Bennington, VT Homes

• 

  

  /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
• 

  

  

  /40

  $125,000

  Sold May 01, 2026

  130 Lincoln St, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,156 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Above List Price
  • $108/SF
  • 39 Days On Market

  Current Estimated Value $129,261

  Last Listing Agent Lisa Friedman Great American Dream Realty

  130 Lincoln St, Bennington, VT 05201
• 

  

  

  /25

  Est $416,949

  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
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  /42

  $277,700

  $1K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 2,142 Sq Ft

  32 Albe Dr, Bennington, VT 05201

  MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

  Beatrice O'Connell Maple Leaf Real Estate

  32 Albe Dr, Bennington, VT 05201
• 

  

  

  /25

  $98,999

  Sold Jul 27, 2026

  78 Ethans Way, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft
  • Built 2024

  Last Sold Summary

  • $120/SF
  • 119 Days On Market

  Last Listing Agent Kate Barry EXP Realty

  78 Ethans Way, Bennington, VT 05201
• 

  

  /39

  Est $402,289

  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
• 

  

  /15

  $165,000

  $4K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  415 County St, Bennington, VT 05201

  STOP RENTING and start building equity! Call your lender today to discover the latest programs that could MAKE HOMEOWNERSHIP A REALITY. Owning may be closer than you think. The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated

  Lori Hurley Four Corner Properties LLC

  415 County St, Bennington, VT 05201
• 

  

  /37

  $500,000

  Sold Jun 30, 2026

  4 Stonehedge Dr, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $157/SF
  • 20 Days On Market

  Current Estimated Value $523,929

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  4 Stonehedge Dr, Bennington, VT 05201
• 

  

  /27

  Est $260,120

  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
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  /60

  $695,000

  • 4 Beds
  • 2 Baths
  • 1,614 Sq Ft

  515 Quarry Rd, Bennington, VT 05201

  Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

  Vicki Wilson Maple Leaf Real Estate

  515 Quarry Rd, Bennington, VT 05201
• 

  

  /26

  $290,000

  Sold Mar 26, 2026

  235 Elm St Unit 3, Bennington, VT 05201

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft
  • Built 1880

  Last Sold Summary

  • 2% Below List Price
  • $110/SF
  • 8 Days On Market

  Current Estimated Value $293,367

  Last Listing Agent Erica Hale Ridgeline Real Estate

  235 Elm St Unit 3, Bennington, VT 05201
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  /5

  Not Listed For Sale

  108 Norton St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft
  • Built 1935

  108 Norton St, Bennington, VT 05201

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Diana LaPerle KW Vermont - Barre
• 

  

  /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
• 

  

  /18

  $286,000

  Sold Jun 12, 2026

  124 Albe Dr, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $259/SF
  • 3 Days On Market

  Current Estimated Value $275,689

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  124 Albe Dr, Bennington, VT 05201
• 

  

  /28

  Est $230,312

  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
• 

  

  /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
• 

  

  /14

  $20,000

  Sold Oct 30, 2025

  79 Skytop Dr Unit 6, Bennington, VT 05201

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • Built 1950

  Last Sold Summary

  • 27% Below List Price
  • $36/SF
  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  79 Skytop Dr Unit 6, Bennington, VT 05201
• 

  

  /30

  Est $242,202

  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
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  /4

  $190,000

  $35K PRICE DROP Pending

  • 5 Beds
  • 2 Baths
  • 1,478 Sq Ft

  32-34 Sage St, Bennington, VT 05257

  Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer. Current tenants keep their units up well.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  32-34 Sage St, Bennington, VT 05257
• 

  

  /23

  $259,000

  Sold Jun 04, 2026

  214 Hickory Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1960

  Last Sold Summary

  • $317/SF
  • 2 Days On Market

  Current Estimated Value $221,888

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  214 Hickory Rd, Bennington, VT 05201
• 

  

  /30

  Est $326,092

  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
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  /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
• 

  

  /54

  $80,000

  Sold Dec 09, 2025

  889 Overlea Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $87/SF
  • 4 Days On Market

  Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  889 Overlea Rd, Bennington, VT 05201
• 

  

  /38

  Est $234,337

  Not Listed For Sale

  134 Imperial Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1915

  134 Imperial Ave, Bennington, VT 05201

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf 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
• 

  

  /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
• 

  

  /33

  Est $172,319

  Not Listed For Sale

  105 Booth Terrace, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 1880

  105 Booth Terrace, Bennington, VT 05201

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Dan Mason Perrott Realty
• 

  

  /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
• 

  

  /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 $672,083

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  /40

  Est $288,084

  Not Listed For Sale

  100 Booth Terrace, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 1905

  100 Booth Terrace, Bennington, VT 05201

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Justine Curry Maple Leaf Real Estate
• 

  

  /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.Each unit has dedicated washer/dryer hookups and fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth. With reliable, long-term

  William Paquin Maple Leaf Real Estate

  110 Short St, 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 $186,699

  Last Listing Agent Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /23

  Est $270,393

  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

  Last Listing Agent William Paquin Maple Leaf Real Estate
• 

  

  /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
• 

  

  /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 $346,218

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  /34

  Est $270,753

  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

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /43

  $499,900

  $50K 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
• 

  

  /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 $305,514

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  4 Rockwood St, Bennington, VT 05201
• 

  

  /30

  Est $286,604

  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

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

  /2

  $58,000

  • 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

Showing Results 161 - 200, Page 5 of 18