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 5 Cherry St estimated to be worth?

Trulia's estimated value for 5 Cherry St in Windsor, VT is $380,000 .

What is the price history for 5 Cherry St?

5 Cherry St in Windsor, VT last sold for $214,900 in November 2017.

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 .

Does 5 Cherry St have laundry facilities?

Yes, 5 Cherry St in Windsor, VT has in-unit laundry.

How big is the lot at 5 Cherry St?

The lot at 5 Cherry St in Windsor, VT is about 0.36 acres (15,682 sq ft).

OFF MARKET

$380,000

Trulia Estimate

4 Beds
1.5 Baths
1,808 sqft (on 0.36 acres)

5 Cherry St, Windsor, VT 05089

Est. Refi. Payment $2,768/mo*

Refinance Your Home

Currently Off Market - Sold Nov 6, 2017 for $214,900

Home Value

Trulia Estimate

$380K

Since last month

$600 (+0.2%)

Since last year

$1K (+0.3%)

Since last sale

$165K (+76.8%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +109% in the last 10 years

Month	Estimated value
2026
September 2026	$380K
September 2026	$380K
August 2026	$379K
July 2026	$388K
June 2026	$393K
May 2026	$391K
April 2026	$380K
March 2026	$377K
February 2026	$364K
January 2026	$364K
2025
December 2025	$366K
November 2025	$373K
October 2025	$372K
September 2025	$379K
August 2025	$385K
July 2025	$396K
June 2025	$395K
May 2025	$376K
April 2025	$368K
March 2025	$359K
February 2025	$351K
January 2025	$350K
2024
December 2024	$351K
November 2024	$359K
October 2024	$372K
September 2024	$371K
August 2024	$369K
July 2024	$371K
June 2024	$366K
May 2024	$371K
April 2024	$363K
March 2024	$351K
February 2024	$343K
January 2024	$344K
2023
December 2023	$341K
November 2023	$352K
October 2023	$356K
September 2023	$358K
August 2023	$362K
July 2023	$359K
June 2023	$355K
May 2023	$343K
April 2023	$332K
March 2023	$324K
February 2023	$316K
January 2023	$309K
2022
December 2022	$313K
November 2022	$318K
October 2022	$321K
September 2022	$322K
August 2022	$324K
July 2022	$327K
June 2022	$326K
May 2022	$322K
April 2022	$312K
March 2022	$304K
February 2022	$293K
January 2022	$291K
2021
December 2021	$290K
November 2021	$289K
October 2021	$289K
September 2021	$286K
August 2021	$286K
July 2021	$282K
June 2021	$263K
May 2021	$229K
April 2021	$229K
March 2021	$222K
February 2021	$229K
January 2021	$229K
2020
December 2020	$245K
October 2020	$250K
September 2020	$246K
August 2020	$244K
July 2020	$241K
June 2020	$236K
May 2020	$232K
April 2020	$230K
March 2020	$231K
February 2020	$230K
January 2020	$231K
2019
December 2019	$230K
November 2019	$228K
October 2019	$227K
September 2019	$228K
August 2019	$227K
July 2019	$226K
June 2019	$225K
May 2019	$225K
April 2019	$223K
March 2019	$209K
February 2019	$209K
January 2019	$214K
2018
December 2018	$221K
November 2018	$223K
October 2018	$223K
September 2018	$220K
August 2018	$220K
July 2018	$220K
June 2018	$219K
May 2018	$219K
April 2018	$219K
March 2018	$218K
February 2018	$218K
January 2018	$216K
2017
December 2017	$215K
November 2017	$215K
October 2017	$211K
September 2017	$208K
August 2017	$208K
July 2017	$205K
June 2017	$215K
May 2017	$215K
April 2017	$185K
March 2017	$188K
February 2017	$185K
January 2017	$183K
2016
December 2016	$183K
November 2016	$183K
October 2016	$182K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
3 Cherry Street, Windsor, VT	0.03	Single-Family Home	$259,000	05/01/26	3	1	1,176
74 Union Street, Windsor, VT	0.26	Single-Family Home	$319,000	07/23/26	4	2	2,142
24 Cherry Street, Windsor, VT	0.10	Single-Family Home	$235,000	09/30/26	3	1	1,095
31 Maple Street, Windsor, VT	0.47	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
4 Bavier Avenue, Windsor, VT	0.23	Single-Family Home	$226,000	08/07/26	3	1	2,088
1 Dorrance Street, Windsor, VT	0.22	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
21 Bavier Avenue, Windsor, VT	0.20	Single-Family Home	$256,500	11/14/25	3	1	1,232
10 McKenzie Drive, Windsor, VT	0.34	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
16 Day Street, Windsor, VT	0.22	Single-Family Home	$94,900	12/04/25	2	1	660
5 Clough Avenue, Windsor, VT	0.32	Single-Family Home	$60,000	12/18/25	3	1	1,392

