# List of oldest buildings and structures in Toronto

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This is a list of the oldest buildings and structures in Toronto, that were constructed before 1920. The history of Toronto dates back to Indigenous settlements in the region approximately 12,000 years ago. However, the oldest standing structures in Toronto were built by European settlers. Remains of a Seneca settlement exist at the federally protected Bead Hill archaeological site, in eastern Toronto.
The first European structure built in Toronto was Magasin Royal, a French trading post established in 1720. In the 1750s, the French built several structures in the area (including Fort Rouillé), although the French would later destroy them in 1759, following their defeat at the Battle of Fort Niagara. In 1793, the government of Upper Canada arranged for the purchase of Toronto from the Mississaugas in order to settle newly landed British American colonists Loyalists, who were exiled from the United States of America after the Revolutionary War. Many of Toronto's oldest structures date back to this early period of British settlement, when it was known as York. The town of York was formally incorporated as the City of Toronto in 1834, with the passage of the Incorporation of the City of Toronto Act.
This list is composed of buildings that are heritage-designated structures or are notable in some way. Toronto has many residential and business buildings which were established prior to 1920 and that are not on this list. These are typically found in the, then, inner-suburbs built between the late 1800s and before 1920, such as Cabbagetown, North Toronto, Parkdale and Rosedale.

## Surviving structures

The oldest intact structure of European settlement may be a piece of St Paul's Cathedral's courtyard railing dating from 1714, designed by Christopher Wren, that is now part of John Howard's tomb in High Park. Howard had it shipped from London in 1875.
The following list does not include structures where only the facade of the building has been preserved.

### 1794 to 1819

The surviving structures were often moved from the original site years after; they are mostly residential or military structures.
| Building | Year completed | Builder | Style | Address | Neighbourhood | District |
| Scadding Cabin | 1794 | John Scadding | Log cabin | — | Exhibition Place | Old Toronto |
| Lavinia Cottage | c. 1800–1819 | | | 23 Jason Road | Thistletown | Etobicoke |
| John Cox Cottage | 1807 | | Log cabin (renovated) | 469 Broadview Avenue | Riverdale | Old Toronto |
| Gibraltar Point Lighthouse | 1809 | | British marine architecture | — | Toronto Islands | Old Toronto |
| Fort York Blockhouse #1 | 1813 | Royal Engineers | 19th century blockhouse | 100 Garrison Road (Fort York) | Fort York | Old Toronto |
| Fort York Blockhouse #2 | 1813 | Royal Engineers | 19th century blockhouse | 100 Garrison Road (Fort York) | Fort York | Old Toronto |
| Fort York Brick Officers Barracks and Mess Room | 1815 | Royal Engineers | 19th century military architecture | 100 Garrison Road (Fort York) | Fort York | Old Toronto |
| Fort York Brick Magazine | 1815 | Royal Engineers | 19th century military architecture | 100 Garrison Road (Fort York) | Fort York | Old Toronto |
| Fort York Stone Powder Magazine | 1815 | Royal Engineers | 19th century military architecture | 100 Garrison Road (Fort York) | Fort York | Old Toronto |
| Fort York Brick Barracks | 1815 | Royal Engineers | 19th century military architecture | 100 Garrison Road (Fort York) | Fort York | Old Toronto |
| Daniel Stong Loghouse | 1816 | Daniel and Elizabeth Stong | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| The Grange | 1817 | D'Arcy Boulton | Georgian | 317 Dundas Street West | Grange Park | Old Toronto |
| Gray Grist Mill | 1819 | William and James Gray | Early-19th century farm architecture | 12 Bushbury Drive | Don Mills | North York |

