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 27 Ascutney St estimated to be worth?

Trulia's estimated value for 27 Ascutney St in Windsor, VT is $209,600 .

What is the price history for 27 Ascutney St?

27 Ascutney St in Windsor, VT last sold for $200,000 in May 2025.

Is Windsor a buyer's or seller's market?

Windsor is currently a seller'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 27 Ascutney St?

The lot at 27 Ascutney St in Windsor, VT is about 0.16 acres (6,970 sq ft).

OFF MARKET

$209,600

Trulia Estimate

3 Beds
2 Baths
1,950 sqft

27 Ascutney St, Windsor, VT 05089

Est. Refi. Payment $1,559/mo*

Refinance Your Home

Currently Off Market - Sold May 2, 2025 for $200,000

Home Value

Trulia Estimate

$210K

Since last month

$1K (-0.6%)

Since last year

$4K (+2.2%)

Since last sale

$9K (+4.4%)

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 +17% in the last 10 years

Month	Estimated value
2026
October 2026	$209K
September 2026	$210K
August 2026	$209K
July 2026	$209K
June 2026	$207K
May 2026	$206K
April 2026	$206K
March 2026	$208K
February 2026	$209K
January 2026	$206K
2025
December 2025	$207K
November 2025	$205K
October 2025	$204K
September 2025	$204K
August 2025	$204K
July 2025	$204K
June 2025	$334K
May 2025	$316K
April 2025	$309K
March 2025	$304K
February 2025	$302K
January 2025	$299K
2024
December 2024	$303K
November 2024	$303K
October 2024	$332K
September 2024	$332K
August 2024	$340K
July 2024	$337K
June 2024	$336K
May 2024	$338K
April 2024	$327K
March 2024	$313K
February 2024	$307K
January 2024	$303K
2023
December 2023	$299K
November 2023	$312K
October 2023	$323K
September 2023	$323K
August 2023	$323K
July 2023	$323K
June 2023	$315K
May 2023	$314K
April 2023	$306K
March 2023	$298K
February 2023	$294K
January 2023	$293K
2022
December 2022	$296K
November 2022	$300K
October 2022	$302K
September 2022	$303K
August 2022	$306K
July 2022	$309K
June 2022	$310K
May 2022	$303K
April 2022	$292K
March 2022	$282K
February 2022	$268K
January 2022	$269K
2021
December 2021	$266K
November 2021	$266K
October 2021	$265K
September 2021	$261K
August 2021	$261K
July 2021	$263K
June 2021	$264K
May 2021	$241K
April 2021	$243K
March 2021	$230K
February 2021	$228K
January 2021	$231K
2020
December 2020	$220K
November 2020	$223K
October 2020	$229K
September 2020	$193K
August 2020	$219K
July 2020	$215K
June 2020	$207K
May 2020	$204K
April 2020	$197K
March 2020	$204K
February 2020	$202K
January 2020	$203K
2019
December 2019	$202K
November 2019	$198K
October 2019	$199K
September 2019	$188K
August 2019	$187K
July 2019	$182K
June 2019	$182K
May 2019	$182K
April 2019	$180K
March 2019	$175K
February 2019	$184K
January 2019	$184K
2018
December 2018	$185K
November 2018	$181K
October 2018	$187K
September 2018	$188K
August 2018	$185K
July 2018	$184K
June 2018	$183K
May 2018	$185K
April 2018	$186K
March 2018	$191K
February 2018	$187K
January 2018	$180K
2017
December 2017	$183K
November 2017	$180K
October 2017	$187K
September 2017	$188K
August 2017	$187K
July 2017	$179K
June 2017	$183K
May 2017	$179K
April 2017	$177K
March 2017	$172K
February 2017	$175K
January 2017	$176K
2016
December 2016	$180K
November 2016	$183K
October 2016	$179K

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
10 McKenzie Drive, Windsor, VT	0.20	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
74 Union Street, Windsor, VT	0.09	Single-Family Home	$319,000	07/23/26	4	2	2,142
3 Cherry Street, Windsor, VT	0.30	Single-Family Home	$259,000	05/01/26	3	1	1,176
24 Cherry Street, Windsor, VT	0.38	Single-Family Home	$235,000	09/30/26	3	1	1,095
1 Dorrance Street, Windsor, VT	0.54	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
5 Clough Avenue, Windsor, VT	0.20	Single-Family Home	$339,000	10/02/26	3	1	1,392
4 Bavier Avenue, Windsor, VT	0.56	Single-Family Home	$226,000	08/07/26	3	1	2,088
21 Bavier Avenue, Windsor, VT	0.52	Single-Family Home	$256,500	11/14/25	3	1	1,232
143 Ascutney Street, Windsor, VT	0.60	Single-Family Home	$354,000	10/14/26	2	1.5	1,092
68 Jarvis Street, Windsor, VT	0.65	Single-Family Home	$165,000	01/23/26	3	1	1,602

