The Clockmaker's Inn was built by Robert Canavan of Scotch Village in 1894 for Rufus Curry - a son of a wealthy Sea Captain and business merchant. The house was occupied by Rufus Curry from 1894 until his death in 1934 and his widow Cornelia continued to live in the house until 1946.

From 1946-1956 the house was used as a nursing home known as Windsor Manor.

 In 1956 it was purchased by David and Esther Allbon who converted the carriage house into a printing shop.

In 1978 Dennis and Veronica Connelly purchased the house and in 1985 opened their home as a Bed and Breakfast calling it the "Clockmaker's Inn" after the book entitled - "The Clockmaker" by Judge Thomas Haliburton, a Windsor native. In the late 1990s the Connellys retired the Bed and Breakfast but continued to live in the home until the Dunham's purchased the historic property in Feburary 2005 and transformed the grand old home into a beautiful Victorian Inn.

 On July 1st 2006, after a year and a half of renovating the house, and converting the Carriage House into a modern loft apartment for Sarah and Sean to live in, The Clockmaker's Inn re-opened its doors to the public.