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The two-storey house located at 56 Barrie St. was built around 1936. It was once the home of Dr. Sinclair. (1)

The mid-block building located on the west side at 60 Barrie St. was built pre-1900 in the Ontario Vernacular Cottage style. The one-storey, three-bay cottage has a symmetrical façade, a square plan, and a centre hall. A box hall was typical for this style. It has a shallow-pitched, hip roof and small window openings with low floor to ceiling heights. The double-hung windows at the ground floor have plain, wood trim and sills. Some 2/2 windows appear to be original. The enclosed porch was added at a later date. It has a single door opening to one side. The house has wood frame construction with vinyl siding (probably wood originally) and a parged, stone foundation. There is a single, brick, masonry chimney at the centre of the house. According to the 2000 inventory, few existing building elements appear to be original (other than the form). It also notes that the cottage probably had few decorative details originally. (1, 3)

The mid-block building located on the west side at 60 Barrie St. was built pre-1900 in the Ontario Vernacular Cottage style. The one-storey, three-bay cottage has a symmetrical façade, a square plan, and a centre hall. A box hall was typical for this style. It has a shallow-pitched, hip roof and small window openings with low floor to ceiling heights. The double-hung windows at the ground floor have plain, wood trim and sills. Some 2/2 windows appear to be original. The enclosed porch was added at a later date. It has a single door opening to one side. The house has wood frame construction with vinyl siding (probably wood originally) and a parged, stone foundation. There is a single, brick, masonry chimney at the centre of the house. According to the 2000 inventory, few existing building elements appear to be original (other than the form). It also notes that the cottage probably had few decorative details originally. (1, 3)

The Davey House is a large, two-storey house located at 79 Barrie St. (on the northeast corner of Barrie St. and Scanlon Avenue). It was built in the Gothic Revival style around 1880. There was a two-storey, frame barn on the back of the lot originally. Bill Davey and his family - Minto "Scott", Leona, Oswald, Archie, and Margaret - lived here many years ago. Bill was a carpenter’s helper for local builder A.J. Saint. Bill was also a noted lumberman, butcher, and hunter. He owned a slaughterhouse on the west side of Simcoe St. (Picadilly Hill) and a butcher shop at the corner of Holland and Moore Streets. Bill died at his hunt camp in his nineties.
The ‘L’-shaped house sits quite near the street line. It has large window openings with high floor to ceiling heights and a medium-pitched, gable roof. Elaborately-carved bargeboard trim and finials, a coloured glass, arched transom over a main-floor window, and the original wood lug sills remain. The house has wood frame construction and a stone foundation. Deterioration of the brick veneer at the grade level indicates a lack of adequate, subsurface drainage. An original rear, one-storey addition with a simple shed roof (once used as a summer kitchen) still remains. According to the 2000 inventory, the replacement windows, doors, and the two-storey addition at the entrance are unsympathetic with the original building. (1, 2, 3)

Dr. Gilbert Blackwell’s House is located on the southwest corner of Barrie and Joseph Streets at 72 Barrie Street. His office faced Joseph Street. The structure was built in 1935 by builder Art Saint in the Arts and Crafts style.
The simple form has an asymmetrical façade and a rectilinear plan. A broad, steeply-pitched, bell-cast roof with a centre dormer extends down to reduce the scale of the building from the street. It also covers the original front porch (which has been enclosed). The structure has wide window openings with low floor to ceiling heights. A wide band of windows across the front of the dormer emphasizes the horizontal lines and massing of this house. Smaller, second-storey windows in the front dormer are offset from the ground-floor windows and have plain, wood sills and trim. The original arched openings in the front porch have been infilled and new windows have been installed. Brackets support the cornice at the roof and there is a central, brick chimney. The house has wood frame construction, stucco cladding and a painted, concrete foundation. A mix of exterior cladding materials is common to this style. The windows, awnings, and the one-storey, rear addition are not original. According to the 2000 inventory, the house is in good condition with some original features. (1, 3)

