Winchester, Massachusetts · Building type

Houses and mansions in Winchester

This tour visits places the Register records as dwellings, among them single houses, rowhouses and mansions. Many are private homes and the stops are meant to be seen from the sidewalk. More of the Winchester register is houses than any other kind of building, 55 listings of it in all.

The stops that carry a construction date run from 1840 to 1909. 15 stops, 1.0 miles end to end.

Distances are straight lines between the coordinates in the National Park Service Register data, so the walk on the street will be longer. Nobody has walked or checked this as a route, and a listing does not mean a place is open to visitors. Stops last changed Sep 18, 2026.

All walking tours in Winchester → · Every listing in Winchester →

15
Stops
1.0 mi
Total, straight line
0.2 mi
Longest leg
6
With a construction date

Map

Coordinates come from the National Park Service National Register spatial data. The solid line joins the stops in walking order and is not a street route. Listings with a restricted address in the Register are never mapped and never become stops. Data refreshed September 19, 2026.

Walking order

  1. 1O. W. Gardner House5 Myrtle St.Building · listed 1989start
  2. 2Edward Sullivan House9 Kendall St.Building · listed 1989369 ft from stop 1
  3. 3S. B. White House8 Stevens St.Building · listed 1989338 ft from stop 2
  4. 4Pressey--Eustis House14 Stevens St.Building · listed 198975 ft from stop 3
  5. 5Amy B. Mitchell House237 Highland Ave.Building · built 1909 · listed 1989329 ft from stop 4
  6. 6Moore House85 Walnut St.Building · built 1845 · listed 19890.2 mi from stop 5
  7. 7Edward A. Brackett House290 Highland Ave.Building · built 1850 · listed 1989503 ft from stop 6
  8. 8Cole House12 Mason St.Building · built 1886 · listed 1989189 ft from stop 7
  9. 9John Mason House10 Hillside Ave. (formerly 8-10 Hillside Ave.)Building · listed 19890.1 mi from stop 8
  10. 10Parker House180 Mystic Valley Pkwy.Building · listed 1989303 ft from stop 9
  11. 11Alfred Vinton House417 Main St.Building · built 1854 · listed 1989373 ft from stop 10
  12. 12Sharon House403 Main St.Building · listed 1989202 ft from stop 11
  13. 13Hutchinson--Blood House394--396 Main St.Building · built 1840 · listed 1989178 ft from stop 12
  14. 14William Simonds House418-420 Main St.Building · listed 1989168 ft from stop 13
  15. 15Jacob Stanton House21 Washington St.Building · listed 1989474 ft from stop 14

1.0 straight-line miles over 14 legs. Printed from registeratlas.com/tours/ma/winchester/function-houses/

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