5,296

Bennington, VT Homes

Section Image
  • 45 Shady Ln, Bennington, VT 05201
    45 Shady Ln, Bennington, VT 05201
    45 Shady Ln, Bennington, VT 05201
    /4

    $45,000

    Sold Oct 06, 2025

    45 Shady Ln, Bennington, VT 05201

    • 4 Beds
    • 1 Bath
    • 1,142 Sq Ft
    • Built 1948

    Last Sold Summary

    • 25% Below List Price
    • $39/SF
    • 7 Days On Market

    Current Estimated Value $103,046

    Last Listing Agent Erika Floriani Hoffman Real Estate

    45 Shady Ln, Bennington, VT 05201
    • 201 Erbs Way, Bennington, VT 05201
      201 Erbs Way, Bennington, VT 05201
      201 Erbs Way, Bennington, VT 05201
      /47

      Est $406,032

      Not Listed For Sale

      201 Erbs Way, Bennington, VT 05201

      • 3 Beds
      • 3.5 Baths
      • 2,686 Sq Ft
      • Built 1974
      201 Erbs Way, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

  • 58 Mount Anthony Rd, Bennington, VT 05201
    58 Mount Anthony Rd, Bennington, VT 05201
    58 Mount Anthony Rd, Bennington, VT 05201
    /53

    $599,000

    $96K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,715 Sq Ft

    58 Mount Anthony Rd, Bennington, VT 05201

    Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

    Monique Geannelis Mahar McCarthy Real Estate

    58 Mount Anthony Rd, Bennington, VT 05201
  • 110 S Branch St, Bennington, VT 05201
    110 S Branch St, Bennington, VT 05201
    110 S Branch St, Bennington, VT 05201
    /43

    $235,000

    Sold Dec 08, 2025

    110 S Branch St, Bennington, VT 05201

    • 6 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1928

    Last Sold Summary

    • 2% Below List Price
    • $98/SF
    • 9 Days On Market

    Current Estimated Value $232,669

    Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

    110 S Branch St, Bennington, VT 05201
    • 505 Cross Rd, Bennington, VT 05201
      505 Cross Rd, Bennington, VT 05201
      505 Cross Rd, Bennington, VT 05201
      /40

      Est $332,239

      Not Listed For Sale

      505 Cross Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,674 Sq Ft
      • Built 2003
      505 Cross Rd, Bennington, VT 05201

      Last Sold Summary

      • 2 Days On Market

  • 212 Dewey St, Bennington, VT 05201
    212 Dewey St, Bennington, VT 05201
    212 Dewey St, Bennington, VT 05201
    /30

    $275,000

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,265 Sq Ft

    212 Dewey St, Bennington, VT 05201

    Move right in or continue operating as a short-term rental—this fully furnished 2-bedroom, 2.5-bath ranch offers comfort, convenience, and flexibility all in one package. Currently used as an Airbnb, all contents are included, making this a true turnkey opportunity. Inside, you’ll find recently refinished hardwood floors, and skylights that fill the home with natural light. A pellet stove for

    William Paquin Maple Leaf Real Estate

    212 Dewey St, Bennington, VT 05201
  • 26 Asa's Way, Bennington, VT 05257
    26 Asa's Way, Bennington, VT 05257
    26 Asa's Way, Bennington, VT 05257
    /24

    $42,000

    Sold Oct 24, 2025

    26 Asa's Way, Bennington, VT 05257

    • Land
    • 20,908 Sq Ft
    • $87,500 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 55 Days On Market

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    26 Asa's Way, Bennington, VT 05257
    • 260 Tower Rd, Bennington, VT 05201
      260 Tower Rd, Bennington, VT 05201
      260 Tower Rd, Bennington, VT 05201
      /40

      Not Listed For Sale

      260 Tower Rd, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 3,976 Sq Ft
      • Built 1981
      260 Tower Rd, Bennington, VT 05201

      Last Sold Summary

      • 115 Days On Market

  • 343 Safford St, Bennington, VT 05201
    343 Safford St, Bennington, VT 05201
    343 Safford St, Bennington, VT 05201
    /12

    $325,000

    Under Contract
    • 2,476 Sq Ft

    343 Safford St, Bennington, VT 05201

    An investment gem or owner-occupied standout in the heart of Bennington, this renovated property features three distinct units, each offering the privacy and feel of a single-family home. Unlike traditional stacked apartments, all three units boast a two-story layout with 2 bedrooms and 1 full bath, ensuring no neighbors above or below. Each features modern finishes, bright living spaces, and a

