100 Webb Street

Closed 9/16/25

Sold

Last Sold Price

$190,000

3 beds1 bath1,416 sqft

100 Webb St, Bennington, VT 05201

Single FamilyProperty Type

0.45 acresLot Size

1943Year Built

$134/sq ftPrice per sq ft

1 carParking Spaces

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.

Sold By Four Corner Properties LLC

Listed by: Lindsey Martin • Maple Leaf Realty

Listing closed: 09/16/2025 12:00 AM • Source: New England Real Estate Network, MLS#: 5042437

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Location

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$1,117 per month

30 year fixed, 6.71% Interest

Principal and Interest

$982

Property Taxes

$135

HOA Dues

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Property Information for 100 Webb Street

Property Details

MLS Type: Residential / Single Family
County: Bennington County
Zoning: VR

Building Information

Stories: 1
Year Built: 1943
Lot Size: 0.45 AC / 19,602 SF

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

Virtual Tour

Property Panorama Virtual Tour: https://tour.neren.com/100-Webb-Street-Bennington-VT-05201/unbranded

Property

Lot Information

Lot Features: Level, In Town, Near Shopping, Neighborhood
Lot Size Acres: 0.45

Road Frontage Length: 248.0
Total Finished Area: 1416.0
Above Grade Finished Area: 1416.0
Above Grade Finished Area Source: Public Records
Above Grade Unfinished Area: 0.0
Below Grade Finished Area: 0.0
Below Grade Unfinished Area: 870.0
BelowGradeUnfinishedAreaSource: Public Records
Lot Size Square Feet: 19602.0
Total Area: 2286.0

Property and Assessments

Property Class: Residential
Property Type: Single Family

Flood Zone: No
PreConstruction: No
Surveyed: Unknown
Year Built: 1943
School District: Southwest Vermont
High School: Mt. Anthony Sr. UHSD 14
Middle/Jr School: Mt. Anthony Union Middle Sch

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
Rooms Total: 6
Bathrooms Full: 1
Bathrooms Half: 0
Bathrooms One Quarter: 0
Bathrooms Three Quarter: 0
Bedrooms Total: 3
Bathrooms Total: 1

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

Date	Event & Source	Price	Appreciation
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	—

Date	Event & Source	Price
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, we 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 Record2025$1,621 ($135 / month)

Home Facts

Beds3Baths1Total Finished SqFt1,416 SqFtAbove Grade Finished SqFt1,416 SqFtStories1Lot Size2,614 SqFtStyleSingle Family ResidenceYear Built1943Year Renovated1943CountyBENNINGTONAPN(015)51-55-11-00

Schools near 100 Webb Street

This home is within Mount Anthony Union High School District #14.


Rating	School	Type	Grades	Distance
1/10	Bennington Elementary School	Public - Serves this home	PK to 5	0.6 mi
3/10	Mt. Anthony Union Middle School	Public - Serves this home	6 to 8	2.0 mi
5/10	Mt. Anthony Senior Uhsd #14	Public - Serves this home	9 to 12	0.8 mi
5/10	Molly Stark School	Public - Nearby school	PK to 5	1.8 mi
NR	Monument School	Public - Nearby school	PK to 5	1.6 mi
NR	Grace Christian School	Private - Nearby school	PK to 12	1.5 mi
NR	The School Of Sacred Heart St Francis De Sales	Private - Nearby school	PK to 8	0.7 mi
NR	Bennington Regional Day Program	Private - Nearby school	3 to 5	0.7 mi


Rating	School	Distance
1/10	Bennington Elementary School PublicPK to 5 Serves this home	0.6 mi
3/10	Mt. Anthony Union Middle School Public6 to 8 Serves this home	2.0 mi
5/10	Mt. Anthony Senior Uhsd #14 Public9 to 12 Serves this home	0.8 mi
5/10	Molly Stark School PublicPK to 5 Nearby school	1.8 mi
NR	Monument School PublicPK to 5 Nearby school	1.6 mi
NR	Grace Christian School PrivatePK to 12 Nearby school	1.5 mi
NR	The School Of Sacred Heart St Francis De Sales PrivatePK to 8 Nearby school	0.7 mi
NR	Bennington Regional Day Program Private3 to 5 Nearby school	0.7 mi

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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Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 100 Webb Street, Bennington, VT 05201	$190,000	3	1	1,416	19,602
127 Webb Street, Bennington, VT 05201	$33,000	–	–	–	11,326
133 South Branch Street, Bennington, VT 05201	–	2	1	968	3,049
141 South Branch Street, Bennington, VT 05201	–	4	2	2,630	28,750
131 South Branch Street, Bennington, VT 05201	–	2	1	1,440	16,117
110 Webb Street, Bennington, VT 05201	–	3	2	1,536	19,602
105 Webb Street, Bennington, VT 05201	–	2	1	924	38,333
115 Webb Street, Bennington, VT 05201	–	1	1	400	10,019
117 South Branch Street, Bennington, VT 05201	–	3	1.5	1,570	12,197
146 South Branch Street, Bennington, VT 05201	$80,500	4	2	1,706	6,098
161 South Branch Street, Bennington, VT 05201	–	3	2.5	1,528	27,443
115 South Branch Street, Bennington, VT 05201	–	4	1.5	1,476	12,632
114 Webb Street, Bennington, VT 05201	$165,000	3	2	1,280	24,393
142 South Branch Street, Bennington, VT 05201	–	4	1	1,385	20,909
138 South Branch Street, Bennington, VT 05201	–	3	1	1,590	21,780
156 South Branch Street, Bennington, VT 05201	$32,500	3	1.5	1,248	10,890

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 09/19/2026 01:51 AM

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