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Bennington Homes for Sale

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  • /32

    $265,000

    $10K PRICE DROP
    • 1,680 Sq Ft

    318 North St, Bennington, VT 05201

    Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

    Jenifer Prouty Hoffman Hoffman Real Estate

    318 North St, Bennington, VT 05201
  • /7

    $997,000

    • Land
    • 23,086 Sq Ft
    • $1,881,132 per Acre

    153 Northside Dr, Bennington, VT 05201

    Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

    Lori Hurley Four Corner Properties LLC

    153 Northside Dr, Bennington, VT 05201
  • /13

    $279,000

    $16K PRICE DROP
    • 2,022 Sq Ft

    124 S Branch St, Bennington, VT 05201

    Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

    Julie Glover Mahar McCarthy Real Estate

    124 S Branch St, Bennington, VT 05201
  • /9

    $279,000

    $16K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,206 Sq Ft

    116 S Branch St Unit 118, Bennington, VT 05201

    Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

    Julie Glover Mahar McCarthy Real Estate

    116 S Branch St Unit 118, Bennington, VT 05201
  • /36

    $198,000

    $22K PRICE DROP
    • Land
    • 54 Acres
    • $3,667 per Acre

    399 Bard Rd, Bennington, VT 05201

    Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level

    Curtis Trousdale Preferred Properties

    399 Bard Rd, Bennington, VT 05201
  • /4

    $379,000

    New Construction $29K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    527 Jennings Brook Dr, Bennington, VT 05201

    Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. Custom Kitchen with granite countertops, custom tile shower unit. The open-concept layout is highlighted by a spacious kitchen and a

    Lilli West Maple Leaf Real Estate

    527 Jennings Brook Dr, Bennington, VT 05201
  • /8

    $65,000

    • Land
    • 1.24 Acres
    • $52,419 per Acre

    2041 East Rd, Bennington, VT 05201

    Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life. Perk test were positive for a inground leaching system, results available.

    Dan Mason Perrott Realty

    2041 East Rd, Bennington, VT 05201
  • /2

    $2,190,000

    • Land
    • 1.16 Acres
    • $1,887,931 per Acre

    301 Northside Dr, Bennington, VT 05201

    Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

    Paul Carroccio TPW Real Estate

    301 Northside Dr, Bennington, VT 05201
  • /25

    $950,000

    $300K PRICE DROP
    • 8,888 Sq Ft

    124 Elm St, Bennington, VT 05201

    A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment. The property includes nine guest accommodations, owner's quarters, expansive common areas,

    Marek Kovac TPW Real Estate

    124 Elm St, Bennington, VT 05201
  • /52

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    113 Main St, Bennington, VT 05201

    Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

    Lindsey Martin Maple Leaf Real Estate

    113 Main St, Bennington, VT 05201
  • /16

    $96,406

    New Construction
    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    32 Cassie Ln, Bennington, VT 05201

    Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    32 Cassie Ln, Bennington, VT 05201

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