Is a car needed in Chester, MA?

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

Are yards well-kept in Chester, MA?

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

Is there wildlife in Chester, MA?

As of early 2026, 91% of users say there's wildlife

Is parking easy in Chester, MA?

As of early 2026, 88% of users say parking is easy

Is Chester, MA quiet?

As of early 2026, 86% of users say it's quiet

Are neighbors friendly in Chester, MA?

As of early 2026, 77% of users say neighbors are friendly

Does Chester, MA show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Is Chester, MA dog-friendly?

As of early 2026, 63% of users say it's dog friendly

Is Chester, MA walkable to restaurants?

As of early 2026, 57% of users say it's walkable to restaurants

Would people walk alone at night in Chester, MA?

As of early 2026, 56% of users say people would walk alone at night

Are there community events in Chester, MA?

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

Does Chester, MA have sidewalks?

As of early 2026, 38% of users say there are sidewalks

Are the streets well-lit in Chester, MA?

As of early 2026, 38% of users say streets are well-lit

Do kids play outside in Chester, MA?

As of early 2026, 38% of users say kids play outside

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

As of early 2026, 13% of users say they plan to stay for at least 5 years

OFF MARKET

20 Main St
Chester, MA 01011

3 Beds
2 Baths
2,000 sqft (on 0.40 acres)

$242,000

Trulia Estimate

as of May 5, 2026

Est. Refi. Payment $1,530/mo*

Refinance Your Home

$242,000

Trulia Estimate

as of May 5, 2026

Est. Refi. Payment $1,530/mo*

Refinance Your Home

3 Beds

2 Baths

2,000 sqft

(on 0.40 acres)

Homes for sale near 20 Main St

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0.7 ACRES
$394,900
5 bd
3 ba
2,832 sqft
56 Middlefield Rd,
Chester, MA 01011
Cynthia Gonzalez, Executive Real Estate, Inc.
$235,000
6 bd
2 ba
4,132 sqft
6 Maple St,
Chester, MA 01011
James Adams, Hilltown Real Estate by Adams Realty
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Apartments for Rent

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Local Information

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Commute Destination

Description

This multi-family home is located at 20 Main St, Chester, MA. 20 Main St is in Chester, MA and in ZIP code 01011. This property has 3 bedrooms, 2 bathrooms and approximately 2,000 sqft of floor space. This property has a lot size of 1.10 acres and was built in 1800.

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

Porch, Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 20 Main St

Interior Features
Interior Details BasementNumber of Rooms: 12Types of Rooms: Breakfast Nook, Dining Room, Family RoomCeiling Fan
Heating & Cooling Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 3Floors: Hardwood
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features
Exterior Home Features Roof: Asphalt, Built UpExterior: WoodPatioPorchSprinkler System
Parking & Garage Parking Spaces: 4Parking: Off Street

Property Information
Year Built Year Built: 1800
Property Type / Style Property Type: Multi FamilyArchitecture: Colonial

Community
Units in Building: 2

Lot Information
Lot Area: 0.40 acres

Price History for 20 Main St

Date	Price	Event	Source
03/05/2021	$95,000	Sold	BCMLS #231664
Recording Date 03/05/2021 County Transfer Tax N/A Total Transfer Tax N/A
02/10/2021	$139,000	Pending	BCMLS #231667

12/01/2020	$139,000	PriceChange	Agent Provided
Price Change $10,000 (-7%)
11/21/2020	$149,000	PriceChange	Agent Provided
Price Change $10,000 (-6%)
10/12/2020	$159,000	PriceChange	Agent Provided
Price Change $21,000 (-12%)
09/26/2020	$180,000	PriceChange	Agent Provided
Price Change $15,000 (-8%)
08/13/2020	$195,000	PriceChange	Agent Provided
Price Change $25,000 (-11%)
07/31/2020	$220,000	Listed For Sale	Agent Provided

06/08/2020	$35,000	Sold	N/A
Recording Date 06/08/2020 Contract Date 05/29/2020 County Transfer Tax N/A Total Transfer Tax N/A
05/08/2020	$89,000	Pending	Agent Provided

