OFF MARKET

Listed by Lindsey Martin • Maple Leaf Real Estate. Bought with Four Corner Properties LLC.

Off Market Sep 2025 for $190K

$242,377

Est. refi paymentEst. refi $1,249/mo

•

1,416

sq ft

100 Webb St, Bennington, VT 05201

About this home

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.

Single-familyProperty Type

1943Year Built

0.45 acresLot Size

$171Est. Price/Sq.Ft.

1 car garageParking

Listed by Lindsey Martin • Maple Leaf Real Estate

Bought with Patrick Sady • Four Corner Properties LLC

Redfin checked: a few seconds ago

•Source:PrimeMLS #5042437

Redfin Estimate

$242,377

$52K since sold in September 2025$11K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.4% lower than the average sale price ($248K) of 6 comparable homes.

SOLD AUG 4, 2026
$77,000
A
3 beds1 bath1,508 sq ft
109 Evergreen Dr, Bennington, VT 05201
SOLD APR 28, 2026
$260,000
B
3 beds1.5 baths1,570 sq ft
940 Gage St, Bennington, VT 05201
SOLD JUL 17, 2026
$168,000
C
3 beds1 bath1,232 sq ft
256 Union St, Bennington, VT 12090
SOLD AUG 27, 2026
$215,000
D
3 beds1 bath1,047 sq ft
99 Coolidge Ave, Bennington, VT 05201
SOLD JUL 21, 2026
$398,000
E
3 beds2 baths1,556 sq ft
231 Washington Ave, Bennington, VT 05201
SOLD MAY 13, 2026
$372,000
F
3 beds1.5 baths1,463 sq ft
303 Prospect St, Bennington, VT 05201

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Earn from this home

Refinance

Est. cash available

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Rent

$1,336/mo

Redfin rental estimate

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Market trends in 05201, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.2%

1.4% MoM

Median sale price

$295K

$2K MoM

Avg. days on market

60d

1 days MoM

Recently sold homes

1 MoM

New listings for sale

$579,000
3 beds2 baths2,501 sq ft
856 Matteson Rd, North Bennington, VT 05201
FOR SALE BY OWNER
$160,000
8 beds2 baths2,334 sq ft
1032 Main St, Bennington, VT 05201
$175,000
2 beds1 bath810 sq ft
220 Gage St, Bennington, VT 05201
See all

Provided by Redfin

Sale history for 100 Webb St

Year

Property tax

Land + Additions

Assessment*

2025

$1,621 (−4.5%)

$10,000 + $74,900

$84,900

2024

$1,697 (+38.5%)

$10,000 + $74,900

$84,900

2023

$1,225 (−37.0%)

$10,000 + $74,900

$84,900

2022

$1,945 (−0.5%)

$10,000 + $74,900

$84,900

2021

$1,955 (+0.2%)

$10,000 + $74,900

$84,900

2020

$1,951 (+5.2%)

$10,000 + $74,900

$84,900

2019

$1,855 (+1.7%)

$10,000 + $74,900

$84,900

2018

$1,824 (−1.0%)

$10,000 + $74,900

$84,900

2017

$1,843 (+1.6%)

$10,000 + $74,900

$84,900

2016

$1,814 (+0.9%)

$10,000 + $74,900

$84,900

2015

$1,797 (+92.2%)

$10,000 + $74,900

$84,900

2014

$935

$10,000 + $74,900

$84,900

2013

$10,000 + $74,900

$84,900

Tax history for 100 Webb St

Year

Property tax

Land + Additions

Assessment*

2025

$1,621 (−4.5%)

$10,000 + $74,900

$84,900

2024

$1,697 (+38.5%)

$10,000 + $74,900

$84,900

2023

$1,225 (−37.0%)

$10,000 + $74,900

$84,900

2022

$1,945 (−0.5%)

$10,000 + $74,900

$84,900

2021

$1,955 (+0.2%)

$10,000 + $74,900

$84,900

2020

$1,951 (+5.2%)

$10,000 + $74,900

$84,900

2019

$1,855 (+1.7%)

$10,000 + $74,900

$84,900

2018

$1,824 (−1.0%)

$10,000 + $74,900

$84,900

2017

$1,843 (+1.6%)

$10,000 + $74,900

$84,900

2016

$1,814 (+0.9%)

$10,000 + $74,900

$84,900

2015

$1,797 (+92.2%)

$10,000 + $74,900

$84,900

2014

$935

$10,000 + $74,900

$84,900

2013

$10,000 + $74,900

$84,900

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

1.5

Lot width

—

Lot depth

—

Lot size

2,614 Sq. Ft.

