Bennington, VT Homes

• 

  

  

  /40

  Est $279,736

  Not Listed For Sale

  25 Center St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1990

  25 Center St, Bennington, VT 05201

  Last Sold Summary

  • 8 Days On Market
• 

  

  

  /52

  $289,000

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
• 

  

  

  /53

  $400,000

  Sold Sep 22, 2025

  495 Fairview St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,309 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $306/SF
  • 12 Days On Market

  Current Estimated Value $393,970

  Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  495 Fairview St, Bennington, VT 05201
• 

  

  

  /58

  Est $287,856

  Not Listed For Sale

  44 Harbour Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,903 Sq Ft
  • Built 1973

  44 Harbour Rd, Bennington, VT 05201

  Last Sold Summary

  • 49 Days On Market
• 

  

  

  /24

  $215,000

  $20K PRICE DROP

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
• 

  

  /60

  $230,500

  Sold Jul 18, 2025

  322 Burgess Rd, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 2,004 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $115/SF
  • 62 Days On Market

  Current Estimated Value $240,262

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  322 Burgess Rd, Bennington, VT 05201
• 

  

  /38

  Est $244,728

  Not Listed For Sale

  5 Tel Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1969

  5 Tel Rd, Bennington, VT 05201

  Last Sold Summary

  • 10 Days On Market
• 

  

  /4

  $350,000

  New Construction Pending

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

  526 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

  526 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /21

  $73,500

  Sold Aug 04, 2025

  0 Sunset Dr Unit 5005504, Bennington, VT 05201

  • Land
  • 7 Acres
  • $10,500 per Acre

  Last Sold Summary

  • 26% Below List Price
  • 297 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate

  0 Sunset Dr Unit 5005504, Bennington, VT 05201
• 

  

  /26

  Est $307,286

  Not Listed For Sale

  1 Tel Cir, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1972

  1 Tel Cir, Bennington, VT 05201

  Last Sold Summary

  • 14 Days On Market
• 

  

  /58

  $1,950,000

  Under Contract

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

  1086 West Rd, Bennington, VT 05201

  Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

  Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
• 

  

  /37

  $256,250

  Sold Sep 03, 2025

  1236 Morgan St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,259 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Above List Price
  • $204/SF
  • 7 Days On Market

  Current Estimated Value $255,663

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  1236 Morgan St, Bennington, VT 05201
• 

  

  /32

  Est $302,446

  Not Listed For Sale

  17 Tel Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 1970

  17 Tel Rd, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market
• 

  

  /15

  $299,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  1803 Harwood Hill Rd, Bennington, VT 05201

  Set on a spacious lot and move-in ready raised ranch offers major updates, flexible living space, and excellent value. Recent improvements include a brand-new septic system, new roof, beautifully renovated kitchen, and new deck — giving buyers peace of mind and modern comfort from day one.The versatile lower level provides additional finished space ideal for a home office, family room, guest

  Lori Hurley Four Corner Properties LLC

  1803 Harwood Hill Rd, Bennington, VT 05201
• 

  

  /45

  $405,000

  Sold Apr 20, 2026

  848 Coleville Rd, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $200/SF
  • 151 Days On Market

  Current Estimated Value $405,457

  Last Listing Agent Beatrice O'Connell Maple Leaf Real Estate

  848 Coleville Rd, Bennington, VT 05201
• 

  

  /40

  Est $187,736

  Not Listed For Sale

  316 Beech St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1948

  316 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 56 Days On Market
• 

  

  /16

  $395,000

  Pending

  • 4,646 Sq Ft

  307 North St, Bennington, VT 05201

  Exceptional mixed-use opportunity in Bennington’s MU-2 District offering flexibility for investors, owner-occupants, or live/work configurations. Sale includes both 307 North Street and 307.5 North Street, two separate buildings situated on one 0.70-acre parcel with strong visibility and approximately 150 feet of frontage along North Street (VT Route 7). The front building (c. 1840) offers

  Jeffrey Dorman

  307 North St, Bennington, VT 05201
• 

  

  /35

  $220,000

  Sold Sep 16, 2025

  115 Jefferson Ave, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Built 1930

  Last Sold Summary

  • 18% Below List Price
  • $142/SF
  • 83 Days On Market

  Current Estimated Value $231,274

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  115 Jefferson Ave, Bennington, VT 05201
• 