### 1820 to 1839

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Ref. |
| Snider Backhouse | 1820 | Henry Snider | Round-log backhouse | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Daniel Stong Smokehouse and Butchery | c. 1820 | Daniel Stong | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Samuel and Ann Mercer House | c. 1820–1830 | Samuel Mercer | Georgian | 72 Old Burnhamthorpe Road | Eringate – Centennial – West Deane | Etobicoke | |
| Bigham/Agar House | c. 1820–1840 | | Saltbox house | 190 Rathburn Road | Princess Gardens | Etobicoke | |
| Campbell House | 1822 | William Campbell | Georgian | 160 Queen Street West | Grange Park | Old Toronto | |
| Edgeley Mennonite Meeting House | 1824 | | Mennonite architecture | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | , |
| William Moore House | 1824 | William Moore | Regency Cottage | 171 Old Forest Hill Road | Forest Hill | Old Toronto | |
| John Bales House | c. 1824 | John Bales | | 4169 Bathurst Street (Earl Bales Park | Armour Heights | North York | |
| George S. Henry House (Oriole Lodge) | c. 1824 | Stillwell Willson | 19th century bungalow | 17 Manorpark Court | Henry Farm | North York | |
| Daniel Stong's Grain Barn | 1825 | | Agricultural architecture | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Todmorden Mills | 1827 | | | 67 Pottery Road | Old East York | East York | |
| Bank of Upper Canada Building | 1827 | William Warren Baldwin | Neoclassical (with later Second Empire roof) | 252 Adelaide Street East | Old Town | Old Toronto | |
| Tollkeepers' Cottage Museum | 1827–1830 | | | 750 Davenport Road | Wychwood Park | Old Toronto | 18 |
| Snider House | c. 1828 | William Snider | Regency Cottage (later altered) | 744 Duplex Avenue | Lytton Park | Old Toronto | |
| Drumsnab House | 1830 | Francis Cayley | Regency Cottage (later altered) | 5 Drumsnab Road | Rosedale | Old Toronto | |
| Bishop's Block Row Houses/Pretzel Bell Tavern | c. 1830 | | | 192 Adelaide Street West | Entertainment District | Old Toronto | |
| Doctor's Home | c. 1830 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Hart House, Jacob Snider House | c. 1830 | | | 35 Nelson Road | York University Heights | North York | 18 |
| Montgomery's Inn | c. 1830 | | Georgian | 4709 Dundas Street West | The Kingsway | Etobicoke | |
| Todmorden Regency Cottage | c. 1830 | | Regency Cottage | 67 Pottery Road (Todmorden Mills) | Old East York | East York | |
| Mackenzie House | c. 1830 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Snider Workshop | c. 1830s | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| 29 Jarvis Street | c. 1830s–1840s | | | 29 Jarvis Street | Old Town | Old Toronto | |
| Thomas and Catherine Snider House | c. 1831 | Thomas and Catherine Snider | | 519 Glengrove Avenue West | Glen Park | North York | |
| Daniel Stong's Second House | 1832 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Hisey Farm Building | 1832 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Islington Senior's Centre | 1832 | | | 4968 Dundas Street West | Islington-City Centre West | Etobicoke | |
| Osgoode Hall | 1832 | John Ewart and William Warren Baldwin | Neoclassical and Palladian | 130 Queen Street West | Discovery District | Old Toronto | |
| Roman Catholic Bishop's residence | 1832 | | | 113 Jarvis Street | Old Town | Old Toronto | |
| Fourth York Post Office | 1833 | James Scott Howard | Georgian | 260 Adelaide Street East | Old Town | Old Toronto | |
| Daniel Brooke Building | 1833 | | Georgian | 150-154 King Street East | Old Town | Old Toronto | |
| C. W. Jeffreys House | c. 1833 | | Ontario Cottage | 4111 Yonge Street | York Mills | North York | |
| McCowan's Log Cabin | 1833 | | Log cabin | 1007 Brimley Road (Thomson Memorial Park) | Bendale | Scarborough | |
| Thomas Thompson Building | 1833 | David B. Dick | | 185 King Street East | Old Town | Old Toronto | |
| Upper Canada College boarding houses | c. 1833 | | | 20 Duncan Street | Entertainment District | Old Toronto | |
| Elihu Pease House | 1834 | | Ontario Cottage | 20 Harrison Garden Boulevard | Willowdale | North York | |
| Elm Bank Farm Second House | 1834 | John Grubb | | 19 Jason Road | Thistletown | Etobicoke | |
| Grubb Farm barn | 1835 | John Grubb | | 32 Jason Road | Thistletown | Etobicoke | |
| Grubb Farm piggery | 1835 | John Grubb | | 34 Jason Road | Thistletown | Etobicoke | |
| Holley House | 1835 | | | 6 Humberview Crescent | Weston | York | |
| Joseph Shepard House | c. 1835 | | | 90 Burndale Avenue | Lansing | North York | |
| Richmond Hill Manse | 1835 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Colborne Lodge | 1836 | John George Howard | Regency Cottage (later altered) | 11 Colborne Lodge Drive | High Park | Old Toronto | |
| 167–169 King Street East | 1836 | | | 167–169 King Street East | Old Town | Old Toronto | |
| 171 King Street East | c. 1836 | Jacob Latham | Georgian | 171 King Street East | Old Town | Old Toronto | |
| Helliwell House | 1837 | | Georgian | 67 Pottery Road (Todmorden Mills) | Old East York | East York | 18 |
| MacKenzie House | c. 1837 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| The Black Bull | 1838 | | | 298 Queen Street West | Grange Park | Old Toronto | |
| Elizabeth Harrison House | 1839 | | | 111 Harrison Road | York Mills | North York | |
| Guildwood Gates (formerly the Gates of New Fort York) | 1839 | | | Northern entrance of Guildwood Parkway | Guildwood | Scarborough | |
| Springfield Farmhouse | 1839 | James Thomson | | 146 St. Andrews Road | Bendale | Scarborough | |
| William Gray First House | 1839 | | | 1413 Don Mills Road | Don Mills | North York | |

