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 2787 Route 44 estimated to be worth?

Trulia's estimated value for 2787 Route 44 in Windsor, VT is $290,300 .

What is the price history for 2787 Route 44?

2787 Route 44 in Windsor, VT last sold for $278,000 in July 2025.

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 2787 Route 44 have laundry facilities?

Yes, 2787 Route 44 in Windsor, VT has in-unit laundry.

How big is the lot at 2787 Route 44?

The lot at 2787 Route 44 in Windsor, VT is about 2.8 acres .

OFF MARKET

2787 Route 44
Windsor, VT 05089

3 Beds
1.5 Baths
1,936 sqft (on 2.80 acres)

$290,300

Trulia Estimate

as of Aug 19, 2026

$290,300

Trulia Estimate

as of Aug 19, 2026

3 Beds

1.5 Baths

1,936 sqft

(on 2.80 acres)

Home Value

Trulia Estimate

$290K

Since last month

$3K (+0.9%)

Since last year

$11K (+4%)

Since last sale

$13K (+4.6%)

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 +30% in the last 10 years

Month	Estimated value
2026
August 2026	$291K
July 2026	$288K
June 2026	$286K
May 2026	$286K
April 2026	$286K
March 2026	$287K
February 2026	$289K
January 2026	$284K
2025
December 2025	$285K
November 2025	$282K
October 2025	$281K
September 2025	$281K
August 2025	$280K
July 2025	$391K
2023
September 2023	$328K
August 2023	$331K
July 2023	$333K
June 2023	$337K
May 2023	$316K
April 2023	$340K
March 2023	$343K
February 2023	$327K
January 2023	$327K
2022
December 2022	$327K
November 2022	$330K
October 2022	$331K
September 2022	$348K
August 2022	$349K
July 2022	$353K
June 2022	$355K
May 2022	$350K
April 2022	$339K
March 2022	$329K
February 2022	$315K
January 2022	$314K
2021
December 2021	$311K
November 2021	$310K
October 2021	$311K
September 2021	$305K
August 2021	$304K
July 2021	$299K
June 2021	$276K
May 2021	$235K
April 2021	$233K
March 2021	$228K
February 2021	$230K
January 2021	$228K
2020
December 2020	$227K
October 2020	$220K
September 2020	$218K
August 2020	$216K
July 2020	$215K
June 2020	$210K
May 2020	$205K
April 2020	$204K
March 2020	$205K
February 2020	$207K
January 2020	$208K
2019
December 2019	$207K
November 2019	$201K
October 2019	$201K
September 2019	$205K
August 2019	$204K
July 2019	$205K
June 2019	$203K
May 2019	$201K
April 2019	$199K
March 2019	$193K
February 2019	$194K
January 2019	$196K
2018
December 2018	$198K
November 2018	$197K
October 2018	$197K
September 2018	$191K
August 2018	$192K
July 2018	$193K
June 2018	$207K
May 2018	$210K
April 2018	$211K
March 2018	$208K
February 2018	$227K
January 2018	$225K
2017
December 2017	$221K
November 2017	$222K
October 2017	$220K
September 2017	$215K
August 2017	$216K
July 2017	$220K
June 2017	$221K
May 2017	$223K
April 2017	$224K
March 2017	$214K
February 2017	$216K
January 2017	$216K
2016
December 2016	$221K
November 2016	$219K
October 2016	$218K
September 2016	$225K
August 2016	$224K

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
96 Dairy Lane, Windsor, VT	1.12	Single-Family Home	$400,000	12/19/25	4	2.5	2,272
586 Ski Tow Road, Brownsville, VT	1.84	Single-Family Home	$460,000	10/02/25	3	2	1,480
4 Bavier Avenue, Windsor, VT	1.63	Single-Family Home	$226,000	08/07/26	3	1	2,088
1159 Ski Tow Road, Brownsville, VT	1.86	Single-Family Home	$315,000	09/19/25	3	2	1,656
1 Dorrance Street, Windsor, VT	1.63	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
217 Brook Rd, West Windsor, VT	1.76	Single-Family Home	$380,000	09/29/25	3	1	924
21 Bavier Avenue, Windsor, VT	1.70	Single-Family Home	$256,500	11/14/25	3	1	1,232
290 Village Lane, Brownsville, VT	2.02	Single-Family Home	$330,000	06/10/26	2	2	1,604
32 Clough Avenue, Windsor, VT	2.07	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
3 Cherry Street, Windsor, VT	1.88	Single-Family Home	$259,000	05/01/26	3	1	1,176

