The structure located at 21 Holland St. West is part of what is known as the Evans Block. The building was raised and Len Saint added a cellar and a foundation. The work was done by Mac Campbell and his team of carpenters. T.W.W. Evans had the building constructed to house his law practice. The upstairs was also used for years by Dr. Ellis, a dentist. The upper floor even served as Bradford Library in the 1930s, run by Mrs. Day. At one time, the offices of Tupling Insurance were also located in this building. In 1957 a fire destroyed several buildings to the east, but this structure was spared. (1, 2)

The mid-block building located at 10 and 12 Holland St. West was built in the Ontario Vernacular style around 1872-1899. The two-storey, commercial, detached ‘row’ building had a narrow rectangular plan with an asymmetrical organization. ‘Main street’ frontage with a typical storefront façade was located at the street line. The plain façade was characterized by a high, flat, ‘boomtown’ façade and cornice with brick dentils. The two bay-façade each had its own entrance and storefront. Existing doors and storefronts are not original. The original, large, second-floor windows (characterized by segmented arch openings and concrete sills) have been partially bricked in, but are still visible from the brick voussoirs. The building has masonry construction with brick cladding and a flat, built-up tar and gravel roof. (1, 3)
The west side of the building (10 Holland St. West and the location of Pizzaville in this 1995 photo) was once the site of a drugstore run by W.L. "Billie" Campbell. Fred Cook helped him for a number of years. Billie’s son, Lou, and druggist Clarence Ritchie took over the business. Eventually Clarence Ritchie ran it on his own before he retired. Fred McKay sold phonographs on the upper floor and there was a pool room run by James Ferguson. The Salvation Army held services here in the 1930’s. (1, 2)
Sutherland’s Grocery Store was once found at 12 Holland St. West (site of Karen’s and Tina’s Flowers in this 1995 photo). Alec Sutherland was a baker. He had a bakeshop on the south side of Simcoe St. that was run for many years by his daughter Jessie and sister Mrs. Bessie Ryan (and her daughter Betty). They eventually retired and moved to St. Catherine’s. There were living quarters upstairs. William Compton and his wife bought the store and ran it as an IGA grocery store. Gord and Marilyn Compton later took over the store. They built a new store on John St. (where Frank Kilkenny’s house had been). The Comptons’ store eventually moved to what was known as the IGA plaza (located at the corner of Collings Ave. and Holland St. West). As of 2014, 12 Holland St. West is the site of The Holland Bloom florist shop. (1, 2)

"A 50 suite senior citizens apartment building will be built in Bradford early next year. Last week, council and the town planning board met with officials of the Ontario Housing Corporation and the plans were revealed. OHC recently purchased five acres of land from the municipality in the west end of town on Miller Park Avenue. The suites will be available to senior citizens who presently reside in Bradford and West Gwillimbury. The rents will be geared to income. The contract for the building is expected to be let later this year and construction to be started in the spring of 1975. Town council has been working for almost four years to obtain the senior citizens apartment. The long delay was due to difficulty in obtaining a suitable site for the project. Last year, the town purchased almost 13 acres of land from the provincial government following the closing of the old Department of Highways garage. The original proposal was for 15 units but it was increased when West Gwillimbury council expressed an interest."

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 building located at 15 Holland St. East was bought by Harold Boyd many years ago. He ran a pool room on the ground floor on the west side. He added a second floor above the pool room for living quarters. Jack Pong owned a restaurant on the east side of the building in the 1930’s. (1, 2)
The two-storey, brick and cement building located at 19 Holland St. East was owned at one time by George Simpkins. He ran a plumbing, heating, electrical, and eavestroughing company upstairs. There was a show room downstairs and the east side was a workshop. George and his family lived on Moore St. across from Joseph Street. Ethel Gapp was his bookkeeper, Ted Gapp was his electrician, and George Manton did the heating work. They drove for miles around the country in a Model T truck. Harry Barron bought the business in the 1930’s and kept the same workmen. Then the business was moved to the southwest corner of Holland and Simcoe Streets. (1, 2)

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)

This two-storey structure is located at 218 Simcoe Road. It is the fourth house on the west side (south of the “Y” in Simcoe Road). Robert Stewart, his wife, and family lived here many years ago. His son George, who married Ethel Waldruff, played lacrosse and was a painter and paper hanger for Billie Sutton. Robert owned 75 acres of land and worked as the town clerk for 25 years. He also farmed (and later rented) his land. Ed Cave and his wife (Ida) and daughter (Violet) moved to this area from Newton Robinson and eventually bought and worked a farm. He delivered milk and had a dairy in town. Ed was a staunch Orangeman who played King Billie riding his white horse at the 12th of July parade. There was a gravel pit on the property. He eventually sold his farm to Mike Sklencar, John Kulha, Steve Brinkos and John Kashmere. They divided the remaining land and sold the lots along Simcoe Road. The large house was converted into four apartments that were used as their living quarters while they each built a house. The structure was still being used as an apartment building in 1995. (1, 2)

