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The building located on the north side at 61 Holland St. West was built in the Romanesque Revival style around the 1880’s. The Scanlon Law Offices building was originally constructed to house the law practice of the two Scanlon brothers. Albert "Ab" Scanlon, a lawyer, and Mrs. Frank (Ethel) Woods, a widow and retired farmer (from the 8th Line) both resided here at one time.
The one-storey building has a rectangular plan, small window openings with high floor to ceiling heights, and a flat roof. The symmetrical façade has a simple, solid form. Round arches are reminiscent of the Roman Empire and rich, decorative details. Originally, there were two entrances contained unobtrusively in simple, rectangular openings on either side of the centre window. This is atypical of the Romanesque Revival style, where the entrance door was more frequently the most prominent element of the façade. The second entrance door to the west of the centre window has been “bricked in”, but its flat, arch opening is still visible by the line of the brick voussoirs. There is a wood-panelled door with an upper, glass light and also a rear entrance. The centre, ground-floor window is a prominent feature. It is exaggerated by the arch form set into the parapet above and subdivided vertically into three parts. Smaller windows to each side are set into segmented, arch openings with brick voussoirs. The windows are double-hung with stone (or concrete) lug sills. A major feature is the heavy parapet with an insert panel decorated richly with brick set in a basket weave pattern. The segmented arch extends the window form into the parapet panel. A cornice line along the bottom of the parapet is decorated with a line of brick dentils. The building has masonry construction, brick cladding, and a cut-stone foundation. According to the 2000 inventory, the structure is in good condition with many, original details remaining. (1, 2, 3)

The William Curry House is a mid-block building located at 73 Holland St. West. It was built in the Gothic Revival style around the 1890’s. Bill Curry, a carpenter, and his wife and children (Harvey and Jessie) moved here from the 14th Line, West Gwillimbury. Members of the Curry family have lived in this house for many decades.
The two-storey, ‘L’-shaped building has large window openings, high floor to ceiling heights, and a medium-pitched, gable roof. The shutters (but probably not the colour) may be original. A wrap-around entrance porch is original and has Regency overtones. Although the windows and doors have been replaced, the original wood, lug sills remain. The building has brick veneer on wood frame construction. Window awnings and attic vents are twentieth-century alterations. The soffit infill, if original, has an altered eaves detail. According to the 2000 inventory, the building is surrounded by a well-maintained, landscaped yard. (1, 2, 3)

The building located at 79 Holland St. West (on the northeast corner of Holland and Church Streets) was built in the Gothic Revival style around 1890-1910. Wilton Johnson and Irwin Ray, retired farmers, once lived in this house. Wilton worked for years for the Clubines. The previous owner was a tombstone maker who sold tombstones throughout all of Simcoe County.
The two-storey, ‘L’-shaped building has a medium-pitched, gable roof with a gable dormer. This is a typical Gothic Revival feature. Uncharacteristically, however, the dormer eaves do not align with the main roof eaves. A broad, hipped, Regency-like porch roof is supported by an eclectic mixture of forms (including a broad cornice band and half, Doric columns on brick pilasters). The porch railing and stairs are not original. There is a coloured-glass, arched transom over the main-floor, gable-end window. The ground-floor windows are wider than those at the second floor. The house has loadbearing, brick masonry construction and a stone foundation. According to the 2000 inventory, the building is an eclectic mixture of styles (suggesting early twentieth-century construction). It also notes that the modern door and railings are unsympathetic with the original design. (1, 2, 3)

Miss Sinclair’s House is a mid-block building located on the south side at 92 Holland Street West. It was built in the 1890’s in the Italianate style. Miss Bertha Sinclair lived in this house for many years. When she died, her nieces Kay and Isabel (daughters of Robert Spence) moved into the house. They were hairdressers. Isabel later moved and part of the house was rented to George and Ethel Stewart. The building was eventually sold to a real estate agent. The office of Dr. Fitzsimmons was also here at one time. Next to this structure was a vacant lot belonging to the Sinclair family. Many years ago there was a Temperance Hall and a church located there.
The two-storey, rectangular, main building has a single-storey, rear addition, a symmetrical façade, and a moderately-pitched, hip roof with a central chimney. The grand, Italianate scale is reflected in the large window openings, high floor to ceiling heights, and the large, 6/6 sash windows. There are deep, projecting eaves with ornately-decorated, paired cornice brackets and ‘false quoins’ (wood detailing meant to resemble masonry). The window cornices are exaggerated. According to the 2000 inventory, the stone foundation, wood frame construction, horizontal, wood-sided exterior finish (resembling masonry), and painted, exterior, wood trim are maintained well. (1, 2, 3).

