R. Horton Builder

  804 N Naughton St Unit 36208951, Chester, SC 29706
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  /32

  $274,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  Elston Plan at Woodhaven at Chester, Chester, SC 29706

  The Elston is a spacious and modern two story home plans featured at Woodhaven at Chester in Chester, SC offering 6 modern elevations. The home features four bedrooms, two and a half bathrooms, and two-car garage. The open concept layer connects the home beautifully, where the inviting foyer will lead you into the heart of the home, where the kitchen and large family room meet to create a

  D.R. Horton Builder

  804 N Naughton St Unit 36208952, Chester, SC 29706
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  /26

  $269,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,764 Sq Ft

  Cali Plan at Woodhaven at Chester, Chester, SC 29706

  The Cali is one of our ranch style plans featured at Woodhaven at Chester in Chester, SC, offering 3 elevations. The Cali’s spacious and modern single-story home design is popular for its open-concept style for living. This home features four bedrooms, two bathrooms, and a two-car garage. The inviting foyer leading directly into the heart of the home greets you upon entering. directly into the

  D.R. Horton Builder

  804 N Naughton St Unit 36208950, Chester, SC 29706
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  /15

  $174,000

  $13K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  556 Roundtree Cir, Chester, SC 29706

  New Paint and Flooring make this 3 Bedroom Brick Ranch shine. There is a new concrete driveway and sidewalk to the front steps. Bedrooms are nice sized with good closet space. The lot is level with large backyard. The large bathroom includes the washer that stays, and a dryer hook-up. Kitchen cabinets have fresh paint, and countertops have been updated. The refrigerator also stays. Dining area

  Roger Ware Ware Land & Timber, LLC

  

  556 Roundtree Cir, Chester, SC 29706
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  /37

  $119,500

  • Land
  • 12 Acres
  • $9,958 per Acre

  0 Cool Branch Rd, Chester, SC 29031

  Escape to your own private country setting in Fairfield County, South Carolina, with this exceptional tract of land offering multiple homesites and endless potential. Whether you're dreaming of building a custom home, establishing a family compound, starting a farm or garden, or creating a recreational getaway, this property delivers the space and versatility to make it happen. Equestrian

  Kyle Keller Carolina Roots Land Co

  0 Cool Branch Rd, Chester, SC 29031
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  /75

  $84,500

  • Land
  • 7.5 Acres
  • $11,267 per Acre

  0 Cool Branch Rd, Chester, SC 29031

  This 7.5-acre homestead tract in Fairfield County, SC offers a rare blend of privacy, natural beauty, and everyday convenience, tucked away in a quiet country setting yet just a short drive from modern amenities. The property provides multiple usable homesites and endless potential, whether you're envisioning a custom-built home, a family compound, a working farm or garden, or a private

  Kyle Keller Carolina Roots Land Co

  0 Cool Branch Rd, Chester, SC 29031
• 

  /2

  $269,500

  • Land
  • 36 Acres
  • $7,486 per Acre

  0 Cool Branch Rd, Chester, SC 29031

  Escape to your own private country setting in Fairfield County, South Carolina, with this exceptional tract of land offering multiple homesites and endless potential. Whether you're dreaming of building a custom home, establishing a family compound, starting a farm or garden, or creating the ultimate hunting and recreational getaway, this property delivers the space and versatility to

  Kyle Keller Carolina Roots Land Co

  0 Cool Branch Rd, Chester, SC 29031
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  /42

  $259,000

  $30K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 2 Baths
  • 2,052 Sq Ft

  1409 Clayton Dr, Chester, SC 29706

  Peaceful country living on 1 acre! 3BR/2BA mobile home on a private driveway in Chester, SC. Features new floors in kitchen, dining & laundry, with carpet replacement needed—great chance to customize. Primary suite includes bonus room perfect for office or nursery. Enjoy 2 screened porches & a 30x40 wired detached garage/workshop. Well water, septic & Duke Power. Excellent investor opportunity or

  Michael Rivera Keller Williams Ballantyne Area

  

  1409 Clayton Dr, Chester, SC 29706
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  /30

  $199,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,788 Sq Ft

  114 Hampton St, Chester, SC 29706

  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!

