100 Webb Street, Bennington, VT 05201
Property image
Property image
OFF MARKET
Listed by Lindsey Martin, Maple Leaf Real Estate, (802) 447-3210 . Bought with Four Corner Properties LLC

$205,400

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,416 sqft (on 0.45 acres)

100 Webb Street, Bennington, VT 05201

Est. Refi. Payment $1,468/mo*
Refinance Your Home
Currently Off Market - Sold Sep 16, 2025 for $190,000

Home Value

Trulia Estimate
$205K
Since last month
Increased$2K (+1%)
Since last year
Increased$16K (+8.4%)
Since last sale
Increased$16K (+8.5%)
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 +125% in the last 10 years
MonthEstimated value
2026
September 2026$206K
August 2026$204K
July 2026$199K
June 2026$200K
May 2026$197K
April 2026$194K
March 2026$194K
February 2026$190K
January 2026$190K
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
0.14
Single-Family Home
$241,000
09/25/25
3
1
1,070
0.33
Single-Family Home
$215,000
08/27/26
3
1
1,047
0.35
Single-Family Home
$260,000
04/28/26
3
1.5
1,570
0.25
Single-Family Home
$206,000
02/20/26
3
2
1,680
0.15
Single-Family Home
$130,000
01/28/26
3
1.5
1,485
0.45
Single-Family Home
$77,000
08/04/26
3
1
1,508
0.19
Single-Family Home
$296,500
11/21/25
3
2
1,896
0.38
Single-Family Home
$168,000
07/17/26
3
1
1,232
0.31
Single-Family Home
$225,000
02/18/26
4
2
1,702

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
0.10
$700,000
10
9
8,300
Recently Sold
0.11
$226,900
3
1
1,680
Off Market
0.10
$248,200
4
1
1,620
Off Market
0.12
$176,300
3
1.5
1,709
Off Market
0.12
$250,800
6
3
2,240
Off Market
0.12
$236,300
3
2
1,271
Off Market
0.07
$275,000
4
2
2,022
For Sale
0.09
$401,400
12
4
5,400
Off Market
0.08
$325,700
7
4
4,264
Off Market
0.09
$269,000
4
2
2,206
For Sale
0.16
$237,200
3
2
1,416
Off Market

Local Information

  • Map ViewExplore the area around 100 Webb Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1943
0.45 acre lot
1,416 sqft
$145/sqft
Garage

About this House

Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown! Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort. From the moment you arrive, you're greeted by the cobblestone driveway leading to the wraparound porch with pillars adorned with regal lion heads, perfect for tea, tales, and twilight daydreams. Inside you’ll find Dragons carved into the stair railings, an open living room, formal dining room, and a sunny breakfast nook tucked in the heart of the kitchen. The fireplace glows with Bennington pottery tiles around the hearth, and a vintage tub pours water from a sculpted fish faucet, offering a splash of whimsy. Discover a rare delight below: a basement projector booth and private children’s puppet theater waiting to be finished. Fantasy meets function in this home Whether you're sipping espresso in the garden or hosting dinner parties in the grand dining room, this home feels like a European escape — without ever leaving town.
100 Webb Street, Bennington, VT 05201 is a 3 bedroom, 1 bathroom, 1,416 sqft single-family home built in 1943. It last sold for $190,000 on Sep 16, 2025 (5% below the $200,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $205,400, with a rent estimate of $2,275/month.

Home Details for 100 Webb Street

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Concrete,Interior Stairs,Interior EntryNumber of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1416 Square Feet
Appliances & Utilities
Utilities: Cable Available, Phone AvailableAppliances: Dryer, Freezer, Electric Range, Refrigerator, WasherDryerLaundry: In BasementRefrigeratorWasher
Heating & Cooling
Heating: Oil,Hot AirNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Fireplace & Spa
Number of Fireplaces: 1Fireplace: 1 FireplaceHas a Fireplace
Gas & Electric
Electric: 100 Amp Service, Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Carpet, Laminate
Levels, Entrance, & Accessibility
Stories: 1.5Levels: One and One HalfFloors: Carpet, Laminate
View
No View

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Covered PorchExterior: Garden, Natural Shade, StorageFoundation: ConcreteGarden
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Has a GarageParking Spaces: 1Parking: Garage
Frontage
Road Frontage: Public
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: Road frontage: 248
Finished Area
Finished Area (above surface): 1416 Square Feet

Property Information

Year Built
Year Built: 1943
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Historic Vintage,New Englander
Building
Construction Materials: Wood Frame, Wood SidingNot a New Construction

Price & Status

Price
List Price: $200,000

Location

Direction & Address
City: Bennington
School Information
Elementary School District: Southwest VermontJr High / Middle School: Mt. Anthony Union Middle SchJr High / Middle School District: Southwest VermontHigh School: Mt. Anthony Sr. UHSD 14High School District: Southwest Vermont

Building

Building Area
Building Area: 2286 Square Feet

Lot Information

Lot Area: 0.45 acres

Miscellaneous

BasementMls Number: 5042437Above Grade Unfinished Area: 1416Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 870Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price and Tax history

DateEventPrice
Sep 16, 2025
Source: PrimeMLS #5042437
Sold
$190,000
Aug 6, 2025
Source: PrimeMLS #5042437
Contingent
$200,000
Jul 16, 2025
Source: PrimeMLS #5042437
PriceChange
$200,000
Price decreased by 7%
Jun 30, 2025
Source: PrimeMLS #5042437
PendingToActive
$215,000
Jun 13, 2025
Source: PrimeMLS #5042437
Contingent
$215,000

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

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 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."
  • 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"
  • 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"
  • 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"
  • 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"
  • 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! "
  • 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 "
  • 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"
  • 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!"
  • renbisson
    "I was born here. I have lived in CA, and visited several areas of the country. I came here to raise my kids."
  • 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."

LGBTQ Local Legal Protections

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-09-20 23:08:23 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

Frequently asked questions about 100 Webb Street

  • What is 100 Webb Street estimated to be worth?
    Trulia's estimated value for 100 Webb Street in Bennington, VT is $205,400.
  • What is the price history for 100 Webb Street?
    100 Webb Street in Bennington, VT last sold for $190,000 in September 2025.
  • 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.
  • Does 100 Webb Street have laundry facilities?
    Yes, 100 Webb Street in Bennington, VT has in-unit laundry.
  • How big is the lot at 100 Webb Street?
    The lot at 100 Webb Street in Bennington, VT is about 0.45 acres (19,602 sq ft).

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