05/08/2020	$89,000	PriceChange	Agent Provided
Price Change $0 (0%)
02/13/2020	$89,000	PriceChange	Agent Provided
Price Change $6,000 (-6%)
01/17/2020	$95,000	PriceChange	Agent Provided
Price Change $5,000 (-5%)
01/14/2020	$100,000	PriceChange	Agent Provided
Price Change $25,000 (-20%)
09/30/2019	$125,000	Listed For Sale	Agent Provided

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Property Tax and Assessment

Year	2025
Tax	$1,996
Assessment	$110,500

Home facts updated by county records

Comparable Sales for 20 Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
45 Middlefield Rd, Chester, MA	0.15	Multi-Family Home	$233,000	08/14/25	5	2	2,732
45-47 Middlefield Rd, Chester, MA	0.16	Multi-Family Home	$233,000	08/14/25	7	2	3,058
75 Russell Stage Rd, Blandford, MA	8.16	Multi-Family Home	$440,000	08/04/25	7	3.5	4,247

Assigned Schools

These are the assigned schools for 20 Main St.

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 Chester

At least 7 Trulia users voted on each feature.

100 % Say car is needed
100 % Say yards are well-kept
91 % Say there's wildlife
88 % Say parking is easy
86 % Say it's quiet
77 % Say neighbors are friendly
75 % Say there's holiday spirit
63 % Say it's dog friendly
57 % Say it's walkable to restaurants
56 % Say people would walk alone at night
50 % Say there are community events
38 % Say there are sidewalks
38 % Say streets are well-lit
38 % Say kids play outside
13 % Say they plan to stay for at least 5 years

Learn more about our methodology.

Jlstathatesso
Resident
6y ago
"There’s plenty of space for dogs to run around without much worry from traffic, but bears and coyotes pose quite the threat."
2
Flag
Mary L. C.
Resident
7y ago
"We have maple fest in the spring with hayrides and also Chester on Track. There are also penny socials and a newer elementary school."
0
Flag

LGBTQ Local Legal Protections

Additional Cost

Homes for rent near 20 Main St

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Off Market Homes Near 20 Main St

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SOLD
MAR 25, 2026
$305,000
2 bd
1.5 ba
1,896 sqft
67 Middlefield Rd,
Chester, MA 01011
Alexander King, Lock and Key Realty Inc.
SOLD
MAR 10, 2026
$197,500
4 bd
2 ba
2,394 sqft
10 William St,
Chester, MA 01011
Nicholas DeCaro, Property Works New England
SOLD
FEB 5, 2026
$196,000
3 bd
1 ba
1,104 sqft
67 Bromley Rd,
Chester, MA 01050
SOLD
JAN 23, 2026
$340,000
2 bd
1 ba
1,350 sqft
73 Ingell Rd,
Chester, MA 01011
Debra A. Petrovsky, Donovan Real Estate
SOLD
DEC 30, 2025
$340,000
2 bd
1 ba
1,360 sqft
689 Skyline Trl,
Chester, MA 01011
Kelley & Katzer Team, Kelley & Katzer Real Estate, LLC
SOLD
DEC 5, 2025
$213,000
3 bd
1 ba
2,068 sqft
11 Maple St,
Chester, MA 01011
Nadine Hiser, KRG - Key Realty Group
SOLD
DEC 1, 2025
$291,000
3 bd
2 ba
1,912 sqft
7 William St,
Chester, MA 01011
James Adams, Hilltown Real Estate by Adams Realty
SOLD
NOV 7, 2025
$270,000
3 bd
1 ba
1,048 sqft
76 Hampden St,
Chester, MA 01011
Patriot Living Group, Lock and Key Realty Inc.
SOLD
SEP 15, 2025
$315,000
3 bd
1 ba
1,458 sqft
9 William St,
Chester, MA 01011
Adam Lajeunesse, Real Broker MA, LLC
SOLD
AUG 22, 2025
$300,000
3 bd
1 ba
1,712 sqft
110 Middlefield Rd,
Chester, MA 01011
Darcie Gasperini, Taylor Agency
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20 Main St, Chester, MA 01011 is a 3 bedroom, 2 bathroom, 2,000 sqft multi-family built in 1800. This property is not currently available for sale. 20 Main St was last sold on Mar 5, 2021 for $95,000. The current Trulia Estimate for 20 Main St is $242,000.

20 Main St
Chester, MA 01011

$242,000

$242,000

Homes for sale near 20 Main St

Apartments for Rent

Local Information