Bennington, VT Homes

• 

  

  

  /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 $339,834

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  

  /23

  Est $256,178

  Not Listed For Sale

  101 Barber St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,574 Sq Ft
  • Built 1920

  101 Barber St, Bennington, VT 05201

  Last Sold Summary

  • 34 Days On Market
• 

  

  

  /4

  $249,900

  Pending

  • 4 Beds
  • 4 Baths
  • 2,080 Sq Ft

  123 Bradford St, Bennington, VT 05201

  4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Great capitalization and income producer.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  123 Bradford St, 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 $290,946

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  4 Rockwood St, Bennington, VT 05201
• 

  

  

  /34

  Est $244,200

  Not Listed For Sale

  99 Barber St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1965

  99 Barber St, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market
• 

  

  /8

  $59,000

  • Land
  • 12,632 Sq Ft
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
• 

  

  /30

  $290,000

  Sold Jul 17, 2025

  221 Grandview St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft
  • Built 1948

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 75 Days On Market

  Current Estimated Value $279,617

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  221 Grandview St, Bennington, VT 05201
• 

  

  /30

  Est $277,886

  Not Listed For Sale

  228 Grandview St, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft
  • Built 1933

  228 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • 108 Days On Market
• 

  

  /37

  $315,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,729 Sq Ft

  105 Albe Dr, Bennington, VT 05201

  Tucked into an established and desirable neighborhood, this well-maintained 3-bedroom, 2-bath home offers the kind of easy, low-maintenance living that’s increasingly hard to find. Built in 1999 and thoughtfully designed with comfort and practicality in mind. The layout provides flexibility for a variety of lifestyles with approximately 1,700 square feet of finished living space, generous room

  Jenifer Prouty Hoffman Hoffman Real Estate

  105 Albe Dr, 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
• 

  

  /32

  Est $325,099

  Not Listed For Sale

  214 Silver St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,466 Sq Ft
  • Built 1860

  214 Silver St, Bennington, VT 05201

  Last Sold Summary

  • 2 Days On Market
• 

  

  /60

  $269,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,934 Sq Ft

  508 Barney Rd, Bennington, VT 05201

  WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area.The septic was

  Dan Mason Perrott Realty

  508 Barney Rd, Bennington, VT 05201
• 

  

  /47

  $240,000

  Sold Sep 24, 2025

  120 Imperial Ave, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 1895

  Last Sold Summary

  • 20% Below List Price
  • $100/SF
  • 114 Days On Market

  Current Estimated Value $265,512

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
• 

  

  /31

  Est $311,646

  Not Listed For Sale

  325 Silver St, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft
  • Built 1956

  325 Silver St, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market
• 

  

  /3

  $74,900

  • Land
  • 2.25 Acres
  • $33,289 per Acre

  0 Brambley Ln, Bennington, VT 05201

  Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, 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 $376,270

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  695 Dermody Rd, Bennington, VT 05201
• 

  

  /22

  Est $296,954

  Not Listed For Sale

  214 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,833 Sq Ft
  • Built 1920

  214 Prospect St, Bennington, VT 05201

  Last Sold Summary

  • 93 Days On Market
• 

  

  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access

  Paul Carroccio TPW Real Estate

  22 Morse Rd, Bennington, VT 05201
• 

  

  /46

  $280,000

  Sold Jun 30, 2025

  4 Pine Rd, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,875 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $149/SF
  • 73 Days On Market

  Current Estimated Value $289,273

  Last Listing Agent Dan Mason Perrott Realty

  4 Pine Rd, Bennington, VT 05201
• 

  

  /11

  Est $146,988

  Not Listed For Sale

  432 South St Unit C5, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft
  • Built 1989

  432 South St Unit C5, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market
• 

  

  /4

  $350,000

  New Construction Under Contract

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

  524 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

  524 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /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 $741,702

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

  77 Monument Ave, Bennington, VT 05201
• 

  

  /36

  Est $167,495

  Not Listed For Sale

  432 South St Unit B5, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft
  • Built 1989

  432 South St Unit B5, Bennington, VT 05201

  Last Sold Summary

  • 5 Days On Market
• 

  

  /32

  $275,000

  • 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
• 

  

  /39

  $275,000

  Sold Jul 31, 2025

  30 Harbour Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $171/SF
  • 69 Days On Market

  Current Estimated Value $270,708

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  30 Harbour Rd, Bennington, VT 05201
• 

