Is a car needed in Chesterfield, MA?

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

Is Chesterfield, MA dog-friendly?

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

Is there wildlife in Chesterfield, MA?

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

Is parking easy in Chesterfield, MA?

As of early 2026, 100% of users say parking is easy

Would people walk alone at night in Chesterfield, MA?

As of early 2026, 100% of users say people would walk alone at night

Does Chesterfield, MA show holiday spirit?

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

Are yards well-kept in Chesterfield, MA?

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

Are there community events in Chesterfield, MA?

As of early 2026, 50% of users say there are community events

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

As of early 2026, 50% of users say they plan to stay for at least 5 years

Are the streets well-lit in Chesterfield, MA?

As of early 2026, 50% of users say streets are well-lit

Does Chesterfield, MA have sidewalks?

As of early 2026, 50% of users say there are sidewalks

Are neighbors friendly in Chesterfield, MA?

As of early 2026, 44% of users say neighbors are friendly

Do kids play outside in Chesterfield, MA?

As of early 2026, 33% of users say kids play outside

OFF MARKET

369 Main Rd
Chesterfield, MA 01012

3 Beds
1.5 Baths
1,959 sqft (on 11.50 acres)

$350,900

Trulia Estimate

as of Jul 16, 2026

Est. Refi. Payment $2,240/mo*

Refinance Your Home

$350,900

Trulia Estimate

as of Jul 16, 2026

Est. Refi. Payment $2,240/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,959 sqft

(on 11.50 acres)

Local Information

Map ViewExplore the area around 369 Main Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 369 Main Rd, Chesterfield, MA. 369 Main Rd is in Chesterfield, MA and in ZIP code 01012. This property has 3 bedrooms, 2 bathrooms and approximately 1,959 sqft of floor space. This property has a lot size of 11.50 acres and was built in 1796.

369 Main Rd, Chesterfield, MA 01012 is a 3 bedroom, 2 bathroom, 1,959 sqft single-family home built in 1796. It last sold for $200,000 on Jul 31, 2019. It is currently off market. The Trulia Estimate is $350,900, with a rent estimate of $3,042/month.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 369 Main Rd

Interior Features
Interior Details BasementNumber of Rooms: 9
Heating & Cooling Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility Floors: Carpet

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Vinyl

Property Information
Year Built Year Built: 1796Year Updated: 1970
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 11.50 acres

Price History for 369 Main Rd

Date	Price	Event	Source
07/31/2019	$200,000	Sold	N/A
Recording Date 07/31/2019 Contract Date 07/29/2019 County Transfer Tax N/A Total Transfer Tax N/A
07/01/2019	$235,000	Pending	Agent Provided

06/26/2019	$235,000	PendingToActive	Agent Provided

06/19/2019	$235,000	Pending	Agent Provided

06/03/2019	$235,000	Listed For Sale	Agent Provided

04/25/2016	$120,500	Sold	N/A
Recording Date 04/25/2016 County Transfer Tax N/A Total Transfer Tax $36
03/04/2016	$129,000	Pending	Agent Provided

02/17/2016	$129,000	Listed For Sale	Agent Provided

10/20/2015	$144,995	ListingRemoved	Agent Provided

09/30/2015	$144,995	PriceChange	Agent Provided
Price Change $5,000 (-3%)
08/27/2015	$149,995	PriceChange	Agent Provided
Price Change $9,755 (-6%)
08/05/2015	$159,750	PriceChange	Agent Provided
Price Change $10,000 (-6%)
07/09/2015	$169,750	PriceChange	Agent Provided
Price Change $9,000 (-5%)
06/29/2015	$178,750	PriceChange	Agent Provided
Price Change $14,000 (-7%)
06/22/2015	$192,750	PriceChange	Agent Provided
Price Change $5,750 (-3%)
05/15/2015	$198,500	Listed For Sale	Agent Provided

