Is Cheshire, MA dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Is a car needed in Cheshire, MA?

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

Are yards well-kept in Cheshire, MA?

As of early 2026, 88% of users say yards are well-kept

Does Cheshire, MA show holiday spirit?

As of early 2026, 86% of users say there's holiday spirit

Are there community events in Cheshire, MA?

As of early 2026, 86% of users say there are community events

Is parking easy in Cheshire, MA?

As of early 2026, 83% of users say parking is easy

Do kids play outside in Cheshire, MA?

As of early 2026, 83% of users say kids play outside

Is there wildlife in Cheshire, MA?

As of early 2026, 83% of users say there's wildlife

Are neighbors friendly in Cheshire, MA?

As of early 2026, 81% of users say neighbors are friendly

Would people walk alone at night in Cheshire, MA?

As of early 2026, 71% of users say people would walk alone at night

Is Cheshire, MA walkable to restaurants?

As of early 2026, 63% of users say it's walkable to restaurants

Does Cheshire, MA have sidewalks?

As of early 2026, 57% of users say there are sidewalks

Is Cheshire, MA quiet?

As of early 2026, 56% of users say it's quiet

Do residents of Cheshire, MA plan to stay at least 5 years?

As of early 2026, 56% of users say they plan to stay for at least 5 years

Are the streets well-lit in Cheshire, MA?

As of early 2026, 44% of users say streets are well-lit

Is Cheshire, MA walkable to grocery stores?

As of early 2026, 25% of users say it's walkable to grocery stores

What is 165 Devonshire Dr estimated to be worth?

Trulia's estimated value for 165 Devonshire Dr in Cheshire, MA is $276,500 .

What is the price history for 165 Devonshire Dr?

165 Devonshire Dr in Cheshire, MA last sold for $5,500 in May 1976.

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

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

What are the closest schools to 165 Devonshire Dr?

The closest schools to 165 Devonshire Dr in Cheshire, MA are Hoosac Valley High School (Middle, rated 3/10), Hoosac Valley Middle School (Elementary, rated 3/10), Plunkett Elementary School (Pre-K, rated 1/10).

How big is the lot at 165 Devonshire Dr?

The lot at 165 Devonshire Dr in Cheshire, MA is about 0.34 acres (14,810 sq ft).

OFF MARKET

$276,500

Trulia Estimate

3 Beds
1 Bath
1,008 sqft (on 0.34 acres)

165 Devonshire Dr, Cheshire, MA 01225

Est. Refi. Payment $1,801/mo*

Refinance Your Home

Currently Off Market - Sold May 4, 1976 for $5,500

Home Value

Trulia Estimate

$277K

Since last month

$5K (-1.8%)

Since last year

$8K (+2.8%)

Since last sale

$271K (+4,921.8%)

