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

SOLD

MAY 1, 2026

Listed by Katie Ladue Gilbert, BHHS Verani Upper Valley, (603) 643-8822 . Bought with BHHS Verani Upper Valley

3 Cherry Street
Windsor, VT 05089

3 Beds
1 Bath
1,176 sqft

$259,000

Last Sold: May 1, 2026

$220/sqft

$259,000

Last Sold: May 1, 2026

$220/sqft

3 Beds

1 Bath

1,176 sqft

Local Information

-- mins to

Commute Destination

Last check for updates: about 2 hours ago

Listed by Katie Ladue Gilbert

BHHS Verani Upper Valley, (603) 643-8822

Allison Griep

BHHS Verani Upper Valley, (603) 643-8822

Bought with: Carter Auch, BHHS Verani Upper Valley, (603) 643-8822

Source: PrimeMLS, MLS#5079791

Description

Classic Vermont character meets everyday convenience in this sweet in-town New Englander. Set in the heart of Windsor, this three-bedroom, one-bath home puts you steps from local shops, dining, and all the charm of one of Vermont's most historic villages. Inside, a fireplace anchors the living space, offering the kind of warmth that makes a New England winter something to look forward to. The thoughtful layout makes the most of every square foot, with comfortable bedrooms and a functional flow throughout. Outside, a detached garage provides coveted covered parking and additional storage — a true Vermont essential. The in-town location means walkability without sacrificing the quiet, neighborly feel that defines life in the Upper Valley. Whether you're a first-time buyer, looking to downsize, or searching for a Vermont retreat, this is a home that delivers on all the right things: location, character, and comfort.

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 01, 2026

Home Highlights

Parking

Garage

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

$220/sqft

Listed

95 days ago

Home Details for 3 Cherry Street

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Unfinished,Interior EntryNumber of Rooms: 6
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout Living Area: 1176 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Dishwasher, Dryer, Gas Range, Refrigerator, WasherDishwasherDryerRefrigeratorWasher
Heating & Cooling Heating: Forced AirNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Forced Air
Gas & Electric Electric: 100 Amp Service
Windows, Doors, Floors & Walls Flooring: Hardwood, Vinyl Plank
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Hardwood, Vinyl Plank
View No View

Exterior Features
Exterior Home Features Roof: Metal Standing SeamPatio / Porch: PorchExterior: Deck, Garden, StorageFoundation: ConcreteGarden
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageParking Spaces: 2Parking: Gravel
Frontage Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 100
Finished Area Finished Area (above surface): 1176 Square Feet

Property Information
Year Built Year Built: 1934
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: New Englander
Building Construction Materials: Wood FrameNot a New Construction

Price & Status
Price List Price: $259,000Price Per Sqft: $220/sqft

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

Building
Building Area Building Area: 1576 Square Feet

Lot Information
Lot Area: 7841 sqft

Miscellaneous
BasementMls Number: 5079791Attribution Contact: Cell: 802-299-7522Above Grade Unfinished Area: 1176Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 400Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price History for 3 Cherry Street

Date	Price	Event	Source
05/01/2026	$259,000	Sold	PrimeMLS #5079791
Recording Date 05/01/2026 County Transfer Tax N/A Total Transfer Tax N/A
03/23/2026	$259,000	Pending	PrimeMLS #5079791

03/18/2026	$259,000	Listed For Sale	PrimeMLS #5079791

03/17/2026	$259,900	ListingRemoved	PrimeMLS #5078706

03/09/2026	$259,900	Listed For Sale	PrimeMLS #5078706

Market trends in Windsor

Last updated May 2026

Avg. sale price

—

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	$188,510

Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,398/mo

List your home for rent

Homes for rent near 3 Cherry Street

See what comparable homes in the neighborhood are renting for.

