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

OFF MARKET

Listed by Jennifer Snyder Fogg, Black House Real Estate, (603) 678-8056 . Bought with KW Vermont Woodstock

2 Ascutney Street
Windsor, VT 05089

3 Beds
1.5 Baths
1,364 sqft (on 0.46 acres)

$316,900

Trulia Estimate

as of Jul 3, 2026

Est. Refi. Payment $2,195/mo*

Refinance Your Home

$316,900

Trulia Estimate

as of Jul 3, 2026

Est. Refi. Payment $2,195/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,364 sqft

(on 0.46 acres)

Local Information

Map ViewExplore the area around 2 Ascutney Street.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Last check for updates: about 24 hours ago

Listed by Jennifer Snyder Fogg

Black House Real Estate, (603) 678-8056

Bought with: Allison Griep, KW Vermont Woodstock, (802) 654-8500

Source: PrimeMLS, MLS#4994827

Description

Absolutely charming Windsor Village home with authentic period detail. With a dining area that has a built-in China Cabinet, beautiful wood floors, natural woodwork and banister, you will immediately fall in love. Although this property sports old world character, the updates are what you are truly looking for; newer windows, vinyl siding, standing seam roof, newly lined septic line, newer heating system, as well as completely rewired in 2010, this home is move in ready! With a nice deck, enclosed porch, oversized 2 car garage and small yard this home is ready to tell your story with you. OPEN HOUSE FRIDAY, May 10, 4p-6p.

2 Ascutney Street, Windsor, VT 05089 is a 3 bedroom, 2 bathroom, 1,364 sqft single-family home built in 1905. It last sold for $270,000 on Jun 14, 2024 (13% above the $239,000 asking price). It is currently off market. The Trulia Estimate is $316,900, with a rent estimate of $2,852/month.

Home Highlights

Parking

Garage

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

180+ days ago

Home Details for 2 Ascutney Street

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Concrete,Basement Stairs,Interior EntryNumber of Rooms: 8
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 1364 Square Feet
Appliances & Utilities Utilities: CableAppliances: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer, Natural Gas Water HeaterDishwasherDryerLaundry: Laundry Hook-ups,1st Floor LaundryMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Oil,Hot AirNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Carpet, Wood
Levels, Entrance, & Accessibility Stories: 2Levels: TwoAccessibility: Zero-Step Entry RampFloors: Carpet, Wood
View No View
Security Security: Smoke Detector(s)

Exterior Features
Exterior Home Features Roof: Standing SeamPatio / Porch: Enclosed PorchExterior: DeckFoundation: Concrete
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Paved,Auto Open,Finished,Storage Above,Driveway,Garage,Detached
Frontage Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 70
Finished Area Finished Area (above surface): 1364 Square Feet

Property Information
Year Built Year Built: 1905
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building Construction Materials: Wood Frame, Clapboard Exterior, Vinyl SidingNot a New Construction

Price & Status
Price List Price: $239,000

Location
Direction & Address City: Windsor
School Information Elementary School District: Windsor School DistrictJr High / Middle School District: Windsor School DistrictHigh School District: Windsor School District

Building
Building Area Building Area: 1364 Square Feet

Lot Information
Lot Area: 0.46 acres

Miscellaneous
BasementMls Number: 4994827Above Grade Unfinished Area: 1364Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square Feet

Price History for 2 Ascutney Street

Date	Price	Event	Source
06/14/2024	$270,000	Sold	PrimeMLS #4994827
Recording Date 06/14/2024 County Transfer Tax N/A Total Transfer Tax N/A
05/13/2024	$239,000	Contingent	PrimeMLS #4994827

05/09/2024	$239,000	Listed For Sale	PrimeMLS #4994827

06/02/2010	$156,000	Sold	N/A
Recording Date 06/02/2010 County Transfer Tax N/A Total Transfer Tax N/A
02/27/2006	$168,000	Sold	N/A
Recording Date 02/27/2006 Contract Date 02/24/2006 County Transfer Tax N/A Total Transfer Tax $1,350
11/21/1988	$86,900	Sold	N/A
Recording Date 11/21/1988 County Transfer Tax N/A Total Transfer Tax $435
09/14/1987	$61,000	Sold	N/A
Recording Date 09/14/1987 County Transfer Tax N/A Total Transfer Tax $305

Market trends in Windsor

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Skip to last item

Results are loading

Skip to first item

Property Tax and Assessment

Year	2024
Tax
Assessment	$234,830

Home facts updated by county records

Comparable Sales for 2 Ascutney Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
32 Clough Avenue, Windsor, VT	0.42	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
10 McKenzie Drive, Windsor, VT	0.30	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
3 Cherry Street, Windsor, VT	0.41	Single-Family Home	$259,000	05/01/26	3	1	1,176
66 Union Street, Windsor, VT	0.21	Single-Family Home	$219,000	09/02/25	3	2	1,743
31 Maple Street, Windsor, VT	0.44	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
9 Main Street, Windsor, VT	0.57	Single-Family Home	$200,001	08/28/25	4	1.5	2,310
21 Bavier Avenue, Windsor, VT	0.63	Single-Family Home	$256,500	11/14/25	3	1	1,232
1 Dorrance Street, Windsor, VT	0.64	Single-Family Home	$315,000	11/21/25	2	1.5	1,649

