In 1861 Thomas Headley, recently arrived from England with his wife Jane Rutherford, their sons Matthew and John and daughter Jane, was living in Stratford, which had grown to town status in 1859. The Canada Company had concluded its settlement of the Huron Tract, which included Stratford and most of Perth County, and the town had been divided into five wards —Avon, Falstaff, Hamlet, Romeo and Shakespeare. The Grand Trunk Railway along with the  Buffalo and Lake Huron line were in operation. Thomas was working as a labourer and daughter Jane, age 18, was earning a living as a milliner.

 
As the years went by the eldest son, Matthew, became a well digger, and in 1872 he married Elizabeth Bateman, a native of Ireland living in Stratford. Elizabeth had grown up in Seaforth, which is where the marriage took place. In the summer of 1875 the couple with their two young daughters, two-year-old Jane and baby Mary Elizabeth, were preparing to move into the new house being built on Lot 20 along the south side of Hibernia Street, a property which would become #227. 

In those early days Stratford was surrounded by land being cleared by pioneer farmers anxious to start establishing their livestock herds and the crops needed to feed them. Just across Hibernia Street on the north side was a 75 acre farm, operated by the sons of one of Stratford’s earliest settlers, John Sharman. Extending to Britannia Street it included the area where the old fair grounds were located. First developed by John’s son Robert and later operated by Robert’s eldest son, Joseph, the farm was the home of a herd of purebred beef cattle imported from England (which he later took with him when he re-located to Manitoba). Joseph’s residence, located on the northwest corner of Hibernia and Avondale Streets, is now a bed and breakfast operation.

A son, William John, joined the Headley family followed by a third daughter, Eveline, and another son, Edward. After living on the Hibernia Street property for about five years they moved to Douglas Street to live beside Matthew's father, Thomas. Henry Barker, a Stratford merchant, became the new owner pf 227 Hibernia. A few years later the Headleys settled on Charles Street near John Street which is where they were living when Matthew died on June 7, 1903 at age 64. His obituary notes that he was one of Stratford's oldest residents, well-known and well-liked.