108 Main Street, Windsor, VT 05089
OFF MARKET
Listed by Rachel Brandli, Fidelity Real Estate Inc., (802) 295-3533 . Bought with Covered Bridge RE

108 Main Street
Windsor, VT 05089

  • 5 Beds
  • 4 Baths
  • 4,096 sqft

$335,300

Trulia Estimate
as of May 9, 2026

$335,300

Trulia Estimate
as of May 9, 2026
5 Beds
4 Baths
4,096 sqft

Homes for sale near 108 Main 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 14 hours ago
Listed by Rachel Brandli
Fidelity Real Estate Inc., (802) 295-3533
Bought with: Gail Childs, Covered Bridge RE, (704) 425-8378
Source: PrimeMLS, MLS#4955144

Description

This charming piece of VT history was originally built as an apothecary in 1804. Now it's a charming, fully occupied, four unit multi-family building consisting of three one-bedroom units and one two-bedroom. Original features and high ceilings. Small yard requires little maintenance. One parking space per unit. Convenient location in a commercial zone. Close to restaurants, schools and hospital.
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 May 01, 2024

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 108 Main Street

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Daylight,No Tenant Access,Unfinished,Walk-Up Access
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 4096 Square Feet
Appliances & Utilities
Utilities: Cable at SiteAppliances: Rented Water Heater
Heating & Cooling
Heating: Oil,Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric
Electric: Circuit Breakers
Levels, Entrance, & Accessibility
Number of Stories: 2.5Levels: 2.5
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleFoundation: Stone
Parking & Garage
No GarageParking: Paved
Frontage
Road Frontage: Private RoadRoad Surface Type: Paved
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: Road frontage: 65
Finished Area
Finished Area (above surface): 4096 Square Feet

Property Information

Year Built
Year Built: 1804
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: Colonial
Building
Construction Materials: Masonry, Brick Exterior, Wood ExteriorNot a New Construction

Price & Status

Price
List Price: $340,000

Location

Direction & Address
City: Windsor
School Information
Elementary School: Windsor State Street SchoolElementary School District: WindsorJr High / Middle School: Windsor High SchoolJr High / Middle School District: WindsorHigh School: Windsor High SchoolHigh School District: Windsor

Building

Building Area
Building Area: 8192 Square Feet

Lot Information

Lot Area: 4792 sqft

Miscellaneous

BasementMls Number: 4955144Above Grade Unfinished Area: 4096Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: OtherBelow Grade Unfinished Area Units: Square Feet

Price History for 108 Main Street

DatePriceEventSource
04/30/2024$310,000Sold
PrimeMLS #4955144
06/01/2023$340,000Listed For SalePrimeMLS #4955144
10/12/2021ListingRemovedPrimeMLS #4882076
09/10/2021$289,000Listed For SalePrimeMLS #4882076
08/02/2004$219,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax
Assessment$309,900
Home facts updated by county records

Comparable Sales for 108 Main Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
102-104 State Street, Windsor, VT
0.32
Multi-Family Home
$250,000
10/02/25
7
4
3,894
64 State Street, Windsor, VT
0.19
Multi-Family Home
$425,000
05/05/26
-
3,700
3-5 Foster Avenue, Windsor, VT
0.19
Multi-Family Home
$235,000
07/11/25
2
2,662
77 Taylor Drive, Windsor, VT
1.78
Multi-Family Home
$335,000
06/02/25
8
4
5,088
7 and 7A Brownsville Road, Hartland, VT
5.00
Multi-Family Home
$560,000
10/20/25
-
2,525
211 north Street, Claremont, NH
7.13
Multi-Family Home
$327,500
04/21/26
3
3,072
232 North Street, Claremont, NH
7.11
Multi-Family Home
$375,000
01/09/26
4
3,082

Assigned Schools

These are the assigned schools for 108 Main 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 Windsor

At least 9 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 92 % Say yards are well-kept

  • 90 % Say it's walkable to grocery stores

  • 83 % Say car is needed

  • 78 % Say it's walkable to restaurants

  • 67 % Say parking is easy

  • 67 % Say people would walk alone at night

  • 64 % Say streets are well-lit

  • 64 % Say it's quiet

  • 64 % Say there are sidewalks

  • 64 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 52 % Say neighbors are friendly

  • 36 % Say they plan to stay for at least 5 years

  • 20 % Say there are community events

Learn more about our methodology.
  • Brianna W.
    "It’s small but fun. It’s got a local salon, pizza chef, and a hospital, fire/police department, and a school all within a mile of each other."
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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 2026-05-08 12:45:15 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 108 Main Street

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Off Market Homes Near 108 Main Street

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108 Main Street, Windsor, VT 05089 is a 5 bedroom, 4 bathroom, 4,096 sqft multi-family built in 1804. This property is not currently available for sale. 108 Main Street was last sold on Apr 30, 2024 for $310,000 (9% lower than the asking price of $340,000). The current Trulia Estimate for 108 Main Street is $335,300.