    Lori Hurley Four Corner Properties LLC

    343 Safford St, Bennington, VT 05201
  • 4 Bank St, Bennington, VT 05201
    4 Bank St, Bennington, VT 05201
    4 Bank St, Bennington, VT 05201
    /46

    $399,000

    Sold Jul 28, 2025

    4 Bank St, Bennington, VT 05201

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft
    • Built 1930

    Last Sold Summary

    • 6% Below List Price
    • $231/SF
    • 55 Days On Market

    Current Estimated Value $394,953

    Last Listing Agent Margretta Fischer Wohler Realty Group

    4 Bank St, Bennington, VT 05201
    • 42 Maple Grove Rd, Bennington, VT 05201
      42 Maple Grove Rd, Bennington, VT 05201
      42 Maple Grove Rd, Bennington, VT 05201
      /40

      Est $401,977

      Not Listed For Sale

      42 Maple Grove Rd, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 2,163 Sq Ft
      • Built 1960
      42 Maple Grove Rd, Bennington, VT 05201

      Last Sold Summary

      • 87 Days On Market

  • 131 Pine Cir, Bennington, VT 05201
    131 Pine Cir, Bennington, VT 05201
    131 Pine Cir, Bennington, VT 05201
    /59

    $419,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,119 Sq Ft

    131 Pine Cir, Bennington, VT 05201

    A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors

    Vicki Wilson Maple Leaf Real Estate

    131 Pine Cir, Bennington, VT 05201
  • 170 Brambley Ln, Bennington, VT 05201
    170 Brambley Ln, Bennington, VT 05201
    170 Brambley Ln, Bennington, VT 05201
    /35

    $329,900

    Sold Aug 28, 2025

    170 Brambley Ln, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,459 Sq Ft
    • Built 1969

    Last Sold Summary

    • $226/SF
    • 4 Days On Market

    Current Estimated Value $320,067

    Last Listing Agent Matt Waddington Hoffman Real Estate

    170 Brambley Ln, Bennington, VT 05201
    • 1063 Middle Pownal Rd, Bennington, VT 05201
      1063 Middle Pownal Rd, Bennington, VT 05201
      1063 Middle Pownal Rd, Bennington, VT 05201
      /38

      Est $380,520

      Not Listed For Sale

      1063 Middle Pownal Rd, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1987
      1063 Middle Pownal Rd, Bennington, VT 05201

      Last Sold Summary

      • 13 Days On Market

  • 856 Matteson Rd, North Bennington, VT 05257
    856 Matteson Rd, North Bennington, VT 05257
    856 Matteson Rd, North Bennington, VT 05257
    /43

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,501 Sq Ft

    856 Matteson Rd, North Bennington, VT 05257

    Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great

    Faith Rhodes Maple Leaf Real Estate

    856 Matteson Rd, North Bennington, VT 05257
  • 1488 Morgan St, Bennington, VT 05201
    1488 Morgan St, Bennington, VT 05201
    1488 Morgan St, Bennington, VT 05201
    /13

    $60,500

    Sold May 18, 2026

    1488 Morgan St, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft
    • Built 1959

    Last Sold Summary

    • 10% Above List Price
    • $48/SF
    • 14 Days On Market

    Current Estimated Value $256,667

    Last Listing Agent Dick Thackston R.H. Thackston & Company

    1488 Morgan St, Bennington, VT 05201
    • 276 Finley Dr, Bennington, VT 05201
      276 Finley Dr, Bennington, VT 05201
      276 Finley Dr, Bennington, VT 05201
      /40

      Est $154,416

      Not Listed For Sale

      276 Finley Dr, Bennington, VT 05201

      • 3 Beds
      • 2.5 Baths
      • 1,866 Sq Ft
      • Built 1987
      276 Finley Dr, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

  • 432 South St Unit D2, Bennington, VT 05201
    432 South St Unit D2, Bennington, VT 05201
    432 South St Unit D2, Bennington, VT 05201
    /27

    $189,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,485 Sq Ft

    432 South St Unit D2, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

    Abi Gregorio

    432 South St Unit D2, Bennington, VT 05201
  • 304 North St Unit 6, Bennington, VT 05201
    304 North St Unit 6, Bennington, VT 05201
    304 North St Unit 6, Bennington, VT 05201
    /54

    $225,000

    Sold Sep 10, 2025

    304 North St Unit 6, Bennington, VT 05201

    • 4 Beds
    • 3 Baths
    • 2,162 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Above List Price
    • $104/SF
    • 15 Days On Market

