Are yards well-kept in Windsor, MA?

As of early 2026, 100% of users say yards are well-kept

Are there community events in Windsor, MA?

As of early 2026, 100% of users say there are community events

Is a car needed in Windsor, MA?

As of early 2026, 100% of users say car is needed

Is there wildlife in Windsor, MA?

As of early 2026, 100% of users say there's wildlife

Are neighbors friendly in Windsor, MA?

As of early 2026, 50% of users say neighbors are friendly

Is parking easy in Windsor, MA?

As of early 2026, 50% of users say parking is easy

Would people walk alone at night in Windsor, MA?

As of early 2026, 50% of users say people would walk alone at night

What is 444 E Windsor Rd estimated to be worth?

Trulia's estimated value for 444 E Windsor Rd is $381,100 .

What is the price history for 444 E Windsor Rd?

444 E Windsor Rd last sold for $35,000 in October 1976.

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

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

What are the closest schools to 444 E Windsor Rd?

The closest schools to 444 E Windsor Rd are Craneville Elementary School (rated 7/10), Nessacus Regional Middle School (rated 7/10), Wahconah Regional High School (rated 6/10).

How big is the lot at 444 E Windsor Rd?

The lot at 444 E Windsor Rd is about 8.7 acres .

OFF MARKET

$381,100

Trulia Estimate

5 Beds
3 Baths
4,212 sqft (on 8.65 acres)

444 E Windsor Rd, Windsor, MA 01270

Est. Refi. Payment $2,577/mo*

Refinance Your Home

Currently Off Market - Sold Oct 28, 1976 for $35,000

Home Value

Trulia Estimate

$381K

Since last month

$10K (+2.7%)

Since last year

$43K (+12.7%)

Since last sale

$347K (+990.3%)

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 +63% in the last 10 years

Month	Estimated value
2026
September 2026	$382K
September 2026	$382K
August 2026	$372K
July 2026	$379K
June 2026	$364K
May 2026	$373K
April 2026	$331K
March 2026	$331K
January 2026	$319K
2025
December 2025	$319K
October 2025	$336K
September 2025	$339K
August 2025	$352K
July 2025	$357K
June 2025	$340K
May 2025	$361K
April 2025	$337K
March 2025	$379K
February 2025	$385K
January 2025	$350K
2024
December 2024	$396K
November 2024	$384K
October 2024	$393K
August 2024	$413K
July 2024	$419K
June 2024	$404K
May 2024	$367K
April 2024	$365K
February 2024	$326K
January 2024	$295K
2023
December 2023	$348K
November 2023	$488K
October 2023	$430K
September 2023	$440K
August 2023	$451K
July 2023	$430K
June 2023	$439K
2021
May 2021	$324K
April 2021	$313K
March 2021	$289K
February 2021	$252K
January 2021	$248K
2020
December 2020	$258K
November 2020	$264K
October 2020	$253K
September 2020	$257K
August 2020	$263K
July 2020	$256K
June 2020	$253K
May 2020	$244K
April 2020	$238K
March 2020	$235K
February 2020	$240K
January 2020	$241K
2019
December 2019	$233K
November 2019	$239K
October 2019	$248K
September 2019	$229K
August 2019	$227K
July 2019	$232K
June 2019	$235K
May 2019	$250K
April 2019	$243K
March 2019	$232K
February 2019	$222K
January 2019	$227K
2018
December 2018	$229K
November 2018	$230K
October 2018	$234K
September 2018	$233K
August 2018	$238K
July 2018	$237K
June 2018	$233K
May 2018	$231K
April 2018	$233K
March 2018	$229K
February 2018	$233K
January 2018	$221K
2017
December 2017	$226K
November 2017	$229K
October 2017	$223K
September 2017	$223K
August 2017	$221K
July 2017	$218K
June 2017	$203K
May 2017	$211K
April 2017	$212K
March 2017	$204K
February 2017	$193K
January 2017	$190K
2016
December 2016	$234K
November 2016	$231K
October 2016	$234K

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
2652 Highway 9 Trl, Windsor, MA	0.82	Single-Family Home	$288,400	10/23/25	2	2	2,080
915 High Street Hill Rd, Windsor, MA	1.27	Single-Family Home	$397,000	10/30/25	4	2	2,728
155 High Street Hill Rd, Windsor, MA	1.42	Single-Family Home	$685,000	10/30/25	3	2.5	2,572
449 High Street Hill Rd, Windsor, MA	1.30	Single-Family Home	$350,000	08/05/26	3	1.5	2,066
961 Peru Rd, Windsor, MA	1.14	Single-Family Home	$300,000	02/03/26	1	1	1,082
49 Access Rd #3B, Windsor, MA	1.34	Single-Family Home	$75,000	05/26/26	2	1	816
1689 E Windsor Rd, Windsor, MA	2.14	Single-Family Home	$385,000	01/09/26	3	1.5	1,632
74 E Windsor Rd, Peru, MA	2.61	Single-Family Home	$292,500	01/05/26	3	1	960
1130 Main Dalton Rd, Windsor, MA	3.62	Single-Family Home	$425,000	08/14/26	4	2	2,616
1752 Donna Lynn Dr, Cummington, GA	2.98	Single-Family Home	$175,000	01/16/26	3	1	1,260

