Bennington Homes

/58
$1,950,000
- 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
/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 $393,662

Last Listing Agent Catherine Cairns Maple Leaf Realty

495 Fairview St, Bennington, VT 05201

/32
Est $207,724 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
- 7% Above List Price
- $162/SF
- 15 Days On Market
Last Sold Price $195,000

Last Listing Agent Gabrielle Burdge

/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
/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 $247,281

Last Listing Agent Vicki Wilson Maple Leaf Realty

322 Burgess Rd, Bennington, VT 05201

/40
Est $247,016 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% Above List Price
- $200/SF
- 7 Days On Market
Last Sold Price $230,500

Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

/7
$175,000
- Land
- 15.49 Acres
- $11,298 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
/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 Realty

0 Sunset Dr Unit 5005504, Bennington, VT 05201

/40
Est $167,772 Not Listed For Sale

239 Beech St, Bennington, VT 05201
- 3 Beds
- 1 Bath
- 989 Sq Ft
- Built 1890
239 Beech St, Bennington, VT 05201

Last Sold Summary
- 116% Above List Price
- $79/SF
- 37 Days On Market
Last Sold Price $77,700

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

/44
$199,000
- 2 Beds
- 2.5 Baths
- 1,156 Sq Ft
106 Park St Unit 2, Bennington, VT 05201

Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for

Vicki Wilson Maple Leaf Realty

106 Park St Unit 2, Bennington, VT 05201
/24
$190,000 Sold May 07, 2025

105 County St, Bennington, VT 05201
- 5 Beds
- 3 Baths
- 2,270 Sq Ft
- Built 1910
Last Sold Summary
- $84/SF
- 6 Days On Market
Current Estimated Value $200,594

Last Listing Agent Erica Hale Ridgeline Real Estate

105 County St, Bennington, VT 05201

/17
Est $371,012 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
- 30% Above List Price
- $132/SF
- 101 Days On Market
Last Sold Price $285,000

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

/21
$235,000
- 4 Beds
- 2 Baths
- 1,652 Sq Ft
209 Grove St Unit 11, Bennington, VT 05201

A must see, well-kept 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, a spacious eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice, level backyard, 2

Julie Glover Mahar McCarthy Real Estate

209 Grove St Unit 11, 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 $253,127

Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

1236 Morgan St, Bennington, VT 05201

/45
Est $418,186 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
- 9% Above List Price
- $203/SF
- 48 Days On Market
Last Sold Price $385,000

Last Listing Agent Abi Gregorio

/25
$975,000
- 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
/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 $224,928

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

115 Jefferson Ave, Bennington, VT 05201

/37
Est $363,019 Not Listed For Sale

163 Morgan St, Bennington, VT 05201
- 3 Beds
- 2 Baths
- 1,714 Sq Ft
- Built 1948
163 Morgan St, Bennington, VT 05201

Last Sold Summary
- 8% Below List Price
- $230/SF
- 6 Days On Market
Last Sold Price $395,000

Last Listing Agent Abi Gregorio

/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
/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 $248,760

Last Listing Agent Floyd Amidon Maple Leaf Realty

19 Robinson Ave, Bennington, VT 05201

/30
Est $197,136 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
- 40% Below List Price
- $126/SF
- 15 Days On Market
Last Sold Price $328,000

Last Listing Agent Angela Bevin Maple Leaf Realty

/25
$289,000
- 7 Beds
- 6 Baths
- 5,712 Sq Ft
136 North St, Bennington, VT 05201

Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail,

Jeffrey Dorman

136 North 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 $316,795

Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

1385 N Bennington Rd, North Bennington, VT 05257

/6
Est $328,979 Not Listed For Sale

240 Grandview St, Bennington, VT 05201
- 3 Beds
240 Grandview St, Bennington, VT 05201

Last Sold Summary
- 656% Above List Price
- $31/SF
- 38 Days On Market
Last Sold Price $43,500

Last Listing Agent Lindsey Martin Maple Leaf Realty

/26
$199,000
- 4 Beds
- 2 Baths
- 1,980 Sq Ft
210 Division St, Bennington, VT 05201

Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

Lilli West Maple Leaf Realty

210 Division St, 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 $269,266

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

82 Oakes St, Bennington, VT 05201

/5
Not Listed For Sale

236 Grandview St, Bennington, VT 05201
- 5 Beds
- Built 1875
236 Grandview St, Bennington, VT 05201

Last Sold Summary
- $16/SF
- 38 Days On Market
Last Sold Price $43,500

Last Listing Agent Lindsey Martin Maple Leaf Realty

/4
$190,000
- 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
/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 $171,656

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

755 Main St, Bennington, VT 05201

/30
Est $299,893 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
- 11% Above List Price
- $158/SF
- 72 Days On Market
Last Sold Price $270,000

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

/4
$350,000 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 Realty

523 Jennings Brook Dr, Bennington, VT 05201
/38
$215,000 Sold Jun 06, 2025

230 Beech St, Bennington, VT 05201
- 3 Beds
- 2 Baths
- 1,271 Sq Ft
- Built 1880
Last Sold Summary
- 4% Below List Price
- $169/SF
- 81 Days On Market
Current Estimated Value $218,908

Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

230 Beech St, Bennington, VT 05201

/24
Est $305,505 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
- 9% Above List Price
- $254/SF
- 6 Days On Market
Last Sold Price $280,000

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

/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.

Dan Mason Perrott Realty

2041 East Rd, 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 $282,564

Last Listing Agent William Paquin Maple Leaf Realty

400 South St, Bennington, VT 05201

/38
Est $392,000 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
- 12% Above List Price
- $220/SF
- 63 Days On Market
Last Sold Price $350,000

Last Listing Agent Brandy Lesser

/40
$289,000
- 6 Beds
- 4 Baths
- 2,520 Sq Ft
111 Booth Terrace, Bennington, VT 05201

Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout.

Abi Gregorio

111 Booth Terrace, Bennington, VT 05201
/38
$193,800 Sold May 30, 2025

134 Imperial Ave, Bennington, VT 05201
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
- Built 1915
Last Sold Summary
- 2% Above List Price
- $192/SF
- 31 Days On Market
Current Estimated Value $193,555

Last Listing Agent Angela Bevin Maple Leaf Realty

134 Imperial Ave, Bennington, VT 05201

/25
Est $392,343 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
- 25% Above List Price
- $202/SF
- 12 Days On Market
Last Sold Price $315,000

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

/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

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