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

165 Main Rd
Williamsburg, MA 01096

2 Beds
1 Bath
1,244 sqft (on 15 acres)

$387,400

Trulia Estimate

as of Jul 23, 2026

Est. Refi. Payment $2,469/mo*

Refinance Your Home

$387,400

Trulia Estimate

as of Jul 23, 2026

Est. Refi. Payment $2,469/mo*

Refinance Your Home

2 Beds

1 Bath

1,244 sqft

(on 15 acres)

Local Information

Map ViewExplore the area around 165 Main Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1978

Lot Size

15 acres

Living Area

1,244 sqft

Price/Sqft

$311

Description

This single-family home is located at 165 Main Rd, Williamsburg, MA. 165 Main Rd is in Williamsburg, MA and in ZIP code 01096. This property has 2 bedrooms, 1 bathroom and approximately 1,244 sqft of floor space. This property has a lot size of 15.00 acres and was built in 1978.

165 Main Rd, Williamsburg, MA 01096 is a 2 bedroom, 1 bathroom, 1,244 sqft single-family home built in 1978. It is currently off market. The Trulia Estimate is $387,400, with a rent estimate of $2,287/month.

Home Details for 165 Main Rd

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

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: WoodPatio

Property Information
Year Built Year Built: 1978Year Updated: 1985
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community
Units in Building: 1

Lot Information
Lot Area: 15.00 acres

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	$4,990
Assessment	$321,500

Home facts updated by county records

Comparable Sales for 165 Main Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
109 East St, Chesterfield, MA	0.73	Single-Family Home	$430,000	08/29/25	3	2	1,352
101 East St, Chesterfield, MA	0.82	Single-Family Home	$591,000	09/26/25	3	2	1,616
100 South St, Chesterfield, MA	1.47	Single-Family Home	$60,000	03/17/26	3	1	1,376
5 Bofat Hill Rd, Williamsburg, MA	1.00	Single-Family Home	$550,000	02/10/26	3	2	2,025
316 Main Rd, Chesterfield, MA	1.30	Single-Family Home	$169,700	06/12/26	4	1	1,947
206 S Chesterfield Rd, Williamsburg, MA	1.71	Single-Family Home	$420,000	09/25/25	2	1	920
39 Cowper Rd, Chesterfield, MA	2.39	Single-Family Home	$415,000	10/24/25	2	1	1,010
81 Lake Dr, Goshen, MA	1.82	Single-Family Home	$449,000	08/27/25	3	1	768
376 Northwest Rd, Westhampton, MA	2.31	Single-Family Home	$460,000	02/17/26	2	2	1,840
330 East St, Williamsburg, MA	1.92	Single-Family Home	$750,000	11/19/25	3	2	2,922

Nearby homes

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

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OFF MARKET
Est. $455,200
3 bd
2 ba
1,352 sqft
109 East St,
Chesterfield, MA 01012
Holly Young, Delap Real Estate LLC
OFF MARKET
63 Sugar Hill Rd,
Williamsburg, MA 01096
Michael Packard, Coldwell Banker Community REALTORS®
SOLD
SEP 26, 2025
$591,000
3 bd
2 ba
1,616 sqft
101 East St,
Chesterfield, MA 01012
Jocelyn Cleary, Canon Real Estate, Inc.
OFF MARKET
Est. $473,800
3 bd
3 ba
2,068 sqft
185 East St,
Chesterfield, MA 01012
Kylene Canon-Smith, Canon Real Estate, Inc.
SOLD
FEB 10, 2026
$550,000
3 bd
2 ba
2,025 sqft
5 Bofat Hill Rd,
Williamsburg, MA 01096
Jonathan Scagel, Venture
OFF MARKET
S Chesterfield Rd,
Goshen, MA 01032
Alexis Noyes, Brick & Mortar
SOLD
APR 17, 2026
$65,000
Stage Rd,
Chesterfield, MA 01012
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
FOR SALE
32.68 ACRES
$529,000
3 bd
1.5 ba
1,781 sqft
3 Stage Rd,
Williamsburg, MA 01096
James A. Molyneux, Molyneux Realty
OFF MARKET
40 East St,
Chesterfield, MA 01012
Alexis Noyes, Brick & Mortar
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

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Additional Cost

Assigned Schools

These are the assigned schools for 165 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 165 Main Rd

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32.68 ACRES
$529,000
3 bd
1.5 ba
1,781 sqft
3 Stage Rd,
Williamsburg, MA 01096
James A. Molyneux, Molyneux Realty
0.44 ACRES
$199,900
3 bd
1 ba
768 sqft
28 Birch Rd,
Goshen, MA 01032
Kathleen Z. Zeamer, 5 College REALTORS®
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.
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
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
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
2.5 ACRES
$369,900
3 bd
1 ba
1,888 sqft
31 Goshen Rd,
Williamsburg, MA 01096
Bradley McGrath, Coldwell Banker Community REALTORS®
OPEN SAT, 11-1PM
2.73 ACRES
$685,000
5 bd
2.5 ba
2,368 sqft
254 Bryant St,
Chesterfield, MA 01012
Aimee Tompkins, Park Square Realty
OPEN SAT, 11-1PM
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.
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Williamsburg
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Off Market Homes Near 165 Main Rd

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SOLD
JUL 15, 2026
$385,000
4 bd
2 ba
1,576 sqft
4 Petticoat Hill Rd,
Williamsburg, MA 01096
Chuck T. Conner, Taylor Agency
SOLD
JUN 24, 2026
$308,000
2 bd
1.5 ba
1,243 sqft
3 N Main St,
Williamsburg, MA 01096
Maria Rosario, Coldwell Banker Realty - Western MA
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
MAR 23, 2026
$247,500
4 bd
2 ba
1,540 sqft
6 Williams St,
Williamsburg, MA 01096
Kim Raczka, 5 College REALTORS® Northampton
SOLD
MAR 6, 2026
$412,000
3 bd
2 ba
1,276 sqft
100 South St,
Williamsburg, MA 01096
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
FEB 10, 2026
$550,000
3 bd
2 ba
2,025 sqft
5 Bofat Hill Rd,
Williamsburg, MA 01096
Jonathan Scagel, Venture
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 11, 2025
$300,000
2 bd
1 ba
828 sqft
58 South St,
Williamsburg, MA 01096
Kim Raczka, 5 College REALTORS® Northampton
See more homes for sale in
Williamsburg
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165 Main Rd
Williamsburg, MA 01096

$387,400

$387,400