The single-family residence located at 84 Barrie St. (on the northwest corner of Barrie and Joseph Streets) was built post-1900 in the Eclectic Edwardian style. The two-storey, ‘L’-shaped building has a hip roof. The projecting, two-storey bay has a wide, projecting gable roof. Edwardian features also include the generous fenestration accentuated by keystones and projecting sills (at the bay windows). Queen Anne features include the variety of textures and materials such as rusticated block on the main building and the wood shingles at the exposed gable. The “wrap-around” nature of the ground-floor verandah and the second-storey balcony are Regency Revival features. Its moulded roof curb is an Italianate feature. This building has load-bearing, block masonry construction and a block foundation. According to the 2000 inventory, the replacement balcony and the post supports are unsympathetic with the original design. (1, 3)

The Nesbitt House is located mid-block on the west side at 88 Barrie Street. The two-storey, ‘L’-shaped building with a hip roof was built around 1920 in the Eclectic Edwardian style. The shallow, two-storey bay with a wide projecting gable roof is a classical, pediment-like form. The porch roof and balcony above are supported by rectangular colonnettes on brick piers. Other Edwardian features are the large, double-hung windows with shorter, upper-sash windows that are proportioned to resemble rectangular transoms. The wood-shingle texture at the exposed gable is an Italianate feature and the roof curb is reminiscent of an Italianate motif. There are precast lug sills and column bases. The house has load-bearing, brick masonry construction, a stone foundation, and painted-wood porch details. According to the 2000 inventory, the house has been maintained well. (1, 3)

The Methodist Manse is located at 96 Barrie St. on the southwest corner of Barrie and Frederick (formerly known as Letitia) Streets. It was built around 1885 in the neoclassical style. The building was used as the Methodist Manse until 1970. It later became a nursing home.
The two-storey, rectangular building has a symmetrical façade, a centre hall plan, and a medium-pitched, gable roof. The two-storey, rear portion is a modern addition. A broad entrance has sidelights and a transom. There are large, 6/6 double-hung windows with wood sills and high floor to ceiling dimensions. Eaves and cornice returns are found at the end gable walls. The porch, as well as the stepped-cornice moulding with quatrefoil decoration and drop finials (a Gothic Revival detail), appear to be twentieth-century additions. Colour variations are seen in the solid-brick construction because of the different batches of brick that were used. The building has a stone foundation. According to the 2000 inventory, additions to the rear of the building over time have been somewhat ad-hoc and are stylistically inconsistent. (1, 3)

The Pringle House is located mid-block on the east side at 99 Barrie Street. It was the home of Walter Pringle, owner and manager of the first Dominion store (on Holland St.) in the 1930’s. The 1½-storey, two-bay ‘bungalow’ was built in the Arts and Crafts style. The construction of this house (and six others) was begun in 1912 by Lieutenant George Stoddart. When Stoddart went overseas during WWI, the projects were completed by builder Art Saint.
The house has a simple form with an asymmetrical façade and a rectilinear plan. It has a bell-cast roof on the centre dormer and a steeply-pitched, truncated gable roof that extends down to reduce the scale of the building. This roof also covers the raised porch and is supported on wood half posts on brick piers. The porch has a simple, wood handrail and baluster. Wood lattice encloses the underside of the porch. A wide band of windows across the front of the dormer emphasizes the horizontal lines and the massing of the house. The building has wide window openings with low floor to ceiling heights. Ground-floor and basement windows and the front door are set into segmented, arched openings with concrete sills. Second-storey windows are offset from the ground-floor windows and have plain, wood sills and trim. The mix of exterior cladding materials and the wood fascia band (expressing the line of the floor structure between the ground and second floors) is common to this style. There are returned eaves at the porch roof. The house has wood frame construction with brick masonry cladding, painted wood shingles on the dormer, and a painted, concrete foundation. The front ground-floor and second-floor windows are not original. According to the 2000 inventory, the house is in good condition with many original features that have been maintained well. (1, 2, 3)

The house located at 105 Barrie St. was once the home of Dennis and Mrs. Nolan, their son James (a car dealer and salesman), and daughters Connie (a teacher at Bradford High School) and Aileen (also a teacher). Dennis Nolan was a Model T. Ford dealer in Cookstown as well as a noted, prize-winning, honey producer. He was also the reeve of Bradford, involved in the drainage of the Holland Marsh, and he worked marshland. At one time Dennis owned the town’s water works. (1, 2)