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 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
Property at 128 Prospect St, Chester, MA 01011
1 / 42
Active

$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
Property at 47 Lyon Hill Rd, Chester, MA 01011
1 / 25
Active
Open

$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.

Property at 254 Route 20, Chester, MA 01011
1 / 29
Active

$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
Property at 2 Taft Rd, Chester, MA 01011
1 / 12
Active

$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
Property at 93 Crane Rd, Chester, MA 01011
1 / 6
Active

$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
Property at 0 Mica Mill Rd, Chester, MA 01011
Active

$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
Property at 50 Smith, Chester, MA 01011
Active
Price drop

$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
Property at 91 Lynes Rd, Chester, MA 01011
1 / 3
Active

$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
Property at lot1 Holcomb Road, Chester, MA 01011
1 / 3
Active

$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
Property at lot 2 Holcomb Road, Chester, MA 01011
1 / 4
Active

$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
Property at lot 3 Holcomb Road, Chester, MA 01011
1 / 5
Active

$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 5, 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 5, 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 49 days on market.

Brokerage Information

Commonwealth Standard Realty Advisors

10 Lincoln St, Newton, MA, 02461

(480) 540-2772

Market Area Served

Needham, Wellesley, Dedham, Natick, Westwood, Dover, Framingham, Wayland, Newton, Ashland, Sherborn and many more.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.