Chesterfield

Chesterfield is a rural hill town in Hampshire County, Massachusetts, United States, 26 miles east of Pittsfield and 110 miles west of Boston. The population was 1,222 at the 2010 census. It is part of the Springfield, Massachusetts Metropolitan Statistical Area.

7 homes for sale in Chesterfield

Name: Open House - 12:30PM-2:00PM
Start: 2026-11-01T12:30:00
End: 2026-11-01T14:00:00
Location: 50 Bray Road, Chesterfield, MA 01012

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1/28 28

Open Sun 12:30PM-2PM

$ 405,000

2 Beds1 Bath846 SqFt

50 Bray Road, Chesterfield, MA 01012

Single Family Home

Listed by Lisa Palumbo of Delap Real Estate LLC
1/21 21

New

$ 425,000

4 Beds1 Bath1,947 SqFt

316 Main Road, Chesterfield, MA 01012

Single Family Home

Listed by Jarod Martin of Greenfield Group Real Estate
1/42 42

Active

$ 1,850,000

5 Beds2.5 Baths3,494 SqFt

31 North Rd, Chesterfield, MA 01012

Single Family Home

Listed by Grace Golden of CR Premier Properties
1/40 40

Price Dropped by $45K

$ 469,000

3 Beds1.5 Baths1,781 SqFt

3 Stage Rd, Chesterfield, MA 01096

Single Family Home

Listed by James A. Molyneux of Molyneux Realty
1/14 14

Active

$ 550,000

3,898 SqFt

432 Main Road, Chesterfield, MA 01012

Commercial

Listed by Michael Packard of Coldwell Banker Community REALTORS®
1/13 13

Active

$ 199,950

7.4 Acres

0 Bissell Rd, Chesterfield, MA 01096

Vacant Land

Listed by Louis Poulin of eRealty Advisors, Inc.
1/5 5

Active

$ 169,000

4 Acres

0 Pynchon Rd, Chesterfield, MA 01012

Vacant Land

Listed by James A. Molyneux of Molyneux Realty