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, 90% 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, 78% of users say it's walkable to restaurants

Is parking easy in Windsor, VT?

As of early 2026, 67% of users say parking is easy

Would people walk alone at night in Windsor, VT?

As of early 2026, 67% of users say people would walk alone at night

Are the streets well-lit in Windsor, VT?

As of early 2026, 64% of users say streets are well-lit

Is Windsor, VT quiet?

As of early 2026, 64% of users say it's quiet

Does Windsor, VT have sidewalks?

As of early 2026, 64% of users say there are sidewalks

Do kids play outside in Windsor, VT?

As of early 2026, 64% of users say kids play outside

Does Windsor, VT show holiday spirit?

As of early 2026, 60% of users say there's holiday spirit

Is there wildlife in Windsor, VT?

As of early 2026, 60% of users say there's wildlife

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 Melissa Robinson, Coldwell Banker LIFESTYLES - Hanover, (603) 643-6406 . Bought with BHHS Verani Upper Valley

38 Ascutney Street
Windsor, VT 05089

5 Beds
2.5 Baths
3,048 sqft (on 0.61 acres)

$569,400

Trulia Estimate

as of May 30, 2026

Est. Refi. Payment $3,864/mo*

Refinance Your Home

$569,400

Trulia Estimate

as of May 30, 2026

Est. Refi. Payment $3,864/mo*

Refinance Your Home

5 Beds

2.5 Baths

3,048 sqft

(on 0.61 acres)

Local Information

-- mins to

Commute Destination

Last check for updates: about 10 hours ago

Listed by Melissa Robinson

Coldwell Banker LIFESTYLES - Hanover, (603) 643-6406

Bought with: Andy Clouse, BHHS Verani Upper Valley, (603) 643-8822

Source: PrimeMLS, MLS#4947641

Description

This beautiful 19th century home has been tastefully updated while retaining much of its period elegance. The main level features a spacious entry way with built in storage, kitchen with custom concrete countertops and plenty of space to entertain as the room leads into a sunroom with pellet stove, 3/4 bath. The main level finishes off with a formal dining room, double-length living room that is currently divided into a cozy, conversation area facing the fireplace with a magnificent mantle while the front half has built-in shelving serving as a study with a picture window view across the Connecticut river to the wooded NH hills beyond. On the 2nd level, there is a primary bedroom with walk-in closet, two other bedrooms and a den with built-in entertainment wall, a bathroom with jetted tub and shower stall plus a separate laundry room. The finished attic with a half bath provides ample space for a bed and sitting room or studio with shelving and more storage.The original, refinished hardwood flooring is to be found in most of the main rooms and hallways with a mix of wood and ceramic flooring elsewhere. The full, dry basement with both in and outside entrances, is a craftsman's paradise, filled with built-in work benches and storage cupboards, plus it remains warm enough to work there year-round. Outside you will find an in-ground pool and gardens with a view, fruit trees, berry bushes and tranquility of a wooded hill providing privacy. Delayed Showings begin Sat. 4/8

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. This description is from May 10, 2023

Home Highlights

Parking

Garage

Outdoor

Porch, Patio, Pool

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

180+ days ago

Home Details for 38 Ascutney Street

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Concrete Floor,Full,Unfinished,Interior Access,Interior EntryNumber of Rooms: 11
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 3048 Square Feet
Appliances & Utilities Appliances: Dishwasher, Disposal, ENERGY STAR Qualified Dryer, Electric Range, Trash Compactor, Washer, Electric Water HeaterDishwasherDisposalLaundry: 2nd Floor LaundryWasher
Heating & Cooling Heating: Oil,SteamNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Fireplace & Spa Number of Fireplaces: 1Fireplace: 1 FireplaceHas a Fireplace
Gas & Electric Electric: 100 Amp Service
Windows, Doors, Floors & Walls Window: ScreensFlooring: Bamboo, Ceramic Tile, Hardwood, Laminate
Levels, Entrance, & Accessibility Stories: 2.5Levels: 2.5Floors: Bamboo, Ceramic Tile, Hardwood, Laminate
View No View