Nearby homes

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

Skip to last item

SOLD
OCT 2, 2025
$250,000
7 bd
4 ba
3,894 sqft
102-104 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $253,200
6 bd
1.5 ba
2,880 sqft
100 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $268,800
4 bd
1.5 ba
1,600 sqft
153 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $124,100
3 bd
1 ba
1,523 sqft
17 Dewey Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $378,700
4 bd
3 ba
1,998 sqft
32 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $236,800
2 bd
2 ba
1,665 sqft
3 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $262,500
2 bd
1.5 ba
945 sqft
1 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $225,400
3 bd
2 ba
1,743 sqft
66 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
DEC 10, 2025
$115,000
5 bd
3.5 ba
4,011 sqft
70-74 State Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 5, 2026
$425,000
3,700 sqft
64 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $409,000
3 bd
1.5 ba
2,273 sqft
18 Pine Street,
Windsor, VT 05089
PrimeMLS, Closed

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 2 Ascutney Street.

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
5y 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

Apartments for Rent

Skip to last item

$1,350/mo
1 bd
1 ba
24 State St #1,
Windsor, VT 05089
NEW - 1 DAY AGO
$1,300/mo
1 bd
1 ba
2326 US Route 5 N #1A,
Windsor, VT 05089
$1,650/mo
2 bd
1 ba
75 Union St #3,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,450/mo
2 bd
1 ba
55 River St #B,
Windsor, VT 05089
$1,136/mo
Studio
1 ba
18 Union St #C,
Windsor, VT 05089
$1,795/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
$2,250/mo
3 bd
1 ba
21-23 Maple St,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
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

Skip to first item

Homes for sale near 2 Ascutney Street

Skip to last item

AUCTION
0.48 ACRES
$515,000
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
11 ACRES
$575,000
4 bd
3 ba
2,229 sqft
511 Route 12A,
Cornish, NH 03745
PrimeMLS, Active
6.8 ACRES
$299,000
2 bd
1 ba
1,152 sqft
466 Estey Lane,
Windsor, VT 05089
PrimeMLS, Active
1.22 ACRES
$413,900
4 bd
2.5 ba
2,888 sqft
273 Route 5 North,
Windsor, VT 05089
PrimeMLS, Active
1.2 ACRES
$239,900
1 bd
1 ba
570 sqft
23 CHASE HILL Road,
Cornish, NH 03745
PrimeMLS, Active
5.25 ACRES
$725,000
3 bd
2 ba
2,618 sqft
21 Squag City Road,
Cornish, NH 03745
PrimeMLS, Active
$110,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
Windsor, VT 05089
PrimeMLS, Active
3.2 ACRES
$599,000
4 bd
3 ba
3,200 sqft
84 Old Barn Lane,
West Windsor, VT 05089
PrimeMLS, Active
1.53 ACRES
$474,800
3 bd
2 ba
1,480 sqft
586 Ski Tow Road,
Brownsville, VT 05037
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

Skip to first item

Off Market Homes Near 2 Ascutney Street

Skip to last item

SOLD
JUN 24, 2026
$290,000
3 bd
2.5 ba
1,614 sqft
127 Mountains Edge Road #211,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
JUN 10, 2026
$330,000
2 bd
2 ba
1,604 sqft
290 Village Lane,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
MAY 21, 2026
$195,000
Hotel Rd,
Brownsville, VT 05037
SOLD
MAY 15, 2026
$459,000
4 bd
1.5 ba
2,349 sqft
579 Town House Road,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
MAY 15, 2026
$195,000
3 bd
1,604 sqft
295 Hotel Road #10/10A,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 5, 2026
$425,000
3,700 sqft
64 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
SOLD
APR 30, 2026
$230,000
3 bd
2 ba
1,434 sqft
19 SPRUCE PARK Drive #19,
Plainfield, NH 03781
PrimeMLS, Closed
SOLD
APR 23, 2026
$185,000
295 Hotel Rd,
Brownsville, VT 05037
SOLD
APR 22, 2026
$295,000
3 bd
3 ba
1,594 sqft
72 Mountains Edge Road #508,
Brownsville, VT 05037
PrimeMLS, Closed
See more homes for sale in
Windsor
Take a look

Skip to first item

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-07-02 11:46:57 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

2 Ascutney Street
Windsor, VT 05089

$316,900

$316,900

Local Information