Homes for Sale in Chester, MA

17 results

17 homes are for sale in Chester, MA (median list price $129,000), as of November 5, 2026.

Property at 23 Maple St, Chester, MA 01011
1 / 24
Active
Price drop

$200,000

Price reduced by

23 Maple St, Chester, MA 01011

2 bds
|
1 ba
|
1652 sqft

$121/sqft · 83 days on market

MLS® 73563768Single Family Residence
Keller Williams Realty - Keira Hildack

$250,000

128 Prospect St, Chester, MA 01011

3 bds
|
1 ba
|
1481 sqft

$169/sqft · 5 days on market

MLS® 73597302Single Family Residence
RE/MAX Compass - Joy Salvini
Property at 27 Maple Ave, Chester, MA 01011
1 / 13
Active
Price drop

$270,000

Price reduced by

27 Maple Ave, Chester, MA 01011

3 bds
|
1.5 ba
|
1384 sqft

$195/sqft · 26 days on market

MLS® 73589335Single Family Residence
RE/MAX Compass, Lee MA - Kathleen A. Engwer
Property at 1 Crane Rd, Chester, MA 01011
1 / 12
Active
Price drop

$135,000

Price reduced by

1 Crane Rd, Chester, MA 01011

4 bds
|
2 ba
|
2151 sqft

$63/sqft · 171 days on market

MLS® 73520586Single Family Residence
Gallagher Real Estate - Melissa L. Blondek

$495,000

47 Lyon Hill Rd, Chester, MA 01011

3 bds
|
2 ba
|
1851 sqft

$267/sqft · 13 days on market

MLS® 73594566Single Family Residence
Donovan Real Estate - Debra A. Petrovsky

What's actually happening in Chester right now?

Forget the national headlines. Get the hyper-local, street-level data on inventory, price drops, and true market value before you make an offer.

$229,900

254 Route 20, Chester, MA 01011

3 bds
|
1.5 ba
|
1968 sqft

$117/sqft · 12 days on market

MLS® 73594709Single Family Residence
Coldwell Banker Realty - Western MA - Dennis Leclair

$39,000

2 Taft Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

31 days on market

MLS® 73586614Single Family Residence
Gallagher Real Estate - Todd Kazunas

$129,900

93 Crane Rd, Chester, MA 01011

0 bds
|
1 ba
|
560 sqft

$232/sqft · 48 days on market

MLS® 73579781Single Family Residence
Coldwell Banker Community REALTORS® - Daniel James Piasecki
Property at 166 Route 20, Chester, MA 01011
1 / 12
Active
Price drop

$80,000

Price reduced by

166 Route 20, Chester, MA 01011

2 bds
|
1.5 ba
|
1328 sqft

$60/sqft · 87 days on market

MLS® 73561688Single Family Residence
Nexthome Elite Realty - Thomas Despard
Property at 95 Lynes Rd, Chester, MA 01011
1 / 4
Active
Price drop

$40,000

Price reduced by

95 Lynes Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

155 days on market

MLS® 73528786Residential
HB Real Estate, LLC - Cheryl Malandrinos

$129,000

0 Mica Mill Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

41 days on market

MLS® 73582709Residential
The LGCY Group LLC - Jaquaine Coe

$40,000

Price reduced by

50 Smith, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

83 days on market

MLS® 73563694Residential
Keller Williams Realty - Nicolle Serafino

$50,000

91 Lynes Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

131 days on market

MLS® 73542747Residential
HB Real Estate, LLC - Cheryl Malandrinos

$365,000

Price reduced by

56 Middlefield Rd, Chester, MA 01011

5 bds
|
3 ba
|
2832 sqft

$129/sqft · 330 days on market

MLS® 73461501Multi Family
Executive Real Estate, Inc. - Cynthia Gonzalez

$45,000

lot1 Holcomb Road, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

127 days on market

MLS® 73543989Residential
Hilltown Real Estate by Adams Realty - James Adams

$45,000

lot 2 Holcomb Road, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

127 days on market

MLS® 73543991Residential
Hilltown Real Estate by Adams Realty - James Adams

$60,000

lot 3 Holcomb Road, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft

127 days on market

MLS® 73543996Residential
Hilltown Real Estate by Adams Realty - James Adams

Homes for sale in Chester, MA: market at a glance

As of November 5, 2026, there are 17 homes for sale in Chester, MA, with a median list price of $129,000. In May 2026, the median sale price for homes in Chester, MA was $230,000.

Homes for sale
17
Median list price
$129,000
Median sale price (May 2026)
$230,000
Median days on market (May 2026)
19 days

Common questions about Chester, MA real estate

How many homes are for sale in Chester, MA?

As of November 5, 2026, there are 17 homes for sale in Chester, MA, including 9 single-family homes and 1 multi-family home.

What is the median home price in Chester, MA?

The median list price of homes for sale in Chester, MA is $129,000. Homes that sold in May 2026 had a median sale price of $230,000.

How long do homes take to sell in Chester, MA?

Homes in Chester, MA that sold in May 2026 had a median of 19 days on market. Homes currently for sale show a median of about 64 days on market.

What types of homes are for sale in Chester, MA?

The homes for sale in Chester, MA include 9 single-family homes and 1 multi-family home.