Exceptional investment opportunity in downtown Bennington! This income-producing multi-family property features eight apartments across two buildings, offering a versatile mix of four 2-bedroom/1-bath units and four 3-bedroom/1-bath units. With eight rental units and an additional unimproved 0.26-acre lot, this property offers investors an opportunity to build long-term wealth while exploring future value-enhancement possibilities. Three apartments have undergone updates/renovation within the past two years, providing a solid foundation for continued investment and potential rental growth. Ideally situated just off Main Street, the property benefits from convenient access to downtown Bennington's shops, restaurants, services, and amenities. A rare opportunity to acquire a substantial multi-unit investment with room to maximize its potential in a desirable downtown location.
4-unit multi-family property. Three units with 2 bedrooms, 1 bathroom each and one unit with, 1-2 bedrooms, 1 bathroom. Off-street parking and various updates, including new boiler and oil tank within the last 2 years. Tenant pays their own electricity. Property is being offered with a separately deeded . 26 parcel which abuts the backyard and can be used to create more housing or kept as a nice wooded barrier for privacy. Owner is also selling a rare 4-unit next door, 129 Webb St, MLS# 4975921.
Year
Property tax
Land + Additions
Assessment*
2025
$3,152 (−4.5%)
$17,200 + $147,900
$165,100
2024
$3,301 (+9.6%)
$17,200 + $147,900
$165,100
2023
$3,012 (−28.4%)
$17,200 + $147,900
$165,100
2022
$4,207 (+55.9%)
$17,200 + $147,900
$165,100
2021
$2,698 (−34.5%)
$17,200 + $147,900
$165,100
2020
$4,121 (+4.0%)
$17,200 + $147,900
$165,100
2019
$3,964 (+1.8%)
$17,200 + $147,900
$165,100
2018
$3,893 (+1.7%)
$17,200 + $147,900
$165,100
2017
$3,826 (+1.0%)
$17,200 + $147,900
$165,100
2016
$3,790 (+1.0%)
$17,200 + $147,900
$165,100
2015
$3,752 (−16.2%)
$17,200 + $147,900
$165,100
2014
$4,477
$17,200 + $147,900
$165,100
2013
$17,200 + $147,900
$165,100
Public record
Beds
8
Baths
4
Stories
2
Lot width
—
Lot depth
—
Lot size
—
Year renovated
—
Finished Sq. Ft.
4,264
Unfinished Sq. Ft.
—
Total Sq. Ft.
4,264
Year built
1850
Style
Condo/Co-op
County
Bennington County
APN
05101567932
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 22, 2026.
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)
27
14
31
14
48
28
58
37
66
47
78
56
82
61
78
55
74
50
61
40
46
31
34
19
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
79/ 100
Good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.3 hrs
4.6 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 127-133 Webb St
There isn’t enough information to generate an accurate estimate at this time. Learn More