Houses for Sale in Chester, MA

16 results

16 single-family homes are for sale in Chester, MA (median list price $104,500), as of November 4, 2026.

$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
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

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

$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

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

As of November 4, 2026, there are 16 single-family homes for sale in Chester, MA, with a median list price of $104,500. In May 2026, the median sale price for homes in Chester, MA (all home types) was $230,000.

Houses for sale
16
Median list price
$104,500
Median sale price (May 2026, all home types)
$230,000
Median days on market (May 2026, all home types)
19 days

Common questions about Chester, MA real estate

How many single-family homes are for sale in Chester, MA?

As of November 4, 2026, there are 16 single-family homes for sale in Chester, MA.

What is the median single-family home price in Chester, MA?

The median list price of single-family homes for sale in Chester, MA is $104,500. Homes (all home types) that sold in May 2026 had a median sale price of $230,000.

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

Homes (all home types) in Chester, MA that sold in May 2026 had a median of 19 days on market. Single-family homes currently for sale show a median of about 48 days on market.