    Current Estimated Value $235,953

    Last Listing Agent Thomas Martins Maple Leaf Real Estate

    304 North St Unit 6, Bennington, VT 05201
    • 402 Middle Pownal Rd, Bennington, VT 05201
      402 Middle Pownal Rd, Bennington, VT 05201
      402 Middle Pownal Rd, Bennington, VT 05201
      /40

      Est $608,022

      Not Listed For Sale

      402 Middle Pownal Rd, Bennington, VT 05201

      • 3 Beds
      • 2.5 Baths
      • 2,706 Sq Ft
      • Built 1880
      402 Middle Pownal Rd, Bennington, VT 05201

      Last Sold Summary

      • 0 Days On Market

  • 78 Ethans Way, Bennington, VT 05201
    78 Ethans Way, Bennington, VT 05201
    78 Ethans Way, Bennington, VT 05201
    /25

    $98,999

    New Construction Under Contract
    • 2 Beds
    • 2 Baths
    • 825 Sq Ft

    78 Ethans Way, Bennington, VT 05201

    Welcome to 78 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polomodel manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. 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 energy-efficient

    Kate Barry EXP Realty

    78 Ethans Way, Bennington, VT 05201
  • 0 Evergreen Dr, Bennington, VT 05201
    0 Evergreen Dr, Bennington, VT 05201
    0 Evergreen Dr, Bennington, VT 05201
    /9

    $65,000

    Sold May 27, 2026

    0 Evergreen Dr, Bennington, VT 05201

    • Land
    • 9.24 Acres
    • $7,035 per Acre

    Last Sold Summary

    • 8 Days On Market

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    0 Evergreen Dr, Bennington, VT 05201
    • 1351 Morgan St, Bennington, VT 05201
      1351 Morgan St, Bennington, VT 05201
      1351 Morgan St, Bennington, VT 05201
      /35

      Est $340,576

      Not Listed For Sale

      1351 Morgan St, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,821 Sq Ft
      • Built 1958
      1351 Morgan St, Bennington, VT 05201

      Last Sold Summary

      • 11 Days On Market

  • 153 Northside Dr, Bennington, VT 05201
    153 Northside Dr, Bennington, VT 05201
    153 Northside Dr, 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
  • 207 Silver St, Bennington, VT 05201
    207 Silver St, Bennington, VT 05201
    207 Silver St, Bennington, VT 05201
    /58

    $299,000

    Sold Jun 01, 2026

    207 Silver St, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1846

    Last Sold Summary

    • $150/SF
    • 143 Days On Market

    Current Estimated Value $294,569

    Last Listing Agent Dan Mason Perrott Realty

    207 Silver St, Bennington, VT 05201
    • 88 Southshire Dr, Bennington, VT 05201
      88 Southshire Dr, Bennington, VT 05201
      88 Southshire Dr, Bennington, VT 05201
      /40

      Est $621,137

      Not Listed For Sale

      88 Southshire Dr, Bennington, VT 05201

      • 3 Beds
      • 3.5 Baths
      • 2,952 Sq Ft
      • Built 1988
      88 Southshire Dr, Bennington, VT 05201

      Last Sold Summary

      • 6 Days On Market

  • 4 Stonehedge Dr, Bennington, VT 05201
    4 Stonehedge Dr, Bennington, VT 05201
    4 Stonehedge Dr, Bennington, VT 05201
    /37

    $525,000

    Pending
    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft

    4 Stonehedge Dr, Bennington, VT 05201

    Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors,

    Kelley Mccarthy Mahar McCarthy Real Estate

    4 Stonehedge Dr, Bennington, VT 05201
  • 224 Garbrooke Dr, Bennington, VT 05201
    224 Garbrooke Dr, Bennington, VT 05201
    224 Garbrooke Dr, Bennington, VT 05201
    /39

    $383,000

    Sold Jul 30, 2025

    224 Garbrooke Dr, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,207 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $174/SF
    • 61 Days On Market

    Current Estimated Value $389,858

    Last Listing Agent Lindsey Martin Maple Leaf Real Estate

    224 Garbrooke Dr, Bennington, VT 05201
    • 377 Southshire Dr, Bennington, VT 05201
      377 Southshire Dr, Bennington, VT 05201
      377 Southshire Dr, Bennington, VT 05201
      /40

      Est $615,292

      Not Listed For Sale

      377 Southshire Dr, Bennington, VT 05201

      • 4 Beds
      • 3.5 Baths
      • 3,183 Sq Ft
      • Built 1988
      377 Southshire Dr, Bennington, VT 05201

