53 Hill Shadow Farm Rd, Bennington, VT 05201
OFF MARKET

$558,000

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,804 sqft (on 2.18 acres)

53 Hill Shadow Farm Rd, Bennington, VT 05201

Est. Refi. Payment $3,692/mo*
Refinance Your Home
Currently Off Market - Sold Jan 23, 2007 for $370,000

Home Value

Trulia Estimate
$558K
Since last month
Increased$4K (+0.7%)
Since last year
Decreased$23K (-3.9%)
Since last sale
Increased$188K (+50.8%)
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 +82% in the last 10 years
MonthEstimated value
2026
August 2026$558K
July 2026$554K
June 2026$559K
May 2026$568K
April 2026$549K
March 2026$548K
February 2026$542K
January 2026$530K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
165 Pippin Knoll, Bennington, VT
0.19
Single-Family Home
$351,000
11/21/25
4
3
2,994
58 Mount Anthony Road, Bennington, VT
0.80
Single-Family Home
$505,000
08/21/26
3
2.5
2,715
495 Fairview Street, Bennington, VT
0.40
Single-Family Home
$400,000
09/22/25
3
2
1,309
126 Fox Hill Road, Bennington, VT
0.66
Single-Family Home
$600,000
11/12/25
5
1.5
2,450
166 Cardinal Lane, Bennington, VT
0.95
Single-Family Home
$295,000
07/22/26
3
2
2,753
695 Dermody Road, Bennington, VT
0.91
Single-Family Home
$355,000
05/29/26
3
1.5
1,748
682-704 Fox Hill Road, Bennington, VT
0.96
Single-Family Home
$838,500
05/29/26
3
2.5
1,728
55 Monument Avenue, Old Bennington, VT
0.89
Single-Family Home
$640,000
12/22/25
3
2.5
2,675
77 Monument Avenue, Old Bennington, VT
0.95
Single-Family Home
$740,000
10/10/25
4
3.5
4,032
458 Fox Hill Road, Bennington, VT
0.96
Single-Family Home
$435,000
10/10/25
4
3
3,040

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
0 Walloomsac Road, Bennington, VT 05201
0.09
-
-
-
-
Off Market
109 Village Lane, Bennington, VT 05201
0.22
$506,900
4
2.5
2,632
Off Market
165 Pippin Knoll, Bennington, VT 05201
0.19
$351,000
4
3
2,994
Recently Sold
17 Jennings Drive, Bennington, VT 05201
0.34
$171,100
3
2
1,800
Off Market
495 Fairview Street, Bennington, VT 05201
0.40
$417,400
3
2
1,309
Off Market
390 Fairview Street, Bennington, VT 05201
0.41
-
-
-
-
Off Market
1086 West Road, Bennington, VT 05201
0.49
$1,800,000
9
6
6,956
Recently Sold
85 Silk Road, Bennington, VT 05201
0.54
$271,800
2
1
1,053
Off Market
1427 Walloomsac Road, Bennington, VT 05201
0.60
$268,400
2
1.5
1,890
Off Market
126 Fox Hill Road, Bennington, VT 05201
0.66
$600,000
5
1.5
2,450
Recently Sold
432 West Road, Bennington, VT 05201
0.68
$640,800
4
2
3,111
Off Market
16 Walloomsac Road, Old Bennington, VT 05201
0.66
$626,500
4
4.5
3,448
Off Market

Local Information

  • Map ViewExplore the area around 53 Hill Shadow Farm Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Lot Size
2.18 acres
Living Area
2,804 sqft
Price/Sqft
$199

About this House

1929 Carriage House in Bennington Totally renovated 1929 Carriage Barn on quiet dead end road boasts charm throughout. 3 bedrooms, 3 full baths, 1st floor laundry, hard wood floors, 2 fireplaces, large eat-in gourmet kitchen with commercial stove. Private terrace and 60' in ground pool with marble deck on 2.18 acres. $397,900. Listing Agent: Suzy Yucht
53 Hill Shadow Farm Rd, Bennington, VT 05201 is a 3 bedroom, 3 bathroom, 2,804 sqft single-family home. It last sold for $370,000 on Jan 23, 2007. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $558,000, with a rent estimate of $3,737/month.