  Jimmy McWaters Rinehart Realty Corporation

  

  114 Hampton St, Chester, SC 29706
• 

  

  /18

  $120,000

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  135 Mill St, Chester, SC 29706

  This charming 3BR/1.5BA brick ranch has so much potential and is ready for its next owner. Whether you're looking for an investment property or a home you can make your own, this one is worth a look. The home features a newer roof installed in 2021 and a current HVAC system installed in November 2025, offering peace of mind on two major components. With a solid layout and plenty of opportunity to

  Latoya Dillard Bloom Realty

  

  135 Mill St, Chester, SC 29706
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  /28

  $217,000

  • 3 Beds
  • 1 Bath
  • 1,015 Sq Ft

  111 Berry St, Chester, SC 29706

  ***Back on the market at no fault of the seller***Charming opportunity in the heart of Chester! Welcome to 111 Berry Street — a property full of upgrades and ready for its next chapter. This home features 3 bedrooms, 1 full bathroom and a functional layout designed for comfortable everyday living. Large windows provide abundant natural light throughout the home. Other updates includes: gutters

  Roderick Fluellen Epique Realty

  111 Berry St, Chester, SC 29706
• 

  

  /43

  $220,000

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  785 Hawthorne Rd, Chester, SC 29706

  Small house nestled on almost two acres of land, with 2 bedrooms, one bathroom. One bedroom could easily be converted into two. There is plenty of space in the outbuilding and barn for storage. Home is located near highly desirable Hawthorne Academy, dining, shopping, and the Chester State Park. You are minutes from downtown Chester.

  Darla Muckenfuss Rinehart Realty Corporation

  

  785 Hawthorne Rd, Chester, SC 29706
• 

  

  /15

  $95,000

  • 2 Beds
  • 1 Bath
  • 918 Sq Ft

  109 Starnes St, Chester, SC 29706

  Welcome to 109 Starnes, a charming “2-bedroom, 1-bath” cottage full of potential. This home is being sold as is, giving the next owner the opportunity to customize the floor plan to fit their needs. Some updates have already been completed by the current owner, including new siding, HVAC, plumbing, electrical panels, and floor joists repair. The flooring and bathroom are ready to be installed,

  Brantly Thomas Jeff Cook Real Estate LPT Realty

  

  109 Starnes St, Chester, SC 29706
• 

  /2

  $41,000

  $2K PRICE DROP

  • Land
  • 15,246 Sq Ft
  • $117,143 per Acre

  714 Belt Rd, Chester, SC 29706

  Perfect .35 acre flat lot in great location! Zone GC (General Commercial). There was a house in this lot that was taken down and now it's ready to build. Lot needs septic and well. Based on previous seller, there was a shared well. Located only 5-7 minutes to the center of Chester.

  Elena Donaldson Keller Williams Ballantyne Area

  

  714 Belt Rd, Chester, SC 29706
• 

  

  /14

  $149,900

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  128 Ella St, Chester, SC 29706

  Clean, well-maintained, and full of charm, this 3-bedroom, 1-bath home is a great opportunity for a first-time buyer, investor or anyone looking to simplify. Inside, you’ll find hardwood floors along with new kitchen counters, sink, and faucet that give the space a fresh feel while keeping its character intact. Outside, the wooded backyard and mature shade trees create a peaceful setting with

  Micah Winn Keller Williams Connected

  

  128 Ella St, Chester, SC 29706
• 

  /2

  $225,000

  • Land
  • 24 Acres
  • $9,375 per Acre

  1848 W End Rd, Chester, SC 29706

  Imagine the possibilities with this beautiful 24-acre property, a blank canvas ready to bring your vision to life. Whether you're dreaming of building your forever home, creating a private family compound, or establishing the farm you've always wanted, this expansive tract offers endless opportunities. With plenty of room for a custom home, barns, gardens, pastures, recreational space, and more,

  Faith Funderburke Faith Funderburke Realty LLC

  

  1848 W End Rd, Chester, SC 29706
• 

  

  /14

  $160,000

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  608 Catawba St, Chester, SC 29706

  Discover the potential of this charming 3-bed, 1-bath home located at 608 Catawba St in Chester, SC. With 1,025 sq ft of living space on a generous 0.38-acre lot, this property is an ideal opportunity for investors, DIY buyers, or anyone looking for an affordable home with room to grow. Several major updates have already been completed, including a brand-new roof, updated HVAC system, and new

  Sheila Eller EXP Realty LLC Rock Hill

  

  608 Catawba St, Chester, SC 29706
• 

  

  /8

  $34,000

  • Land
  • 1.37 Acres
  • $24,818 per Acre

  0 Mt Pleasant Church Rd Hwy Unit SPN340061, Chester, SC 29706

  Baylen Scherer EXP Realty LLC

  0 Mt Pleasant Church Rd Hwy Unit SPN340061, Chester, SC 29706
• 

  

