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 21 Dewey Ave estimated to be worth?

Trulia's estimated value for 21 Dewey Ave in Windsor, VT is $321,600 .

What is the price history for 21 Dewey Ave?

21 Dewey Ave in Windsor, VT last sold for $169,000 in July 2006.

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 .

How big is the lot at 21 Dewey Ave?

The lot at 21 Dewey Ave in Windsor, VT is about 0.18 acres (7,840 sq ft).

OFF MARKET

21 Dewey Ave
Windsor, VT 05089

Studio

$321,600

Trulia Estimate

as of Aug 23, 2026

$321,600

Trulia Estimate

as of Aug 23, 2026

Studio

Home Value

Trulia Estimate

$322K

Since last month

$2K (-0.6%)

Since last year

$2K (+0.6%)

Since last sale

$153K (+90.3%)

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 +84% in the last 10 years

Month	Estimated value
2026
August 2026	$322K
July 2026	$324K
June 2026	$329K
May 2026	$331K
April 2026	$315K
March 2026	$311K
February 2026	$305K
January 2026	$301K
2025
December 2025	$301K
November 2025	$305K
October 2025	$302K
September 2025	$313K
August 2025	$320K
July 2025	$329K
June 2025	$337K
May 2025	$311K
April 2025	$295K
March 2025	$291K
February 2025	$277K
January 2025	$283K
2024
December 2024	$265K
November 2024	$265K
October 2024	$299K
September 2024	$279K
August 2024	$274K
July 2024	$304K
June 2024	$307K
May 2024	$302K
April 2024	$299K
March 2024	$289K
February 2024	$281K
January 2024	$277K
2023
December 2023	$262K
November 2023	$292K
October 2023	$280K
September 2023	$280K
August 2023	$294K
July 2023	$290K
June 2023	$290K
May 2023	$254K
April 2023	$248K
March 2023	$243K
February 2023	$236K
January 2023	$232K
2022
December 2022	$234K
November 2022	$236K
October 2022	$238K
September 2022	$239K
August 2022	$240K
July 2022	$241K
June 2022	$239K
May 2022	$234K
April 2022	$226K
March 2022	$223K
February 2022	$218K
January 2022	$218K
2021
December 2021	$217K
November 2021	$217K
October 2021	$217K
September 2021	$216K
August 2021	$224K
July 2021	$228K
June 2021	$220K
May 2021	$202K
April 2021	$195K
March 2021	$187K
February 2021	$188K
January 2021	$182K
2020
December 2020	$180K
November 2020	$188K
October 2020	$185K
September 2020	$184K
August 2020	$191K
July 2020	$185K
June 2020	$184K
May 2020	$180K
April 2020	$175K
March 2020	$177K
February 2020	$177K
January 2020	$177K
2019
December 2019	$176K
November 2019	$176K
October 2019	$176K
September 2019	$176K
August 2019	$177K
July 2019	$174K
June 2019	$173K
May 2019	$173K
April 2019	$172K
March 2019	$164K
February 2019	$161K
January 2019	$164K
2018
December 2018	$164K
November 2018	$166K
October 2018	$169K
September 2018	$171K
August 2018	$170K
July 2018	$165K
June 2018	$171K
May 2018	$171K
April 2018	$172K
March 2018	$172K
February 2018	$168K
January 2018	$165K
2017
December 2017	$166K
November 2017	$169K
October 2017	$169K
September 2017	$170K
August 2017	$170K
July 2017	$169K
June 2017	$170K
May 2017	$169K
April 2017	$168K
March 2017	$168K
February 2017	$168K
January 2017	$168K
2016
December 2016	$168K
November 2016	$169K
October 2016	$168K
September 2016	$170K
August 2016	$175K

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
3 Cherry Street, Windsor, VT	0.35	Single-Family Home	$259,000	05/01/26	3	1	1,176
26 Cherry St, Windsor, VT	0.39	Single-Family Home	$150,000	11/03/25		-	-
74 Union Street, Windsor, VT	0.23	Single-Family Home	$319,000	07/23/26	4	2	2,142
66 Union Street, Windsor, VT	0.26	Single-Family Home	$219,000	09/02/25	3	2	1,743
10 McKenzie Drive, Windsor, VT	0.37	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
31 Maple Street, Windsor, VT	0.53	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
16 Day Street, Windsor, VT	0.52	Single-Family Home	$94,900	12/04/25	2	1	660
70-74 State Street, Windsor, VT	0.40	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
6 Bavier Avenue, Windsor, VT	0.59	Single-Family Home	$200,000	08/27/25	2	1	786
1 Dorrance Street, Windsor, VT	0.54	Single-Family Home	$315,000	11/21/25	2	1.5	1,649

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
17 Dewey Avenue, Windsor, VT 05089	0.03	$125,200	3	1	1,523	Off Market
153 State Street, Windsor, VT 05089	0.10	$267,800	4	1.5	1,600	Off Market
2 Ascutney Street, Windsor, VT 05089	0.16	$314,300	3	1.5	1,364	Off Market
32 Ascutney Street, Windsor, VT 05089	0.16	$381,500	4	3	1,998	Off Market
18 County Road, Windsor, VT 05089	0.21	$344,500	3	2	1,400	Off Market
74 Union Street, Windsor, VT 05089	0.23	$319,000	4	2	2,142	Recently Sold
3 Fitch Court, Windsor, VT 05089	0.24	$238,500	2	2	1,665	Off Market
66 Union Street, Windsor, VT 05089	0.26	$226,800	3	2	1,743	Off Market
102-104 State Street, Windsor, VT 05089	0.29	$299,400	7	4	3,894	Off Market
100 State Street, Windsor, VT 05089	0.30	$252,500	6	1.5	2,880	Off Market
3 Cherry Street, Windsor, VT 05089	0.35	$259,000	3	1	1,176	Recently Sold
10 McKenzie Drive, Windsor, VT 05089	0.37	$271,000	3	1.5	1,320	Recently Sold

Local Information

Map ViewExplore the area around 21 Dewey Ave.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

About this House

This single-family home is located at 21 Dewey Ave, Windsor, VT. 21 Dewey Ave is in Windsor, VT and in ZIP code 05089. This property has a lot size of 7840 sqft.

21 Dewey Ave, Windsor, VT 05089 is a studio single-family home. It last sold for $169,000 on Jul 12, 2006. It is currently off market. The Trulia Estimate is $321,600, with a rent estimate of $2,840/month.

Home Details for 21 Dewey Ave

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 7840 sqft

Price and Tax history

Date	Event	Price
Jul 12, 2006 Source: N/A	Sold	$169,000

Year	Property tax	Tax assessment
2025	$6,755	$262,550

Additional Cost

Market trends in Windsor

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

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."
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 21 Dewey Ave

What is 21 Dewey Ave estimated to be worth?
Trulia's estimated value for 21 Dewey Ave in Windsor, VT is $321,600.
What is the price history for 21 Dewey Ave?
21 Dewey Ave in Windsor, VT last sold for $169,000 in July 2006.
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.
How big is the lot at 21 Dewey Ave?
The lot at 21 Dewey Ave in Windsor, VT is about 0.18 acres (7,840 sq ft).