The two-storey, brick house located at 108 Holland St. West was built by John Maurino on what was originally a 100-acre farm owned by John Skinner. Skinner lived on Church St. (at the southeast corner of John Street). There was a creek behind the original barn and a pond used for watering stock, etc. It was also used as a hockey and skating rink in the winter many years ago. The land was eventually sold to John Maurino. He added a two-storey shed and a new barn to the property at the time he built the house that is seen in this photo from 1995. Maurino and his wife (a sister of Cavallo, the local harness and shoemaker) farmed the land with their children Augustus, Aida, Frank, Lena and Laura. (1, 2)

Builder A.J. (Arthur) Saint and his wife Margaret once lived in the structure located at 113 Holland St. West. Art bought the house in 1931 and completely remodeled it. He added a walk-in refrigerator and a two-car garage in the old summer kitchen and woodshed. At the back of the lot at that time there was a two-storey barn that Art turned into a workshop. He had three children (Keith, Helen and Karen). Art died in 1952 and the house was sold a couple of years later to John DePeuter. It was later remodeled and bricked again as seen in this photo from 1995. (1, 2)

The building located at 120 Holland St. West in this photo from 1995 replaces one built by Watson (a cement block and sidewalk builder) just before, or during, WWI. That structure had a barn and shed for stock and chickens at the back. The Slothin family moved here from Toronto around the time of the Depression. They had one daughter and a son named Max. At one time Elgar Houghton and his wife lived here with their daughter (Muriel) and sons (Gordon and Lloyd). He drove a team (before he got a truck) and delivered gas for Imperial Oil. Paul Gres, his wife, and family (market gardeners) lived here years later. This house and property (around 25 acres) was still owned by the Gres family in 1995. (1, 2)

The Turner House is located at 185 Holland Street West (on the northwest corner of Holland and Toronto Streets). It was built in the 1880’s in the Eclectic Gothic Revival style. The two-storey, ‘L’-shaped building has an asymmetrical façade. The gable roofs above the front façade projection and at the centre of the façade facing Toronto Street are Gothic Revival features. A medium-pitched, hipped main roof with curb detail and wide eaves are Italianate features. The entrance is from an enclosed, asymmetrical porch with a shallow-pitched roof. The porch may originally have been open. Double-hung windows (of various sizes) are set into rectangular openings with plain, wood frames and sills. Painted, wood half-timbers decorate the front and side façades below the gables. There is a discontinuous eaves line, post and beam construction, and a parged, stone foundation. The stucco cladding has been replaced with insulbrick siding. According to the 2000 inventory, some original wood siding is visible below the gables. It also notes that other than the form and some details, there are few original features. (1, 3)

Miss Sinclair’s House is a mid-block building located on the south side at 92 Holland Street West. It was built in the 1890’s in the Italianate style. Miss Bertha Sinclair lived in this house for many years. When she died, her nieces Kay and Isabel (daughters of Robert Spence) moved into the house. They were hairdressers. Isabel later moved and part of the house was rented to George and Ethel Stewart. The building was eventually sold to a real estate agent. The office of Dr. Fitzsimmons was also here at one time. Next to this structure was a vacant lot belonging to the Sinclair family. Many years ago there was a Temperance Hall and a church located there.
The two-storey, rectangular, main building has a single-storey, rear addition, a symmetrical façade, and a moderately-pitched, hip roof with a central chimney. The grand, Italianate scale is reflected in the large window openings, high floor to ceiling heights, and the large, 6/6 sash windows. There are deep, projecting eaves with ornately-decorated, paired cornice brackets and ‘false quoins’ (wood detailing meant to resemble masonry). The window cornices are exaggerated. According to the 2000 inventory, the stone foundation, wood frame construction, horizontal, wood-sided exterior finish (resembling masonry), and painted, exterior, wood trim are maintained well. (1, 2, 3)

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).