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 23 Dewey Ave estimated to be worth?

Trulia's estimated value for 23 Dewey Ave in Windsor, VT is $249,600 .

What is the price history for 23 Dewey Ave?

23 Dewey Ave in Windsor, VT last sold for $117,000 in September 2003.

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 23 Dewey Ave?

The lot at 23 Dewey Ave in Windsor, VT is about 1 acre .

OFF MARKET

23 Dewey Ave
Windsor, VT 05089

Studio

$249,600

Trulia Estimate

as of Aug 11, 2026

$249,600

Trulia Estimate

as of Aug 11, 2026

Studio

(on 1 acre)

Local Information

Map ViewExplore the area around 23 Dewey Ave.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

1 acre

About this House

This single-family home is located at 23 Dewey Ave, Windsor, VT. 23 Dewey Ave is in Windsor, VT and in ZIP code 05089. This property has a lot size of 1 acre.

23 Dewey Ave, Windsor, VT 05089 is a studio single-family home. It last sold for $117,000 on Sep 24, 2003. It is currently off market. The Trulia Estimate is $249,600, with a rent estimate of $2,903/month.

Home Details for 23 Dewey Ave

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

Lot Information
Lot Area: 1 acre

Price History for 23 Dewey Ave

Date	Price	Event	Source
09/24/2003	$117,000	Sold	N/A
Recording Date 09/24/2003 Contract Date 09/19/2003 County Transfer Tax N/A Total Transfer Tax $713
11/27/2001	$94,000	Sold	N/A
Recording Date 11/27/2001 Contract Date 11/26/2001 County Transfer Tax N/A Total Transfer Tax $1,175

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	$205,970

Home facts updated by county records

Comparable Sales for 23 Dewey Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
16 Ascutney St, Windsor, VT	0.08	Single-Family Home	$227,940	05/04/26		-	-
70-74 State Street, Windsor, VT	0.43	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
74 Union Street, Windsor, VT	0.24	Single-Family Home	$319,000	07/23/26	4	2	2,142
26 Cherry St, Windsor, VT	0.36	Single-Family Home	$150,000	11/03/25		-	-
32 Clough Avenue, Windsor, VT	0.45	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
66 Union Street, Windsor, VT	0.26	Single-Family Home	$219,000	09/02/25	3	2	1,743
19 1/2 Union St, Windsor, VT	0.49	Single-Family Home	$63,200	06/10/26		-	-
16 Day Street, Windsor, VT	0.49	Single-Family Home	$94,900	12/04/25	2	1	660
3 Cherry Street, Windsor, VT	0.33	Single-Family Home	$259,000	05/01/26	3	1	1,176
10 McKenzie Drive, Windsor, VT	0.38	Single-Family Home	$271,000	11/13/25	3	1.5	1,320

Nearby homes

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

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OFF MARKET
Est. $125,200
3 bd
1 ba
1,523 sqft
17 Dewey Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $270,600
4 bd
1.5 ba
1,600 sqft
153 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $382,700
4 bd
3 ba
1,998 sqft
32 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $315,700
3 bd
1.5 ba
1,364 sqft
2 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $341,700
3 bd
2 ba
1,400 sqft
18 County Road,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
JUL 23, 2026
$319,000
4 bd
2 ba
2,142 sqft
74 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $239,500
2 bd
2 ba
1,665 sqft
3 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $261,100
2 bd
1.5 ba
945 sqft
1 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $227,900
3 bd
2 ba
1,743 sqft
66 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $300,900
7 bd
4 ba
3,894 sqft
102-104 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $259,700
6 bd
1.5 ba
2,880 sqft
100 State Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 1, 2026
$259,000
3 bd
1 ba
1,176 sqft
3 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 23 Dewey Ave.

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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$1,500 - $1,700/mo
1-2 bd
1 ba
360 Tecumseh Road West | 360 Tecumseh Rd W,
Windsor, VT 05089
$1,325/mo
1 bd
1 ba
9 State Street | 9 State St,
Windsor, VT 05089
$1,425/mo
1 bd
1 ba
112-114 State St #114A,
Windsor, VT 05089
$1,325/mo
1 bd
1 ba
24 State St #2,
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
289 County Rd #f320a52c6,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
65 State St #f320a52c6,
Windsor, VT 05089
APPLY INSTANTLY
PET FRIENDLY
$2,500/mo
3 bd
2.5 ba
178 Pierce Hill Rd #2,
Brownsville, VT 05037
PET FRIENDLY
$2,700/mo
4 bd
2.5 ba
178 Pierce Hill Rd #1,
Brownsville, VT 05037
APPLY INSTANTLY
PET FRIENDLY
$1,495/mo
1 bd
1 ba
51 River St #1,
Windsor, VT 05089
See more homes for rent in
Windsor
Take a look

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Homes for sale near 23 Dewey Ave

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0.48 ACRES
$500,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
4.96 ACRES
$1,399,000
4 bd
3.5 ba
4,000 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Active
$109,000
1 bd
1 ba
504 sqft
52 Jarvis Street,
Windsor, VT 05089
PrimeMLS, Active
11 ACRES
$575,000
4 bd
3 ba
2,229 sqft
511 Route 12A,
Cornish, NH 03745
PrimeMLS, Active
$99,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
Windsor, VT 05089
PrimeMLS, Active
2.51 ACRES
$279,000
2 bd
1 ba
783 sqft
15 Rt. 5 North,
Windsor, VT 05089
PrimeMLS, Active
3.2 ACRES
$574,900
4 bd
3 ba
3,200 sqft
84 Old Barn Lane,
West Windsor, VT 05089
PrimeMLS, Active
5.51 ACRES
$1,295,000
7 bd
5 ba
5,774 sqft
310 Pierce Hill Road,
Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 23 Dewey Ave

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SOLD
AUG 7, 2026
$226,000
3 bd
1 ba
2,088 sqft
4 Bavier Avenue,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
AUG 7, 2026
$273,000
3 bd
1 ba
1,008 sqft
61 Kennedy Drive,
Windsor, VT 05089
PrimeMLS, Closed
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 13, 2026
$175,000
3 bd
2 ba
1,527 sqft
271 Tandy Brook Rd,
Cornish, NH 03745
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
See more homes for sale in
Windsor
Take a look

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Frequently asked questions about 23 Dewey Ave

What is 23 Dewey Ave estimated to be worth?
Trulia's estimated value for 23 Dewey Ave in Windsor, VT is $249,600.
What is the price history for 23 Dewey Ave?
23 Dewey Ave in Windsor, VT last sold for $117,000 in September 2003.
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 23 Dewey Ave?
The lot at 23 Dewey Ave in Windsor, VT is about 1 acre.

23 Dewey Ave
Windsor, VT 05089

$249,600

$249,600