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
• 

  

  

  /14

  $278,000

  Sold Aug 04, 2025

  400 South St, Bennington, VT 05201

  • 3 Beds
  • 3 Baths
  • 1,461 Sq Ft
  • Built 1825

  Last Sold Summary

  • 7% Above List Price
  • $190/SF
  • 38 Days On Market

  Current Estimated Value $279,966

  Last Listing Agent William Paquin Maple Leaf Real Estate

  400 South St, Bennington, VT 05201
• 

  

  

  /30

  Est $317,855

  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
• 

  

  

  /42

  $277,700

  $1K PRICE DROP

  • 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
• 

  

  

  /30

  $310,000

  Sold Jul 25, 2025

  198 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 2,032 Sq Ft
  • Built 1930

  Last Sold Summary

  • 11% Below List Price
  • $153/SF
  • 54 Days On Market

  Current Estimated Value $318,225

  Last Listing Agent Margretta Fischer Wohler Realty Group

  198 Weeks St, Bennington, VT 05201
• 

  

  /24

  Est $303,807

  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
• 

  

  /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
• 

  

  /57

  $275,000

  Sold Aug 07, 2025

  115-117 Norton St, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • Built 1930

  Last Sold Summary

  • $162/SF
  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  115-117 Norton St, Bennington, VT 05201
• 

  

  /38

  Est $416,000

  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
• 

  

  /30

  $300,000

  $25K PRICE DROP Under Contract

  • 1 Bed
  • 1.5 Baths
  • 1,120 Sq Ft

  113 South St Unit 302, Bennington, VT 05201

  Whether you’re seeking a full-time downtown lifestyle, a lock-and-leave home base for travel, or you’re ready to make the leap from renting to owning, this is the kind of property that checks every box—location, character, and simplicity. Offered publicly for the first time, Unit 302 is filled with natural light from tall windows that frame the energy of downtown Bennington. Soaring ceilings,

  Jenifer Prouty Hoffman Hoffman Real Estate

  113 South St Unit 302, 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 $286,283

  Last Listing Agent Erica Hale Ridgeline Real Estate

  235 Elm St Unit 3, Bennington, VT 05201
• 

  

  /25

  Est $382,179

  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
• 

  

  /36

  $355,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  149 Jewett Dr, Bennington, VT 05201

  Tucked just outside of town with sweeping views in every direction, this 4-bedroom, 2-bath raised ranch offers the space and setting you're looking for. Hardwood floors run throughout the main level, where the sun-filled living room features a cozy wood-burning fireplace—perfect for gathering on chilly evenings. The finished lower level provides flexible space to grow, including the third and

  Faith Rhodes Maple Leaf Real Estate

  149 Jewett Dr, 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 $271,451

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  124 Albe Dr, Bennington, VT 05201
• 

  

  /39

  Est $423,661

  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
• 

  

  /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
• 

  

  /26

  $193,500

  Sold Aug 06, 2025

  305 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1937

  Last Sold Summary

  • 3% Below List Price
  • $119/SF
  • 17 Days On Market

  Current Estimated Value $196,104

  Last Listing Agent Matt Waddington Hoffman Real Estate

  305 Weeks St, Bennington, VT 05201
• 

  

  /27

  Est $241,900

  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
• 

  

  /4

  $350,000

  New Construction Pending

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

  523 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

  523 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /38

  $291,065

  Sold Jul 11, 2025

  121 Fillmore St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1946

  Last Sold Summary

  • 1% Above List Price
  • $168/SF
  • 66 Days On Market

  Current Estimated Value $295,111

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  121 Fillmore St, 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
• 

  

  /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
• 

  

  /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
• 

  

  /28

  Est $195,909

  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
• 

  

  /59

  $249,900

  • 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
• 

  

  /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 $231,145

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  214 Hickory Rd, Bennington, VT 05201
• 

  

  /30

  Est $232,791

  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
• 

  

  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, 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
• 

  

  /30

  Est $333,867

  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
• 

  

  /29

  $399,000

  $16K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /38

  Est $195,278

  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
• 

  

  /20

  $499,000

  • 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
• 

  

  /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 $679,151

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  /33

  Est $153,458

  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
• 

  

  /43

  $550,000

  Under Contract

  • 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
• 

  

  /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 $192,472

  Last Listing Agent Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /40

  Est $292,200

  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
• 

  

  /14

  $125,000

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  Faith Rhodes Maple Leaf Real Estate

  347 Hickory Rd, Bennington, VT 05201

Showing Results 161 - 200, Page 5 of 18