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
2 Cherry St, Windsor, VT 05089	0.03	$273,400	Studio	-	-	Off Market
8 Cherry St, Windsor, VT 05089	0.03	$286,700	4	3	1,764	Off Market
4 Crystal St, Windsor, VT 05089	0.03	$321,300	6	2	-	Off Market
6 Cherry St, Windsor, VT 05089	0.03	$269,700	Studio	-	-	Off Market
3 Cherry Street, Windsor, VT 05089	0.03	$259,000	3	1	1,176	Recently Sold
10 Cherry St, Windsor, VT 05089	0.03	$458,700	Studio	-	-	Off Market
8 Terrace St, Windsor, VT 05089	0.03	$277,800	Studio	-	-	Off Market
4 Terrace St, Windsor, VT 05089	0.04	$279,800	Studio	-	-	Off Market
2 Terrace St, Windsor, VT 05089	0.04	$276,700	Studio	-	-	Off Market
2 Crystal St, Windsor, VT 05089	0.04	$212,300	Studio	-	-	Off Market
14 Cherry St, Windsor, VT 05089	0.04	$199,200	2	1	850	Off Market
4 Pleasant St, Windsor, VT 05089	0.04	$277,100	Studio	-	-	Off Market
11 Cherry St, Windsor, VT 05089	0.05	$359,600	8	4	2,600	Off Market
35 Crystal St, Windsor, VT 05089	0.05	$303,800	Studio	-	-	Off Market
9 Elm St, Windsor, VT 05089	0.05	$261,700	3	1.5	1,400	Off Market
16 Cherry St, Windsor, VT 05089	0.05	$211,600	Studio	-	-	Off Market
11 Elm St, Windsor, VT 05089	0.06	$223,600	Studio	-	-	Off Market
5 Elm St, Windsor, VT 05089	0.06	$227,400	3	1	1,200	Off Market
18 Cherry St, Windsor, VT 05089	0.06	$223,500	3	1	925	Off Market
10 Elm St, Windsor, VT 05089	0.07	$224,800	3	2	1,050	Off Market

Local Information

Map ViewExplore the area around 5 Cherry St.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1937

0.36 acre lot

1,808 sqft

$210/sqft

Garage

About this House

This single-family home is located at 5 Cherry St, Windsor, VT. 5 Cherry St is in Windsor, VT and in ZIP code 05089. This property has 4 bedrooms, 2 bathrooms and approximately 1,808 sqft of floor space. This property has a lot size of 0.36 acres and was built in 1937.

5 Cherry St, Windsor, VT 05089 is a 4 bedroom, 2 bathroom, 1,808 sqft single-family home built in 1937. It last sold for $214,900 on Nov 6, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $380,000, with a rent estimate of $3,117/month.

Home Details for 5 Cherry St

Interior Features
Heating & Cooling Heating: Baseboard, Oil, Wood PelletHeating Fuel: Baseboard
Interior Details Types of Rooms: Walk In Closet, Dining Room, Library, Sun Room
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace
Levels, Entrance, & Accessibility Floors: Tile, Hardwood

Property Information
Year Built Year Built: 1937
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Exterior Features
Exterior Home Features DeckExterior: WoodGarden
Parking & Garage GarageParking: Garage Detached

Lot Information
Lot Area: 0.36 acres

Price and Tax history

Date	Event	Price
Nov 6, 2017 Source: PrimeMLS #4647842	Sold	$214,900
Aug 5, 2017 Source: Agent Provided	Pending	$214,900
Jul 18, 2017 Source: Agent Provided	PriceChange	$214,900 Price decreased by 4%
May 2, 2017 Source: Agent Provided	Listed For Sale	$225,000

Year	Property tax	Tax assessment
2025	$7,466	$290,170

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

Around this home

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."
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5 Cherry St

What is 5 Cherry St estimated to be worth?
Trulia's estimated value for 5 Cherry St in Windsor, VT is $380,000.
What is the price history for 5 Cherry St?
5 Cherry St in Windsor, VT last sold for $214,900 in November 2017.
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.
Does 5 Cherry St have laundry facilities?
Yes, 5 Cherry St in Windsor, VT has in-unit laundry.
How big is the lot at 5 Cherry St?
The lot at 5 Cherry St in Windsor, VT is about 0.36 acres (15,682 sq ft).