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

What is 21 Cherry Street estimated to be worth?

Trulia's estimated value for 21 Cherry Street in Windsor, VT is $245,100 .

What is the price history for 21 Cherry Street?

21 Cherry Street in Windsor, VT last sold for $198,000 in December 2023.

Is Windsor a buyer's or seller's market?

Windsor is currently a buyer's market, based on recent for-sale activity.

What do residents say about Windsor?

Residents describe Windsor, VT as dog-friendly, well-kept, and walkable to grocery stores. See recently sold homes in Windsor, VT .

OFF MARKET

Listed by Leila Tarantelli, KW Coastal and Lakes & Mountains Realty/Hanover, (603) 610-8500 . Bought with KW Vermont - Montpelier

21 Cherry Street
Windsor, VT 05089

2 Beds
2 Baths
1,354 sqft

$245,100

Trulia Estimate

as of Aug 9, 2026

$245,100

Trulia Estimate

as of Aug 9, 2026

2 Beds

2 Baths

1,354 sqft

Local Information

Map ViewExplore the area around 21 Cherry Street.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Multi-Family

Year Built

1910

Living Area

1,354 sqft

Price/Sqft

$181

Parking

Open Parking

Last check for updates: about 13 hours ago

Listed by Leila Tarantelli

KW Coastal and Lakes & Mountains Realty/Hanover, (603) 610-8500

Bought with: Linda Winter, KW Vermont - Montpelier, (802) 654-8500

Source: PrimeMLS, MLS#4976750

About this House

This Sears home has stood the test of time of that bygone era where quality home building was the pride of America. One of the first pioneers in the prefab world, Sears homes were built with quality materials as the bones of this home so proudly show. The roof line is straight, the floors are level, the basement is dry and the little details such as stain glass windows and wood staircases still function as they did in the early 1900's. Converted into a two unit home several years back, this home has been a steady income producer for the owner over the last several years. As life changes so do needs thus this home is ready for its new stewards. The first floor apartment is vacant in the event an owner would like to occupy it and offset their mortgage with the income produced from the 2nd floor tenant. Rentals being in high demand, the first floor unit will have no problem finding an occupant should the owner desire. Walking distance from beautiful Mill Pond with a public beach for your use, the location can't be beat!

21 Cherry Street, Windsor, VT 05089 is a 2 bedroom, 2 bathroom, 1,354 sqft multi-family built in 1910. It last sold for the $198,000 asking price on Dec 12, 2023. It is currently off market. The Trulia Estimate is $245,100, with a rent estimate of $1,790/month.

Home Details for 21 Cherry Street

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Concrete Floor,Full,Interior Stairs,Unfinished,Interior Access,Exterior Entry,Basement Stairs,Interior Entry
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 1354 Square Feet
Appliances & Utilities Utilities: Cable, SatelliteAppliances: Electric Water Heater
Heating & Cooling Heating: Oil,Baseboard,Hot Water,House Unit,Zoned,Radiant,Radiant Floor,RadiatorNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric Electric: 200+ Amp Service, Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Wood
Levels, Entrance, & Accessibility Number of Stories: 2Levels: TwoFloors: Wood
View No View

Exterior Features
Exterior Home Features Roof: Asphalt ShinglePatio / Porch: Covered PorchFoundation: Brick, Concrete
Parking & Garage No CarportNo GarageHas Open ParkingParking: Paved,Driveway,On Site,Unassigned
Frontage Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 60
Finished Area Finished Area (above surface): 1354 Square Feet

Property Information
Year Built Year Built: 1910
Property Type / Style Property Type: Residential IncomeProperty Subtype: Multi FamilyArchitecture: Craftsman
Building Construction Materials: Wood Frame, Clapboard ExteriorNot a New Construction
Property Information Not Included in Sale: Garage that spans both lots will be torn down and is not being conveyed with the sale.

Price & Status
Price List Price: $198,000

Location
Direction & Address City: Windsor

Building
Building Area Building Area: 2036 Square Feet

Lot Information
Lot Area: 8276.4 sqft

Miscellaneous
BasementMls Number: 4976750Above Grade Unfinished Area: 1354Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 682Below Grade Unfinished Area Source: AssessorBelow Grade Unfinished Area Units: Square Feet

Price History for 21 Cherry Street

Date	Price	Event	Source
12/12/2023	$198,000	Sold	PrimeMLS #4976750
Recording Date 12/12/2023 County Transfer Tax N/A Total Transfer Tax N/A
11/09/2023	$198,000	Contingent	PrimeMLS #4976750

11/04/2023	$198,000	Listed For Sale	PrimeMLS #4976750

04/30/2007	$180,000	Sold	N/A
Recording Date 04/30/2007 Contract Date 04/27/2007 County Transfer Tax N/A Total Transfer Tax $1,500

