100 Webb Street, Bennington, VT 05201
SOLD
SEP 16, 2025
Listed by Lindsey Martin, Maple Leaf Real Estate, (802) 447-3210 . Bought with Four Corner Properties LLC

100 Webb Street
Bennington, VT 05201

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

$190,000

Last Sold: Sep 16, 2025
5% below list $200K
$134/sqft

$190,000

Last Sold: Sep 16, 2025
5% below list $200K
$134/sqft
3 Beds
1 Bath
1,416 sqft
(on 0.45 acres)

Homes for sale near 100 Webb Street

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 13 hours ago
Listed by Lindsey Martin
Maple Leaf Real Estate, (802) 447-3210
Bought with: Patrick J Sady, Four Corner Properties LLC, (508) 320-9014
Source: PrimeMLS, MLS#5042437

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from September 16, 2025

Home Highlights

Parking
Garage
Outdoor
Porch
A/C
Heating only
HOA
None
Price/Sqft
$134/sqft
Listed
180+ days ago

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: $200,000Price Per Sqft: $134/sqft

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 History for 100 Webb Street

DatePriceEventSource
09/16/2025$190,000Sold
PrimeMLS #5042437
08/06/2025$200,000ContingentPrimeMLS #5042437
07/16/2025$200,000PriceChange
PrimeMLS #5042437
06/30/2025$215,000PendingToActivePrimeMLS #5042437
06/13/2025$215,000ContingentPrimeMLS #5042437
05/22/2025$215,000Listed For SalePrimeMLS #5042437
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Property Tax and Assessment

Year2024
Tax
Assessment$84,900
Home facts updated by county records

Comparable Sales for 100 Webb Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
230 Beech Street, Bennington, VT
0.12
Single-Family Home
$215,000
06/06/25
3
2
1,271
20 Rockwood Street, Bennington, VT
0.14
Single-Family Home
$241,000
09/25/25
3
1
1,070
30 Harbour Road, Bennington, VT
0.33
Single-Family Home
$275,000
07/31/25
3
1
1,608
130 Beech Street, Bennington, VT
0.16
Single-Family Home
$217,000
07/10/25
3
2
1,416
82 Oakes Street, Bennington, VT
0.22
Single-Family Home
$265,000
06/25/25
2
1
1,512
134 Imperial Avenue, Bennington, VT
0.47
Single-Family Home
$193,800
05/30/25
3
1
1,008
940 Gage Street, Bennington, VT
0.35
Single-Family Home
$260,000
04/28/26
3
1.5
1,570
116 Morgan Street, Bennington, VT
0.25
Single-Family Home
$206,000
02/20/26
3
2
1,680
755 Main Street, Bennington, VT
0.15
Single-Family Home
$130,000
01/28/26
3
1.5
1,485

Assigned Schools

These are the assigned schools for 100 Webb Street.
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 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

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

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 2026-05-07 15:09:41 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.

Homes for rent near 100 Webb Street

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Off Market Homes Near 100 Webb Street

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100 Webb Street, Bennington, VT 05201 is a 3 bedroom, 1 bathroom, 1,416 sqft single-family home built in 1943. This property is not currently available for sale. 100 Webb Street was last sold on Sep 16, 2025 for $190,000 (5% lower than the asking price of $200,000). The current Trulia Estimate for 100 Webb Street is $193,500.