Exterior Features
Exterior Home Features Roof: Asphalt ShinglePatio / Porch: Patio, Porch, Covered PorchFencing: FullExterior: GardenFoundation: ConcreteGardenHas a Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Gravel,Driveway,Garage,Detached
Pool Pool: In GroundPool
Frontage Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 75
Finished Area Finished Area (above surface): 3048 Square Feet

Property Information
Year Built Year Built: 1885
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: New Englander
Building Construction Materials: Wood Frame, Clapboard Exterior, Wood SidingNot a New Construction
Property Information Usage of Home: Residential

Price & Status
Price List Price: $449,000
Status Change & Dates Possession Timing: Close Of Escrow

Location
Direction & Address City: Windsor
School Information Elementary School: Windsor State Street SchoolElementary School District: Windsor School DistrictJr High / Middle School: Windsor High SchoolJr High / Middle School District: Windsor School DistrictHigh School: Windsor High SchoolHigh School District: Windsor School District

Building
Building Area Building Area: 4556 Square Feet

Lot Information
Lot Area: 0.61 acres

Miscellaneous
BasementMls Number: 4947641Attic: Attic with Hatch/SkuttleAttribution Contact: Cell: 603-667-7761Above Grade Unfinished Area: 3048Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 1508Below Grade Unfinished Area Source: AssessorBelow Grade Unfinished Area Units: Square Feet

Price History for 38 Ascutney Street

Date	Price	Event	Source
05/10/2023	$485,000	Sold	PrimeMLS #4947641
Recording Date 05/10/2023 County Transfer Tax N/A Total Transfer Tax N/A
04/05/2023	$449,000	Listed For Sale	PrimeMLS #4947641

11/09/2022	$439,000	Sold	PrimeMLS #4923435
Recording Date 11/09/2022 County Transfer Tax N/A Total Transfer Tax N/A
10/11/2022	$439,000	Contingent	PrimeMLS #4923435

09/18/2022	$439,000	PriceChange	PrimeMLS #4923435
Price Change $10,000 (-2%)
08/02/2022	$449,000	Listed For Sale	PrimeMLS #4923435

09/12/1996	$87,000	Sold	N/A
Recording Date 09/12/1996 Contract Date 09/06/1996 County Transfer Tax N/A Total Transfer Tax $435
03/17/1988	$77,000	Sold	N/A
Recording Date 03/17/1988 County Transfer Tax N/A Total Transfer Tax $385

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Property Tax and Assessment

Year	2024
Tax
Assessment	$473,500

Home facts updated by county records

Comparable Sales for 38 Ascutney Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
3 Fitch Court, Windsor, VT	0.12	Single-Family Home	$229,000	06/25/25	2	2	1,665
32 Clough Avenue, Windsor, VT	0.26	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
30 Union Street, Windsor, VT	0.33	Single-Family Home	$350,000	05/30/25	4	4.5	3,990
338 US Route 5 South, Windsor, VT	0.65	Single-Family Home	$240,000	07/21/25	6	2	2,504
42 Elm Street, Windsor, VT	0.33	Single-Family Home	$275,000	06/09/25	3	2	1,264
70-74 State Street, Windsor, VT	0.38	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
66 Union Street, Windsor, VT	0.10	Single-Family Home	$219,000	09/02/25	3	2	1,743
10 McKenzie Drive, Windsor, VT	0.21	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
31 Maple Street, Windsor, VT	0.37	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
9 Main Street, Windsor, VT	0.74	Single-Family Home	$200,001	08/28/25	4	1.5	2,310

Nearby homes

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

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OFF MARKET
Est. $377,400
4 bd
3 ba
1,998 sqft
32 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
SEP 2, 2025
$219,000
3 bd
2 ba
1,743 sqft
66 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $261,100
2 bd
1.5 ba
945 sqft
1 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $236,200
2 bd
2 ba
1,665 sqft
3 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
SOLD
MAY 1, 2026
$259,000
3 bd
1 ba
1,176 sqft
3 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $282,500
3 bd
1 ba
1,025 sqft
20 Elm 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
OFF MARKET
Est. $286,900
4 bd
2 ba
3,266 sqft
17 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $123,500
3 bd
1 ba
1,523 sqft
17 Dewey Avenue,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
AUG 28, 2025
$292,500
3 bd
1.5 ba
1,606 sqft
32 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 38 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 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

