Does Old Bennington, VT show holiday spirit?

As of early 2026, 100% of users say there's holiday spirit

Is Old Bennington, VT dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Does Old Bennington, VT have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Would people walk alone at night in Old Bennington, VT?

As of early 2026, 100% of users say people would walk alone at night

Is parking easy in Old Bennington, VT?

As of early 2026, 100% of users say parking is easy

Do kids play outside in Old Bennington, VT?

As of early 2026, 88% of users say kids play outside

Is Old Bennington, VT quiet?

As of early 2026, 75% of users say it's quiet

Are neighbors friendly in Old Bennington, VT?

As of early 2026, 67% of users say neighbors are friendly

Is a car needed in Old Bennington, VT?

As of early 2026, 67% of users say car is needed

Are the streets well-lit in Old Bennington, VT?

As of early 2026, 60% of users say streets are well-lit

Is there wildlife in Old Bennington, VT?

As of early 2026, 50% of users say there's wildlife

Are yards well-kept in Old Bennington, VT?

As of early 2026, 50% of users say yards are well-kept

Is Old Bennington, VT walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Are there community events in Old Bennington, VT?

As of early 2026, 33% of users say there are community events

Is Old Bennington, VT walkable to grocery stores?

As of early 2026, 25% of users say it's walkable to grocery stores

What is 21 West Rd estimated to be worth?

Trulia's estimated value for 21 West Rd in Bennington, VT is $156,500 .

What is the price history for 21 West Rd?

21 West Rd in Bennington, VT last sold for $22,200 in November 2014.

Is Bennington a buyer's or seller's market?

Bennington is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 21 West Rd?

The closest schools to 21 West Rd in Bennington, VT are Monument School (Pre-K/Elementary), Mt. Anthony Senior Uhsd #14 (High, rated 5/10), Mt. Anthony Union Middle School (rated 3/10).

Does 21 West Rd have air conditioning?

Yes, 21 West Rd in Bennington, VT has air conditioning.

How big is the lot at 21 West Rd?

The lot at 21 West Rd in Bennington, VT is about 11 acres .

OFF MARKET

$156,500

Trulia Estimate

3 Beds
2 Baths
880 sqft (on 11 acres)

21 West Rd, Bennington, VT 05201

Est. Refi. Payment $1,136/mo*

Refinance Your Home

Currently Off Market - Sold Nov 12, 2014 for $22,200

Home Value

Trulia Estimate

$157K

Since last month

$14K (-8%)

Since last year

$24K (+17.8%)

Since last sale

$134K (+605%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +433% in the last 10 years

Month	Estimated value
2026
September 2026	$157K
August 2026	$170K
July 2026	$136K
June 2026	$155K
May 2026	$139K
April 2026	$123K
March 2026	$143K
January 2026	$134K
2025
December 2025	$142K
November 2025	$138K
October 2025	$139K
September 2025	$133K
August 2025	$152K
July 2025	$149K
2020
July 2020	$34K
June 2020	$35K
May 2020	$35K
2019
November 2019	$34K
September 2019	$36K
August 2019	$35K
July 2019	$34K
June 2019	$35K
May 2019	$35K
April 2019	$35K
March 2019	$35K
February 2019	$36K
January 2019	$35K
2018
December 2018	$36K
November 2018	$36K
October 2018	$36K
September 2018	$35K
August 2018	$34K
July 2018	$34K
June 2018	$34K
May 2018	$33K
April 2018	$33K
March 2018	$34K
February 2018	$34K
January 2018	$34K
2017
December 2017	$33K
November 2017	$32K
October 2017	$33K
September 2017	$33K
August 2017	$32K
July 2017	$33K
June 2017	$33K
May 2017	$33K
April 2017	$32K
March 2017	$34K
February 2017	$32K
January 2017	$30K
2016
December 2016	$34K
November 2016	$34K
October 2016	$33K
September 2016	$29K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
126 Fox Hill Road, Bennington, VT	0.30	Single-Family Home	$600,000	11/12/25	5	1.5	2,450
339 Chester Knoll Drive, Bennington, VT	0.42	Single-Family Home	$300,000	10/16/25	3	1.5	1,365
341 Chester Knoll Drive, Bennington, VT	0.43	Single-Family Home	$285,500	06/12/26	3	1.5	1,365
55 Monument Avenue, Old Bennington, VT	0.18	Single-Family Home	$640,000	12/22/25	3	2.5	2,675
321 Chester Knoll Drive, Bennington, VT	0.41	Single-Family Home	$385,000	09/23/25	3	2	1,702
318 Chester Knoll Drive, Bennington, VT	0.44	Single-Family Home	$300,000	04/02/26	3	2	1,865
139 McKinley Street, Bennington, VT	0.64	Single-Family Home	$250,000	10/14/25	3	1.5	1,264
317 Chester Knoll Drive, Bennington, VT	0.43	Single-Family Home	$388,800	06/10/26	4	2	1,620
34 Monument Avenue, Bennington, VT	0.27	Single-Family Home	$625,000	08/31/26	4	2.5	2,692
136 McKinley Street, Bennington, VT	0.61	Single-Family Home	$154,500	01/13/26	3	1	854

