The Oldest Houses in Windsor
45 resources stand on the state's historic inventory here: 32 of them buildings, with 2 recorded as demolished and excluded below. The assessors' rolls corroborate the age: about 4 parcels in town carry pre-1800 construction dates.
The Oldest on the Inventory
- 1785Dawes, Samuel House · 800 Windsor Bush Rd · Federal
- 1790Winslow, Henry N. House · Windigo Rd · Federal
- 1795Allen, Capt. J. Farm · River Rd · Federal
- 1795Ford, N. House · River Rd · Federal
- 1796Whitmarsh, James House · 254 Flintstone Rd · Federal
- 1800Beales, Gideon - Cahill, Andrew House · 40 Pierce Rd · Federal
- 1800Beales, Calvin Wheelock House · 154 Windsor Bush Rd · Federal
- 1800Hollis, Jephithal House · 780 Windsor Bush Rd · Federal
- 1810Capen, Howland Dawes Farm · 1195 East Windsor Rd · Federal
- 1810Fairfield, J. H. House · 665 North St · Federal
- 1810Dawes, Harvey House · 968 Windsor Bush Rd
- 1810Windsor Historical Commission Museum · 1985 Rt 9
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 Windsor Is Built In
- Federal13
- Greek Revival4
- Colonial Revival2
- Shingle Style1
Inventoried buildings by recorded style, the survey's lens, not a census of every roof in town.
What Listing Actually Means Here
1 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 3 historic areas in town: Winslow Farm - Windigo Camp; Windsor State Forest - Windsor Jambs; Windsor State Forest - Steep Bank Brook.
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.