Plaqued Houses and Buildings
235 Trafalgar Road - Simpson House
The Melancthon Simpson House was built in 1839.
Property Details:
This property was purchased from William Chisholm by William Dolby in 1838 and the house was built about a year later, probably as one of a pair built by John Potter who lived next door. In 1846 it was purchased by Melancthon Simpson. Simpson was a Methodist born in Upper Canada in 1823. His wife was Esther Terry, daughter of Elizabeth Silverthorn and John Terry and niece of both William Chisholm and Merrick Thomas. Melancthon and his brother, John, bought a shipyard about 1849 and built schooners ranging from the 141-ton Lily to the 230-ton Sea Gull which sailed to South Africa and back. The Sea Gull carried a deck cargo of prefab houses and Canadian Whisky in the hold. Apparently they were unable to sell the whisky in South Africa but it sold well in New York City on the way back. After moving away from Oakville, Simpson built the steamship Segwun which is still plying Lake Muskoka today.

In 1858 the Simpsons sold the house but got it back in 1866. They resold it a year later. In 1882 the property right through to Reynolds Street and including a barn was purchased by John Freestone for $525 cash. He worked at the basket factory and his mother looked after portions of his weekly pay for him. In 1915 Freestone built a new house on Reynolds Street.

In 1920 the house was sold to Faith Chisholm Robinson and has been owned by the family for over 100 years. In the 1930s it was the home of Lightbourn’s School for girls, now St Mildred’s Lightbourn.

It is a fine example of a Regency Cottage and is the earliest in Oakville. The low-slope hip roof and tent-shaped verandah roof flanked by two shuttered French windows identifies the style. The verandah originally covered three sides of the house and the lawn was level with the sidewalk. Curved walls by the sidelights allow light into an otherwise narrow hallway. Several additions have been made over the years.
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235 Trafalgar Road, 1991235 Trafalgar Road, 1991
Trafalgar Road #235Trafalgar Road #235
235 Trafalgar Road, 1957235 Trafalgar Road, 1957
Mr. and Mrs. John Freestone, c 1920sMr. and Mrs. John Freestone, c 1920s
Faith Fell (nee Chisholm) (1894-1973)Faith Fell (nee Chisholm) (1894-1973)