Market trends in Chesterfield

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

1MoM

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Property Tax and Assessment

Year	2025
Tax	$4,136
Assessment	$266,500

Home facts updated by county records

Comparable Sales for 369 Main Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
316 Main Rd, Chesterfield, MA	0.46	Single-Family Home	$169,700	06/12/26	4	1	1,947
100 South St, Chesterfield, MA	0.75	Single-Family Home	$60,000	03/17/26	3	1	1,376
109 East St, Chesterfield, MA	1.63	Single-Family Home	$430,000	08/29/25	3	2	1,352
101 East St, Chesterfield, MA	1.57	Single-Family Home	$591,000	09/26/25	3	2	1,616
85 Damon Pond Rd, Chesterfield, MA	1.56	Single-Family Home	$425,000	08/12/25	3	2.5	2,249
11 Farmhouse Rd, Chesterfield, MA	1.51	Single-Family Home	$435,000	08/12/25	3	2.5	2,100
31 Farmhouse Rd, Chesterfield, MA	1.67	Single-Family Home	$300,000	11/25/25	2	1	1,024
196 Ireland St, West Chesterfield, MA	2.60	Single-Family Home	$440,000	09/03/25	3	2	1,489
46 Bray Rd, Chesterfield, MA	1.94	Single-Family Home	$235,000	09/22/25	2	1	871
5 Bofat Hill Rd, Williamsburg, MA	2.35	Single-Family Home	$550,000	02/10/26	3	2	2,025

Nearby homes

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

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OFF MARKET
Est. $345,100
2 bd
1 ba
1,308 sqft
21 South St,
Chesterfield, MA 01012
Karen McAmis, Maple and Main Realty, LLC
OFF MARKET
Est. $106,900
2 bd
1 ba
965 sqft
33 South St,
Chesterfield, MA 01012
Donald Mailloux, Coldwell Banker Community REALTORS®
OFF MARKET
Est. $419,200
3 bd
2 ba
2,043 sqft
11 Bryant St,
Chesterfield, MA 01012
Kempf-Vanderburgh Realty Consultants, Kempf-Vanderburgh Realty Consultants, Inc.
OFF MARKET
Est. $512,000
4 bd
2 ba
2,593 sqft
419 Main Rd,
Chesterfield, MA 01012
Michael Packard, Coldwell Banker Community REALTORS®
OFF MARKET
Est. $446,900
2 bd
1.5 ba
1,531 sqft
73 North Rd,
Chesterfield, MA 01012
Amy Heflin, Keller Williams Realty
FOR SALE
NEW
OPEN SAT, 11-1PM
32.68 ACRES
$529,000
3 bd
1.5 ba
1,781 sqft
3 Stage Rd,
Williamsburg, MA 01096
James A. Molyneux, Molyneux Realty
SOLD
JUN 12, 2026
$169,700
4 bd
1 ba
1,947 sqft
316 Main Rd,
Chesterfield, MA 01012
Jarod Martin, Greenfield Group Real Estate
OFF MARKET
Est. $370,900
3 bd
1 ba
1,260 sqft
386 Main Rd,
Chesterfield, MA 01012
The Jackson & Nale Team, REMAX Connections - Belchertown
OFF MARKET
Est. $703,800
3 bd
2 ba
1,988 sqft
108 South St,
Chesterfield, MA 01012
MJC Home Team, Keller Williams Boston MetroWest
OFF MARKET
108 Two South St,
Chesterfield, MA 01012
MJC Home Team, Keller Williams Boston MetroWest
FOR SALE
3D VIEW
55 ACRES
$1,850,000
5 bd
2.5 ba
3,494 sqft
31 North Rd,
Chesterfield, MA 01012
Grace Golden, Equine Homes Real Estate, LLC
OFF MARKET
Est. $323,800
3 bd
1 ba
1,094 sqft
11 Damon Pond Rd,
Chesterfield, MA 01012
James P. Kwiecinski, The Murphys REALTORS®, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 369 Main Rd.

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 Chesterfield

At least 1 Trulia users voted on each feature.