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
29 Ascutney St, Windsor, VT 05089	0.03	$516,900	6	4	3,592	Off Market
29 Ascutney St #2, Windsor, VT 05089	0.03	$310,300	2	1	-	Off Market
29 Ascutney St #1, Windsor, VT 05089	0.03	$298,200	2	1	900	Off Market
25 Ascutney St, Windsor, VT 05089	0.03	$337,600	4	2	1,616	Off Market
23 Ascutney St, Windsor, VT 05089	0.03	$303,700	Studio	-	-	Off Market
33 Ascutney St, Windsor, VT 05089	0.03	$224,800	Studio	-	-	Off Market
45-47 Ascutney Blvd #1, Windsor, VT 05089	0.04	-	2	1	-	Off Market
45-47 Ascutney Blvd #3, Windsor, VT 05089	0.04	-	2	1	800	Off Market
45-47 Ascutney Blvd #5, Windsor, VT 05089	0.04	-	2	1	-	Off Market
45-47 Ascutney Blvd #4, Windsor, VT 05089	0.04	-	2	1	-	Off Market
28 Ascutney St, Windsor, VT 05089	0.05	$290,900	Studio	-	-	Off Market
21 Ascutney St, Windsor, VT 05089	0.05	$224,800	2	1.5	1,309	Off Market
9 Fitch Ct, Windsor, VT 05089	0.05	$230,500	Studio	-	-	Off Market
30 Ascutney St, Windsor, VT 05089	0.05	$287,100	Studio	-	-	Off Market
22 Ascutney St, Windsor, VT 05089	0.05	$280,100	Studio	-	-	Off Market
32 Ascutney Street, Windsor, VT 05089	0.05	$382,100	4	3	1,998	Off Market
5 Fitch Ct, Windsor, VT 05089	0.05	-	Studio	-	-	Off Market
35 Ascutney St, Windsor, VT 05089	0.06	$307,900	4	1.5	1,774	Off Market
20 Ascutney St, Windsor, VT 05089	0.06	$302,700	3	2	1,538	Off Market
17 Ascutney St, Windsor, VT 05089	0.07	$299,600	5	2	1,980	Off Market

Local Information

Map ViewExplore the area around 27 Ascutney St.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1915

1,950 sqft

$107/sqft

About this House

This beautifully maintained Classic New Englander on one of Windsor??s more desirable streets is absolutely filled with period charm. Pristine natural woodwork, maple floors throughout, double French doors, stained and leaded glass windows. Large country kitchen features original bead board pantry and built-in cupboards. Sizeable finished room on third floor for studio, office or additional guest space. Just steps to swimming and skating on Kennedy Pond, elementary school, and town fitness center. Double carport, front and rear covered porches, and three season porch. A wonderful home! Subject to third party approval.

27 Ascutney St, Windsor, VT 05089 is a 3 bedroom, 2 bathroom, 1,950 sqft single-family home built in 1915. It last sold for $200,000 on May 2, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $209,600, with a rent estimate of $2,478/month.

Home Details for 27 Ascutney St

Exterior Features
Exterior Home Features Roof: Other

Property Information
Year Built Year Built: 1915
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 6970 sqft

Price and Tax history

Date	Event	Price
May 2, 2025 Source: N/A	Sold	$200,000
Jul 9, 2013 Source: N/A	Sold	$150,000
Feb 13, 2013 Source: Agent Provided	ListingRemoved	$150,000
Jan 29, 2013 Source: Agent Provided	PriceChange	$150,000 Price decreased by 21%
Aug 30, 2012 Source: Agent Provided	PriceChange	$189,000 Price decreased by 5%
Jul 11, 2012 Source: Agent Provided	Listed For Sale	$199,000
Jun 7, 2007 Source: N/A	Sold	$199,500
Jul 6, 2005 Source: N/A	Sold	$189,500
Feb 10, 1987 Source: N/A	Sold	$61,500

Year	Property tax	Tax assessment
2025	$7,129	$277,090

Additional Cost

Market trends in Windsor

Last updated September 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Sourced by Trulia Market Trends

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

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.

64% say there's holiday spirit
64% say there are sidewalks
52% say neighbors are friendly

Trulia Trick or TreatStart Ghost Hunt

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 27 Ascutney St

What is 27 Ascutney St estimated to be worth?
Trulia's estimated value for 27 Ascutney St in Windsor, VT is $209,600.
What is the price history for 27 Ascutney St?
27 Ascutney St in Windsor, VT last sold for $200,000 in May 2025.
Is Windsor a buyer's or seller's market?
Windsor is currently a seller'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 27 Ascutney St?
The lot at 27 Ascutney St in Windsor, VT is about 0.16 acres (6,970 sq ft).