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	$205,660

Home facts updated by county records

Comparable Sales for 21 Cherry Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
102-104 State Street, Windsor, VT	0.60	Multi-Family Home	$250,000	10/02/25	7	4	3,894
64 State Street, Windsor, VT	0.71	Multi-Family Home	$425,000	05/05/26		-	3,700
7 and 7A Brownsville Road, Hartland, VT	4.98	Multi-Family Home	$560,000	10/20/25		-	2,525
248 Main Street, Claremont, NH	7.27	Multi-Family Home	$175,000	01/15/26	3	2	1,405
110 Lafayette Street, Claremont, NH	7.29	Multi-Family Home	$300,000	04/16/26	6	2	2,160
4 Freedom Street, Claremont, NH	7.37	Multi-Family Home	$120,000	03/04/26		-	1,840
211 north Street, Claremont, NH	7.18	Multi-Family Home	$327,500	04/21/26		3	3,072
232 North Street, Claremont, NH	7.15	Multi-Family Home	$375,000	01/09/26		4	3,082

Nearby homes

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

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OFF MARKET
Est. $286,900
3 bd
2 ba
1,264 sqft
42 Elm Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $287,400
4 bd
1.5 ba
1,400 sqft
4 Kiniry 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
DEC 4, 2025
$94,900
2 bd
1 ba
660 sqft
16 Day Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $324,000
4 bd
1.5 ba
2,554 sqft
119 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
NOV 21, 2025
$315,000
2 bd
1.5 ba
1,649 sqft
1 Dorrance Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $383,200
3 bd
1.5 ba
1,493 sqft
3 Bavier 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. $207,500
2 bd
1 ba
786 sqft
6 Bavier Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $244,700
2 bd
1 ba
696 sqft
141 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
FOR SALE
NEW
$350,000
2 bd
1.5 ba
1,092 sqft
143 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Active

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Additional Cost

Assigned Schools

These are the assigned schools for 21 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
6y 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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$1,325/mo
1 bd
1 ba
9 State Street | 9 State St,
Windsor, VT 05089
$1,325 - $1,350/mo
1 bd
1 ba
24 State Street | 24 State St,
Windsor, VT 05089
$1,425/mo
1 bd
1 ba
112-114 State St #114A,
Windsor, VT 05089
$1,895/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,500 - $1,700/mo
1-2 bd
1 ba
360 Tecumseh Road West | 360 Tecumseh Rd W,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
65 State St #f320a52c6,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
289 County Rd #f320a52c6,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
92 Cedar Hill Dr #f320a52c6,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
APPLY INSTANTLY
PET FRIENDLY
$2,500/mo
3 bd
2.5 ba
178 Pierce Hill Rd #2,
Brownsville, VT 05037
PET FRIENDLY
$2,700/mo
4 bd
2.5 ba
178 Pierce Hill Rd #1,
Brownsville, VT 05037
See more homes for rent in
Windsor
Take a look

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Homes for sale near 21 Cherry Street

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$442,999
3 bd
2 ba
1,961 sqft
6 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
5.83 ACRES
$1,576,000
9,455 sqft
14/16 Summarsell Drive,
Hartland, VT 05048
PrimeMLS, Active
1 ACRE
$452,600
3 ba
2,915 sqft
282 Skunk Hollow Road,
Hartland, VT 05048
PrimeMLS, Active
0.36 ACRES
$280,000
2,440 sqft
89 Belding Street,
Claremont, NH 03743
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 21 Cherry Street

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SOLD
JUL 24, 2026
$300,000
3 bd
3 ba
1,594 sqft
70 Mountains Edge Road #606,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
JUL 23, 2026
$319,000
4 bd
2 ba
2,142 sqft
74 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
JUL 13, 2026
$175,000
3 bd
2 ba
1,527 sqft
271 Tandy Brook Rd,
Cornish, NH 03745
SOLD
JUL 6, 2026
$260,000
00 Tandy Brook Road #12,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
JUL 1, 2026
$222,030
1214 State St,
Windsor, VT 05089
SOLD
JUN 30, 2026
$200,000
245 Orchard Ln,
Windsor, VT 05089
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 22, 2026
$260,000
95 Mountains Edge Rd #102,
Brownsville, VT 05037
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
See more homes for sale in
Windsor
Take a look

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Frequently asked questions about 21 Cherry Street

What is 21 Cherry Street estimated to be worth?
Trulia's estimated value for 21 Cherry Street in Windsor, VT is $245,100.
What is the price history for 21 Cherry Street?
21 Cherry Street in Windsor, VT last sold for $198,000 in December 2023.
Is Windsor a buyer's or seller's market?
Windsor is currently a buyer's market, based on recent for-sale activity.
What do residents say about Windsor?
Residents describe Windsor, VT as dog-friendly, well-kept, and walkable to grocery stores. See recently sold homes in Windsor, VT.

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 2026-08-08 11:38:38 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.

21 Cherry Street
Windsor, VT 05089

$245,100

$245,100