Historic photos from around Rosedale, Toronto

Originally the estate of William Botsford Jarvis, Rosedale is one of Toronto oldest, and wealthiest neighbourhoods. Built among three ravines, Rosedale was originally separated by the Rosedale ravine - the older, south Rosedale, home to Branksome Hall, was developed as early as 1864 when the Jarvis family sold the land. It was then connected to north Rosedale, home to St. Andrews College (before it moved to Aurora) and the Rosedale Golf Club, when a bridge was built in 1909 across Park Drive Ravine.

List of all areas in Toronto or take a look at the historic photos by date. New! You can now access the photos by street address A subset of the photos have also been arranged by subject.

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1796		Castle Frank near York - Elizabeth Simcoe painting of original pine log cabin, modelled on classical Greek temple - burned down 1829 (Categorized under: Estates and Houses ) 228 years ago - Wednesday, July 20, 1796 - Rosedale at 725 Bloor Street East Link to archive record - Map location (From Archives of Ontario)
1861		Rosedale garden party by William Botsford Jarvis - Rosedale Rd., w. side, between Avondale Rd. and Cluny Ave. 163 years ago - Wednesday, October 23, 1861 - Rosedale Max temp: 8.3°C - Min temp: 6.7°C (weather details) Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1870		Gate leading to The Dale - Dale Ave., s. side, w. of McKenzie Ave.; n. of Bloor St. E., w. of Castle Frank Rd. (Categorized under: Ornamental gate ) 154 years ago - 1870 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1872		Collapsed wooden bridge on Park Rd., bridge over Rosedale Ravine, n. of Collier St. 152 years ago - 1872 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1880		Pricess Mill on Prices Creek, Rosedale Ravine (North) Roxborough Drive & Mt. Pleasant 144 years ago - 1880 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1885		Huntley St., bridge, north of Bloor St. looking s.w. - also known as the White Bridge 139 years ago - 1885 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1890		South Glen Road Bridge : corner of Dale and Glen Road 134 years ago - 1890 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1890		Rosedale Ravine : showing the Sherbourne Street Bridge 134 years ago - 1890 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1890		Gooderham estate - North Glen Road Bridge at South Drive (Categorized under: Estates and Houses --- Ornamental gate ) 134 years ago - 1890 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1890		Gooderham estate (1885-95) North Glen Road Bridge at South Drive (Categorized under: Estates and Houses ) 134 years ago - 1890 - Rosedale Link to archive record - Map location (From Archives of Ontario)
1900		Edmund A. Meredith house, west side of Rosedale Rd. north of Pine Hill Rd. 124 years ago - 1900 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1900		Backyard of John Hoskin's house - The Dale - with greenhouse? 124 years ago - 1900 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1901		Cluny Avenue and Crescent Road looking east 123 years ago - Wednesday, November 13, 1901 - Rosedale Max temp: 4.4°C - Min temp: -1.1°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1905		H. H. Fudger Residence - colour perspective - 40 Maple Aveune 119 years ago - 1905 - Rosedale Link to archive record - Map location (From Archives of Ontario)
1905		H. H. Fudger Residence; Billiard Room, detail 119 years ago - 1905 - Rosedale Link to archive record - Map location (From Archives of Ontario)
1908		Footpath across Don Valley where the viaduct is now 116 years ago - 1908 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1909		Panoramic view of the first Grey Cup Football Game 1909 - Rosedale Park, Toronto 115 years ago - Saturday, December 4, 1909 - Rosedale Max temp: 3.9°C - Min temp: -0.6°C (weather details) Link to archive record - Map location (From the University of Toronto Archives)
