Is Windsor, VT dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Are yards well-kept in Windsor, VT?

As of early 2026, 92% of users say yards are well-kept

Is Windsor, VT walkable to grocery stores?

As of early 2026, 91% of users say it's walkable to grocery stores

Is a car needed in Windsor, VT?

As of early 2026, 83% of users say car is needed

Is Windsor, VT walkable to restaurants?

As of early 2026, 80% of users say it's walkable to restaurants

Would people walk alone at night in Windsor, VT?

As of early 2026, 69% of users say people would walk alone at night

Does Windsor, VT show holiday spirit?

As of early 2026, 64% of users say there's holiday spirit

Do kids play outside in Windsor, VT?

As of early 2026, 64% of users say kids play outside

Does Windsor, VT have sidewalks?

As of early 2026, 64% of users say there are sidewalks

Are the streets well-lit in Windsor, VT?

As of early 2026, 64% of users say streets are well-lit

Is there wildlife in Windsor, VT?

As of early 2026, 60% of users say there's wildlife

Is parking easy in Windsor, VT?

As of early 2026, 60% of users say parking is easy

Is Windsor, VT quiet?

As of early 2026, 58% of users say it's quiet

Are neighbors friendly in Windsor, VT?

As of early 2026, 52% of users say neighbors are friendly

Do residents of Windsor, VT plan to stay at least 5 years?

As of early 2026, 36% of users say they plan to stay for at least 5 years

Are there community events in Windsor, VT?

As of early 2026, 20% of users say there are community events

What is 108 Main Street estimated to be worth?

Trulia's estimated value for 108 Main Street in Windsor, VT is $357,300 .

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.

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

$357,300

Trulia Estimate

as of Aug 8, 2026

Est. Refi. Payment $1,887/mo*

Refinance Your Home

$357,300

Trulia Estimate

as of Aug 8, 2026

Est. Refi. Payment $1,887/mo*

Refinance Your Home

5 Beds

4 Baths

4,096 sqft

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

Property Type

Multi-Family

Year Built

1804

Living Area

4,096 sqft

Price/Sqft

$87

Last check for updates: about 7 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

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). It is currently off market. The Trulia Estimate is $357,300, with a rent estimate of $1,990/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 History for 108 Main Street

Date	Price	Event	Source
04/30/2024	$310,000	Sold	PrimeMLS #4955144
Recording Date 04/30/2024 County Transfer Tax N/A Total Transfer Tax N/A
06/01/2023	$340,000	Listed For Sale	PrimeMLS #4955144

10/12/2021		ListingRemoved	PrimeMLS #4882076

09/10/2021	$289,000	Listed For Sale	PrimeMLS #4882076

08/02/2004	$219,000	Sold	N/A
Recording Date 08/02/2004 Contract Date 07/30/2004 County Transfer Tax N/A Total Transfer Tax $2,738

Market trends in Windsor

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Property Tax and Assessment

Year	2024
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
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 homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $218,200
1 bd
1.5 ba
1,056 sqft
14 Central Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $265,300
2 bd
2.5 ba
2,009 sqft
149 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $242,800
3 bd
1 ba
1,331 sqft
159 Marcy Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $405,400
6 bd
5 ba
3,176 sqft
40 Village Green,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $275,000
2,662 sqft
36 River Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $244,600
2 ba
2,662 sqft
3-5 Foster Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $227,900
3,500 sqft
9 Durkee Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 5, 2026
$425,000
3,700 sqft
64 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $285,600
4 bd
1.5 ba
2,116 sqft
43 River Street,
Windsor, VT 05089
PrimeMLS, Closed
FOR SALE
$109,000
1 bd
1 ba
504 sqft
52 Jarvis Street,
Windsor, VT 05089
PrimeMLS, Active
SOLD
DEC 10, 2025
$115,000
5 bd
3.5 ba
4,011 sqft
70-74 State Street,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

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 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.
Resident
6y ago
"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

Apartments for Rent

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$1,325/mo
1 bd
1 ba
9 State Street | 9 State St,
Windsor, VT 05089
$1,325 - $1,350/mo
1 bd
1 ba
24 State Street | 24 State St,
Windsor, VT 05089
$1,425/mo
1 bd
1 ba
112-114 State St #114A,
Windsor, VT 05089
$1,895/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
65 State St #f320a52c6,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
92 Cedar Hill Dr #f320a52c6,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
289 County Rd #f320a52c6,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
See more homes for rent in
Windsor
Take a look

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Homes for sale near 108 Main Street

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$442,999
3 bd
2 ba
1,961 sqft
6 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
5.83 ACRES
$1,576,000
9,455 sqft
14/16 Summarsell Drive,
Hartland, VT 05048
PrimeMLS, Active
1 ACRE
$452,600
3 ba
2,915 sqft
282 Skunk Hollow Road,
Hartland, VT 05048
PrimeMLS, Active
0.36 ACRES
$280,000
2,440 sqft
89 Belding Street,
Claremont, NH 03743
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 108 Main Street

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SOLD
JUL 24, 2026
$300,000
3 bd
3 ba
1,594 sqft
70 Mountains Edge Road #606,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
JUL 23, 2026
$319,000
4 bd
2 ba
2,142 sqft
74 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
JUL 14, 2026
$374,000
2 bd
2 ba
1,192 sqft
39 Parsonage Road,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
JUL 6, 2026
$260,000
00 Tandy Brook Road #12,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
JUL 1, 2026
$222,030
1214 State St,
Windsor, VT 05089
SOLD
JUN 30, 2026
$200,000
245 Orchard Ln,
Windsor, VT 05089
SOLD
JUN 24, 2026
$290,000
3 bd
2.5 ba
1,614 sqft
127 Mountains Edge Road #211,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
JUN 22, 2026
$260,000
95 Mountains Edge Rd #102,
Brownsville, VT 05037
SOLD
MAY 21, 2026
$195,000
Hotel Rd,
Brownsville, VT 05037
SOLD
MAY 15, 2026
$459,000
4 bd
1.5 ba
2,349 sqft
579 Town House Road,
Cornish, NH 03745
PrimeMLS, Closed
See more homes for sale in
Windsor
Take a look

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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 $357,300.
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.

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 2026-08-07 18:45:20 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.

108 Main Street
Windsor, VT 05089

$357,300

$357,300