  /39

  $274,900

  $14K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,339 Sq Ft

  107 Hinton St, Chester, SC 29706

  Welcome to 107 Hinton St., a beautifully preserved Victorian residence in the heart of historic Chester. Reintroduced to the market following significant upgrades, this timeless property reflects a thoughtful investment in quality improvements while preserving the architectural integrity that defines its character. Set on approximately 0.45 acres, the four-bedroom, three-bath home offers 3,339

  Robin Nitsche Premier Sotheby's International Realty

  

  107 Hinton St, Chester, SC 29706
• 

  

  /5

  $270,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  764 Old York Rd, Chester, SC 29706

  Construction is nearing completion, and this one is worth seeing! Located in Chester County near the Charlotte metro, this beautifully designed semi-custom home offers the opportunity to enjoy more space, a quieter setting, and convenient access to Rock Hill and the greater Charlotte area. The home features 3 bedrooms, 2 full baths, and a spacious 0.55-acre lot with no HOA. Inside, the

  Ari Simpson Bloom Realty

  

  764 Old York Rd, Chester, SC 29706
• 

  

  /36

  $299,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,161 Sq Ft

  853 Nancys Place, Chester, SC 29706

  Enjoy the peace and privacy of country living on this beautiful 10-acre property with a pond, a mix of open fields and mature woods, and endless possibilities. Spend your days fishing, kayaking, paddling around, or simply relaxing by the water while taking in the peaceful views. The well-kept 3-bedroom, 2-bath home offers a comfortable layout that's ready for its next owner. Established pecan

  Micah Winn Keller Williams Connected

  

  853 Nancys Place, Chester, SC 29706
• 

  

  /13

  $225,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  110 Crestwood Dr, Chester, SC 29706

  Sold As-Is. Sweet 1456 sq ft. two-bedroom two bath home in a quiet neighborhood near downtown Chester. It has a room right off the kitchen that can be used as an office or another bedroom. Updated stainless steel appliances. Washer and Dryer will convey with property. Fireplace in the living room was recently cleaned, great for cool nights in the Carolinas. Hardwood floors throughout the house

  Andre Allen The Virtual Realty Group

  110 Crestwood Dr, Chester, SC 29706
• 

  

  /5

  $49,000

  • Land
  • 2.92 Acres
  • $16,781 per Acre

  1178 Great Falls Hwy, Chester, SC 29706

  This 2.92 acre lot that is only minutes from I-77 or downtown Chester has beautiful large shade trees and loads of privacy! There is plenty of space for work shops or sheds. Come plan your dream home on this large, gently rolling property.Builder available to complete your new home to your specifications. Disclaimer: CMLS has not reviewed and, therefore, does not endorse vendors who may appear in

  Kristina Dillon CD Realty

  1178 Great Falls Hwy, Chester, SC 29706
• 

  

  /25

  $59,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 853 Sq Ft

  30 E Elliott St, Chester, SC 29706

  Calling all investors, flippers, and handy buyers. This 2-bedroom, 1-bath Craftsman bungalow is located right in the city limits of Chester, SC, just a short walk from the charming downtown area with local shops and restaurants. At approximately 900 sqft on a single level, this home is a prime candidate for a full renovation with strong upside potential. The home features a covered front porch

  Kyle Johnson Acacia Realty Advisors, LLC

  30 E Elliott St, Chester, SC 29706
• 

  

  /41

  $230,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft

  518 Melton St, Chester, SC 29706

  Charming Renovated Home in Chester! Welcome to 518 Melton St in Chester, SC, a beautifully updated home that blends classic character with modern upgrades. This inviting property offers 3 bedrooms and 2 full bathrooms with tons of living space, providing a comfortable layout perfect for families or first-time buyers. Step inside to find luxury vinyl plank flooring in the main living areas and a

  Farrah Hall Costello Real Estate and Investments LLC

  

  518 Melton St, Chester, SC 29706
• 

  

  /23

  $199,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,309 Sq Ft

  612 Ballard St, Chester, SC 29706

  Price Improvement — Now is the Time!Some homes just have a soul — and this one has it in spades. This timeless all-brick charmer sits quietly on a tree-lined lot where magnificent mature oaks set the scene before you even step inside. Whether you're a first-time buyer or savvy investor, this property offers the kind of character and quality that simply isn't built anymore.Step onto the

  Michelle Graves LPT Realty, LLC

  

  612 Ballard St, Chester, SC 29706

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