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

74 Ascutney St
Windsor, VT 05089

4 Beds
1.5 Baths
1,176 sqft

$289,400

Trulia Estimate

as of Jul 19, 2026

$289,400

Trulia Estimate

as of Jul 19, 2026

4 Beds

1.5 Baths

1,176 sqft

Local Information

Map ViewExplore the area around 74 Ascutney St.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This is one of the most loved streets in Windsor with easy walking distance to town, school, the ponds, and Paradise Park, all on sidewalks. A nice, simple, manicured lawn, and paved driveway pair with plenty of bedrooms, and a mudroom, and you are HOME. This one is truly move in ready.

74 Ascutney St, Windsor, VT 05089 is a 4 bedroom, 2 bathroom, 1,176 sqft single-family home built in 1920. It last sold for $177,500 on Feb 22, 2019. It is currently off market. The Trulia Estimate is $289,400, with a rent estimate of $2,829/month.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 74 Ascutney St

Interior Features
Heating & Cooling Heating: Electric, OilHeating Fuel: Electric
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DryerRefrigeratorWasher
Levels, Entrance, & Accessibility Floors: Hardwood, Laminate

Exterior Features
Exterior Home Features Roof: Asphalt
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1920
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 6969 sqft

Price History for 74 Ascutney St

Date	Price	Event	Source
02/22/2019	$177,500	Sold	PrimeMLS #4719443
Recording Date 02/22/2019 County Transfer Tax N/A Total Transfer Tax N/A
07/18/2006	$120,000	Sold	N/A
Recording Date 07/18/2006 Contract Date 07/18/2006 County Transfer Tax N/A Total Transfer Tax $1,500
07/31/1987	$54,500	Sold	N/A
Recording Date 07/31/1987 County Transfer Tax N/A Total Transfer Tax $273

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	$185,700

Home facts updated by county records

Comparable Sales for 74 Ascutney St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
3 Cherry Street, Windsor, VT	0.08	Single-Family Home	$259,000	05/01/26	3	1	1,176
6 Kiniry St, Windsor, VT	0.24	Single-Family Home	$176,000	07/28/25	3	1	1,400
10 McKenzie Drive, Windsor, VT	0.23	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
21 Bavier Avenue, Windsor, VT	0.28	Single-Family Home	$256,500	11/14/25	3	1	1,232
66 Union Street, Windsor, VT	0.19	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
32 Clough Avenue, Windsor, VT	0.18	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
1 Dorrance Street, Windsor, VT	0.33	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
6 Bavier Avenue, Windsor, VT	0.34	Single-Family Home	$200,000	08/27/25	2	1	786
5 Clough Avenue, Windsor, VT	0.21	Single-Family Home	$60,000	12/18/25	3	1	1,392

Nearby homes

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

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SOLD
MAY 1, 2026
$259,000
3 bd
1 ba
1,176 sqft
3 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $312,100
3 bd
1.5 ba
1,606 sqft
32 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $247,100
2 bd
2 ba
1,354 sqft
21 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $282,300
3 bd
4 ba
2,052 sqft
4 Old Mill Pond Road #4,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $227,200
3 bd
2 ba
1,743 sqft
66 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $287,600
4 bd
2 ba
3,266 sqft
17 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $262,700
2 bd
1.5 ba
945 sqft
1 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
DEC 18, 2025
$60,000
3 bd
1 ba
1,392 sqft
5 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $381,600
4 bd
3 ba
1,998 sqft
32 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $316,600
3 bd
5 ba
1,754 sqft
8 Old Mill Pond Road,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $282,800
4 bd
1.5 ba
1,400 sqft
4 Kiniry Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
NOV 13, 2025
$271,000
3 bd
1.5 ba
1,320 sqft
10 McKenzie Drive,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 74 Ascutney St.

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
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Apartments for Rent

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$1,325/mo
1 bd
1 ba
9 State Street | State St,
Windsor, VT 05089
$1,350/mo
1 bd
1 ba
24 State St #1,
Windsor, VT 05089
$1,300/mo
1 bd
1 ba
2326 US Route 5 N #1A,
Windsor, VT 05089
$1,450/mo
2 bd
1 ba
55 River St #B,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,136/mo
Studio
1 ba
18 Union St #C,
Windsor, VT 05089
$1,500 - $1,700/mo
1-2 bd
1 ba
360 Tecumseh Road West | Tecumseh Rd W,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
289 County Rd #f320a52c6,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
NEW - 2 DAYS AGO
APPLY INSTANTLY
$1,325/mo
Total price
1 bd
1 ba
Address Not Disclosed,
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
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Homes for sale near 74 Ascutney St

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4.96 ACRES
$1,399,000
4 bd
3.5 ba
4,000 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Active
AUCTION
0.48 ACRES
$510,000
6 bd
4 ba
4,933 sqft
2 Pine 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
6.8 ACRES
$299,000
2 bd
1 ba
1,152 sqft
466 Estey Lane,
Windsor, VT 05089
PrimeMLS, Active
$110,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
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
1.22 ACRES
$413,900
4 bd
2.5 ba
2,888 sqft
273 Route 5 North,
Windsor, VT 05089
PrimeMLS, Active
5.25 ACRES
$725,000
3 bd
2 ba
2,618 sqft
21 Squag City Road,
Cornish, NH 03745
PrimeMLS, Active
3.2 ACRES
$599,000
4 bd
3 ba
3,200 sqft
84 Old Barn Lane,
West Windsor, VT 05089
PrimeMLS, Active
5.51 ACRES
$1,345,000
7 bd
5 ba
5,774 sqft
310 Pierce Hill Road,
Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
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