100 Webb St

Bennington, VT 05201

$190,000
Last Sold Price
3
Beds
1,416 Sq. Ft.
$134 / Sq. Ft.
1,416
Sq. Ft.
$134
per Sq. Ft.
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Closed 9/16/25
Closed 9/16/25

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,...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.
  1. Listed by Lindsey Martin • Maple Leaf Realty

Sold By Four Corner Properties LLC

Property Details for 100 Webb Street

Zoning
VR
LISTING UPDATED: 09/16/2025 07:29 PM

Property Details for 100 Webb Street

StatusClosed
MLS #5042437
Days on Market59
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1943
Lot Size0.45 AC / 19,602 SF
CountyBennington County
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Location

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Building Information for 100 Webb Street

Stories1Year Built1943Building Size-Lot Size0.45 AC / 19,602 SF

Payment Calculator

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$1,175 per month

30 year fixed, 6.15% Interest

Principal and Interest

$926

Property Taxes

$249

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 100 Webb Street

Summary
Location and General Information
  • City: Bennington
  • County: VT-Bennington
  • Directions: From Downtown Bennington drive east on Main St. Take a right onto Beech St. In 0.2 miles turn left onto Rollin St. Then Right onto Webb. The house will be on the right.
  • Latitude: 42.877373000001000
  • Longitude: -73.181635999999997
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05201
Taxes and HOA Information
  • SPAN Number: 051-015-67918
  • Taxes TBD: Yes
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Other
Property
Lot Information
  • Lot Features: Level, In Town, Near Shopping, Neighborhood
  • Lot Size Acres: 0.45
  • Road Frontage Length: 248.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1943
Utilities
  • Electric: 100 Amp Service, Circuit Breaker(s)
  • Sewer: Public
  • Water Source: Public
  • Utilities: Cable Available, Telephone Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: Brown
  • Construction Materials: Wood Frame, Wood Siding
  • Roof: Architectural Shingle
Interior Features
  • Appliances: Dryer, Freezer, Electric Range, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Concrete, Interior Stairs
  • Rooms: Level 1: Level 1: Full Bathroom, Level 1: Dining Room, Level 1: Eat-in Kitchen, Level 1: Living Room
  • Rooms: Level 2: Level 2: Bedroom
  • Flooring: Carpet, Laminate
  • Heating: Oil, Hot Air
  • Cooling: None
  • Total Stories: 1.5
Room Information
Room 1
  • Room Level: 1
  • Room Type: Eat-in Kitchen
Room 2
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Level: 1
  • Room Type: Bathroom Full
Room 5
  • Room Level: 2
  • Room Type: Bedroom
Room 6
  • Room Level: 2
  • Room Type: Bedroom
Room 7
  • Room Level: 2
  • Room Type: Bedroom

Property History for 100 Webb Street

DateEvent & SourcePriceAppreciation
Sep 16, 2025

Sold (Public Record)

Public Record #1914065363

$190,000—
Sep 16, 2025

Sold

New England Real Estate Network #5042437

$190,000—
Aug 6, 2025

Pending

New England Real Estate Network #5042437

—
May 22, 2025

Listed (Active)

New England Real Estate Network #5042437

$215,000—
DateEvent & SourcePrice
09/16/2025

Sold (Public Record)

Public Record #1914065363

$190,000
09/16/2025

Sold

New England Real Estate Network #5042437

$190,000
08/06/2025

Pending

New England Real Estate Network #5042437

—
05/22/2025

Listed (Active)

New England Real Estate Network #5042437

$215,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 100 Webb Street

Taxable ValueLand$10,000Additions$74,900Total$84,900
Tax Record2024$2,987 ($249 / month)
Home Facts
Beds3Baths1Total Finished SqFt1,416 SqFtAbove Grade Finished SqFt1,416 SqFtStories2Lot Size2,614 SqFtStyleSingle Family ResidenceYear Built1943CountyBENNINGTONAPN(015)51-55-11-00Fireplace TypeHas Fireplace

Schools near 100 Webb Street

This home is within Mount Anthony Union High School District #14.
Rating
School
Type
Grades
Distance
Bennington Elementary School
Public - PK to 5
Mt. Anthony Union Middle School
Public - 6 to 8
Mt. Anthony Senior Uhsd #14
Public - 9 to 12
Molly Stark School
Public - PK to 5
Rating
School
Distance
Bennington Elementary School
PublicPK to 5

Mt. Anthony Union Middle School
Public6 to 8

Mt. Anthony Senior Uhsd #14
Public9 to 12

Molly Stark School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Maple Leaf Realty

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 03/12/2026 04:58 AM