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The building located at 46 Simcoe Road (on the corner of Thomas St. and Simcoe Road) was built pre-1900 in the Ontario Vernacular Cottage style. James Church, and then Jimmie Jackson, his wife, and son once lived in this house. Jimmie worked for the town, was a noted drain expert, and did road work. Mrs. Jackson remained in the house for many years after her husband died. It was also once the home of Lorne Faris (a jeweller) and his wife (Ona). Lorne converted the shed that was on the property into a garage. John Kanyo Jr. lived here when he was first married. After the Kanyo family, it became the home of Budd Robson. Years later, Mr. and Mrs. Emerson Madill (retired farmers from the south side of the 10th Concession near Highway 400) resided here.

The one-storey, three-bay ‘cottage’ has a simple form with a symmetrical façade, a rectilinear plan, and a shallow-pitched, gable roof. It has a centre hall entrance from a covered, open, front-entrance porch which is accessed from the side. Originally, the porch stairs were in the centre and aligned with the front door. The hip roof on the porch is supported on turned posts. Decorative, wood fascia is found at the porch roof. There is a plain, wood handrail and balusters and the porch foundation is enclosed with wood lattice. The building has narrow window openings with low floor to ceiling heights. Windows are set into rectangular openings with plain, wood trim and sills. The house has wood frame construction with brick cladding and a parged, concrete foundation. Originally, the cladding was stucco. According to the 2000 inventory, the house is in good condition with some original features that have been maintained well. (1, 2, 3)

The mid-block building located at 47/49 Simcoe Road was built around 1830-1860 in the Neoclassical Duplex style. Originally, there was a long, one-storey, frame house located at this site. It had a verandah on the northwest side, a picket fence along the street, a large barn on the south side of the house, a garden at the back and it was the home of Lew McConkey Sr. (a grain and seed merchant), his wife, and son. Lew had an office on the north side of Holland Street. New owner Paul Sadlon had Len Saint build a garage and a storage building at the back. Paul and his wife were market gardeners. Their son owned Bruce Sadlon Motors. The house was later converted into two apartments. Jack Gibney and his wife (Sadie Copeland) and their three daughters (Doris, Joyce and Muriel) lived here at one time. He was a horse trainer and worked for Dick Crake for many years. Jack replaced Alfred Payne (a bachelor who lived at the Queen’s Hotel). The current duplex was built on the same property after the house was demolished. Harold Gwyn, owner of a plumbing and heating business, was the owner of this newer building at the time this photo was taken in 1996.
The two-storey, four-bay, semi-detached house has a rectangular plan, a formal, symmetrical façade, and a medium-pitched, gable roof that has a central chimney (not original). Slightly-raised, separated, side-hall entrances are located at either end of the façade. This gives greater privacy than paired entrances, but it places habitable rooms along the party wall. The doors are set into plain, rectangular openings and are not original. There are large window openings with low floor to ceiling heights. Equal-sized, ground-floor and second-floor windows (not original) with high sills are set into plain, rectangular openings. The openings have plain, wood frames and sills. Similar window openings above the entrance doors may have once existed and then been covered. The building has wood frame construction with vinyl siding (not original), a cut- stone foundation, and a basement. According to the 2000 inventory, few original details remain other than the building’s form. It also notes that the slightly-sagging roof suggests insufficient structural supports in the centre of each house. (1, 2, 3)

The building located at 1 Holland St. West was originally built as a hotel (Central Hotel, Uneeda Hotel, H. Hulse Hotel). Tom and Len Saint worked on the construction of the building. George Webb ran the hotel for a while before he moved to Saskatchewan. Tom Bell was the manager for many years until he retired and moved to the east side of Simcoe Street. Around 1917 it became the Imperial Bank of Commerce. A large safe and living quarters for the bank staff were located upstairs. The entrance to the apartment was on the west side of the building. John McDowell and his family lived here in the 1930’s. The bank was robbed by the notorious “Boyd Gang” in the 1940’s. At one time the front offices were used by the police, and the back offices were used by Mr. Scanlon (a lawyer). The bank closed in 1972 and was moved further west on Holland Street. This building then became a real estate office, a convenience store, and as of 2014, the Coffee Culture Café. (1, 2)

The original building located at 4 Holland St. West (on the southwest corner of Holland and Simcoe Streets) was built in the 1840’s and was situated on land originally owned by James Drury. He was one of the early immigrants who reached Upper Canada. Drury rented the corner lot to Thomas Driffill (a blacksmith), who opened a hardware store at that location. The lot was later sold to Robert Cooke, who leased the property to Driffill for another 20 years. Thomas Driffill became the village of Bradford’s first reeve when it was incorporated in 1857. The great fire of 1871 destroyed all but the building’s foundation. It was rebuilt incorporating the intact, old vault and locally-made bricks. Thomas Driffill bought the building in 1885, eventually retired, and left the business to his sons, Joseph and James, who eventually sold it to Andrew Thompson, Driffill's partner. It became Thompson's Hardware. A series of different owners and different types of enterprises followed. William Barron bought the building in 1946 and relocated his hardware business to this site. He made several renovations, including adding a new stone façade, new plate glass windows, and an elevator to facilitate deliveries to the tinsmithing shop upstairs. He retired and left the business to his son Norman. The building later became a motorcycle shop, and eventually, for several years, the Winchester Arms Restaurant. (1, 2, 4, “Four Holland Street West: A Short History” by Lorraine Philip - Bradford West Gwillimbury Public Library, Local History Collection).

The mid-block building once located at 49 Drury St. was built in the neoclassical style around 1880. James Currie (a retired farmer, businessman, carpenter and noted gardener) and his wife lived here many years ago. Gilbert Lukes, his wife, and some of his family also lived here at one time.
The two-storey, rectangular building had a symmetrical façade, a centre hall plan, and a medium-pitched, gable roof. It had large window openings with high floor to ceiling heights. The large, 2/2 double-hung, wood windows had wood lug sills. Aluminum storm windows were modern additions. The house had symmetrically-placed chimneys at both ends of the roof. The metal roof had minimal eaves projection. There were decorative brick dentils at the cornices and stepped brick corbels at the projecting, end gable walls (firewall-type construction). The building had solid, brick construction. At one time the house had a woodshed (with a toilet inside), a chicken run, and a chicken house attached to the barn (with a horse and cow stable), car garage (and loft above) on the laneway. The house was demolished in June, 1997. (1, 2, 3)