1910		St. Andrew's College field day west side of Schofield Avenue, north of the Glen Road bridge, north Rosedale. 114 years ago - 1910 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1910		Rosedale Hotel on Yonge street at Shaftensbury Avenue, just north of the CPR level crossing (Categorized under: Hotels ) 114 years ago - 1910 - Rosedale at 1145 Yonge Street n.e. corner at Shaftesbury Ave. Link to archive record - Map location (From the City of Toronto Archives)
1910		Saturday afternoon lacrosse match crowds crossing the Old Glen Road bridge 114 years ago - 1910 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1910		Edgar Walker house on Yonge, with part of Emily Walkers brickmakers suppliers factory at left 114 years ago - 1910 - Rosedale at 1238 Yonge Street south west corner of Walker Ave. Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1910		Two grand homes still standing on Chestnut Park in Rosedale 114 years ago - 1910 - Rosedale at 78 Chestnut Park backing on to the Yellow Creek Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1912		Crowd looking at electric automobile in accident on Glen Road Bridge 112 years ago - 1912 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1912		Electric automobile in accident on Glen Road Bridge 112 years ago - 1912 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1912		Looking up at the electric automobile in accident on Glen Road Bridge 112 years ago - 1912 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1912		St. Andrews College School (2nd building built 1907) North Rosedale (Categorized under: Schools ) 112 years ago - 1912 - Rosedale at 20 Scholfield Ave Link to archive record - Map location (From the Library and Archives Canada)
1912		Rosedale Ravine and Howard St. Bridge with house on the hill (Categorized under: Bridges ) 112 years ago - 1912 - Rosedale at 700 Rosedale Valley Road (approximately) Link to archive record - Map location (From the Library and Archives Canada)
1912		Rosedale Ravine - Rosedale Valley road : first ravine 112 years ago - Wednesday, December 18, 1912 - Rosedale Max temp: 7.8°C - Min temp: 1.7°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1912		Rosedale Ravine : general view of ravine 112 years ago - Wednesday, December 18, 1912 - Rosedale Max temp: 7.8°C - Min temp: 1.7°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1913		Rosedale Ravine - north from Roxborough Street Bridge 111 years ago - Friday, February 14, 1913 - Rosedale Max temp: 2.8°C - Min temp: -7.8°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1913		7 Rosedale Lane (south side, first house off Yonge Street) 111 years ago - Thursday, May 15, 1913 - Rosedale at 7 Rosedale Lane just east of Yonge Street Max temp: 9.4°C - Min temp: 4.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1913		7 Rosedale Lane (rear view) 111 years ago - Thursday, May 15, 1913 - Rosedale at 7 Rosedale Lane just east of Yonge Street Max temp: 9.4°C - Min temp: 4.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1914		Chestnut Park Road and Roxborough Street 110 years ago - Friday, October 30, 1914 - Rosedale Max temp: 8.3°C - Min temp: 1.7°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1914		Rosedale Hotel NE corner of Yonge Street and Shaftensbury Avenue, (Categorized under: Hotels ) 110 years ago - Saturday, November 21, 1914 - Rosedale at 1145 Yonge Street n.e. corner at Shaftesbury Ave. Max temp: 1.1°C - Min temp: -5.6°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1915		Rosedale Section - Rosedale Ravine Drive cemetery property (St. James Cemetery) 109 years ago - Saturday, April 24, 1915 - Rosedale Max temp: 21.1°C - Min temp: 8.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1916		Rosedale Hotel with sign - Yonge Street track extension looking north to Shaftesbury Avenue (Categorized under: Hotels ) 108 years ago - Tuesday, August 29, 1916 - Rosedale at 1145 Yonge Street n.e. corner at Shaftesbury Ave. Max temp: 25.6°C - Min temp: 8.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1919		Chestnut Park Road - Rosedale 105 years ago - Tuesday, May 6, 1919 - Rosedale Max temp: 11.7°C - Min temp: 5.0°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1919		Chestnut Park Road north from Roxborough Street East 105 years ago - Tuesday, May 6, 1919 - Rosedale Max temp: 11.7°C - Min temp: 5.0°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1919		Chestnut Park Road north from Roxborough Street East 105 years ago - Tuesday, May 6, 1919 - Rosedale Max temp: 11.7°C - Min temp: 5.0°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1920		Rosedale Public School 104 years ago - 1920 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1920		Rosedale Hotel from railway bridge on Yonge Street looking north (Categorized under: Hotels ) 104 years ago - 1920 - Rosedale at 1145 Yonge Street n.e. corner at Shaftesbury Ave. Link to archive record - Map location (From the City of Toronto Archives)