  

  /38

  Est $213,024

  Not Listed For Sale

  230 Beech St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1880

  230 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 81 Days On Market
• 

  

  /38

  $309,900

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  2 Pine Rd, Bennington, VT 05201

  Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  2 Pine Rd, Bennington, VT 05201
• 

  

  /60

  $245,000

  Sold Sep 22, 2025

  19 Robinson Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1954

  Last Sold Summary

  • 11% Below List Price
  • $186/SF
  • 3 Days On Market

  Current Estimated Value $247,111

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  19 Robinson Ave, Bennington, VT 05201
• 

  

  /17

  Est $160,640

  Not Listed For Sale

  224 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,709 Sq Ft
  • Built 1900

  224 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 103 Days On Market
• 

  

  /29

  $395,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft

  231 Washington Ave, Bennington, VT 05201

  Charming vintage 1920s Arts & Crafts-style cottage in a prime village location. This inviting home offers seven main rooms, including three bedrooms and two baths, blending timeless character with modern comfort. The updated kitchen features abundant storage and flows nicely into the living spaces, highlighted by beautiful wood floors and a cozy fireplace. Central air ensures year-round comfort.

  Kelley Mccarthy Mahar McCarthy Real Estate

  231 Washington Ave, Bennington, VT 05201
• 

  

  /23

  $388,800

  Sold Jun 10, 2026

  317 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2026

  Last Sold Summary

  • $240/SF

  Last Listing Agent Lilli West Maple Leaf Real Estate

  317 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /35

  Est $202,289

  Not Listed For Sale

  218 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft
  • Built 1890

  218 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 48 Days On Market
• 

  

  /54

  $495,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /37

  $233,000

  Sold Aug 04, 2025

  73 Woodford City Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Above List Price
  • $221/SF
  • 73 Days On Market

  Last Listing Agent Abi Gregorio

  73 Woodford City Rd, Bennington, VT 05201
• 

  

  /32

  Est $181,515

  Not Listed For Sale

  103 Evergreen Dr, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1945

  103 Evergreen Dr, Bennington, VT 05201

  Last Sold Summary

  • 15 Days On Market
• 

  

  /45

  $275,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  951 Gage St, Bennington, VT 05201

  This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

  Dan Mason Perrott Realty

  951 Gage St, Bennington, VT 05201
• 

  

  /49

  $313,000

  Sold Jul 21, 2025

  1385 N Bennington Rd, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $153/SF
  • 53 Days On Market

  Current Estimated Value $314,777

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1385 N Bennington Rd, North Bennington, VT 05257
• 

  

  /40

  Est $247,233

  Not Listed For Sale

  313 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1960

  313 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market
• 

  

  /7

  $145,000

  $30K PRICE DROP

  • Land
  • 15.49 Acres
  • $9,361 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
• 

  

  /36

  $265,000

  Sold Jun 25, 2025

  82 Oakes St, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • Built 1991

  Last Sold Summary

  • $175/SF
  • 57 Days On Market

  Current Estimated Value $271,870

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  82 Oakes St, Bennington, VT 05201
• 

  

  /17

  Est $369,776

  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
• 

  

  /55

  $225,000

  • 4 Beds
  • 2 Baths
  • 1,518 Sq Ft

  142 Pine Cir, Bennington, VT 05201

  Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom

  Justine Curry Maple Leaf Real Estate

  142 Pine Cir, Bennington, VT 05201
• 

  

  /16

  $130,000

  Sold Jan 28, 2026

  755 Main St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft
  • Built 1890

  Last Sold Summary

  • 10% Below List Price
  • $88/SF
  • 141 Days On Market

  Current Estimated Value $140,495

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

  755 Main St, Bennington, VT 05201
• 

  

  /45

  Est $403,156

  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
• 

  

  /25

  $950,000

  $300K PRICE DROP

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

  Marek Kovac TPW Real Estate

  124 Elm St, 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 $121,230

  Last Listing Agent Lisa Friedman Great American Dream Realty

  130 Lincoln St, Bennington, VT 05201
• 

  

  /30

  Est $213,048

  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

Showing Results 121 - 160, Page 4 of 18