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
M14-L11 E Windsor Rd, Windsor, MA 01270	0.06	-	-	-	-	Off Market
E Windsor Rd, Windsor, MA 01270	0.11	$30,000	-	-	-	Recently Sold
353 E Windsor Rd, Windsor, MA 01270	0.20	$449,600	4	1	2,501	Off Market
429 E Windsor Rd, Windsor, MA 01270	0.24	$215,800	3	1	1,024	Off Market
Nobodys Rd, Windsor, MA 01270	0.26	-	Studio	-	-	Off Market
663 E Windsor Rd, Windsor, MA 01270	0.30	$585,800	3	3	2,984	Off Market
663 E Windsor Rd, Windsor, MA 01270	0.30	-	-	-	-	Off Market
663 E Windsor Rd, Windsor, MA 01270	0.30	-	-	-	-	Off Market
Route 9, Windsor, MA 01270	0.32	-	-	-	-	Off Market
604 E Windsor Rd, Windsor, MA 01270	0.32	$449,100	3	1.5	1,764	Off Market
269 E Windsor Rd, Windsor, MA 01270	0.35	$599,600	3	2	2,038	Off Market
285 E Windsor Rd, Windsor, MA 01270	0.36	$174,600	1	1	563	Off Market
130 E Windsor Rd, Windsor, MA 01270	0.53	-	4	2	1,148	Off Market
835 Windsor Bush Rd, Windsor, MA 01270	0.54	-	3	1	1,152	Off Market
859 E Windsor Rd, Windsor, MA 01270	0.54	$228,100	1	1	945	Off Market
154 Windsor Bush Rd, Windsor, MA 01270	0.55	$769,500	4	3.5	3,348	Off Market
750 E Windsor Rd, Windsor, MA 01270	0.56	-	3	1	960	Off Market
143 WINDSOR BUSH RD, WINDSOR , MA 01270	0.57	-	2	2	1,014	Off Market
975 E Windsor Rd, Windsor, MA 01270	0.59	$1,597,600	4	4.5	4,977	Off Market
919 E Windsor Rd, Windsor, MA 01270	0.60	$272,100	2	1	960	Off Market

Local Information

Map ViewExplore the area around 444 E Windsor Rd.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1900

8.65 acre lot

4,212 sqft

$90/sqft

About this House

This single-family home is located at 444 E Windsor Rd, Windsor, MA. 444 E Windsor Rd is in Windsor, MA and in ZIP code 01270. This property has 5 bedrooms, 3 bathrooms and approximately 4,212 sqft of floor space. This property has a lot size of 8.65 acres and was built in 1900.

444 E Windsor Rd, Windsor, MA 01270 is a 5 bedroom, 3 bathroom, 4,212 sqft single-family home built in 1900. It last sold for $35,000 on Oct 28, 1976. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $381,100, with a rent estimate of $4,649/month.

Home Details for 444 E Windsor Rd

Interior Features
Interior Details BasementNumber of Rooms: 13
Heating & Cooling Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Wood

Property Information
Year Built Year Built: 1900
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 8.65 acres

Price and Tax history

Date	Event	Price
Oct 28, 1976 Source: N/A	Sold	$35,000

Year	Property tax	Tax assessment
2025	$1,184	$104,437

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Around this home

Craneville Elementary School
K-5
Public
450 Students
Central Berkshire School District
7/10
GreatSchools Rating
Parent Rating Average
Racial differences and bullying have been becoming a big issue . No equality, teacher kids are treated so special . Strong and rebellious kids always win . Being nice and kind is no where seen or appreciated. Students have no respect to their teachers. Role modeling or importance of olders or parents.
Other Review
2y ago
2 Reviews

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 1 Trulia users voted on each feature.

100 % Say yards are well-kept
100 % Say there are community events
100 % Say car is needed
100 % Say there's wildlife
50 % Say neighbors are friendly
50 % Say parking is easy
50 % Say people would walk alone at night

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 444 E Windsor Rd

What is 444 E Windsor Rd estimated to be worth?
Trulia's estimated value for 444 E Windsor Rd is $381,100.
What is the price history for 444 E Windsor Rd?
444 E Windsor Rd last sold for $35,000 in October 1976.
Is Windsor a buyer's or seller's market?
Windsor is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 444 E Windsor Rd?
The closest schools to 444 E Windsor Rd are Craneville Elementary School (rated 7/10), Nessacus Regional Middle School (rated 7/10), Wahconah Regional High School (rated 6/10).
How big is the lot at 444 E Windsor Rd?
The lot at 444 E Windsor Rd is about 8.7 acres.

