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

$348,100

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 4,096 sqft

108 Main Street, Windsor, VT 05089

Est. Refi. Payment $2,513/mo*
Refinance Your Home
Currently Off Market - Sold Apr 30, 2024 for $310,000

Home Value

Trulia Estimate
$348K
Since last month
Increased$5K (+1.5%)
Since last year
Increased$1K (+0.4%)
Since last sale
Increased$38K (+12.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +87% in the last 10 years
MonthEstimated value
2026
September 2026$348K
August 2026$343K
July 2026$358K
June 2026$350K
May 2026$350K
April 2026$336K
March 2026$337K
February 2026$341K
January 2026$324K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
14 Central Street, Windsor, VT 05089
0.06
$217,800
1
1.5
1,056
Off Market
149 Main Street, Windsor, VT 05089
0.11
$254,100
2
2.5
2,009
Off Market
159 Marcy Court, Windsor, VT 05089
0.14
$236,200
3
1
1,331
Off Market
40 Village Green, Windsor, VT 05089
0.16
$395,100
6
5
3,176
Off Market
36 River Street, Windsor, VT 05089
0.19
$276,100
Studio
-
2,662
Off Market
3-5 Foster Avenue, Windsor, VT 05089
0.19
$244,200
Studio
2
2,662
Off Market
9 Durkee Street, Windsor, VT 05089
0.18
$226,700
Studio
-
3,500
Off Market
64 State Street, Windsor, VT 05089
0.19
$425,000
Studio
-
3,700
Recently Sold
43 River Street, Windsor, VT 05089
0.20
$286,500
4
1.5
2,116
Off Market
70-74 State Street, Windsor, VT 05089
0.21
$115,000
5
3.5
4,011
Recently Sold
51-53 River Street, Windsor, VT 05089
0.22
$274,500
4
4
2,509
Off Market

Local Information

  • Map ViewExplore the area around 108 Main Street.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1804
4,096 sqft
$85/sqft

About this House

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.
108 Main Street, Windsor, VT 05089 is a 5 bedroom, 4 bathroom, 4,096 sqft multi-family built in 1804. It last sold for $310,000 on Apr 30, 2024 (9% below the $340,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $348,100, with a rent estimate of $2,145/month.

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 and Tax history

DateEventPrice
Apr 30, 2024
Source: PrimeMLS #4955144
Sold
$310,000
Jun 1, 2023
Source: PrimeMLS #4955144
Listed For Sale
$340,000
Oct 12, 2021
Source: PrimeMLS #4882076
ListingRemoved
Sep 10, 2021
Source: PrimeMLS #4882076
Listed For Sale
$289,000
Aug 2, 2004
Source: N/A
Sold
$219,000

Market trends in Windsor

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
3MoM

Around this home

What Locals Say about Windsor

At least 10 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 92 % Say yards are well-kept

  • 91 % Say it's walkable to grocery stores

  • 83 % Say car is needed

  • 80 % Say it's walkable to restaurants

  • 69 % Say people would walk alone at night

  • 64 % Say there's holiday spirit

  • 64 % Say kids play outside

  • 64 % Say there are sidewalks

  • 64 % Say streets are well-lit

  • 60 % Say there's wildlife

  • 60 % Say parking is easy

  • 58 % Say it's quiet

  • 52 % Say neighbors are friendly

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

  • 20 % Say there are community events

Sourced by Trulia users. 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."
    0
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LGBTQ Local Legal Protections

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 2026-09-21 08:09:49 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.

Frequently asked questions about 108 Main Street

  • What is 108 Main Street estimated to be worth?
    Trulia's estimated value for 108 Main Street in Windsor, VT is $348,100.
  • What is the price history for 108 Main Street?
    108 Main Street in Windsor, VT last sold for $310,000 in April 2024.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Windsor?
    Residents describe Windsor, VT as dog-friendly, well-kept, and walkable to grocery stores. See recently sold homes in Windsor, VT.
  • Does 108 Main Street have parking?
    Yes, 108 Main Street in Windsor, VT has on-site parking.

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Windsor, VT

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