Chesterfield

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

31 North Rd
Chesterfield, MA $1,850,000

31 North Rd

Chesterfield, MA

$1,850,000
  • 5 Beds
  • 2/1 Baths
  • 3,494 Sqft
409 Main Rd
Chesterfield, MA $699,000

409 Main Rd

Chesterfield, MA

$699,000
  • 5 Beds
  • 3 Baths
  • 3,752 Sqft
432 Main Road
Chesterfield, MA $550,000

432 Main Road

Chesterfield, MA

$550,000
  • 2.00 Baths
  • 3,898 Sqft
3 Stage Rd
Chesterfield, MA $469,000

3 Stage Rd

Chesterfield, MA

$469,000
  • 3 Beds
  • 1/1 Baths
  • 1,781 Sqft
316 Main Road
Chesterfield, MA $425,000

316 Main Road

Chesterfield, MA

$425,000
  • 4 Beds
  • 1 Baths
  • 1,947 Sqft
50 Bray Road
Chesterfield, MA $405,000

50 Bray Road

Chesterfield, MA

$405,000
  • 2 Beds
  • 1 Baths
  • 846 Sqft
66 Fuller Rd
Chesterfield, MA $325,000

66 Fuller Rd

Chesterfield, MA

$325,000
  • 3 Beds
  • 1 Baths
  • 1,531 Sqft
134 Indian Hollow Rd
Chesterfield, MA $220,000

134 Indian Hollow Rd

Chesterfield, MA

$220,000
  • 2 Beds
  • 1 Baths
  • 1,116 Sqft

Chesterfield

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