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
16 West Road, Bennington, VT 05201	0.09	$1,495,000	7	5.5	6,392	Recently Sold
3 Seminary Lane, Bennington, VT 05201	0.12	$641,500	5	3.5	3,782	Off Market
432 West Road, Bennington, VT 05201	0.17	$640,600	4	2	3,111	Off Market
55 Monument Avenue, Old Bennington, VT 05201	0.18	$640,000	3	2.5	2,675	Recently Sold
77 Monument Avenue, Old Bennington, VT 05201	0.18	$799,300	4	3.5	4,032	Off Market
34 Monument Avenue, Bennington, VT 05201	0.27	$625,000	4	2.5	2,692	Recently Sold
126 Fox Hill Road, Bennington, VT 05201	0.30	$641,600	5	1.5	2,450	Off Market
115 Monument Avenue, Old Bennington, VT 05201	0.29	$384,300	3	2.5	1,496	Off Market
16 Walloomsac Road, Old Bennington, VT 05201	0.37	$622,500	4	4.5	3,448	Off Market
1 Monument Avenue, Old Bennington, VT 05201	0.39	$885,000	4	2	3,560	Off Market
328 Chester Knoll Drive, Bennington, VT 05201	0.39	$386,000	3	3.5	2,148	Recently Sold
134 Monument Avenue, Bennington, VT 05201	0.40	$665,000	3	2.5	2,868	Recently Sold

Local Information

Map ViewExplore the area around 21 West Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1913

11 acre lot

880 sqft

$178/sqft

About this House

Ideally located just minutes outside of Bennington this home offers an unbeatable combination of comfort, convenience and affordability. Less than 5 miles from Bennington College. Rent includes cold water, sewer and removal of trash/recyclables. Please call Abe at 802-442-1887 to schedule a time to see the home that could end your search. Photos are of a similar home

$50 refundable application fee. Credit and background checks. Pets require prior approval. No smoking

21 West Rd, Bennington, VT 05201 is a 3 bedroom, 2 bathroom, 880 sqft single-family home built in 1913. It last sold for $22,200 on Nov 12, 2014. More recently, it was listed as a rental in April 2019 with an asking price of $875 per month. That rental listing was removed on February 27, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $156,500, with a rent estimate of $2,257/month.

Home Details for 21 West Rd

Interior Features
Heating & Cooling Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Appliances & Utilities DishwasherRefrigerator
Interior Details Ceiling Fan

Exterior Features
Exterior Home Features Roof: Asphalt, Metal
Parking & Garage Parking: Off Street

Property Information
Year Built Year Built: 1913
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 11.00 acres

Price and Tax history

Date	Event	Price
Feb 27, 2021 Source: N/A	ListingRemoved
Apr 9, 2019 Source: N/A	ListingRemoved	$875
Apr 7, 2019 Source: N/A	Listed For Rent	$875
Nov 26, 2017 Source: Agent Provided	ListingRemoved	$2,200,000
Feb 10, 2017 Source: Agent Provided	Listed For Sale	$2,200,000
Nov 12, 2014 Source: N/A	Sold	$22,200

Year	Property tax	Tax assessment
2025	$1,006	$34,600

Additional Cost

Market trends in Old Bennington

Last updated August 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Around this home

Monument School
PK-5
Public
147 Students
Southwest Vermont Union Elementary School District #87
NA
GreatSchools Rating
Parent Rating Average
When I was there one of the teachers made me cry and didn’t say sorry or I didn’t mean to make you cry They only “apologized” after I told someone they made 3 other kids cry that year. One of the teachers yelled at me when I didn’t hold the door for someone the person wasn’t disabled it was I wasn’t being a gentlemen I was in the 3rd grade. One of the kids didn’t do any work and was fine one kid slept the most classes and was ok. My friend was bullied for crying, the teacher didn’t do much. They banned a game for having a “bad” name. This was the 4th grade we would get in trouble for playing. My 2nd grade teacher threw a chair and broke a plastic bin they scared me and my friends at the table. There are good things like natures classroom and some field trips and going outside and the museum right by the school but that gets boring and repetitive. Some teachers are nice and that does help. There are fun trips that we went on . That’s all
Other Review
3y ago
5 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Old Bennington

At least 4 Trulia users voted on each feature.

