311 Prospect Street.
Date unknownHistoric vernacular house
The Story
Approaching Newmarket from the south, there is a point where the familiar road begins to feel like the old town. For generations, the house at 311 Prospect Street has stood at that approach.
At the corner of Prospect Street and Pearson Avenue, the house is recognizable for its sharply pitched front gable, tall brick chimney, projecting bay window and welcoming porch. Its form has survived the changing streetscape around it, even as details of its earliest years remain difficult to establish.
Across the intersection stood the former Newmarket High School. For generations of students heading home at the end of the school day, this corner house would have been one of the first familiar sights beyond the school grounds. The school site has taken on a different life, but the house remains, one of those features that quietly helps give a street its character.
It also appears prominently in a painting of Prospect Street by local artist Jianming Chen. The artist’s treatment of the light is romantic, but the building and its relationship to the road are immediately recognizable. That painting was the starting point for this investigation.
An archival Newmarket Historical Society photograph, captioned “Prospect Street looking North from Pearson Street,” shows 311 Prospect Street at the right of the image. The distinctive gable and curved tops of the upper windows remain recognizable today.
We do not yet have a reliable construction date or the name of the original builder. What the surviving records do give us, however, is a clearer picture of one household that lived here: Donald and Daisy Fines, documented at 311 Prospect Street by 1957.
02Three views of a familiar corner
Then & Now
The People
Watchmaker · jeweller · optician
Donald & Daisy Fines
Donald Harvey Fines was already working as a watchmaker when he appeared in the 1931 Canadian census, then living at 317 Park Avenue. Later that year, he married Daisy Frances Morgason in Richmond Hill.
Advertisements trace Donald’s business along Main Street. A 1936 merchant directory places his jewellery business at 13 Main Street; in 1952 he advertised at 15 Main Street, and in 1957 and 1965 at 242 Main Street. His advertisements offered watches and diamonds as well as optical services.
Donald and Daisy were living at 311 Prospect Street by 1957 and were still there in 1974, when Donald was retired. A 1959 newspaper notice offers another glimpse of their family life: the couple were named in a report of a large Fines family reunion at the original family homestead in Whitchurch Township.
Earlier voters lists, from 1945 and 1949, place the couple at 14 Prospect Street. That may have been an earlier number for this house, but a direct link between the two addresses has not yet been demonstrated.
04Dates of Note
A Historical Timeline
Donald Harvey Fines, a watchmaker and jeweller, is recorded as single and renting at 317 Park Avenue in the census. On October 24 he marries Daisy Frances Morgason in Richmond Hill. This predates their confirmed Prospect Street records.
A directory of Newmarket merchants lists D. H. Fines as a jeweller at 13 Main Street, on the west side.
Donald and Daisy Fines are listed at 14 Prospect Street in a federal voters list; this address is not yet proven to be the present 311 Prospect.
Another voters list places Donald and Daisy at 14 Prospect Street.
A jewellery advertisement lists D. H. Fines at 15 Main Street.
A voters list identifies Donald Fines, jeweller, at 311 Prospect Street. A Centennial advertisement lists his watchmaking, jewellery and optical services at 242 Main Street.
A June 25 Newmarket Era report names Mr. and Mrs. D. H. Fines of 311 Prospect Street in an account of the Fines family reunion at an older Whitchurch homestead.
The house and its setting
A familiar approach.
For years, this corner marked a transition from the outskirts into old Newmarket. The former high school stood across Pearson Avenue, while 311 Prospect offered a recognizable domestic counterpoint.
Its presence in Jianming Chen’s painting is a reminder that an ordinary house can become part of a town’s shared picture of itself, whether or not it ever acquired a grand name.
Research
Sources & notes
1931 Census of Canada, Donald Harvey Fines
Records Donald H. Fines, watchmaker, unmarried and renting at 317 Park Avenue. Evidence for his occupation before his marriage, not for residence at 311 Prospect.Ontario marriage registration, Donald Harvey Fines and Daisy Frances Morgason, October 24, 1931
Documents their marriage at Richmond Hill. The couple’s later residence on Prospect Street is established from separate records.Federal voters lists, York North and York–Simcoe, 1945–1974
Places Donald and Daisy at 14 Prospect in 1945 and 1949, then at 311 Prospect by 1957 and in 1962 and 1974. Whether 14 and 311 refer to the same property has not been proven.Newmarket merchants directory (1936); Newmarket Centennial 1857–1957, p. 84; D. H. Fines advertisement (1952)
Evidence of Fines’s jewellery, watchmaking and optical business at different Main Street addresses, including 13 Main, 15 Main and 242 Main.Newmarket Era, June 25, 1959, p. 19; February 10, 1965, p. 11
Contemporary newspaper evidence for the Fines family and their business, including a 1959 family reunion report identifying Donald and Daisy at 311 Prospect Street.Newmarket Historical Society, “Prospect Street looking North from Pearson Street”
Archival streetscape photograph showing 311 Prospect Street on the right, identified by its location and surviving architectural features. The photograph’s exact date remains uncertain.Jianming Chen, Prospect Street painting
The work that prompted research into this house. Reproduced for The Old Houses of Newmarket with the artist’s permission.
About the address and early history
The 1945 and 1949 voters lists give 14 Prospect Street, while records from 1957 onward give 311 Prospect Street. A renumbering is possible, but the addresses should not be treated as identical without property or municipal records that establish the connection.
The construction date, original builder and first residents of the house have not yet been securely identified.
Images. The painting of Prospect Street by Jianming Chen is reproduced with the artist’s permission. The circa-1910s Prospect-at-Pearson photograph is from the Newmarket Historical Society Archives. The October 2026 photographs of the house and the approach along Prospect Street were taken for The Old Houses of Newmarket. The D. H. Fines jewellery advertisement appeared in the February 10, 1965 edition of the Newmarket Era.
Historical record · House 004