  

  /18

  Est $152,564

  Not Listed For Sale

  432 South St Unit A11, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft
  • Built 1989

  432 South St Unit A11, Bennington, VT 05201

  Last Sold Summary

  • 170 Days On Market
• 

  

  /34

  $275,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,526 Sq Ft

  302 Prospect St, Bennington, VT 05201

  Welcome to this lovely Colonial home, formerly a charming carriage house, nestled in one of Bennington’s most desirable walkable neighborhoods. Offering over 1,500 square feet of inviting living space, this well maintained home features 3 bedrooms, 2 bathrooms, and a versatile bonus room perfect for a home office or potential fourth bedroom. Inside, you’ll find beautiful wood floors and trim,

  Mary Beth French Hoffman Real Estate

  302 Prospect St, 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 $250,137

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  139 Mckinley St, Bennington, VT 05201
• 

  

  /26

  Est $167,184

  Not Listed For Sale

  432 South St Unit A2, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft
  • Built 1989

  432 South St Unit A2, Bennington, VT 05201

  Last Sold Summary

  • 142 Days On Market
• 

  

  /31

  $274,900

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,210 Sq Ft

  26 Knoll Crest Ln, Bennington, VT 05201

  Beautifully updated Cape-style home nestled in a quiet, sought-after neighborhood with picturesque views of Mount Anthony. Full of charm and character, this move-in-ready home perfectly blends comfort, style, and convenience. Tucked away on a dead-end street, it’s ideally located near SVMC hospital, public transportation, scenic hiking trails, and Bennington’s vibrant Main Street, which offers

  Matt Waddington Hoffman Real Estate

  26 Knoll Crest Ln, 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 $341,284

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

  43 Spur Rd, Bennington, VT 05201
• 

  

  /4

  Not Listed For Sale

  406 South St, Bennington, VT 05201

  • 6 Beds
  • 6 Baths
  • 2,690 Sq Ft
  • Built 1900

  406 South St, Bennington, VT 05201

  Last Sold Summary

  • 27 Days On Market
• 

  

  /59

  $399,900

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,896 Sq Ft

  23 Pageant St, Bennington, VT 05201

  This c. 1936 4BR/2BA home has been beautifully updated to blend timeless architectural character with modern comfort and convenience. Meticulously maintained throughout, it features gleaming hardwood floors, vintage details and thoughtful updates designed for today’s lifestyle. The stunning granite kitchen offers rich cherry cabinetry and stainless steel appliances, all new in 2024, creating a

  Vicki Wilson Maple Leaf Real Estate

  23 Pageant St, Bennington, VT 05201
• 

  

  /44

  $40,000

  Sold Oct 31, 2025

  273 Union St, Bennington, VT 05201

  • 5 Beds
  • 1 Bath
  • 1,952 Sq Ft
  • Built 1910

  Last Sold Summary

  • 60% Below List Price
  • $20/SF
  • 108 Days On Market

  Current Estimated Value $144,028

  Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  273 Union St, Bennington, VT 05201
• 

  

  /32

  Est $263,800

  Not Listed For Sale

  402 South St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,262 Sq Ft
  • Built 1940

  402 South St, Bennington, VT 05201

  Last Sold Summary

  • 721 Days On Market
• 

  

  /15

  $269,000

  Under Contract

  • 2,500 Sq Ft

  626 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  626 Main St, Bennington, VT 05201
• 

  

  /27

  $274,000

  Sold Jan 22, 2026

  26 Sage St, Bennington, VT 05257

  • 9 Beds
  • 3 Baths
  • 3,176 Sq Ft
  • Built 1820

  Last Sold Summary

  • 8% Below List Price
  • $86/SF
  • 55 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  26 Sage St, Bennington, VT 05257
• 

  

  /38

  Est $175,864

  Not Listed For Sale

  314 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,301 Sq Ft
  • Built 1920

  314 Weeks St, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market
• 

  

  /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
• 

  

  /33

  $355,000

  Sold Sep 19, 2025

  60 Knoll Crest Ln, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 1948

  Last Sold Summary

  • $171/SF
  • 22 Days On Market

  Current Estimated Value $356,566

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

  60 Knoll Crest Ln, Bennington, VT 05201

Showing Results 201 - 240, Page 6 of 18