1920		Roxborough Drive bridge 104 years ago - Wednesday, July 28, 1920 - Rosedale Max temp: 24.4°C - Min temp: 11.1°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1921		Summer picnics in Rosedale Park 103 years ago - Friday, July 1, 1921 - Rosedale Max temp: 28.3°C - Min temp: 18.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1924		Laying track in the Rosedale Loop, looking south-west 100 years ago - Thursday, April 24, 1924 - Rosedale Max temp: 17.2°C - Min temp: 3.3°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1924		Construction of Rosedale Loop on Sherbourne, looking south to Bloor 100 years ago - Wednesday, April 30, 1924 - Rosedale Max temp: 10.6°C - Min temp: 4.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1924		Construction of the Rosedale Loop, looking south-west 100 years ago - Wednesday, April 30, 1924 - Rosedale Max temp: 10.6°C - Min temp: 4.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1924		Sketch and floorplan of Rosedale Park shelter (Categorized under: Architectural drawings ) 100 years ago - 1924 - Rosedale at 20 Scholfield Ave Link to archive record - Map location (From the City of Toronto Archives)
1925		Rosedale Loop on Sherbourne, looking north, (Way Department) 99 years ago - Friday, May 22, 1925 - Rosedale Max temp: 20.0°C - Min temp: 4.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1925		Rosedale Loop looking south to Sherbourne Bridge, (Way Department) 99 years ago - Friday, May 22, 1925 - Rosedale Max temp: 20.0°C - Min temp: 4.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1926		Rosedale Loop west side of Sherbourne Street, looking west, (Way Department) 98 years ago - Monday, June 7, 1926 - Rosedale Max temp: 21.7°C - Min temp: 7.2°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1927		Rosedale Park - shelter building with fountain 97 years ago - Monday, July 11, 1927 - Rosedale Max temp: 28.9°C - Min temp: 16.1°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1928		Construction of the new Glen Road, bridge, north of South Drive 96 years ago - Thursday, March 1, 1928 - Rosedale Max temp: 0.6°C - Min temp: -5.6°C - 5.1cm of snowfall (weather details) Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1931		Canadian Pacific Railway level crossing at McLennan Hill in North Rosedale with crossing gates tower at left (Ingenium Archives, CN Images of Canada Collection, 36143) 93 years ago - 1931 - Rosedale at 120 Ridge Drive At MacLenan Ave and Old Bridle Path Link to archive record - Map location (From the Ingenium Archives)
1942		Rosehill Reservoir Cleaning and War protection 82 years ago - Wednesday, November 4, 1942 - Rosedale Max temp: 5.6°C - Min temp: 0.0°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1945		Rosedale Hotel at 1145 Yonge St - painted (Categorized under: Hotels ) 79 years ago - 1945 - Rosedale at 1145 Yonge Street n.e. corner at Shaftesbury Ave. Link to archive record - Map location (From the City of Toronto Archives)
1945		H.H. Fudger House at 40 Maple Avenue designed by Edmund Burke, built 1897 79 years ago - Tuesday, August 28, 1945 - Rosedale Max temp: 22.8°C - Min temp: 17.8°C (weather details) Link to archive record - Map location (From York University Archives)
