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The mid-block building located at 23 John St. West was built pre-1900 in the Ontario Vernacular Cottage style. It was the home of retired farmer Walter King (during and after the war) until his death.
The one-storey, three-bay cottage has a rectangular plan, a centre hall, a symmetrical façade and a gable roof. It had a kitchen at the rear originally. There are single windows (with low floor to ceiling heights) to the primary rooms on each side of the porch at the front. The wood trim is original, but the windows and the door are replacements. Metal supports for the porch roof are not original, but the roof itself may be authentic. The house has wood frame construction with vinyl siding. The original wood siding is probably still under the newer cladding. According to the 2000 inventory, few existing building elements appear to be original other than the building’s form. It also notes that this modest cottage probably had few decorative details originally. (1, 2, 3)

The one-storey, frame house located at 45 John St. West originally had a kitchen and a woodshed at the rear and a veranda at the front. It was the home of Stan Cairns' parents Isaac and Grace (Fisher). The family lived here before and after World War II. (1, 2)

The small, frame house located at 52 John St. West was built by Art Saint after World War II for his father (Frank) and sister (Lena). After Frank’s death, Lena moved to Toronto and the house was sold. (1, 2)

The mid-block building located on the south side at 126 John St. West was built in the 1880’s in the Gothic Revival Cottage style. Originally, there was a back lane for Jim Woods' house and barn next to this house. Pratt lived here many years ago with his wife and two sons. Elgar Houghton bought this house around the time of World War II. He lived there for a time and then he had the house converted into four apartments which were rented. He later sold the building.
The 1½-storey, five-bay cottage has a rectangular plan with a centre hall, an asymmetrical façade with an off-centre gable over the entrance, and a medium-pitched, gable roof. There is a simple, rectangular entrance (at grade level) with windows to the primary rooms on each side. The existing roof over the entry is not original. Small windows at the ground and second floors are not original. They are set into segmented, arch openings with plain, wood frames and painted, stone lug sills. Brick, masonry construction is clad with stucco (not original) and the structure has a parged, stone foundation. According to the 2000 inventory, this modest house has few original details other than the building’s form. (1, 2, 3)

This house is located at 139 John St. West (on the northwest corner of John and Essa Streets). It was built in the 1900’s by carpenter Dalt Coburn. Originally, there was a laneway behind the house that ran west to Toronto St. and a vacant lot next door. The 1½-storey, frame house had many gables. There was a fire here at one time. Dalt raised his family (including son Des) here before moving to Cookstown in the early 1930’s. James Pelovich and his son Jim lived here in 1935. Later George Sadovchuk and his mother (Stephanie Semenuk Sadovchuk) lived here. Stephanie was James Pelovich's mother. George remodelled the house extensively. The veranda at the top was removed and the brick was matched. (1, 2)

This one-storey house is located at 156 John St. West. The original cladding was stucco and there was a kitchen at the back. Mrs. Belfry owned the building many years ago. After her death, Merle Woodcock bought (and repaired) the house. John Holancin and his wife Zuzana (Balint) and large family lived here for a number of years. They were market gardeners on Highway #9. (1, 2)

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 units located at 70 Simcoe Road (north side) and 72 Simcoe Road (south side) are part of an apartment building that was erected in 1980. The property was originally the site of a large, frame house that had a woodshed, chicken house, and a horse and cow stable on the back lane (Elizabeth Street). It was the home of Mr. Peachman (a farmer), his wife and sons (Wilbert, Harvey and Louis) many years ago. He was a day worker and a labourer. Charles Jackson and his wife (retired farmers) later lived here with their family before the house was demolished. (1, 2)

The two-storey house located at 78 Simcoe Road was once the home of Bob Root, his wife Sarah, and children (Bill and Mildred). The family moved here from Newton Robinson many years ago. He was a pump maker and a repairman. Howard Robson, Evelyn, Alvin, Garret and Phyllis, Budd and Shirley also lived here at one time. Howard worked on the railway and then at Bender Caskets in Newmarket. He retired and later died in this house. His wife looked after (and nursed) Miss Sterling (Stirling?), an unmarried woman who left her money to many people when she died in the 1930’s. (1, 2)