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 +95% in the last 10 years

Month	Estimated value
2026
August 2026	$276K
August 2026	$276K
July 2026	$281K
June 2026	$281K
May 2026	$281K
April 2026	$276K
March 2026	$273K
February 2026	$265K
January 2026	$262K
2025
December 2025	$261K
November 2025	$263K
October 2025	$266K
September 2025	$268K
August 2025	$269K
July 2025	$276K
June 2025	$276K
May 2025	$272K
April 2025	$271K
March 2025	$253K
February 2025	$248K
January 2025	$243K
2024
December 2024	$250K
November 2024	$256K
October 2024	$258K
September 2024	$258K
August 2024	$265K
July 2024	$266K
June 2024	$265K
May 2024	$259K
April 2024	$251K
March 2024	$249K
February 2024	$240K
January 2024	$239K
2023
December 2023	$239K
November 2023	$247K
October 2023	$250K
September 2023	$255K
August 2023	$257K
July 2023	$250K
June 2023	$247K
May 2023	$245K
April 2023	$237K
March 2023	$233K
February 2023	$225K
January 2023	$224K
2022
December 2022	$225K
November 2022	$227K
October 2022	$229K
September 2022	$230K
August 2022	$229K
July 2022	$231K
June 2022	$230K
May 2022	$226K
April 2022	$214K
March 2022	$195K
February 2022	$171K
January 2022	$170K
2021
December 2021	$185K
November 2021	$184K
October 2021	$187K
September 2021	$186K
August 2021	$189K
July 2021	$193K
June 2021	$196K
May 2021	$197K
April 2021	$194K
March 2021	$184K
February 2021	$182K
January 2021	$180K
2020
December 2020	$176K
November 2020	$175K
October 2020	$176K
September 2020	$173K
August 2020	$175K
July 2020	$173K
June 2020	$172K
May 2020	$170K
April 2020	$166K
March 2020	$167K
February 2020	$167K
January 2020	$164K
2019
December 2019	$164K
November 2019	$162K
October 2019	$162K
September 2019	$161K
August 2019	$162K
July 2019	$154K
June 2019	$157K
May 2019	$148K
April 2019	$153K
March 2019	$157K
February 2019	$156K
January 2019	$151K
2018
December 2018	$149K
November 2018	$141K
October 2018	$136K
September 2018	$141K
August 2018	$149K
July 2018	$146K
June 2018	$144K
May 2018	$143K
April 2018	$143K
March 2018	$144K
February 2018	$144K
January 2018	$145K
2017
December 2017	$146K
November 2017	$149K
October 2017	$147K
September 2017	$143K
August 2017	$149K
July 2017	$156K
June 2017	$151K
May 2017	$150K
April 2017	$146K
March 2017	$143K
February 2017	$136K
January 2017	$138K
2016
December 2016	$139K
November 2016	$143K
October 2016	$143K
September 2016	$141K

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
83 Devonshire Dr, Cheshire, MA	0.15	Single-Family Home	$302,000	12/12/25	3	2	1,584
47 Ingalls Rd, Cheshire, MA	0.23	Single-Family Home	$340,000	08/11/26	3	1.5	1,652
106 Ingalls Rd, Cheshire, MA	0.28	Single-Family Home	$335,000	05/27/26	3	2	2,193
136 Ingalls Rd, Cheshire, MA	0.29	Single-Family Home	$416,500	12/08/25	3	1.5	2,254
268 Devonshire Dr, Cheshire, MA	0.14	Single-Family Home	$509,000	06/12/26	4	2.5	2,892
120 Willow Cove Rd, Cheshire, MA	1.04	Single-Family Home	$450,000	07/15/26	2	1	955
222 Brough Rd, Cheshire, MA	0.79	Single-Family Home	$585,000	08/17/26	3	3.5	1,776
14 Glassworks Rd, Lanesborough, MA	1.54	Single-Family Home	$265,000	02/02/26	4	1	1,231
74 South St, Cheshire, MA	2.07	Single-Family Home	$295,000	10/24/25	3	2	2,010
39 N Mountain Rd, Lanesborough, MA	1.31	Single-Family Home	$685,000	11/14/25	4	3.5	2,952

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
119 Yorkshire Dr, Cheshire, MA 01225	0.03	$305,700	3	1	1,371	Off Market
100 Yorkshire Dr, Cheshire, MA 01225	0.08	$286,200	3	1	1,176	Off Market
236 Devonshire Dr, Cheshire, MA 01225	0.11	$351,500	2	2	1,431	Off Market
213 Devonshire Dr, Cheshire, MA 01225	0.10	$461,100	4	2	1,685	Off Market
149 Wilshire Dr, Cheshire, MA 01225	0.13	$543,400	4	3	4,302	Off Market
131 Wilshire Dr, Cheshire, MA 01225	0.14	$517,100	4	4	3,814	Off Market
268 Devonshire Dr, Cheshire, MA 01225	0.14	$509,000	4	2.5	2,892	Recently Sold
83 Devonshire Dr, Cheshire, MA 01225	0.15	$302,000	3	2	1,584	Recently Sold
45-47 Wilshire Dr, Cheshire, MA 01225	0.20	$326,800	4	2	1,728	Off Market
47 Ingalls Rd, Cheshire, MA 01225	0.23	$340,000	3	1.5	1,652	Recently Sold
106 Ingalls Rd, Cheshire, MA 01225	0.28	$335,000	3	2	2,193	Recently Sold
136 Ingalls Rd, Cheshire, MA 01225	0.29	$416,500	3	1.5	2,254	Recently Sold

