27 Ascutney St, Windsor, VT 05089
OFF MARKET

27 Ascutney St
Windsor, VT 05089

  • 3 Beds
  • 2 Baths
  • 1,950 sqft

$209,800

Trulia Estimate
as of Aug 14, 2026

$209,800

Trulia Estimate
as of Aug 14, 2026
3 Beds
2 Baths
1,950 sqft

Home Value

Trulia Estimate
$210K
Since last month
Increased$3K (+1.6%)
Since last year
Increased$7K (+3.3%)
Since last sale
Increased$10K (+5.1%)
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 +21% in the last 10 years
MonthEstimated value
2026
August 2026$210K
July 2026$209K
June 2026$207K
May 2026$206K
April 2026$206K
March 2026$208K
February 2026$209K
January 2026$206K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
66 Union Street, Windsor, VT
0.09
Single-Family Home
$219,000
09/02/25
3
2
1,743
31 Maple Street, Windsor, VT
0.36
Single-Family Home
$215,000
10/06/25
3
1.5
1,900
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
32 Clough Avenue, Windsor, VT
0.30
Single-Family Home
$292,500
08/28/25
3
1.5
1,606
3 Cherry Street, Windsor, VT
0.30
Single-Family Home
$259,000
05/01/26
3
1
1,176
1 Dorrance Street, Windsor, VT
0.54
Single-Family Home
$315,000
11/21/25
2
1.5
1,649
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
9 Main Street, Windsor, VT
0.65
Single-Family Home
$200,001
08/28/25
4
1.5
2,310

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
32 Ascutney Street, Windsor, VT 05089
0.05
$382,700
4
3
1,998
Off Market
74 Union Street, Windsor, VT 05089
0.09
$319,000
4
2
2,142
Recently Sold
3 Fitch Court, Windsor, VT 05089
0.07
$239,500
2
2
1,665
Off Market
66 Union Street, Windsor, VT 05089
0.09
$227,900
3
2
1,743
Off Market
2 Ascutney Street, Windsor, VT 05089
0.12
$315,700
3
1.5
1,364
Off Market
17 Dewey Avenue, Windsor, VT 05089
0.16
$125,200
3
1
1,523
Off Market
5 Clough Avenue, Windsor, VT 05089
0.20
$339,000
3
1
1,392
For Sale
10 McKenzie Drive, Windsor, VT 05089
0.20
$271,000
3
1.5
1,320
Recently Sold
17 Clough Avenue, Windsor, VT 05089
0.24
$283,000
4
2
3,266
Off Market
153 State Street, Windsor, VT 05089
0.20
$265,600
4
1.5
1,600
Off Market
102-104 State Street, Windsor, VT 05089
0.20
$292,900
7
4
3,894
Off Market
100 State Street, Windsor, VT 05089
0.20
$253,500
6
1.5
2,880
Off Market

Local Information

  • Map ViewExplore the area around 27 Ascutney St.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1915
Living Area
1,950 sqft
Price/Sqft
$108

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. It is currently off market. The Trulia Estimate is $209,800, with a rent estimate of $2,902/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

DateEventPrice
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%

Market trends in Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
6
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Around this home

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.
    "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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Apartments for Rent

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Homes for sale near 27 Ascutney St

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Off Market Homes Near 27 Ascutney St

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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 $209,800.
  • 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 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 27 Ascutney St?
    The lot at 27 Ascutney St in Windsor, VT is about 0.16 acres (6,970 sq ft).