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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)

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).

This mid-block structure is located at 23 and 25 John St. East. It was built around 1830-1860 in the Neoclassical Duplex style. Lewis Algeo, one of the first Irish settlers in West Gwillimbury and a retired farmer, once lived in the west side of the building. T. S. Graham lived in the east side in the early 1900’s. James Glynn lived here around 1916. He left it to James Nolan, son of Denis and Catherine Nolan (reeve of West Gwillimbury), his wife Clare(a piano teacher), and their son, Dennis. The east side was also once the home of Miss Dora Noble, a nurse at the new hospital in Newmarket. She lived here with her retired father (James Noble) until he passed away.
The two-storey, six-bay, semi-detached structure has a rectangular plan with a side hall entrance. It has a two-storey, ‘L’-shaped, rear extension and a medium-pitched, gable roof with chimneys set into each gable end. The formal, symmetrical façade has a series of openings arranged equally across the front. It has paired, entrance doors with side halls along the common, party wall. The raised entrances are set close to the street with side stairs and railings that are not original. Each door has a high transom light set into a plain, rectangular opening. There are large window openings with high floor to ceiling heights. Equal-sized ground and second-floor windows with high sills are set into rectangular openings with plain, wood frames and lug sills. The windows are not original. Wood frame construction is covered with vinyl siding and the building has a cut-stone foundation with a basement. Originally, the cladding was stucco. According to the 2000 inventory, few original details remain other than the building’s form. It also notes that the chimney is not original. An aggressive fire damaged much of the structure on April 6, 2015. Several residents were left homeless as a result of the fire (Bradford Times, April 7, 2015). The structure has since been demolished. (1, 2, 3)

The mid-block building located at 71 John St. East was built around 1900 in the Edwardian Classicism style. It was once the home of Sam Stein and his son and daughter. He was the owner of the Toronto Manufacturing Co. (maker of baby carriages and wicker furniture). His business was located on the northwest corner of Dissette St. until around 1929. After its end, the house was rented to a number of O.P.P. officers and their families, including Ivan Spence and Sam Irwin (a talented violin player). It was also the home of Joe Kanyo (a market gardener) and his family at one time. Leonard Saint built a large cement garage at the rear of the house. It had a basement for storing vegetables and a ground-level room for vehicles. The house was eventually sold and redesigned into rental apartments.
The large, 2½-storey house has a rectangular plan with a side hall, an asymmetrical façade and a simple, formal composition. It has a prominent, gable roof. The Classical roof form is expressed as a pediment with extended eaves and mixed with the Queen Anne texture of wood shingles. A raised, entrance portico with a flat roof and balustrade with access from the second- floor portico roof is set on a plain entablature ornamented with a band of dentils and set on double posts on brick piers. The single door is off-centre. There are large window openings with high floor to ceiling heights. Multi-paned, double-hung windows are reminiscent of the Queen Anne style. Ground and second-floor windows are set into segmented, arch openings with brick voussoirs and concrete, lug sills. The third-floor windows have wood entablature and plain, wood trim and sills. Wood frame construction is covered with smooth brick and wood-shingle cladding. There is a parged, stone foundation. The portico steps, foundation and balustrade, and entrance door are not original. According to the 2000 inventory, the house is in good condition. It also notes that the original form and many details are still intact. (1, 2, 3)

The mid-block structure located at 79 John St. East was built around 1860-1890’s in the Gothic Revival style. Originally, there was a shed and garage attached to the house at the rear and a vacant lot on the east side. This building was the home of Charles Aitcheson and his wife Carol for many years. He was a painter and decorator and he worked for Bill Sutton. Cyril Mestagh was the next owner of the house. He and his wife Jennie and their daughters (Vera and Gladys Irene) lived here. Cyril was a small, market gardener and a well-known grower. He hauled vegetables to the Toronto market. The house was sold when Cyril retired.
The 1½-storey structure has an ‘L’-shaped plan with a centre hall, a one-storey, rear, kitchen wing and a medium-pitched, gable roof. The asymmetrical façade has an off-centre, front gable above the façade projection. There is a raised, front porch with a shed roof set onto wood posts on brick. The steps, door, windows, and enclosing walls of the porch are not original. This building has small windows with high floor to ceiling heights. A wide, Regency-style, ground- floor window has a wide, centre opening flanked by narrow lights. It is set into a rectangular opening with a plain, wood frame and sill. An upper window is centred above the lower window in the projecting bay. It is also set into a rectangular opening with a plain, wood frame and sill. Only the 2/2 windows in the structure are original. The building has wood frame construction, vinyl siding (not original), and a parged, stone foundation. According to the 2000 inventory, some original details still remain. (1, 2, 3)

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)

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 one-storey building with a flat roof located at 21 Barrie St. has been used by many businesses over the years. Tommy Lautonee owned the blacksmith and carriage factory once situated in this structure. George Geddes was the blacksmith there until late in 1937. There was a stable door at the south end of the building and two sets of windows running along the front. There was also a large door going to the rear where there was a stall for shoeing uncooperative horses and a large flat stone circle with a hole in the middle (for pestling steel rims on wheels). In later years, the Bradford Witness (owned by Stewart and Ina McKenzie) moved from Holland St. to this structure. The newspaper also ran a printing shop here. Harvey Marks was a typesetter. Frank Edney and Fallis also helped. After Stewart passed away, Ina ran the business until she retired. (1, 2)

The one-storey building with a flat roof located at 23 Barrie St. (as seen in the photo) replaces the round, metal building originally found on this site. It was an implement store and later the home of a pop business moved here by Keenty O’Keife (?) and run by Dave Smith (who helped deliver in and around the county). The building became a Chinese restaurant owned by Jack Pong around 1938. He ran it until after WWII (when he moved to Holland Street). (1, 2)