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

286 Main Rd
Williamsburg, MA 01096

3 Beds
1 Bath
1,567 sqft (on 31.39 acres)

$392,800

Trulia Estimate

as of Jun 7, 2026

Est. Refi. Payment $2,467/mo*

Refinance Your Home

$392,800

Trulia Estimate

as of Jun 7, 2026

Est. Refi. Payment $2,467/mo*

Refinance Your Home

3 Beds

1 Bath

1,567 sqft

(on 31.39 acres)

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 286 Main Rd, Williamsburg, MA. 286 Main Rd is in Williamsburg, MA and in ZIP code 01096. This property has 3 bedrooms, 1 bathroom and approximately 1,567 sqft of floor space. This property has a lot size of 31.39 acres and was built in 1971.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

No Info

Outdoor

Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 286 Main Rd

Interior Features
Interior Details BasementNumber of Rooms: 6
Heating & Cooling Heating: CoalHeating Fuel: Coal
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: MetalDeckExterior: Wood

Property Information
Year Built Year Built: 1971Year Updated: 1980
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary

Community
Units in Building: 1

Lot Information
Lot Area: 31.39 acres

Market trends in Chesterfield

Last updated April 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

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Property Tax and Assessment

Year	2025
Tax	$3,765
Assessment	$242,570

Home facts updated by county records

Comparable Sales for 286 Main Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
100 South St, Chesterfield, MA	0.62	Single-Family Home	$60,000	03/17/26	3	1	1,376
101 East St, Chesterfield, MA	0.82	Single-Family Home	$591,000	09/26/25	3	2	1,616
109 East St, Chesterfield, MA	0.85	Single-Family Home	$430,000	08/29/25	3	2	1,352
5 Bofat Hill Rd, Williamsburg, MA	1.56	Single-Family Home	$550,000	02/10/26	3	2	2,025
39 Cowper Rd, Chesterfield, MA	2.26	Single-Family Home	$415,000	10/24/25	2	1	1,010
81 Lake Dr, Goshen, MA	1.99	Single-Family Home	$449,000	08/27/25	3	1	768
23 Hyde Hill Rd, Goshen, MA	2.51	Single-Family Home	$400,000	06/26/25	3	2	1,667
206 S Chesterfield Rd, Williamsburg, MA	1.96	Single-Family Home	$420,000	09/25/25	2	1	920
85 Damon Pond Rd, Chesterfield, MA	2.03	Single-Family Home	$425,000	08/12/25	3	2.5	2,249
12 Cherry Rd, Goshen, MA	2.02	Single-Family Home	$234,500	06/26/25	2	1	624

Nearby homes

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

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OFF MARKET
Est. $683,100
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
OFF MARKET
63 Sugar Hill Rd,
Williamsburg, MA 01096
Michael Packard, Coldwell Banker Community REALTORS®
SOLD
APR 17, 2026
$65,000
Stage Rd,
Chesterfield, MA 01012
James A. Molyneux, Molyneux Realty
OFF MARKET
40 East St,
Chesterfield, MA 01012
Alexis Noyes, Brick & Mortar
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.
SOLD
AUG 29, 2025
$430,000
3 bd
2 ba
1,352 sqft
109 East St,
Chesterfield, MA 01012
Holly Young, Delap Real Estate LLC
OFF MARKET
Est. $78,900
2 bd
1 ba
965 sqft
33 South St,
Chesterfield, MA 01012
Donald Mailloux, Coldwell Banker Community REALTORS®
OFF MARKET
Est. $346,300
2 bd
1 ba
1,308 sqft
21 South St,
Chesterfield, MA 01012
Karen McAmis, Maple and Main Realty, LLC
OFF MARKET
Est. $414,100
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. $446,100
2 bd
1.5 ba
1,531 sqft
73 North Rd,
Chesterfield, MA 01012
Amy Heflin, Keller Williams Realty
OFF MARKET
Est. $506,100
4 bd
2 ba
2,593 sqft
419 Main Rd,
Chesterfield, MA 01012
Michael Packard, Coldwell Banker Community REALTORS®

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Additional Cost

Assigned Schools

These are the assigned schools for 286 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 286 Main Rd

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OFF MARKET
Est. $161,800
2 bd
1 ba
1,547 sqft
316 Main Rd,
Chesterfield, MA 01012
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
OPEN SUN, 12-2PM
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
$599,900
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
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
2.19 ACRES
$450,000
4 bd
2 ba
2,056 sqft
55 Cummington Rd,
West Chesterfield, MA 01084
Patriot Living Group, Lock and Key Realty Inc.
1.6 ACRES
$110,000
4 bd
1 ba
2,160 sqft
35 Goshen Rd,
Williamsburg, MA 01096
Stephen Snow, Steve Snow Real Estate
NEW - 1 DAY AGO
18.11 ACRES
$525,000
3 bd
2 ba
2,310 sqft
496 Old Post Rd,
Worthington, MA 01098
Grace Golden, Equine Homes Real Estate, LLC
FOR SALE BY OWNER
$498,000
2 bd
1 ba
675 sqft
69 Aberdeen Rd,
Goshen, MA 01032
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Off Market Homes Near 286 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 27, 2026
$580,000
3 bd
2 ba
2,080 sqft
8 Ring Rd,
Worthington, MA 01084
Holly Young, Delap Real Estate LLC
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 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
NOV 19, 2025
$536,500
3 bd
1.5 ba
2,127 sqft
275 Northwest Rd,
Westhampton, MA 01027
Dawn Ezold, Naples Realty Group
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.
See more homes for sale in
Williamsburg
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Homes for rent near 286 Main Rd

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286 Main Rd, Williamsburg, MA 01096 is a 3 bedroom, 1 bathroom, 1,567 sqft single-family home built in 1971. This property is not currently available for sale. The current Trulia Estimate for 286 Main Rd is $392,800.

286 Main Rd
Williamsburg, MA 01096

$392,800

$392,800

Local Information