Local Information

Map ViewExplore the area around 165 Devonshire Dr.
Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1976

0.34 acre lot

1,008 sqft

$274/sqft

About this House

This single-family home is located at 165 Devonshire Dr, Cheshire, MA. 165 Devonshire Dr is in Cheshire, MA and in ZIP code 01225. This property has 3 bedrooms, 1 bathroom and approximately 1,008 sqft of floor space. This property has a lot size of 0.34 acres and was built in 1976.

165 Devonshire Dr, Cheshire, MA 01225 is a 3 bedroom, 1 bathroom, 1,008 sqft single-family home built in 1976. It last sold for $5,500 on May 4, 1976. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $276,500, with a rent estimate of $2,449/month.

Home Details for 165 Devonshire Dr

Interior Features
Interior Details BasementNumber of Rooms: 5
Heating & Cooling Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 1

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Other

Property Information
Year Built Year Built: 1976
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community
Units in Building: 1

Lot Information
Lot Area: 0.34 acres

Price and Tax history

Date	Event	Price
May 4, 1976 Source: N/A	Sold	$5,500

Year	Property tax	Tax assessment
2025	$2,319	$208,400

Additional Cost

Market trends in Cheshire

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Plunkett Elementary School
PK-3
Public
366 Students
Hoosac Valley Regional
1/10
GreatSchools Rating
Parent Rating Average
We were not at all impressed with this school and after one year, chose to send our children to a different school. The class sizes are too large, the teachers seem overburdened, the classroom activities mundane.
Parent Review
15y 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 Cheshire

At least 4 Trulia users voted on each feature.

100 % Say it's dog friendly
100 % Say car is needed
88 % Say yards are well-kept
86 % Say there's holiday spirit
86 % Say there are community events
83 % Say parking is easy
83 % Say kids play outside
83 % Say there's wildlife
81 % Say neighbors are friendly
71 % Say people would walk alone at night
63 % Say it's walkable to restaurants
57 % Say there are sidewalks
56 % Say it's quiet
56 % Say they plan to stay for at least 5 years
44 % Say streets are well-lit
25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Satunsheryl
Prev. Resident
6y ago
"Cheshire Ladies Readers Club, St. Mary Church Christmas Eve, Holiday Tea, Town Hall meeting where residents are heard"
1
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LGBTQ Local Legal Protections

Frequently asked questions about 165 Devonshire Dr

What is 165 Devonshire Dr estimated to be worth?
Trulia's estimated value for 165 Devonshire Dr in Cheshire, MA is $276,500.
What is the price history for 165 Devonshire Dr?
165 Devonshire Dr in Cheshire, MA last sold for $5,500 in May 1976.
Is Cheshire a buyer's or seller's market?
Cheshire is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 165 Devonshire Dr?
The closest schools to 165 Devonshire Dr in Cheshire, MA are Hoosac Valley High School (Middle, rated 3/10), Hoosac Valley Middle School (Elementary, rated 3/10), Plunkett Elementary School (Pre-K, rated 1/10).
How big is the lot at 165 Devonshire Dr?
The lot at 165 Devonshire Dr in Cheshire, MA is about 0.34 acres (14,810 sq ft).

