Chesterfield

Massachusetts

VIEW 15 COMMUNITY LISTINGS

A rural Hampshire County hill town, Chesterfield is situated along the scenic Westfield River and offers a small-town atmosphere amid an abundance of scenic beauty.

Named after the Earl of Chesterfield, the rural hill town of Chesterfield in Hampshire County boasts a population of about 1,200 residents. The community, comprising about 31.2 square miles, is situated 25 miles east of Pittsfield, 50 miles north of Hartford, Connecticut and 100 miles west of Boston. Chesterfield, which was first settled in 1790 and incorporated in 1762, was primarily an agricultural community in its early days, known for the production of Merino wool. The town also had several tanneries and sawmills which were the dominant industries in the early 19th century, attracting a small population of Irish immigrants. With the arrival of the 20th century, however, the town’s agricultural roots regained economic prosperity, and Chesterfield experienced an influx of summer residents. A popular point of interest is the Chesterfield Gorge, situated along the Westfield River.

Named after the Earl of Chesterfield, the rural hill town of Chesterfield in Hampshire County boasts a population of about 1,200 residents. The community, comprising about 31.2 square miles, is situated 25 miles east of Pittsfield, 50 miles north of Hartford, Connecticut and 100 miles west of Boston. Chesterfield, which was first settled in 1790 and incorporated in 1762, was primarily an agricultural community in its early days, known for the production of Merino wool. The town also had several tanneries and sawmills which were the dominant industries in the early 19th century, attracting a small population of Irish immigrants. With the arrival of the 20th century, however, the town’s agricultural roots regained economic prosperity, and Chesterfield experienced an influx of summer residents. A popular point of interest is the Chesterfield Gorge, situated along the Westfield River.

Named after the Earl of Chesterfield, the rural hill town of Chesterfield in Hampshire County boasts a population of about 1,200 residents. The community, comprising about 31.2 square miles, is situated 25 miles east of Pittsfield, 50 miles north of Hartford, Connecticut and 100 miles west of Boston. Chesterfield, which was first settled in 1790 and incorporated in 1762, was primarily an agricultural community in its early days, known for the production of Merino wool. The town also had several tanneries and sawmills which were the dominant industries in the early 19th century, attracting a small population of Irish immigrants. With the arrival of the 20th century, however, the town’s agricultural roots regained economic prosperity, and Chesterfield experienced an influx of summer residents. A popular point of interest is the Chesterfield Gorge, situated along the Westfield River.

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Featured Listings

330 East St
Chesterfield, MA $985,000

330 East St

Chesterfield, MA

$985,000
  • 3 Beds
  • 2 Baths
  • 2,922 Sqft
31 Farm House Rd
Chesterfield, MA $454,500

31 Farm House Rd

Chesterfield, MA

$454,500
  • 2 Beds
  • 1 Baths
  • 1,024 Sqft
11 Farmhouse Road
Chesterfield, MA $450,000

11 Farmhouse Road

Chesterfield, MA

$450,000
  • 3 Beds
  • 2/1 Baths
  • 2,100 Sqft
574 Main Rd
Chesterfield, MA $449,900

574 Main Rd

Chesterfield, MA

$449,900
  • 3 Beds
  • 2 Baths
  • 1,658 Sqft
8 Antin Rd
Chesterfield, MA $350,000

8 Antin Rd

Chesterfield, MA

$350,000
  • 2 Beds
  • 1 Baths
  • 1,068 Sqft
11 Bryant St
Chesterfield, MA $288,000

11 Bryant St

Chesterfield, MA

$288,000
  • 3 Beds
  • 2 Baths
  • 2,043 Sqft
134 Indian Hollow Rd
Chesterfield, MA $220,000

134 Indian Hollow Rd

Chesterfield, MA

$220,000
  • 2 Beds
  • 1 Baths
  • 1,116 Sqft
43 Don Emerson Rd
Chesterfield, MA $219,000

43 Don Emerson Rd

Chesterfield, MA

$219,000
  • 2 Beds
  • 1 Baths
  • 508 Sqft

Chesterfield

Area Map

Chesterfield is within Pioneer Valley, Massachusetts and borders Cummington.

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Featured Communities Within

Pioneer Valley

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Chesterfield

Market Snapshot

Median Sales Price

June 2023 - Single Family Homes

$790K

Percentage of Asking Price

June 2023 Single Family Homes

103%
103%