The Oldest Houses in Chester
296 resources stand on the state's historic inventory here: 246 of them buildings, with 10 recorded as demolished and excluded below. The assessors' rolls corroborate the age: about 16 parcels in town carry pre-1800 construction dates.
The Oldest on the Inventory
- 1747Ventura Lodge · 74 Blandford Rd · Colonial
- 1752Fay House · 156 Middlefield Rd · ColonialNational Register
- 1763Lyman, Steven House · 103 Lyman Rd · Georgian
- 1765Hamilton, James House · 15 Abbott Hill Rd · Colonial
- 1765Otis, James House · 25 Ed Lebleau Rd
- 1765Elder, Samuel House · 555 Skyline Trl · Georgian
- 1767Searles House · 345 Skyline Trl · ColonialNational Register
- 1769Phinney Farm · 156 Bromley Rd · Colonial
- 1769Mullholland, James House · 40 Holcomb Rd · Georgian
- 1769Bascom, Rev. Aaron House · 348 Skyline Trl · GeorgianNational Register
- 1769Smith, John House · 65 Lyman Rd · Georgian
- 1770Shepard, Dr. David House · 1 Crane 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 Chester Is Built In
- Greek Revival27
- Victorian Eclectic18
- Queen Anne13
- Federal12
- Italianate10
- Georgian9
- Colonial7
- Colonial Revival7
Inventoried buildings by recorded style, the survey's lens, not a census of every roof in town.
What Listing Actually Means Here
209 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. 1 carry recorded preservation restrictions that run with the deed. 1 is a National Historic Landmark. The inventory maps 11 historic areas in town: Chester Center Historic District; North Chester; Chester Factory Village Historic District….
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.