      Last Sold Summary

      • 14 Days On Market

  • 116 S Branch St Unit 118, Bennington, VT 05201
    116 S Branch St Unit 118, Bennington, VT 05201
    116 S Branch St Unit 118, 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
  • 126 Fox Hill Rd, Bennington, VT 05201
    126 Fox Hill Rd, Bennington, VT 05201
    126 Fox Hill Rd, Bennington, VT 05201
    /42

    $600,000

    Sold Nov 12, 2025

    126 Fox Hill Rd, Bennington, VT 05201

    • 5 Beds
    • 1.5 Baths
    • 2,450 Sq Ft
    • Built 1850

    Last Sold Summary

    • 25% Below List Price
    • $245/SF
    • 148 Days On Market

    Current Estimated Value $606,954

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    126 Fox Hill Rd, Bennington, VT 05201
    • 179 Southshire Dr, Bennington, VT 05201
      179 Southshire Dr, Bennington, VT 05201
      179 Southshire Dr, Bennington, VT 05201
      /40

      Est $564,901

      Not Listed For Sale

      179 Southshire Dr, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 2,336 Sq Ft
      • Built 1984
      179 Southshire Dr, Bennington, VT 05201

      Last Sold Summary

      • 8 Days On Market

  • 124 S Branch St, Bennington, VT 05201
    124 S Branch St, Bennington, VT 05201
    124 S Branch St, Bennington, VT 05201
    /13

    $279,000

    $16K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 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. With

    Julie Glover Mahar McCarthy Real Estate

    124 S Branch St, Bennington, VT 05201
  • 72 Ethans Way, Bennington, VT 05201
    72 Ethans Way, Bennington, VT 05201
    72 Ethans Way, Bennington, VT 05201
    /20

    $89,499

    Sold Sep 24, 2025

    72 Ethans Way, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 825 Sq Ft
    • Built 2024

    Last Sold Summary

    • 10% Below List Price
    • $108/SF
    • 120 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    72 Ethans Way, Bennington, VT 05201
    • 1065 Burgess Rd, Bennington, VT 05201
      1065 Burgess Rd, Bennington, VT 05201
      1065 Burgess Rd, Bennington, VT 05201
      /37

      Est $308,149

      Not Listed For Sale

      1065 Burgess Rd, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,400 Sq Ft
      • Built 1974
      1065 Burgess Rd, Bennington, VT 05201

      Last Sold Summary

      • 51 Days On Market

  • 525 Jennings Brook Dr, Bennington, VT 05201
    525 Jennings Brook Dr, Bennington, VT 05201
    525 Jennings Brook Dr, Bennington, VT 05201
    /5

    $350,000

    New Construction Pending
    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    525 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. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

    Lilli West Maple Leaf Real Estate

    525 Jennings Brook Dr, Bennington, VT 05201
  • 303 Prospect St, Bennington, VT 05201
    303 Prospect St, Bennington, VT 05201
    303 Prospect St, Bennington, VT 05201
    /35

    $372,000

    Sold May 13, 2026

    303 Prospect St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,463 Sq Ft
    • Built 1949

    Last Sold Summary

    • 1% Above List Price
    • $254/SF
    • 11 Days On Market

    Current Estimated Value $361,535

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    303 Prospect St, Bennington, VT 05201
    • 543 Gore Rd, Bennington, VT 05201
      543 Gore Rd, Bennington, VT 05201
      543 Gore Rd, Bennington, VT 05201
      /31

      Est $431,841

      Not Listed For Sale

      543 Gore Rd, Bennington, VT 05201

      • 3 Beds
      • 3 Baths
      • 1,963 Sq Ft
      • Built 1990
      543 Gore Rd, Bennington, VT 05201

      Last Sold Summary

      • 87 Days On Market

  • 319 Chester Knoll Dr, Bennington, VT 05201
    319 Chester Knoll Dr, Bennington, VT 05201
    319 Chester Knoll Dr, Bennington, VT 05201
    /15

    $389,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,516 Sq Ft

    319 Chester Knoll Dr, Bennington, VT 05201

    Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

    Lilli West Maple Leaf Real Estate

    319 Chester Knoll Dr, Bennington, VT 05201
  • 940 Gage St, Bennington, VT 05201
    940 Gage St, Bennington, VT 05201
    940 Gage St, Bennington, VT 05201
    /18

    $260,000

    Sold Apr 28, 2026

    940 Gage St, Bennington, VT 05201

    • 3 Beds
    • 1.5 Baths
    • 1,570 Sq Ft
    • Built 1945

    Last Sold Summary

    • 13% Below List Price
    • $166/SF
    • 58 Days On Market

    Current Estimated Value $278,811

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    940 Gage St, Bennington, VT 05201

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