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Homes for Sale in Chester, MA

16 results

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

$210,000

23 Maple St, Chester, MA 01011

2 bds
|
1 ba
|
1652 sqft
MLS® 73563768Single Family Residence
Keller Williams Realty - Keira Hildack
Property at 254 Route 20, Chester, MA 01011
1 / 29
Active

$229,900

254 Route 20, Chester, MA 01011

2 bds
|
1.5 ba
|
1968 sqft
MLS® 73594709Single Family Residence
RE/MAX Compass - Dennis Leclair
Property at 47 Lyon Hill Rd, Chester, MA 01011
1 / 24
Active

$495,000

47 Lyon Hill Rd, Chester, MA 01011

3 bds
|
2 ba
|
1851 sqft
MLS® 73594566Single Family Residence
Donovan Real Estate - Debra A. Petrovsky
Property at 2 Taft Rd, Chester, MA 01011
1 / 12
Active

$39,000

2 Taft Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft
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
MLS® 73579781Single Family Residence
Coldwell Banker Community REALTORS® - Daniel James Piasecki

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 166 Route 20, Chester, MA 01011
1 / 12
Active
Price

$80,000

166 Route 20, Chester, MA 01011

2 bds
|
1.5 ba
|
1328 sqft
MLS® 73561688Single Family Residence
Nexthome Elite Realty - Thomas Despard
Property at 95 Lynes Rd, Chester, MA 01011
1 / 4
Active
Price

$40,000

95 Lynes Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft
MLS® 73528786Residential
HB Real Estate, LLC - Cheryl Malandrinos
Property at 27 Maple Ave, Chester, MA 01011
1 / 13
Active

$290,000

27 Maple Ave, Chester, MA 01011

3 bds
|
1.5 ba
|
1384 sqft
MLS® 73589335Single Family Residence
RE/MAX Compass, Lee MA - Kathleen A. Engwer
Property at 1 Crane Rd, Chester, MA 01011
1 / 12
Active
Price

$150,000

1 Crane Rd, Chester, MA 01011

4 bds
|
2 ba
|
2151 sqft
MLS® 73520586Single Family Residence
Gallagher Real Estate - Melissa L. Blondek
Property at 0 Mica Mill Rd, Chester, MA 01011
Active

$129,000

0 Mica Mill Rd, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft
MLS® 73582709Residential
The LGCY Group LLC - Jaquaine Coe
Property at 50 Smith, Chester, MA 01011
Active
Price

$40,000

50 Smith, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft
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
MLS® 73542747Residential
HB Real Estate, LLC - Cheryl Malandrinos
Property at 56 Middlefield Rd, Chester, MA 01011
1 / 39
Active
Price

$365,000

56 Middlefield Rd, Chester, MA 01011

5 bds
|
3 ba
|
2832 sqft
MLS® 73461501Multi Family
Executive Real Estate, Inc. - Cynthia Gonzalez
Property at lot1 Holcomb Road, Chester, MA 01011
1 / 3
Active

$45,000

lot1 Holcomb Road, Chester, MA 01011

0 bds
|
0 ba
|
-- sqft
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
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
MLS® 73543996Residential
Hilltown Real Estate by Adams Realty - James Adams

Brokerage Information

Gibson Sotheby's International Realty

526B Boston Post Road, Sudbury, MA, 01776

(207) 939-1067

License #9630186-RE-S

Market Area Served

Concord, Carlisle, Lexington, Newton, Wellesley, Weston, Somerville, Belmont, Cambridge, Bedford, Lincoln, Arlington, Sudbury 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.

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Amanda Allen Nurse

I'm Amanda Allen Nurse, a Concord, MA real estate agent with Gibson Sotheby's, guiding move-up families and home sellers across MetroWest from first search to closing.

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Gibson Sotheby's International Realty

© 2026 Amanda Allen Nurse. All rights reserved.
License #9630186-RE-S. Equal Housing Opportunity. Information deemed reliable but not guaranteed.

Service Areas

  • Somerville, MA
  • Belmont, MA
  • Cambridge, MA
  • Arlington, MA
  • Weston, MA
  • Newton, MA
  • Wellesley, MA
  • Sudbury, MA

Office

  • Sudbury

    526B Boston Post Road

    Sudbury, MA 01776

    9784438484

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

As of October 28, 2026, there are 16 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 was $230,000.

Homes for sale
16
Median list price
$104,500
Median sale price (May 2026)
$230,000
Median days on market (May 2026)
19 days
  • Chester market report
  • Chester single-family homes for sale
  • Chester multi-family homes for sale

Homes for sale near Chester

  • Middlefield, MA
  • Huntington, MA
  • Blandford, MA
  • Otis, MA
  • Worthington, MA
  • Becket, MA
  • Montgomery, MA
  • Peru, MA

Common questions about Chester, MA real estate

How many homes are for sale in Chester, MA?

As of October 28, 2026, there are 16 homes for sale in Chester, MA, including 8 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 $104,500. 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 25 days on market.

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

The homes for sale in Chester, MA include 8 single-family homes and 1 multi-family home.