Home Details for 53 Hill Shadow Farm Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 2.18 acres

Price and Tax history

DateEventPrice
Jun 6, 2010
Source: Agent Provided
ListingRemoved
$397,900
Mar 17, 2010
Source: Agent Provided
PriceChange
$397,900
Price decreased by 3%
Feb 14, 2010
Source: Agent Provided
PriceChange
$409,900
Price decreased by 2%
Sep 19, 2009
Source: Agent Provided
PriceChange
$419,900
Price decreased by 9%
Aug 9, 2008
Source: Agent Provided
PriceChange
$459,000
Price decreased by 6%

Market trends in Bennington

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
36
3MoM

Around this home

What Locals Say about Bennington

At least 58 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 82 % Say car is needed

  • 79 % Say yards are well-kept

  • 78 % Say parking is easy

  • 71 % Say there are sidewalks

  • 69 % Say there's holiday spirit

  • 66 % Say there's wildlife

  • 63 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 59 % Say people would walk alone at night

  • 56 % Say neighbors are friendly

  • 48 % Say streets are well-lit

  • 44 % Say it's quiet

  • 38 % Say they plan to stay for at least 5 years

  • 33 % Say there are community events

  • 28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Jowasieleuski
    "I have lived here 20 years and it has gone down hill in this time. No real growth here. Drug use is rampant and jobs are few and far."
    3
    Flag
  • Thomayera
    "Nothing special about Bennington it may be pretty some times but that’s about it. When it’s pretty we have too many tourists so no win"
    1
    Flag
  • Thomayera
    "Lived on this part of Gage street for 10 years now. It’s been pretty decent. Had some theft once but other than that was okay"
    1
    Flag
  • Kjae_pristine
    "I lived in Bennington over 20 years. Bennington has a different type of living. One minute you are in the center of town the next minute you are in the country with nothing but mountains to look at"
    0
    Flag
  • Bryonbleau0217
    "Minimal traffic,I travel less then 5 miles to work most business are within walking distance.all town roads and no highways are needed if you work and live in Bennington"
    0
    Flag
  • s. lowers
    "There are other dogs around, all over. So when one barks, they all do. They’re friendly most of the time though, but I guess your dog would pull when walking? I don’t know. I’m sure everything will be great! "
    0
    Flag
  • Shennajeann
    "Not many people travel up and down the road, and the neighbors are very nice. My neighbors inform me if anybody is on my property or anything "
    0
    Flag
  • Tiggacrandall79276
    "the Neighborhood is clean and there is no drug activity here it's quite next to the Jr high school. and watch them play baseball or football"
    1
    Flag
  • Starlene G.
    "people genuinely stay to them self's ,very quiet ,always seem to be rushing around though ,and they stay busy!😊 very clean and nice place to live ,every thing is pretty much accessible!"
    0
    Flag
  • renbisson
    "I was born here. I have lived in CA, and visited several areas of the country. I came here to raise my kids."
    0
    Flag
  • mymusic54
    "Live here - very quiet, close to App hiking trail, new Highway, still super quiet and convenient travel in all directions. Although in town, beautiful countryside within miles."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 53 Hill Shadow Farm Rd

  • What is 53 Hill Shadow Farm Rd estimated to be worth?
    Trulia's estimated value for 53 Hill Shadow Farm Rd in Bennington, VT is $558,000.
  • What is the price history for 53 Hill Shadow Farm Rd?
    53 Hill Shadow Farm Rd in Bennington, VT last sold for $370,000 in January 2007.
  • Is Bennington a buyer's or seller's market?
    Bennington is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Bennington?
    Residents describe Bennington, VT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Bennington, VT.
  • How big is the lot at 53 Hill Shadow Farm Rd?
    The lot at 53 Hill Shadow Farm Rd in Bennington, VT is about 2.2 acres.

Explore by feature - Pet Friendly

7 pet-friendly rentals in Bennington, VT

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Off Market Homes Near 53 Hill Shadow Farm Rd

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