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 the estimated monthly payment for 153 Main Street?

Based on a $184,900 list price with 20% down at today's rates, the estimated monthly payment for 153 Main Street in Windsor, VT is approximately $1,348 (about $968 principal & interest, $305 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.

What do residents say about Windsor?

Residents describe Windsor, VT as dog-friendly, well-kept, and walkable to grocery stores. See homes for sale in Windsor, VT .

What are the closest schools to 153 Main Street?

The closest schools to 153 Main Street in Windsor, VT are Albert Bridge School (West Windsor) (Pre-K/Elementary), Windsor School (K-12, rated 4/10).

What is 153 Main Street estimated to be worth?

Trulia's estimated value for 153 Main Street in Windsor, VT is $243,800 .

Does 153 Main Street have parking?

Yes, 153 Main Street in Windsor, VT has on-site parking.

FOR SALE

NEW - 4 HRS AGO

153 Main Street
Windsor, VT 05089

Studio
2,470 sqft

$184,900

Studio

2,470 sqft

Home Highlights

Price/Sqft

$75

Listed

Less than a day ago

Climate Control

Hot Water, Zoned Heating

Local Information

Map ViewExplore the area around 153 Main Street.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Last check for updates: about 2 hours ago

Listing courtesy of Don Chabot

Town and Country Realty, (603) 542-5188

Source: PrimeMLS, MLS#5106186

Also Listed on PrimeMLS.

About this House

RECENT RENOVATIONS INCLUDE A NEW HOT WATER HEATING SYSTEM, NEW PARTIAL ROOF AND FULLY REPAINTED INTERIOR. TWO - 2BR's APARTMENTS AND ONE - 3BR's APARTMENT. ESTIMATED GROSS RENTS $5,100.00 PER MONTH. SHORT NOTICE SHOWINGS AVAILABLE. READY FOR OCCUPANCY.

Home Details for 153 Main Street

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: Concrete,Dirt,Dirt Floor,Unfinished,Walk-Out Access
Dimensions and Layout Living Area: 2470 Square Feet
Appliances & Utilities Utilities: Cable at Site, Satellite, Telephone at Site
Heating & Cooling Heating: Oil,Hot Water,ZonedNo 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: Asphalt Shingle MetalFoundation: Brick, Stone
Parking & Garage No GarageParking: Dirt
Frontage Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 67
Finished Area Finished Area (above surface): 2470 Square Feet

Days on Market
Days on Market: <1 day on Trulia

Property Information
Year Built Year Built: 1782
Property Type / Style Property Type: Residential IncomeProperty Subtype: Multi FamilyStructure Type: Apartment BuildingArchitecture: Apartment Building
Building Construction Materials: Vinyl SidingNot a New Construction
Property Information Condition: Updated/Remodeled

Price & Status
Price List Price: $184,900Price Per Sqft: $75

Location
Direction & Address City: Windsor

Agent Information
Listing Agent Listing ID: 5106186

Building
Building Area Building Area: 3370 Square Feet

Lot Information
Lot Area: 6098.4 sqft

Miscellaneous
BasementMls Number: 5106186Above Grade Unfinished Area: 2470Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 900Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Around this home

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
Flag

Market trends in Windsor

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Home Value

Trulia Estimate

$244K

Since last month

$9K (+3.7%)

Since last year

$9K (+3.7%)

Since last sale

$171K (+254.8%)

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 +98% in the last 10 years

Month	Estimated value
2026
August 2026	$238K
July 2026	$230K
2024
July 2024	$107K
June 2024	$106K
May 2024	$242K
April 2024	$229K
March 2024	$219K
January 2024	$242K
2023
December 2023	$249K
November 2023	$241K
October 2023	$246K
September 2023	$244K
August 2023	$240K
July 2023	$249K
June 2023	$232K
May 2023	$240K
April 2023	$238K
March 2023	$230K
February 2023	$229K
January 2023	$230K
2022
December 2022	$230K
November 2022	$230K
October 2022	$225K
September 2022	$242K
August 2022	$243K
July 2022	$242K
June 2022	$238K
May 2022	$233K
April 2022	$229K
March 2022	$224K
February 2022	$217K
January 2022	$215K
2021
December 2021	$212K
November 2021	$214K
October 2021	$212K
September 2021	$209K
August 2021	$209K
July 2021	$208K
June 2021	$200K
May 2021	$185K
April 2021	$177K
March 2021	$170K
February 2021	$171K
January 2021	$177K
2020
December 2020	$194K
November 2020	$192K
October 2020	$177K
September 2020	$177K
August 2020	$178K
July 2020	$172K
June 2020	$170K
May 2020	$163K
April 2020	$167K
March 2020	$172K
February 2020	$136K
January 2020	$135K
2019
December 2019	$135K
November 2019	$137K
October 2019	$140K
September 2019	$136K
August 2019	$134K
July 2019	$132K
June 2019	$133K
May 2019	$131K
April 2019	$129K
March 2019	$121K
February 2019	$122K
January 2019	$123K
2018
December 2018	$126K
November 2018	$127K
October 2018	$127K
September 2018	$127K
August 2018	$127K
July 2018	$128K
June 2018	$132K
May 2018	$131K
April 2018	$129K
March 2018	$128K
February 2018	$126K
January 2018	$122K
2017
December 2017	$122K
November 2017	$121K
October 2017	$122K
September 2017	$122K
August 2017	$122K
July 2017	$121K
June 2017	$119K
May 2017	$122K
April 2017	$124K
March 2017	$126K
February 2017	$134K
January 2017	$125K
2016
December 2016	$120K
November 2016	$121K
October 2016	$123K
September 2016	$123K
August 2016	$120K

