237 Cheshire Rd, Windsor, MA 01270
OFF MARKET

$524,100

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,544 sqft (on 4.46 acres)

237 Cheshire Rd, Windsor, MA 01270

Est. Refi. Payment $3,346/mo*
Refinance Your Home
Currently Off Market - Sold Jun 1, 1999 for $171,000

Home Value

Trulia Estimate
$524K
Since last month
Decreased$5K (-0.8%)
Since last year
Increased$5K (+0.9%)
Since last sale
Increased$355K (+207.4%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$526K
August 2026$523K
July 2026$530K
June 2026$533K
May 2026$528K
April 2026$519K
March 2026$507K
February 2026$497K
January 2026$492K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
1340 North St, Windsor, MA
1.42
Single-Family Home
$350,100
08/11/26
2
1.5
1,043
205 Windsor Rd, Savoy, MA
1.57
Single-Family Home
$360,000
02/03/26
3
2
1,650
137 Windsor Rd, Savoy, MA
1.79
Single-Family Home
$376,000
10/10/25
3
2
1,152
30 Jackson Rd, Savoy, MA
1.78
Single-Family Home
$205,000
08/18/26
2
1
1,421
86 Sandmill Hl, Cheshire, MA
2.30
Single-Family Home
$515,000
09/19/25
3
2
1,822
86 Sand Mill Hill Rd, Cheshire, MA
2.31
Single-Family Home
$515,000
09/19/25
3
2
1,576
829 Main Rd, Savoy, MA
2.65
Single-Family Home
$419,900
11/14/25
4
3
2,419
141 Griffin Hill Rd, Savoy, MA
1.97
Single-Family Home
$715,000
07/01/26
3
3
2,078
788 Flintstone Rd, Windsor, MA
2.37
Single-Family Home
$600,000
10/16/25
4
3
1,914
1416 Windsor Rd, Cheshire, MA
2.60
Single-Family Home
$175,000
01/14/26
3
1
1,000

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
249 Bates Rd, Windsor, MA 01270
0.81
$1,539,100
4
4.5
5,000
Off Market
576 North St, Windsor, MA 01270
1.35
$452,000
4
2
2,444
Off Market
775 North St, Windsor, MA 01270
1.38
$443,800
3
2
1,472
Off Market
733 North St, Windsor, MA 01270
1.39
$692,400
3
2.5
2,350
Off Market
1340 North St, Windsor, MA 01270
1.42
$350,100
2
1.5
1,043
Recently Sold
North St, Windsor, MA 01270
1.46
$99,900
-
-
-
For Sale
1496 North St, Windsor, MA 01270
1.51
$570,900
4
2.5
2,241
Off Market

Local Information

  • Map ViewExplore the area around 237 Cheshire Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1994
4.46 acre lot
2,544 sqft
$206/sqft

About this House

This single-family home is located at 237 Cheshire Rd, Windsor, MA. 237 Cheshire Rd is in Windsor, MA and in ZIP code 01270. This property has 4 bedrooms, 2 bathrooms and approximately 2,544 sqft of floor space. This property has a lot size of 4.46 acres and was built in 1994.
237 Cheshire Rd, Windsor, MA 01270 is a 4 bedroom, 2 bathroom, 2,544 sqft single-family home built in 1994. It last sold for $171,000 on Jun 1, 1999. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $524,100, with a rent estimate of $3,662/month.

Home Details for 237 Cheshire Rd

Interior Features

Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 4.46 acres

Price and Tax history

DateEventPrice
Jun 1, 1999
Source: N/A
Sold
$171,000

Market trends in Windsor

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
7

Around this home

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 237 Cheshire Rd

  • What is 237 Cheshire Rd estimated to be worth?
    Trulia's estimated value for 237 Cheshire Rd in Windsor, MA is $524,100.
  • What is the price history for 237 Cheshire Rd?
    237 Cheshire Rd in Windsor, MA last sold for $171,000 in June 1999.
  • 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 237 Cheshire Rd?
    The closest schools to 237 Cheshire Rd in Windsor, MA 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 237 Cheshire Rd?
    The lot at 237 Cheshire Rd in Windsor, MA is about 4.5 acres.

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Off Market Homes Near 237 Cheshire Rd

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