Year renovated

—

Sq. Ft.

1,416

Year built

1943

Style

Single Family Residential

County

Bennington County

APN

05101567918

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 1

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 1

Basement Information
Basement: Yes
Basement Access: Interior
Concrete, Stairs - Interior

Other Interior Features
# of Rooms: 6
Flooring: Carpet, Laminate

Equipment & Appliance Information
Dryer, Freezer, Range - Electric, Refrigerator, Washer

Room 1 Information
Eat-in Kitchen
Eat-In Kitchen
Level: 1

Room 2 Information
Dining Room
Level: 1

Room 3 Information
Living Room
Level: 1

Room 4 Information
Full Bath
Level: 1

Room 5 Information
Bedroom
Level: 2

Room 6 Information
Bedroom
Bedroom
Level: 2

Room 7 Information
Bedroom
Level: 2

Exterior

Building Information
Architectural Style: Historic Vintage, New Englander
Construction Status: Existing
Construction Materials: Wood Frame, Wood Siding
Approximate Sq. Ft. Total Finished: 1416
Approximate Sq. Ft. Total: 2286
Color: Brown
Roof: Shingle - Architectural

Driveway
Other

Lot, Zoning, & Easement Information
Lot Features: Level, In Town, Near Shopping, Neighborhood

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1943

Financial

Tax Information
SPAN Number: 051-015-67918
Taxes TBD: Yes

Other Tax Information
Page Deed: 86-88

Utilities

Heating & Cooling Information
Heat: Oil, Hot Air

Sewer Information
Public

Electric Information
100 Amp, Circuit Breaker(s)

Water Information
Water Source: Public

Other Utilities Information
Internet: High Speed Intrnt -Avail
Cable - Available, Telephone Available

Location

School Information
School District: Southwest Vermont
Middle/Jr School: Mt. Anthony Union Middle Sch
School - High: Mt. Anthony Sr. UHSD 14

Road Information
Road Frontage Type: Public
Road Frontage: Yes
Road Frontage Length: 248

Other Location Information
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.

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 1,416
Stories: 1.5
Lot Size: 2,614 square feet
Style: Single Family Residential
Year Built: 1943
Year Renovated: —
County: Bennington County
APN: 05101567918

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Mt. Anthony Union Middle School

Public 6-8 • Assigned • 2.0mi

3/10

Mt. Anthony Senior Uhsd #14

Public 9-12 • Assigned • 0.8mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

7 days above 88° expected this year, 16 days in 30 years

3/10 Wind Factor

6% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Bennington, VT • 05201

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 3.6 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$231,000 – $279,000

Sell confidently with a local market expert in Bennington. 3 minutes to get started.

Nearby similar homes

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New listings for sale in 05201

$579,000

3 beds2 baths2,501 sq ft

856 Matteson Rd, North Bennington, VT 05201

FOR SALE BY OWNER

$160,000

8 beds2 baths2,334 sq ft

1032 Main St, Bennington, VT 05201

$175,000

2 beds1 bath810 sq ft

220 Gage St, Bennington, VT 05201

Home values near 100 Webb St

Data from public records.

Address	Redfin Estimate
114 Webb Street, Bennington, VT 3 Beds \| 2 Baths \| 1280 Sq. Ft.	$236,085
139 Webb Street, Bennington, VT 3 Beds \| 1 Baths \| 932 Sq. Ft.	$152,073

Address	Redfin Estimate
105 Webb Street, Bennington, VT 2 Beds \| 1 Baths \| 924 Sq. Ft.	$188,894
115 Webb Street, Bennington, VT 1 Beds \| 1 Baths \| 400 Sq. Ft.	$101,667

Address	Redfin Estimate
110 Webb Street, Bennington, VT 3 Beds \| 2 Baths \| 1786 Sq. Ft.	$275,594
102 Fillmore Street, Bennington, VT 2 Beds \| 1 Baths \| 1190 Sq. Ft.	$217,394

Property information provided by PrimeMLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05201, VT

Sale history for 100 Webb St

Tax history for 100 Webb St

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05201

Home values near 100 Webb St

More real estate resources