Sutherland’s Grocery Store was once found at 12 Holland St. West (site of Karen’s and Tina’s Flowers in this 1995 photo). Alec Sutherland was a baker. He had a bakeshop on the south side of Simcoe St. that was run for many years by his daughter Jessie and sister Mrs. Bessie Ryan (and her daughter Betty). They eventually retired and moved to St. Catherine’s. There were living quarters upstairs. William Compton and his wife bought the store and ran it as an IGA grocery store. Gord and Marilyn Compton later took over the store. They built a new store on John St. (where Frank Kilkenny’s house had been). The Comptons’ store eventually moved to what was known as the IGA plaza (located at the corner of Collings Ave. and Holland St. West). As of 2014, 12 Holland St. West is the site of The Holland Bloom florist shop. (1, 2)
The two-storey, commercial, ‘row’ building located mid-block on the south side at 16 Holland St. West was built around 1872-1899 in the Ontario Vernacular style. The second floor had space for offices or living quarters. Whimster and Wilcox operated a clothing and garment store at this location many years ago. Charles Wilson worked for them. John McDowall moved to the area from Midland and ran a clothing store there sometime in the 1930’s or 1940’s. He had three children (Norrie, Jack and Pat). They lived in quarters above the Bank of Commerce and later moved to the apartment over the store.
The building has a wide, rectangular plan with a symmetrical organization. ‘Main street’ frontage with a typical, storefront façade is located at the street line. The symmetrical, three-bay façade originally had a high, articulated cornice of corbelled and dentilled brick (typical of rich detailing). Its ground floor was characterized by the rhythm of flat pilasters along the street edge. The existing doors and storefront are not original. Three, large window openings with segmented arch openings and concrete lug sills at the second-floor level have been partially filled. The windows are also not original. Built-up tar and gravel covers the flat roof. Masonry construction with brick cladding has been considerably altered in appearance. It is also no longer the site of Carmen’s Backyard Restaurant, as seen in this photo from 1995. (1, 2, 3)

The Dr. Clement House is located at 41 Simcoe Road (on the southeast corner of Simcoe Road and Centre Street). It was built around 1830-1860 (1840’s?) in the Classic Revival style. Dr. Clement lived and died here after practising in the 1870-80’s. He was buried in Clement Cemetery on the 2nd Line in Innisfil (east of Highway 11). His wife Rachel lived here until her death. The house was then rented to Walton, a railroad man for the C.N.R. The barn and garden behind the building ran to William St. (as did all the properties on the east side). Sam Catania and his wife Sarah lived here in later years. They converted the house into two apartments and had a dry cleaning business in the garage that was eventually destroyed by fire. Sam sold the house to Bruce and Barbara Verney. They were still living here when this photo was taken in 1995. Bruce was a chiropractor. A building used as a dry cleaner was constructed later on the property. Jack Pong (a restaurant owner on Holland St.) built a house on the back of this property that extended to Centre Street.
The street level has apparently been raised considerably around this house as the current 1½-storey, two-bay house was originally 2½ storeys. It has an asymmetrical façade and entrance, a simplified ‘temple’ form, and a medium-pitched, gable roof. The pediment roof shape has return eaves facing the front. A hip roof on the raised entrance portico is supported on wood beams with decorative, wood dentils. The corner columns have wooden ‘flutes’ and are mounted on brick pedestals. A wood-panelled door is flanked by narrow sidelights and is topped by a transom light. The house has small window openings with low floor to ceiling heights. Small, upper-floor windows are set into rectangular openings with plain, wood frames and sills. A ground-floor, bay window is an angled projection with a hip roof. The brick masonry foundation appears to be a replacement. A horizontal belt line at the top of the foundation is expressed with wood trim. The structure has wood frame construction with stucco cladding and a cut-stone foundation. Bricks found at the bay window foundation and at the entrance porch are probably not original. According to the 2000 inventory, the house is in good condition with many original details. (1, 2, 3, 4)

The building located at 5 Holland St. East (near the northeast corner of Holland and Barrie Streets) has solid-brick construction. The office of veterinarian Dr. Stephenson (who lived on Queen Street across from the public school) was on the ground floor at this address. Grain buyers worked upstairs. They had their own stairway and a huge, walk-in safe. Later, that space was turned into an apartment that became the home of Rae Green after WWII. Around 1928 or 1930, Fred Buck (a pharmacist) opened a drugstore on the ground floor. It later became Brackens Drugstore and was run by Mr. Harrison. (1, 2)
The building located at 9 Holland St. East (beside 5 Holland St. East) also has solid-brick construction. It was the site of Dennis Nolan and Jim’s Model T Ford dealership. There was a garage with an elevator. Overhauling was done in the basement and painting was done upstairs. Hugh Bannerman pumped gas and Rose MacEwan was the bookkeeper. Nolan had as many as 10 employees working for him at one time. Mr. Martin moved in around WWII and opened a used furniture and appliance store here. It was later sold to Bob Sewery, a WWI veteran. (1, 2)