Apartments for Rent

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NEW - 21 HRS AGO
$2,000/mo
Fees may apply
3 bd
2 ba
105 S Main St #1,
Lanesborough, MA 01237
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Cheshire
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Off Market Homes Near 165 Devonshire Dr

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SOLD
SEP 8, 2026
$195,900
4 bd
1 ba
1,227 sqft
174 Wells Rd,
Cheshire, MA 01225
Lisa Mendel, BURNHAM GOLD REAL ESTATE, LLC
SOLD
AUG 31, 2026
$255,000
4 bd
2 ba
2,072 sqft
40 Depot St,
Dalton, MA 01226
John M. Ciepiela, BISHOP WEST REAL ESTATE
SOLD
AUG 31, 2026
$170,000
1 bd
1 ba
965 sqft
28 Baker St,
Lanesborough, MA 01237
Lisa M Peltier, ROBERTS & ASSOC. REALTY, INC
SOLD
AUG 25, 2026
$320,000
4 bd
2 ba
2,654 sqft
1 Riverview Dr,
Dalton, MA 01226
Kolleen E. Schmitt, Keller Williams Realty
SOLD
AUG 14, 2026
$205,000
2 bd
1 ba
735 sqft
688 Cheshire Rd,
Lanesborough, MA 01224
Douglas Collins, Lamacchia Realty, Inc. - Dalton
SOLD
AUG 11, 2026
$340,000
3 bd
1.5 ba
1,652 sqft
47 Ingalls Rd,
Cheshire, MA 01225
Laiken Rapisarda, Lamacchia Realty, Inc. - Dalton
SOLD
AUG 11, 2026
$225,000
2 bd
2 ba
1,100 sqft
60 North St #16,
Dalton, MA 01226
Douglas Collins, Lamacchia Realty, Inc. - Dalton
SOLD
AUG 11, 2026
$189,900
3 bd
2 ba
1,280 sqft
395 Cheshire Rd #102,
Pittsfield, MA 01201
Jason Nocher, NOCHER REALTY
SOLD
AUG 6, 2026
$268,000
3 bd
2 ba
1,352 sqft
73 Westchester Ave,
Pittsfield, MA 01201
Jim ''Chico'' Gelinas, GELINAS REAL ESTATE
SOLD
AUG 6, 2026
$270,000
3 bd
1.5 ba
1,596 sqft
169 Park Ave,
Dalton, MA 01226
Juli Anne Atwood, Lamacchia Realty, Inc. - Dalton
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Cheshire
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Homes for sale near 165 Devonshire Dr

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2.1 ACRES
$649,900
2 bd
3 ba
2,481 sqft
40 Willow Cove Rd,
Cheshire, MA 01225
Robin Moore, 413 REAL ESTATE
$105,000
3 bd
1 ba
1,281 sqft
57 Church St,
Cheshire, MA 01225
Letizia Dutra, Cameron Real Estate Group
0.53 ACRES
$299,900
3 bd
1 ba
1,335 sqft
115 Main St,
Cheshire, MA 01225
Cory Evangelisto, NOCHER REALTY
102 ACRES
$2,200,000
5 bd
2 ba
12,225 sqft
350 Old Cheshire Rd,
Lanesborough, MA 01237
Lisa Bouchard Hoe, THE KINDERHOOK GROUP
1.7 ACRES
$289,900
3 bd
1.5 ba
1,560 sqft
192 Curran Rd,
Cheshire, MA 01225
Brenda Anne Durant, KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
0.63 ACRES
$395,000
3 bd
3 ba
2,584 sqft
335 North St,
Cheshire, MA 01225
Herbert Butzke, Engel & Volkers Wellesley
1.3 ACRES
$599,000
3 bd
2 ba
2,686 sqft
56 Victoria Ln,
Lanesborough, MA 01237
Jessica L. Rizzo, Lamacchia Realty, Inc. - Dalton
2.36 ACRES
$349,900
3 bd
1.5 ba
2,063 sqft
477 N State Rd,
Cheshire, MA 01225
Cheryl Ryan, BISHOP WEST REAL ESTATE
$295,000
3 bd
1 ba
1,342 sqft
17 Howe Rd,
Pittsfield, MA 01201
Amanda Lee Kmetz, ROBERTS & ASSOC. REALTY, INC
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