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
64 State Street, Windsor, VT	0.29	Multi-Family Home	$425,000	05/05/26		-	3,700
102-104 State Street, Windsor, VT	0.39	Multi-Family Home	$250,000	10/02/25	7	4	3,894
7 and 7A Brownsville Road, Hartland, VT	5.11	Multi-Family Home	$560,000	10/20/25		-	2,525
4 Freedom Street, Claremont, NH	7.19	Multi-Family Home	$120,000	03/04/26		-	1,840
248 Main Street, Claremont, NH	7.14	Multi-Family Home	$175,000	01/15/26	3	2	1,405
211 north Street, Claremont, NH	7.01	Multi-Family Home	$327,500	04/21/26		3	3,072
232 North Street, Claremont, NH	6.99	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
159 Marcy Court, Windsor, VT 05089	0.02	$241,800	3	1	1,331	Off Market
149 Main Street, Windsor, VT 05089	0.02	$262,000	2	2.5	2,009	Off Market
9 Durkee Street, Windsor, VT 05089	0.05	$225,400	Studio	-	3,500	Off Market
14 Central Street, Windsor, VT 05089	0.12	$219,000	1	1.5	1,056	Off Market
108 Main Street, Windsor, VT 05089	0.13	$355,500	5	4	4,096	Off Market
29 National Street, Windsor, VT 05089	0.20	$229,000	2	1	1,008	For Sale
68 Jarvis Street, Windsor, VT 05089	0.21	$165,000	3	1	1,602	Recently Sold
30 Union Street, Windsor, VT 05089	0.17	$366,600	4	4.5	3,990	Off Market
3-5 Foster Avenue, Windsor, VT 05089	0.22	$245,500	Studio	2	2,662	Off Market
38 Jarvis Street, Windsor, VT 05089	0.22	$139,000	1	1	768	Recently Sold
31 Maple Street, Windsor, VT 05089	0.19	$222,900	3	1.5	1,900	Off Market

Price and Tax history

Date	Event	Price
Aug 21, 2026 Source: PrimeMLS #5106186	Listed For Sale	$184,900
Apr 2, 2025 Source: N/A	Sold	$67,166
Nov 10, 2021 Source: N/A	Sold	$33,640
Apr 1, 2020 Source: Agent Provided	ListingRemoved	$0
Jan 22, 2020 Source: Agent Provided	Listed For Sale	$0
May 22, 2006 Source: N/A	Sold	$155,000
Jan 13, 2005 Source: N/A	Sold	$112,000

Year	Property tax	Tax assessment
2025	$5,830	$227,360

LGBTQ Local Legal Protections

Additional Cost

Don Chabot, Town and Country Realty, (603) 542-5188

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 2026-08-21 10:34:38 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.

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Frequently asked questions about 153 Main Street

What is the estimated monthly payment for 153 Main Street?
Based on a $184,900 list price with 20% down at today's rates, the estimated monthly payment for 153 Main Street in Windsor, VT is approximately $1,348 (about $968 principal & interest, $305 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
What do residents say about Windsor?
Residents describe Windsor, VT as dog-friendly, well-kept, and walkable to grocery stores. See homes for sale in Windsor, VT.
What are the closest schools to 153 Main Street?
The closest schools to 153 Main Street in Windsor, VT are Albert Bridge School (West Windsor) (Pre-K/Elementary), Windsor School (K-12, rated 4/10).
What is 153 Main Street estimated to be worth?
Trulia's estimated value for 153 Main Street in Windsor, VT is $243,800.
Does 153 Main Street have parking?
Yes, 153 Main Street in Windsor, VT has on-site parking.

153 Main Street, Windsor, VT 05089 is a studio, 2,470 sqft multi-family built in 1782. This property is currently available for sale and was listed by PrimeMLS on Aug 21, 2026. The MLS # for this home is MLS# 5106186.

153 Main Street
Windsor, VT 05089

$184,900