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."
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LGBTQ Local Legal Protections

Apartments for Rent

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$1,400/mo
1 bd
1 ba
2326 US Route 5 North | 2326 US Route 5 N #C,
Windsor, VT 05089
$1,050 - $1,375/mo
Studio-2 bd
1 ba
55 River St,
Windsor, VT 05089
NEW - 7 HRS AGO
$1,225/mo
2 bd
1 ba
45-47 Ascutney Blvd #4,
Windsor, VT 05089
$1,650/mo
2 bd
1 ba
75 Union St #3,
Windsor, VT 05089
$1,136/mo
Studio
1 ba
18 Union St #C,
Windsor, VT 05089
$1,950/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
24 Durkee St #B,
Windsor, VT 05089
$1,800/mo
2 bd
1 ba
77 Union St #2,
Windsor, VT 05089
See more homes for rent in
Windsor
Take a look

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Explore by feature

$1,675/mo
1 bd
1 ba
68 Ascutney St,
Windsor, VT 05089
$2,950/mo
3 bd
1 ba
69 Belknap Ln,
Windsor, VT 05089
$1,325/mo
1 bd
1 ba
17 State St,
Windsor, VT 05089
$1,400/mo
1 bd
1 ba
2326 US Route 5 North | 2326 US Route 5 N #C,
Windsor, VT 05089
$1,950/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
$1,800/mo
2 bd
1 ba
77 Union St #2,
Windsor, VT 05089
6 rentals with a washer/dryer in Windsor, VT

Homes for sale near 38 Ascutney Street

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AUCTION
0.48 ACRES
$535,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
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
5.3 ACRES
$699,000
3 bd
2 ba
1,706 sqft
53 Sunset Strip 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
$115,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
Windsor, VT 05089
PrimeMLS, Active
15.12 ACRES
$625,000
5 bd
3 ba
3,510 sqft
330 Parsonage Road,
Cornish, NH 03745
PrimeMLS, Active
1.53 ACRES
$474,800
3 bd
2 ba
1,480 sqft
586 Ski Tow Road,
Brownsville, VT 05037
PrimeMLS, Active
0.84 ACRES
$369,000
2 bd
2 ba
1,192 sqft
39 Parsonage Road,
Cornish, NH 03745
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 38 Ascutney Street

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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 5, 2026
$425,000
3,700 sqft
64 State Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
APR 22, 2026
$295,000
3 bd
3 ba
1,594 sqft
72 Mountains Edge Road #508,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
APR 16, 2026
$650,000
3 bd
3 ba
3,018 sqft
528 Town House Rd,
Cornish, NH 03745
SOLD
APR 15, 2026
$650,000
3 bd
2.5 ba
3,816 sqft
528 Town House Road,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
APR 3, 2026
$530,000
4 bd
2.5 ba
2,468 sqft
223 Taylor Drive,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAR 13, 2026
$380,000
2 bd
1.5 ba
1,156 sqft
1507 Rte 12A,
Plainfield, NH 03781
PrimeMLS, Closed
SOLD
FEB 2, 2026
$299,000
2 bd
1 ba
936 sqft
22 Hammond Hill Road,
West Windsor, VT 05089
PrimeMLS, Closed
SOLD
JAN 29, 2026
$425,000
3 bd
1.5 ba
1,920 sqft
466 Parsonage Road,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
JAN 23, 2026
$426,000
4 bd
2.5 ba
1,832 sqft
473 Taylor Drive,
Windsor, VT 05089
PrimeMLS, Closed
See more homes for sale in
Windsor
Take a look

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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 2026-05-29 10:28:17 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.

Homes for rent near 38 Ascutney Street

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38 Ascutney Street, Windsor, VT 05089 is a 5 bedroom, 3 bathroom, 3,048 sqft single-family home built in 1885. This property is not currently available for sale. 38 Ascutney Street was last sold on May 10, 2023 for $485,000 (8% higher than the asking price of $449,000). The current Trulia Estimate for 38 Ascutney Street is $569,400.

38 Ascutney Street
Windsor, VT 05089

$569,400

$569,400

Local Information