100 % Say car is needed
100 % Say it's dog friendly
100 % Say there's wildlife
100 % Say parking is easy
100 % Say people would walk alone at night
100 % Say there's holiday spirit
100 % Say yards are well-kept
50 % Say there are community events
50 % Say they plan to stay for at least 5 years
50 % Say streets are well-lit
50 % Say there are sidewalks
44 % Say neighbors are friendly
33 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 369 Main Rd

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NEW
OPEN SAT, 11-1PM
32.68 ACRES
$529,000
3 bd
1.5 ba
1,781 sqft
3 Stage Rd,
Williamsburg, MA 01096
James A. Molyneux, Molyneux Realty
55 ACRES
$1,850,000
5 bd
2.5 ba
3,494 sqft
31 North Rd,
Chesterfield, MA 01012
Grace Golden, Equine Homes Real Estate, LLC
3.21 ACRES
$898,000
3 bd
2.5 ba
1,968 sqft
82 Willcutt Rd,
Chesterfield, MA 01012
Jeanne Troxell Munson, The Murphys REALTORS®, Inc.
9.09 ACRES
$679,000
3 bd
2.5 ba
2,303 sqft
7 Sundown Dr,
Williamsburg, MA 01096
Jacob Wint, William Pitt Sotheby's International Realty
0.66 ACRES
$250,000
4 bd
1 ba
945 sqft
54 Bray Rd,
Chesterfield, MA 01012
Shelly Hardy, Brick & Mortar Northampton
6.5 ACRES
$549,900
2 bd
1.5 ba
1,112 sqft
32 Pond Hill Rd,
Goshen, MA 01032
Alex Anthony, Alex Anthony R.E.
2.73 ACRES
$695,000
5 bd
2.5 ba
2,368 sqft
254 Bryant St,
Chesterfield, MA 01012
Aimee Tompkins, Park Square Realty
OPEN SAT, 11-1PM
0.44 ACRES
$199,900
3 bd
1 ba
768 sqft
28 Birch Rd,
Goshen, MA 01032
Kathleen Z. Zeamer, 5 College REALTORS®
17.87 ACRES
$440,000
2 bd
1 ba
1,364 sqft
345 Harvey Rd,
Worthington, MA 01098
Jocelyn Cleary, Canon Real Estate, Inc.
1.03 ACRES
$159,000
2 bd
1 ba
906 sqft
11 S Chesterfield Rd,
Goshen, MA 01032
Michael P Mendyk, Michael Mendyk Real Estate
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Chesterfield
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Off Market Homes Near 369 Main Rd

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SOLD
APR 17, 2026
$440,000
3 bd
2 ba
1,384 sqft
221 Northwest Rd,
Westhampton, MA 01027
SOLD
APR 16, 2026
$469,900
3 bd
3 ba
1,232 sqft
12 Pine Rd,
Goshen, MA 01032
Trailside Team, The Murphys REALTORS® , Inc.
SOLD
FEB 17, 2026
$460,000
2 bd
2 ba
1,840 sqft
376 Northwest Rd,
Westhampton, MA 01027
The Aimee Kelly Crew, eXp Realty
SOLD
JAN 5, 2026
$475,000
3 bd
3 ba
2,997 sqft
178 Northwest Rd,
Westhampton, MA 01027
Kylene Canon-Smith, Canon Real Estate, Inc.
SOLD
DEC 19, 2025
$420,000
3 bd
1 ba
960 sqft
527 Old Post Rd,
Worthington, MA 01098
James A. Molyneux, Molyneux Realty
SOLD
NOV 25, 2025
$300,000
2 bd
1 ba
1,024 sqft
31 Farmhouse Rd,
Chesterfield, MA 01012
Shelly Hardy, Brick & Mortar Northampton
SOLD
OCT 24, 2025
$415,000
2 bd
1 ba
1,010 sqft
39 Cowper Rd,
Chesterfield, MA 01012
David A Murphy, The Murphys REALTORS®, Inc.
SOLD
OCT 15, 2025
$490,000
3 bd
1.5 ba
2,763 sqft
95 Ball Rd,
Goshen, MA 01032
Linda Webster, Coldwell Banker Community REALTORS®
SOLD
SEP 25, 2025
$420,000
2 bd
1 ba
920 sqft
206 S Chesterfield Rd,
Williamsburg, MA 01096
Karen McAmis, 5 College REALTORS® Northampton
SOLD
SEP 22, 2025
$235,000
2 bd
1 ba
871 sqft
46 Bray Rd,
Chesterfield, MA 01012
Linda Webster, Coldwell Banker Community REALTORS®
See more homes for sale in
Chesterfield
Take a look

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369 Main Rd
Chesterfield, MA 01012

$350,900

$350,900

Local Information