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5-Bedroom Homes for Sale in Chester, SC

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  • /48

    $1,000,000

    • 6 Beds
    • 9 Baths
    • 3,614 Sq Ft

    1421 Ashford Rd, Chester, SC 29706

    Welcome to your private country oasis! This spacious 6-bedroom, 6 full bath, 3 half bath custom home offers approximately 4,414 sqft of flexible living space on 10 serene acres. Built in 2007, the property features second living quarters ideal for multi-generational living or guests, a private in-ground pool perfect for relaxing or entertaining, and a wired barn/workshop ready for hobbies or

    David Carter Jeff Cook Real Estate LPT Realty

    1421 Ashford Rd, Chester, SC 29706
  • /27

    $2,700,000

    • 62 Beds
    • 62 Baths
    • 28,000 Sq Ft

    153 W End St, Chester, SC 29706

    Assumable Freddie Mac Note with amazing 3.53% fixed rate to 2031 for qualified buyers! Well-maintained apartments with 90+% of units updated in recent years. Other improvements include water sub-metering project, repaving of asphalt parking lots, ongoing hvac replacement as needed, a roof replacement, installation of a commercial-grade backflow preventer system, and upgraded electric meters by

    Jim Townsend Townsend Realty Group

    153 W End St, Chester, SC 29706
  • /48

    $625,000

    • 7 Beds
    • 5 Baths
    • 4,947 Sq Ft

    128 W End St, Chester, SC 29706

    The well-sought after "Chester Estate" is up For Sale and Fully Updated! A rare opportunity to own a one of a kind gem offering a perfect combination of Traditional Elegance and modern features that showcase class and sophistication. The Home has 2 Living Quarters with a Private outdoor separate access along with indoor access to the Basement Suite! As you enter, you are greeted to a Grand Foyer

    Tyler Goldsmith Better Homes and Gardens Real Estate Paracle

    128 W End St, Chester, SC 29706
  • /39

    $315,000

    • 5 Beds
    • 4 Baths
    • 3,249 Sq Ft

    119 Foote St, Chester, SC 29706

    Step into a piece of history with this beautifully preserved 1907 home, offering 5 spacious bedrooms, 2.5 bathrooms, and over 3,200 square feet of character-rich living space. From original woodwork and period details to high ceilings and large windows, this home exudes warmth and elegance.Enjoy the charm of a classic wraparound front porch, perfect for morning coffee, and relax in the

    Jeremy Ordan Allen Tate Charlotte South

    119 Foote St, Chester, SC 29706
  • /31

    $419,900

    • 5 Beds
    • 3.5 Baths
    • 2,322 Sq Ft

    679 Fairforest Rd, Chester, SC 29706

    Opportunity in the heart of Chester, S.C. This private 4.89-acre retreat offers the perfect blend of peaceful country living with the convenience of nearby restaurants and shopping. The spacious home features two primary bedrooms and the potential for a second living quarters, complete with existing plumbing hookups. Car enthusiasts will appreciate the ample garage space, ideal for a workshop or

    Saige Maxwell Saige Real Estate

    679 Fairforest Rd, Chester, SC 29706
  • /16

    $185,000

    • 5 Beds
    • 4 Baths
    • 4,032 Sq Ft

    121 York St, Chester, SC 29706

    LOCATION. HISTORY. OPPORTUNITY. This is your chance to own a piece of history in the heart of Chester! You have to see it for yourself to take in its full charm and character. Located on a street lined with other beautiful historic homes, this is one of the closest to the charming downtown area. All major systems have been updated, most recently the HVAC in 2025. Renovations have been started but

    Caroline Stallings Rinehart Realty Corporation

    121 York St, Chester, SC 29706
  • /29

    $325,000

    • 5 Beds
    • 4 Baths
    • 3,044 Sq Ft

    173 Columbia St, Chester, SC 29706

    Investors take note, this home great for a house hack! Live in one unit and have tenants help offset your costs. In close proximity to downtown Chester and Adjacent to the Chester Aquatic Center Unit A of this triplex has 3 bedrooms, an office (could be fourth bed), and two full bathrooms. Unit B, also on the first floor (rear of the home) is a studio apartment. Unit C is a two bedroom one bath

    Tom O'Neil EXP Realty LLC Rock Hill

    173 Columbia St, Chester, SC 29706
  • /28

    $320,990 New Construction

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

    834 N Naughton St, Chester, SC 29706

    THIS HOME IS UNDER CONSTRUCTION The Robie is a spacious 2-story home showcasing 5 bedrooms, 3 bathrooms, & 2-car garage. Open floorplan features 1st floor guest suite with full bath, second floor loft area and upstairs laundry room. At the heart of the home is the beautiful kitchen with granite countertops, stainless steel appliances, WALK-IN PANTRY and LARGE CENTER ISLAND. Upstairs you will find

    Maria Wilhelm DR Horton Inc

    834 N Naughton St, Chester, SC 29706
  • /28

    $319,990 New Construction

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

    575 N Sparkleberry St, Chester, SC 29706

    READY NEW HOME-The Robie is a spacious 2-story home showcasing 5 bedrooms, 3 bathrooms, & 2-car garage. Open floorplan features 1st floor guest suite with full bath, second floor loft area and upstairs laundry room. At the heart of the home is the beautiful kitchen w/ stainless steel appliances, WALK-IN PANTRY and LARGE CENTER ISLAND. Upstairs you will find the large primary suite with walk-in

    Maria Wilhelm DR Horton Inc

    575 N Sparkleberry St, Chester, SC 29706
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