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$1,750/mo
2 bd
1 ba
873 sqft
77 Union St #2,
Windsor, VT 05089
$1,650/mo
2 bd
1 ba
75 Union St #3,
Windsor, VT 05089
$1,575/mo
2 bd
1 ba
45-47 Ascutney Blvd #4,
Windsor, VT 05089
$2,250/mo
3 bd
1 ba
21-23 Maple St,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$2,900/mo
3 bd
1 ba
69 Belknap Ln,
Windsor, VT 05089
2 bd
2 ba
65 State St #f320a52c6,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
24 Durkee St #B,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
$1,795/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
See more homes for rent in
Windsor
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Comparable Sales for 3 Cherry Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
21 Bavier Avenue, Windsor, VT	0.22	Single-Family Home	$256,500	11/14/25	3	1	1,232
10 McKenzie Drive, Windsor, VT	0.31	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
6 Bavier Avenue, Windsor, VT	0.27	Single-Family Home	$200,000	08/27/25	2	1	786
1 Dorrance Street, Windsor, VT	0.25	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
32 Clough Avenue, Windsor, VT	0.25	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
16 Day Street, Windsor, VT	0.25	Single-Family Home	$94,900	12/04/25	2	1	660
66 Union Street, Windsor, VT	0.26	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

Nearby homes

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

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OFF MARKET
Est. $281,600
3 bd
1 ba
1,025 sqft
20 Elm Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $248,600
2 bd
2 ba
1,354 sqft
21 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $274,000
4 bd
1.5 ba
1,400 sqft
4 Kiniry Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $282,800
3 bd
2 ba
1,264 sqft
42 Elm Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $326,200
4 bd
1.5 ba
2,554 sqft
119 Ascutney Street,
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
SOLD
NOV 14, 2025
$256,500
3 bd
1 ba
1,232 sqft
21 Bavier Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $278,300
3 bd
4 ba
2,052 sqft
4 Old Mill Pond Road #4,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $376,700
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. $260,800
2 bd
1.5 ba
945 sqft
1 Fitch Court,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 3 Cherry 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."
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Apartments for Rent

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$1,350/mo
1 bd
1 ba
24 State St #1,
Windsor, VT 05089
$1,575/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
$1,450/mo
2 bd
1 ba
55 River St #B,
Windsor, VT 05089
$1,795/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
$1,750/mo
2 bd
1 ba
77 Union St #2,
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
See more homes for rent in
Windsor
Take a look

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Explore by feature - Washer/dryer

$2,250/mo
3 bd
1 ba
21-23 Maple St,
Windsor, VT 05089
$1,675/mo
1 bd
1 ba
68 Ascutney St,
Windsor, VT 05089
$2,900/mo
3 bd
1 ba
69 Belknap Ln,
Windsor, VT 05089
$1,795/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
$1,750/mo
2 bd
1 ba
77 Union St #2,
Windsor, VT 05089

Homes for sale near 3 Cherry Street

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4.96 ACRES
$1,399,000
4 bd
3.5 ba
3,720 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Active
AUCTION
0.48 ACRES
$515,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
$110,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
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
5.25 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
1.53 ACRES
$474,800
3 bd
2 ba
1,480 sqft
586 Ski Tow Road,
Brownsville, VT 05037
PrimeMLS, Active
5.51 ACRES
$1,345,000
7 bd
5 ba
5,774 sqft
310 Pierce Hill Road,
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
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 3 Cherry Street

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SOLD
JUN 10, 2026
$139,000
1 bd
1 ba
768 sqft
38 Jarvis Street,
Windsor, VT 05089
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
$195,000
3 bd
1,604 sqft
295 Hotel Road #10/10A,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
APR 30, 2026
$142,500
3 bd
2 ba
1,549 sqft
66 Country Skyline Boulevard,
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
SOLD
APR 17, 2026
$185,000
2 bd
1.5 ba
850 sqft
295 Hotel Road #15,
Windsor, VT 05089
PrimeMLS, Closed
See more homes for sale in
Windsor
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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 2026-06-22 00:14:27 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.

3 Cherry Street, Windsor, VT 05089 is a 3 bedroom, 1 bathroom, 1,176 sqft single-family home built in 1934. This property is not currently available for sale. 3 Cherry Street was last sold on May 1, 2026 for $259,000 (0% higher than the asking price of $259,000). The current Trulia Estimate for 3 Cherry Street is $260,000.

3 Cherry Street
Windsor, VT 05089

$259,000

$259,000

Local Information