1946		Castle Frank - demolished in 1962 - Sir Albert Edward Kemp - Bloor St. E., s. side, e. of Castlefrank Crescent (formerly 72 Castle Frank Road) (Categorized under: Estates and Houses ) 78 years ago - 1946 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1950		Northwest corner Roxborough & Mt. Pleasant Road 74 years ago - Friday, July 7, 1950 - Rosedale Max temp: 27.8°C - Min temp: 14.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1950		Southwest corner Roxborough & Mt. Pleasant Road 74 years ago - Friday, July 7, 1950 - Rosedale Max temp: 27.8°C - Min temp: 14.4°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1951		Glen Road, bridge between Howard St. and Dale Avenue, looking south from Dale Avenue 73 years ago - 1951 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1952		Guiseley House - Joseph Cawthra - 5 Elm Ave., s.e. corner Mt. Pleasant Rd (Categorized under: Estates and Houses ) 72 years ago - Wednesday, October 1, 1952 - Rosedale Max temp: 23.3°C - Min temp: 12.2°C (weather details) Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1953		The Dale - John Hoskin's house - Dale Ave., s. side, w. of McKenzie Ave.; looking w. 71 years ago - 1953 - Rosedale Link to archive record - Map location (From the Toronto Public Library Still not back as of March 2024)
1953		6 photos from Rosedale and King subway stations 71 years ago - Monday, June 15, 1953 - Rosedale Max temp: 23.9°C - Min temp: 11.7°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		Southeast corner Roxborough & Yonge Street 71 years ago - Wednesday, July 15, 1953 - Rosedale Max temp: 30.0°C - Min temp: 18.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		4 and 6 Roxborough Street East 71 years ago - Wednesday, July 15, 1953 - Rosedale at 4 Roxborough Street East Max temp: 30.0°C - Min temp: 18.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		4 Roxborough Street East 71 years ago - Wednesday, July 15, 1953 - Rosedale at 4 Roxborough Street East Max temp: 30.0°C - Min temp: 18.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		3 and 5 Roxborough Street East 71 years ago - Wednesday, July 15, 1953 - Rosedale at 3 Roxborough Street East Max temp: 30.0°C - Min temp: 18.9°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		43 photos of the vitrolite glass tiles being installed in the Rosedale subway Station 71 years ago - Friday, September 18, 1953 - Rosedale Max temp: 17.2°C - Min temp: 6.1°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		Ground cover north of Rosedale Subway Station 71 years ago - Tuesday, September 29, 1953 - Rosedale Max temp: 16.7°C - Min temp: 10.0°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1953		Underpinning of the Rosedale Subway Station 71 years ago - Friday, November 20, 1953 - Rosedale Max temp: 15.6°C - Min temp: 6.1°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1960		Paisley Shop just before it was demolished in 1960 - built 1841 64 years ago - 1960 - Rosedale at 925 Yonge Street n,e, corner at Baxter Street Link to archive record - Map location (From Archives of Ontario)
1966		TTC subway bridge over Rosedale Valley Road, between Sherbourne and Castle Frank stations 58 years ago - 1966 - Rosedale Link to archive record - Map location (From the City of Toronto Archives)
1969		Office building of Resources Engineering of Canada Ltd., Consulting Engineers 55 years ago - 1969 - Rosedale at 1047 Yonge Street n.e. corner at Roxborough Avenue Link to archive record - Map location (From the City of Toronto Archives)
1971		Yonge Street United Church after 1971 fire (built 1873) 53 years ago - Thursday, May 20, 1971 - Rosedale at 1219 Yonge Street n.e. corner at Summerhil Link to archive record - Map location (From the City of Toronto Archives)
1971		Yonge Street United church front entrance after fire 53 years ago - Thursday, May 20, 1971 - Rosedale at 1219 Yonge Street Link to archive record - Map location (From the City of Toronto Archives)
1973		View of CPR overpass on Yonge Street with Liquor Control Board sign 51 years ago - Tuesday, July 17, 1973 - Rosedale Max temp: 25.6°C - Min temp: 17.2°C (weather details) Link to archive record - Map location (From the City of Toronto Archives)
1985		TTC subway train heading south from Rosedale subway station beside Aylmer Ave - Aubrey Mattingly Transportation Collection, MAT-05307 (Categorized under: Streetcars and buses ) 39 years ago - 1985 - Rosedale at 17 Aylmer Ave n.e. of Yonge Street and Church Street Link to archive record - Map location (From the Ingenium Archives)