27 Ascutney St, Windsor, VT 05089
OFF MARKET

27 Ascutney St
Windsor, VT 05089

  • 3 Beds
  • 2 Baths
  • 1,950 sqft

$206,200

Trulia Estimate
as of May 17, 2026
Est. Refi. Payment $1,433/mo*
Refinance Your Home

$206,200

Trulia Estimate
as of May 17, 2026
Est. Refi. Payment $1,433/mo*
Refinance Your Home
3 Beds
2 Baths
1,950 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 27 Ascutney St

DatePriceEventSource
05/02/2025$200,000Sold
N/A
07/09/2013$150,000Sold
N/A
02/13/2013$150,000ListingRemovedAgent Provided
01/29/2013$150,000PriceChange
Agent Provided
08/30/2012$189,000PriceChange
Agent Provided
07/11/2012$199,000Listed For SaleAgent Provided
06/07/2007$199,500Sold
N/A
07/06/2005$189,500Sold
N/A
02/10/1987$61,500Sold
N/A
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Property Tax and Assessment

Year2024
Tax
Assessment$277,090
Home facts updated by county records

Comparable Sales for 27 Ascutney St

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
3 Fitch Court, Windsor, VT
0.07
Single-Family Home
$229,000
06/25/25
2
2
1,665
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
6 Kiniry St, Windsor, VT
0.46
Single-Family Home
$176,000
07/28/25
3
1
1,400
42 Elm Street, Windsor, VT
0.42
Single-Family Home
$275,000
06/09/25
3
2
1,264
1 Dorrance Street, Windsor, VT
0.54
Single-Family Home
$315,000
11/21/25
2
1.5
1,649
21 Bavier Avenue, Windsor, VT
0.52
Single-Family Home
$256,500
11/14/25
3
1
1,232

Assigned Schools

These are the assigned schools for 27 Ascutney St.
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What Locals Say about Windsor

At least 9 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 92 % Say yards are well-kept

  • 90 % Say it's walkable to grocery stores

  • 83 % Say car is needed

  • 78 % Say it's walkable to restaurants

  • 67 % Say parking is easy

  • 67 % Say people would walk alone at night

  • 64 % Say streets are well-lit

  • 64 % Say it's quiet

  • 64 % Say there are sidewalks

  • 64 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 52 % Say neighbors are friendly

  • 36 % Say they plan to stay for at least 5 years

  • 20 % Say there are community events

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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Homes for rent near 27 Ascutney St

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Off Market Homes Near 27 Ascutney St

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27 Ascutney St, Windsor, VT 05089 is a 3 bedroom, 2 bathroom, 1,950 sqft single-family home built in 1915. This property is not currently available for sale. 27 Ascutney St was last sold on May 2, 2025 for $200,000. The current Trulia Estimate for 27 Ascutney St is $206,200.