Bennington, VT Homes

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  /60

  $285,000

  Sold Feb 18, 2026

  150 Fillmore St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $203/SF
  • 54 Days On Market

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  150 Fillmore St, Bennington, VT 05201
• 

  

  

  /17

  Est $390,408

  Not Listed For Sale

  10 Margaret Ln, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,154 Sq Ft
  • Built 1978

  10 Margaret Ln, Bennington, VT 05201

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  

  /4

  $80,000

  • 4 Beds
  • 2 Baths
  • 1,465 Sq Ft

  107 Lyons St, Bennington, VT 05201

  Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Lyons St, Bennington, VT 05201
• 

  

  

  /40

  $665,000

  Sold May 13, 2026

  134 Monument Ave, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 1927

  Last Sold Summary

  • 4% Below List Price
  • $232/SF
  • 178 Days On Market

  Current Estimated Value $666,652

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  

  /45

  Est $435,528

  Not Listed For Sale

  320 Crescent Blvd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,895 Sq Ft
  • Built 1960

  320 Crescent Blvd, Bennington, VT 05201

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /37

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  291 Springhill Rd, Bennington, VT 05201

  Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons.

  Faith Rhodes Maple Leaf Real Estate

  291 Springhill Rd, Bennington, VT 05201
• 

  

  /40

  $185,000

  Sold May 12, 2026

  317 Pleasant St, Bennington, VT 05201

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1900

  Last Sold Summary

  • 14% Below List Price
  • $84/SF
  • 125 Days On Market

  Current Estimated Value $191,120

  Last Listing Agent Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /30

  Est $235,188

  Not Listed For Sale

  101 Coulter St, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,603 Sq Ft
  • Built 1947

  101 Coulter St, Bennington, VT 05201

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  

  /8

  $65,000

  Under Contract

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

  0 East Rd Unit 26, 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

  0 East Rd Unit 26, Bennington, VT 05201
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  /44

  $340,000

  Sold Jan 23, 2026

  989 Carpenter Hill Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $205/SF
  • 85 Days On Market

  Current Estimated Value $353,127

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  /30

  Est $327,761

  Not Listed For Sale

  402 Jefferson Heights, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft
  • Built 1953

  402 Jefferson Heights, Bennington, VT 05201

  Last Sold Summary

  • 72 Days On Market

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

  

  /36

  $349,900

  Under Contract

  • 2,584 Sq Ft

  219-221 Washington Ave, Bennington, VT 05201

  Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful

  Matt Waddington Hoffman Real Estate

  219-221 Washington Ave, Bennington, VT 05201
• 

  

  /48

  $296,500

  Sold Nov 21, 2025

  4 Rockwood St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $156/SF
  • 6 Days On Market

  Current Estimated Value $307,593

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  4 Rockwood St, Bennington, VT 05201
• 

  

  /24

  Est $316,689

  Not Listed For Sale

  15 Greenview Dr, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,102 Sq Ft
  • Built 1993

  15 Greenview Dr, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /59

  $249,900

  Under Contract

  • 3,569 Sq Ft

  406 Gage St, Bennington, VT 05201

  Bring this historic gem back to life and unlock its incredible potential! Rich with the timeless character and charm of a late-1800s home, this unique property features spacious rooms and many original architectural details waiting to shine again. The building includes three two-bedroom units, including a generously sized two-story unit with a kitchenette and full bathroom on the upper level.

  Justine Curry Maple Leaf Real Estate

  406 Gage St, Bennington, VT 05201
• 

  

  /48

  $230,000

  Sold Sep 11, 2026

  104 Short St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,128 Sq Ft
  • Built 1843

  Last Sold Summary

  • $204/SF
  • 19 Days On Market

  Current Estimated Value $231,175

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate

  104 Short St, Bennington, VT 05201
• 

  

  /26

  Est $282,159

  Not Listed For Sale

  519 South St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft
  • Built 1930

  519 South St, Bennington, VT 05201

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /29

  $399,000

  $16K PRICE DROP Under Contract

  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  Vicki Wilson Maple Leaf Real Estate

  126 Washington Ave, Bennington, VT 05201
• 

  

  /21

  $120,000

  Sold Mar 09, 2026

  1319 Vail Rd, Bennington, VT 05201

  • Land
  • 20 Acres
  • $6,000 per Acre

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  1319 Vail Rd, Bennington, VT 05201
• 

  

  /38

  Est $389,165

  Not Listed For Sale

  150 Pine Cir, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft
  • Built 2005

  150 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Brandy Lesser
• 

  

  /32

  $350,000

  • 2,586 Sq Ft

  110 Short St, Bennington, VT 05201

  Secure a smart, low-maintenance income property featuring four well-kept units—two 2-bedroom and two 1-bedroom—on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Three of the four units have dedicated washer/dryer hookups and each unit is fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth.

