Cheshire · The Old House Atlas
The Oldest Houses in Cheshire
180 resources stand on the state's historic inventory here: 106 of them buildings, with 5 recorded as demolished and excluded below. The assessors' rolls corroborate the age: about 10 parcels in town carry pre-1800 construction dates.
The Oldest on the Inventory
- 1768Coman, Daniel - Bennett, Joseph House · 1051-1053 Wells Rd · Colonial
- 1768Low, Capt. Samuel House · 800 Jenks Rd · Georgian
- 1770Brown, Nicholas House · 411 Jenks Rd · Federal
- 1770Weskit - Cole House · 478 West Mountain Rd · Colonial
- 1775Richardson - Brayton House · 184 Stafford Hill Rd · Colonial
- 1776Bowen, Valentine House · 10 Stafford Hill Rd · Greek Revival
- 1780Whitmarsh, Toleman House · 198 West Mountain Rd
- 1790Bradford - Cole House · 477 North State Rd · Colonial
- 1790Tiffany Green · 38 South St · Second Empire
- 1791Cushing - Martin House · 450 North State Rd · Colonial
- 1791Jenks, Jesse Farm · 761 Wells Rd · Georgian
- 1792Richardson House · 725 North State Rd · Federal
Dates are the surveyor's attribution, often approximate. Names are the inventory's own historic designations. These are private homes unless a museum says otherwise, admire from the road.
What Cheshire Is Built In
- Greek Revival30
- Federal22
- Colonial7
- Colonial Revival5
- Italianate5
- Second Empire4
- Gothic Revival3
- Greek Revival; Victorian Eclectic3
Inventoried buildings by recorded style, the survey's lens, not a census of every roof in town.
What Listing Actually Means Here
73 of the town's inventoried resources are on the National Register, an honour that, for a private owner, restricts almost nothing. No local historic district binds owners here. The inventory maps 5 historic areas in town: Cheshire Town Center; Farnams Village Historic District; Mount Greylock State Reservation….
Old Houses Nearby
The nearest towns, and the age of their housing stock.
From the Desk
RE413 News: what to check before you buy an old house here. Built from the same public record as the figures on this page.
Sources
- Massachusetts Historical Commission inventory; assessors' parcel rolls for the age corroboration. Checked 2026-08-05.
"Figures through" is the period the publisher's data describes; "checked" is only when we last asked. The full sourcing: sources and method.