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The house located at 39 Drury St. (at the southeast corner of Drury and Thomas Streets) was built pre-1900 in the Ontario Vernacular Cottage style. Bob (“Red”) Armstrong, a bachelor, once lived here. Jim Webb eventually bought the property and rented the structure to Victor Hunter (a carpenter) and his family. Frank Park (a handyman) kept his horse in the small barn on the property. Charles Hounsome (a railway section man) also lived here at one time. Lloyd Houston (a butcher) and his wife Jean lived here after the wars.
The one-storey, three-bay cottage has a shallow-pitched, gable roof, a symmetrical façade, and a rectangular plan with a centre hall. A box hall was typical for this style. The simple entrance has a single door set into a rectangular opening. It opens directly into the house from grade level and there is no porch (or weather protection) to shelter the entrance. The windows have low floor to ceiling heights. There are double-hung, 2/2 windows on either side of the entrance that appear to be original. They are set into simple, rectangular openings with plain, wood frames and sills. Wood frame construction is covered with vinyl siding. The original cladding was wood. The house has a parged, stone foundation. There is a single, brick masonry chimney at the centre of house. According to the 2000 inventory, this simple cottage probably had few decorative details originally. It also notes that the concrete block chimney on the exterior south wall is a later addition. (1, 2, 3)

The structure located at 29 Holland St. West was vacant for many years. Howard Bowser bought and restored it as a shop with living quarters upstairs. Ted and Audrey Gapp lived here for a number of years. Helen Bantam ran a ladies’ shop downstairs and lived upstairs. She may have bought it from Bowser. At the time of this photo (1995), it was a barber shop.
The building located at 31 and 33 Holland St. West (on the northeast corner of Holland and Moore Streets) was built around 1880 in the Ontario Vernacular style. It was constructed on the site of the former Edmanson Bakery (33 Holland St. West). The bakery was the origin of the big fire on May 23, 1871 that destroyed much of downtown Bradford. E.P. Snow had a harness and saddle shop at 31 Holland St. West for many years. He lived on the north side of John Street. Later it was bought by Secondo Cavallo, who ran a shoemaking business at this location. He lived on the south side of John Street. Cavallo’s daughter (Aida) ran the business for a few years and then it was sold. Lash Davey and Bill ran a butcher shop at 33 Holland St. West for several years. They had a slaughter house on Piccadilly Hill (Simcoe St. South). James Webb, a butcher and lacrosse player, later ran his shop here. Webb was joined by his son Jim, who eventually took over the business and employed Harold Boyd. Jim originally had an ice house at the back of the property. A freezer locker was built later by Len Saint at the back. The building and business were eventually owned for many years by the Pezzanitti family.
The one-storey, commercial, semi-detached ‘row’ building has a wide, rectangular plan with an asymmetrical organization. There is “Main Street” frontage with a typical, storefront façade located at the street line. A plain façade is characterized by a high, flat, ‘boomtown’ façade with brick dentils. The two-bay façade is dominated above the storefronts by an applied, pressed- metal cornice with stone brackets at each end. Existing doors and storefronts are not original. Wide, glass, storefront windows with stone sills are also not original. The building has masonry construction with brick cladding, a stone foundation, and a flat, built-up tar and gravel roof. According to the 2000 inventory, the modest building is in good condition. (1, 2, 3)

The corner building located close to the street (on the north side) at 71 and 73 Holland St. East was built in the Neoclassical Duplex style in 1831. This building was known as the Edmanson Hotel. It is the earliest hotel and possibly the oldest building in Bradford. In this photo (from 1996) it is a residential duplex.
The 71 Holland St. East half was once a boarding place for travellers coming into town by train. These travellers then went on to the surrounding hamlets. There was a garage and shed on Nelson Street. Dave Ogilvie later lived here with his wife (a McKinstry). Their son Gordon was born there in 1911. They eventually moved to the northwest corner of John and Nelson Streets. Butcher George Webb bought it and he and his wife (a Collings) had six children – George, Agatha, Jim, Bertie, Ben and Mary (Mrs. H. Hillary). Mary was still living in the house in 1996.
The 73 Holland St. East half was the home of Jim Webb and his wife Muriel (Houghton). Their son James was in partnership with his father. When Jim died, James took over the butcher shop until he died suddenly. Muriel lived there for a while after that until the house was sold.
The two-storey, six-bay, semi-detached house has a rectangular plan and a shallow-pitched, gable roof with gable end and centre chimneys. The formal façade is symmetrical. Slightly-raised entrances are paired at the centre of the façade and recessed for greater privacy. The entrances have round, arched openings with inset steps and the doors are set into high, rectangular openings and have high transoms. The upper portion of each original, wood-panelled door is glazed. The building has large window openings with low floor to ceiling heights. Large, front windows have high sills that are set into plain, rectangular openings with plain, wood frames and sills. Upper-storey windows are offset from the ground floor. The lower windows were changed in the 1930’s. Those in the west half have multiple panes in the original style. The building has wood frame construction, stucco siding, a parged-stone foundation and a basement. The stucco was added by Len Saint in the 1930’s. The chimney on the west side is original. According to the 2000 inventory, the building is in good condition. (1, 2, 3, 4)