106 Leonard St, Bennington, VT 05201
OFF MARKET

$259,600

Trulia Estimate
  • Studio

106 Leonard St, Bennington, VT 05201

Refinance Your Home
Currently Off Market - Sold Nov 17, 2003 for $125,000

Home Value

Trulia Estimate
$260K
Since last month
Increased$8K (+3.3%)
Since last year
Increased$14K (+5.7%)
Since last sale
Increased$135K (+107.8%)
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$260K
August 2026$260K
July 2026$251K
June 2026$259K
May 2026$264K
April 2026$254K
March 2026$251K
February 2026$250K
January 2026$256K
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
103 Leonard Street, Bennington, VT
0.05
Single-Family Home
$279,000
12/09/25
3
2.5
1,723
130 Lincoln Street, Bennington, VT
0.30
Single-Family Home
$125,000
05/01/26
4
1
1,156
21 Pageant Street, Bennington, VT
0.14
Single-Family Home
$325,000
07/29/26
4
2
1,443
136 McKinley Street, Bennington, VT
0.24
Single-Family Home
$154,500
01/13/26
3
1
854
23 Pageant Street, Bennington, VT
0.16
Single-Family Home
$399,900
07/31/26
4
2
1,896
14 Robinson Avenue, Bennington, VT
0.33
Single-Family Home
$220,000
06/23/26
3
1
1,254
115 River Street, Bennington, VT
0.39
Single-Family Home
$75,500
12/05/25
4
1.5
1,887
19 Robinson Avenue, Bennington, VT
0.31
Single-Family Home
$245,000
09/22/25
3
1
1,320
209 Depot Street, Bennington, VT
0.43
Single-Family Home
$190,230
08/21/26
4
2
1,840
23 Robinson Avenue, Bennington, VT
0.30
Single-Family Home
$335,000
09/29/25
3
1.5
1,682

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
103 Leonard Street, Bennington, VT 05201
0.05
$279,000
3
2.5
1,723
Recently Sold
1 Woodland Drive, Bennington, VT 05201
0.06
$299,000
3
2
1,368
Off Market
143 Convent Avenue, Bennington, VT 05201
0.08
$388,700
4
3
2,786
Off Market
146 Convent Avenue, Bennington, VT 05201
0.12
$263,900
3
1
1,720
Off Market
21 Pageant Street, Bennington, VT 05201
0.14
$325,000
4
2
1,443
Recently Sold
24 Pageant Street, Bennington, VT 05201
0.16
$396,300
4
2.5
2,008
Off Market
23 Pageant Street, Bennington, VT 05201
0.16
$399,900
4
2
1,896
Recently Sold
2 Sharon Drive, Bennington, VT 05201
0.17
$428,600
3
2.5
2,431
Off Market
139 McKinley Street, Bennington, VT 05201
0.23
$267,500
3
1.5
1,264
Off Market
105 County Street, Bennington, VT 05201
0.24
$229,400
5
3
2,270
Off Market
24 Robinson Avenue, Bennington, VT 05201
0.27
$277,500
4
2
1,472
Off Market
136 McKinley Street, Bennington, VT 05201
0.24
$154,500
3
1
854
Recently Sold

Local Information

  • Map ViewExplore the area around 106 Leonard St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
0.29 acre lot

About this House

This single-family home is located at 106 Leonard St, Bennington, VT. 106 Leonard St is in Bennington, VT and in ZIP code 05201. This property has a lot size of 0.29 acres.
106 Leonard St, Bennington, VT 05201 is a studio single-family home. It last sold for $125,000 on Nov 17, 2003. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $259,600, with a rent estimate of $2,637/month.

Home Details for 106 Leonard St

Property Information

Property Type / Style
Property Type: Single Family Home

Exterior Features

Parking & Garage
Parking: Off Street

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Nov 17, 2003
Source: N/A
Sold
$125,000
Dec 8, 1994
Source: N/A
Sold
$93,000
Feb 9, 1988
Source: N/A
Sold
$45,000

Market trends in Bennington

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

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 106 Leonard St

  • What is 106 Leonard St estimated to be worth?
    Trulia's estimated value for 106 Leonard St in Bennington, VT is $259,600.
  • What is the price history for 106 Leonard St?
    106 Leonard St in Bennington, VT last sold for $125,000 in November 2003.
  • 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 106 Leonard St?
    The lot at 106 Leonard St in Bennington, VT is about 0.29 acres (12,632 sq ft).
  • Does 106 Leonard St have parking?
    Yes, 106 Leonard St in Bennington, VT has on-site parking.

Explore by feature - Pet Friendly

7 pet-friendly rentals in Bennington, VT

Explore by feature - Air Conditioning

6 rentals with air conditioning in Bennington, VT

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