Apartments for Rent

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APPLY INSTANTLY
PET FRIENDLY
$1,950/mo
Total price
2 bd
1 ba
24 W Main St #1,
Cummington, MA 01026
See more homes for rent in
Windsor
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Off Market Homes Near 444 E Windsor Rd

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SOLD
SEP 30, 2026
$430,000
4 bd
2 ba
1,296 sqft
48 Canterbury Ln,
Hinsdale, MA 01235
Sherry Street, REALTY STREET, LLC
SOLD
AUG 28, 2026
$386,000
2 bd
2 ba
1,296 sqft
221 Ashmere Rd,
Hinsdale, MA 01235
Victoria A Standring, Lamacchia Realty, Inc. - Dalton
SOLD
AUG 14, 2026
$425,000
4 bd
2 ba
2,616 sqft
1130 Main Dalton Rd,
Windsor, MA 01270
Brenda Anne Durant, KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
SOLD
AUG 5, 2026
$350,000
3 bd
1.5 ba
2,066 sqft
449 High Street Hill Rd,
Windsor, MA 01270
Kolleen E. Schmitt, KELLER WILLIAMS REALTY
SOLD
AUG 3, 2026
$305,000
3 bd
1 ba
1,117 sqft
4 David Dr,
Peru, MA 01235
Jessie Downer, Lamacchia Realty, Inc. - Dalton
SOLD
JUL 8, 2026
$360,000
3 bd
2 ba
1,568 sqft
78 E Main Rd,
Peru, MA 01235
Jessie Carlino, MACCARO REAL ESTATE
SOLD
MAR 27, 2026
$333,000
1 bd
1 ba
1,031 sqft
13 Jordan Rd,
Cummington, MA 01026
Barbara Osborne, ASHMERE REALTY, INC.
SOLD
FEB 3, 2026
$300,000
1 bd
1 ba
1,082 sqft
961 Peru Rd,
Windsor, MA 01270
Carla Ness, Delap Real Estate LLC
SOLD
JAN 9, 2026
$385,000
3 bd
1.5 ba
1,632 sqft
1689 E Windsor Rd,
Windsor, MA 01270
Tanya LeRose, THE KINDERHOOK GROUP
SOLD
JAN 5, 2026
$292,500
3 bd
1 ba
960 sqft
74 E Windsor Rd,
Peru, MA 01235
Maureen Kirby, NOCHER REALTY
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Windsor
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Homes for sale near 444 E Windsor Rd

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OPEN SAT, 1-2:30PM
3.24 ACRES
$724,900
5 bd
3.5 ba
3,744 sqft
255 High Street Hill Rd,
Windsor, MA 01270
Reciprocal Reciprocal, Berkshire Reciprocal
OPEN SAT, 11-12:30PM
2.5 ACRES
$499,900
3 bd
3 ba
2,142 sqft
1273 Old Route 9,
Windsor, MA 01270
John M. Ciepiela, BISHOP WEST REAL ESTATE
1 ACRE
$239,900
3 bd
2 ba
1,104 sqft
6 Frary Rd,
Peru, MA 01235
Jesse Dimitropolis, RE/MAX COMPASS
3 ACRES
$395,000
3 bd
1 ba
1,236 sqft
1760 Route 9,
Windsor, MA 01270
THE KAHN TEAM, BISHOP WEST REAL ESTATE
OPEN SAT, 11-12:30PM
3.5 ACRES
$300,000
2 bd
1 ba
960 sqft
1640 State Highway 9,
Windsor, MA 01270
Andrew Manns, Lamacchia Realty, Inc. - Dalton
NEW - 23 HRS AGO
5.49 ACRES
$799,000
5 bd
4.5 ba
5,209 sqft
23 E Windsor Rd,
Worthington, MA 01098
James Adams, Hilltown Real Estate by Adams Realty
8.1 ACRES
$129,900
1 bd
1 ba
547 sqft
96 West St,
Plainfield, MA 01070
Nadine Hiser, KRG - Key Realty Group
$595,275
4 bd
3 ba
3,600 sqft
275 Pine Cone Ln,
Hinsdale, MA 01235
Barbara Osborne, ASHMERE REALTY, INC.
5 ACRES
$104,900
3 bd
1.5 ba
1,120 sqft
1155 Main Rd,
Savoy, MA 01256
Sara Bresett, NOCHER REALTY
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