  William Paquin Maple Leaf Real Estate

  110 Short St, Bennington, VT 05201
• 

  

  /18

  $350,000

  Sold Sep 11, 2026

  526 Jennings Brook Dr, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft
  • Built 2026

  Last Sold Summary

  • $294/SF
  • 0 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  526 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /25

  Est $417,687

  Not Listed For Sale

  145 Pine Cir, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 1,560 Sq Ft
  • Built 1975

  145 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group
• 

  

  /20

  $475,000

  $24K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft

  425 Main St, Bennington, VT 05201

  15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

  Chris Long BHG Masiello Brattleboro

  425 Main St, Bennington, VT 05201
• 

  

  /36

  $355,000

  Sold May 29, 2026

  695 Dermody Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,748 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $368,459

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  695 Dermody Rd, Bennington, VT 05201
• 

  

  /39

  Est $437,300

  Not Listed For Sale

  153 Pine Cir, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,528 Sq Ft
  • Built 1968

  153 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Brandy Lesser
• 

  

  /48

  $450,000

  $100K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 3,105 Sq Ft

  193 Finley Dr, Bennington, VT 05201

  Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes

  Jenifer Prouty Hoffman Hoffman Real Estate

  193 Finley Dr, Bennington, VT 05201
• 

  

  /46

  $261,000

  Sold Aug 19, 2026

  2867 Chapel Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $200/SF
  • 6 Days On Market

  Current Estimated Value $259,894

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  2867 Chapel Rd, Bennington, VT 05201
• 

  

  /27

  Est $284,651

  Not Listed For Sale

  317 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1940

  317 Prospect St, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  /2

  $58,000

  Under Contract

  • Land
  • 20,908 Sq Ft
  • $120,833 per Acre

  33 Asa's Way, Bennington, VT 05257

  This lot in beautiful North Bennington is ready to go! Building plans have been drawn up and available to come with the property for an approx. 2200 sq ft 3 bed, 2 bath home with decks facing the mountains. This lot has the electric, water, and sewer available at the street. Beyond having school choice for the elementary it also boasts being the second highest elevation lot in the development,

  William Paquin Maple Leaf Real Estate

  33 Asa's Way, Bennington, VT 05257
• 

  

  /52

  $740,000

  Sold Oct 10, 2025

  77 Monument Ave, Bennington, VT 05201

  • 4 Beds
  • 3.5 Baths
  • 4,032 Sq Ft
  • Built 1807

  Last Sold Summary

  • 5% Below List Price
  • $184/SF
  • 16 Days On Market

  Current Estimated Value $796,808

  Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  77 Monument Ave, Bennington, VT 05201
• 

  

  /28

  Est $235,586

  Not Listed For Sale

  234 Grandview St, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 3,809 Sq Ft
  • Built 1850

  234 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /22

  $232,500

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft

  903 Gage St, Bennington, VT 05201

  You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home.Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate,

  Pauline Green

  903 Gage St, Bennington, VT 05201
• 

  

  /58

  $1,800,000

  Sold Jul 24, 2026

  1086 West Rd, Bennington, VT 05201

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft
  • Built 1866

  Last Sold Summary

  • 8% Below List Price
  • $259/SF
  • 91 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
• 

  

  /30

  Est $254,070

  Not Listed For Sale

  110 Booth Terrace, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,114 Sq Ft
  • Built 1924

  110 Booth Terrace, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /55

  $975,000

  • 3 Beds
  • 3 Baths
  • 3,326 Sq Ft

  2100 Monument Ave, Bennington, VT 05201

  Stunning Monument Avenue home offering unparalleled craftsmanship, exceptional style, and beautiful mountain and meadow views. This remarkable ranch-inspired design is equally impressive inside and out, with thoughtfully designed spaces and exceptional millwork throughout. The cook’s kitchen features soapstone countertops, stainless steel appliances, and abundant natural light from large windows.

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  2100 Monument Ave, Bennington, VT 05201
• 

  

  /39

  $250,000

  Sold Oct 14, 2025

  139 Mckinley St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Below List Price
  • $198/SF
  • 25 Days On Market

  Current Estimated Value $269,062

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  139 Mckinley St, Bennington, VT 05201
• 

  

  /30

  Est $336,534

  Not Listed For Sale

  233 Grandview St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft
  • Built 1950

  233 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Thomas Martins Maple Leaf Real Estate
• 

  

  /30

  $595,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,379 Sq Ft

  1278 Harrington Rd, Bennington, VT 05201

  Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and

  Kelley Mccarthy Mahar McCarthy Real Estate

  1278 Harrington Rd, Bennington, VT 05201
• 

  

  /34

  $399,900

  Sold Oct 06, 2025

  43 Spur Rd, Bennington, VT 05201

  • 2 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • $235/SF
  • 8 Days On Market

  Current Estimated Value $334,320

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

  43 Spur Rd, Bennington, VT 05201

Showing Results 161 - 200, Page 5 of 18