100 % Say there's holiday spirit
100 % Say it's dog friendly
100 % Say there are sidewalks
100 % Say people would walk alone at night
100 % Say parking is easy
88 % Say kids play outside
75 % Say it's quiet
67 % Say neighbors are friendly
67 % Say car is needed
60 % Say streets are well-lit
50 % Say there's wildlife
50 % Say yards are well-kept
50 % Say it's walkable to restaurants
33 % Say there are community events
25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Hannah.toromino
Visitor
7y ago
"My husband used to live right down the street with his dad, stepmom, and step-brother. Very friendly neighborhood with quiet atmosphere."
18
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LGBTQ Local Legal Protections

Frequently asked questions about 21 West Rd

What is 21 West Rd estimated to be worth?
Trulia's estimated value for 21 West Rd in Bennington, VT is $156,500.
What is the price history for 21 West Rd?
21 West Rd in Bennington, VT last sold for $22,200 in November 2014.
Is Bennington a buyer's or seller's market?
Bennington is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 21 West Rd?
The closest schools to 21 West Rd in Bennington, VT are Monument School (Pre-K/Elementary), Mt. Anthony Senior Uhsd #14 (High, rated 5/10), Mt. Anthony Union Middle School (rated 3/10).
Does 21 West Rd have air conditioning?
Yes, 21 West Rd in Bennington, VT has air conditioning.
How big is the lot at 21 West Rd?
The lot at 21 West Rd in Bennington, VT is about 11 acres.

Explore by feature - Air Conditioning

8 rentals with air conditioning in Bennington, VT

SPECIAL OFFER
PET FRIENDLY
$1,750 - $2,650/mo
Studio-2 bd
1 ba
757 Main Street | 757 Main St,
Bennington, VT 05201
$1,975/mo
Total price
2 bd
2 ba
1,100 sqft
34 West Rd #1,
Bennington, VT 05201
APPLY INSTANTLY
$900/mo
1 bd
1 ba
331 sqft
Address Not Disclosed,
Bennington, VT 05201
APPLY INSTANTLY
FURNISHED
$1,650/mo
2 bd
1 ba
1,150 sqft
111 Harvard St,
Bennington, VT 05201
APPLY INSTANTLY
FURNISHED
$1,750/mo
1 bd
1.5 ba
1,100 sqft
215 Benmont Ave #G,
Bennington, VT 05201
APPLY INSTANTLY
$1,500/mo
1 bd
1 ba
900 sqft
530 Main St #1,
Bennington, VT 05201
APPLY INSTANTLY
$1,400/mo
2 bd
1 ba
800 sqft
108 Spring St,
Bennington, VT 05201
APPLY INSTANTLY
$1,300/mo
2 bd
1 ba
690 sqft
247 Depot St #4,
Bennington, VT 05201

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Bennington, VT

SPECIAL OFFER
PET FRIENDLY
$1,750 - $2,650/mo
Studio-2 bd
1 ba
757 Main Street | 757 Main St,
Bennington, VT 05201
$1,975/mo
Total price
2 bd
2 ba
1,100 sqft
34 West Rd #1,
Bennington, VT 05201
APPLY INSTANTLY
FURNISHED
$1,650/mo
2 bd
1 ba
1,150 sqft
111 Harvard St,
Bennington, VT 05201
APPLY INSTANTLY
$1,500/mo
1 bd
1 ba
900 sqft
530 Main St #1,
Bennington, VT 05201
APPLY INSTANTLY
$1,400/mo
2 bd
1 ba
800 sqft
108 Spring St,
Bennington, VT 05201
PET FRIENDLY
$2,100/mo
Total price
3 bd
2 ba
1,624 sqft
61 Bell St,
Bennington, VT 05201
PET FRIENDLY
$2,125/mo
Total price
3 bd
1.5 ba
980 sqft
9 Mountain View Rd,
Bennington, VT 05201