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
2742 Route 44, Windsor, VT 05089	0.08	$248,500	1	1	1,248	Off Market
159 Estey Lane, Windsor, VT 05089	0.21	$294,800	2	2	1,154	Off Market
3460 Route 44, West Windsor, VT 05089	0.63	$351,600	3	2	3,264	Off Market
3528 Route 44, Windsor, VT 05089	0.76	$618,500	3	2	2,578	Off Market
3652 Route 44, Windsor, VT 05089	0.91	$632,500	3	2	2,986	Off Market
1804 Rte 44, Windsor, VT 05089	0.91	$313,700	2	2	1,500	Off Market
1807 Route 44, Windsor, VT 05089	0.92	$188,400	3	1.5	1,182	Off Market
333 Brook Road, Windsor, VT 05089	0.92	$331,400	4	1.5	1,008	Off Market
108 Cubb Court, Windsor, VT 05089	0.94	$96,232	2	2	777	For Sale
23 Cubb Court, Windsor, VT 05089	0.94	$87,826	1	1	643	For Sale
505 Back Mountain Road #14, Windsor, VT 05089	0.95	$99,000	1	1	240	For Sale
517 Back Mountain Road, Windsor, VT 05089	0.96	$96,232	2	2	777	Recently Sold

Local Information

Map ViewExplore the area around 2787 Route 44.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1963

Lot Size

2.8 acres

Living Area

1,936 sqft

Price/Sqft

$150

Parking

Garage

About this House

This single-family home is located at 2787 Route 44, Windsor, VT. 2787 Route 44 is in Windsor, VT and in ZIP code 05089. This property has 3 bedrooms, 2 bathrooms and approximately 1,936 sqft of floor space. This property has a lot size of 2.80 acres and was built in 1963.

2787 Route 44, Windsor, VT 05089 is a 3 bedroom, 2 bathroom, 1,936 sqft single-family home built in 1963. It last sold for $278,000 on Jul 21, 2025. It is currently off market. The Trulia Estimate is $290,300, with a rent estimate of $3,232/month.

Home Details for 2787 Route 44

Interior Features
Heating & Cooling Heating: Electric, Oil, Wood PelletHeating Fuel: Electric
Interior Details Types of Rooms: Dining Room, Family Room
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace
Levels, Entrance, & Accessibility Floors: Tile, Hardwood, Laminate

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: WoodGardenPatio
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1963
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary

Lot Information
Lot Area: 2.80 acres

Price and Tax history

Date	Event	Price
Jul 21, 2025 Source: N/A	Sold	$278,000
Nov 3, 2022 Source: PrimeMLS #4931948	ListingRemoved
Sep 30, 2022 Source: PrimeMLS #4931948	Listed For Sale	$339,000
Oct 19, 2018 Source: PrimeMLS #4679066	Sold	$196,500
Jul 19, 2018 Source: Agent Provided	PriceChange	$199,900 Price decreased by 7%
Mar 2, 2018 Source: Agent Provided	Listed For Sale	$214,900

Year	Property tax	Tax assessment
2024	Unavailable	$312,840

Additional Cost

Market trends in Windsor

Last updated July 2026

Avg. sale price

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Sale-to-List Price

—

Price per sq ft

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Available listings

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."
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Frequently asked questions about 2787 Route 44

What is 2787 Route 44 estimated to be worth?
Trulia's estimated value for 2787 Route 44 in Windsor, VT is $290,300.
What is the price history for 2787 Route 44?
2787 Route 44 in Windsor, VT last sold for $278,000 in July 2025.
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 2787 Route 44 have laundry facilities?
Yes, 2787 Route 44 in Windsor, VT has in-unit laundry.
How big is the lot at 2787 Route 44?
The lot at 2787 Route 44 in Windsor, VT is about 2.8 acres.