### 1840 to 1849

| Building | Year completed | Builder | Style | Address | Neighbourhood | District |
| 20 Beechwood Crescent | 1840 | George Taylor | | 20 Beechwood Crescent | Old East York | East York |
| 33 Jarvis Street | 1840 | | | 29 Jarvis Street | Old Town | Old Toronto |
| 98 Front Street East | 1840 | | | 98 Front Street East | Old Town | Old Toronto |
| 100 Front Street East | 1840 | | | 100 Front Street East | Old Town | Old Toronto |
| Limehouse Back House | 1840 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| William Hume Blake House (Woodlawn) | 1840 | John George Howard | | 35 Woodlawn Avenue West | Summerhill | Old Toronto |
| Henry Snider Cider Mill | c. 1840 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| Broom Maker Shop | 1840–45 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| Hedman House | c. 1840s | | | 171 Old Forest Hill Road | Forest Hill | Old Toronto |
| Thornbeck-Bell House | c. 1840s | | Georgian | 80 Bell Estate Road | Scarborough Junction | Scarborough |
| Scott House | 1841 | | | 520 Progress Avenue | Scarborough City Centre | Scarborough |
| Stanley Barracks Officers' Quarters | 1841 | | 19th century military architecture | 115 Princes' Boulevard | Exhibition Place | Old Toronto |
| 71 King Street East | 1842 | John George Howard | | 71 King Street East | St. Lawrence | Old Toronto |
| 83 King Street East | 1842 | John George Howard | | 83 King Street East | St. Lawrence | Old Toronto |
| 85 King Street East | 1842 | John George Howard | | 85 King Street East | St. Lawrence | Old Toronto |
| 105 King Street East | 1842 | William Thomas | Georgian Revival | 105 King Street East | St. Lawrence | Old Toronto |
| 109 King Street East | 1842 | William Thomas | Georgian Revival | 109 King Street East | St. Lawrence | Old Toronto |
| 111 King Street East | 1842 | William Thomas | | 111 King Street East | St. Lawrence | Old Toronto |
| 125 King Street | 1842 | William Thomas | Georgian Revival | 125 King Street East | St. Lawrence | Old Toronto |
| Albany Club (originally Victoria Row) | 1842 | John George Howard | | 91 King Street East | St. Lawrence | Old Toronto |
| James McDonnell Building | 1842 | | | 79–81 King Street East | St. Lawrence | Old Toronto |
| John F. Smith Building | 1842 | | | 75–77 King Street East | St. Lawrence | Old Toronto |
| Paul Bishop's House | 1842 | | | 363–365 Adelaide Street East | Old Town | Old Toronto |
| Roblin's Mill | 1842 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| 173 King Street | 1843 | | Georgian Revival | 173 King Street East | Old Town | Old Toronto |
| 175–179 King Street | 1843 | | Georgian Revival | 175–179 King Street East | Old Town | Old Toronto |
| Etobicoke Township Hall | 1843 | | Georgian Revival | 4946 Dundas Street West | Islington–City Centre West | Etobicoke |
| John Perkins Bull House | 1843 | | Georgian Revival | 450 Rustic Road | Maple Leaf | North York |
| Little Trinity Anglican Church | 1843 | Henry Bowyer Lane | Gothic Revival | 425 King Street East | Corktown | Old Toronto |
| Burwick House | 1844 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| Farnham Lodge | 1844 | | | 50 Farnham Avenue | Deer Park | Old Toronto |
| James Coulter House | 1844 | | | 63 George Street | Mimico | Etobicoke |
| St. John's Anglican Church | 1844 | | Gothic Revival | 19 Don Ridge Drive | York Mills | North York |
| St. George's on-the-Hill Anglican Church | 1844 | | | 4600 Dundas St. West | Humber Valley Village | Etobicoke |
| St. Lawrence Market Square Gallery (originally Toronto City Hall) | 1844 | John Wilson Siddall | Gothic Revival and Second Empire | 95 Front Street East | St. Lawrence | Old Toronto |
| Bell Estate | 1845 | | Georgian Revival | 671–679 Warden Avenue | Scarborough Junction | Scarborough |
| Charles Coxwell Small House | 1845 | Charles Coxwell Small | | 298–300 King Street East | Old Town | Old Toronto |
| James Vance/Sheldon Ward House | 1845 | | | 115–117 Berkeley Street | Old Town | Old Toronto |
| Methodist Episcopal Church Oddfellows Hall | 1845 | | | 24 Church Street | Weston | York |
| St. George the Martyr Church clock tower | 1845 | Henry Bowyer Lane | Gothic Revival | 197 John Street | Grange Park | Old Toronto |
| Osterhout Log Cabin | c. 1845 | Augustus Jones | Log cabin | 201 Guildwood Parkway (Guild Park and Gardens) | Guildwood | Scarborough |
| Bishop's Palace of St. Michael's Cathedral | 1846 | William Thomas | Gothic Revival | 200 Church Street | Garden District | Old Toronto |
| Henry Hough Carriage Works | 1846 | Henry Hough | | 1007 Brimley Road (Thomson Memorial Park) | Bendale | Scarborough |
| Weston Plank Road Co. | 1846 | | | 2371 Weston Road | Weston | York |
| Church of the Holy Trinity | 1847 | Henry Bowyer Lane | Gothic Revival | 19 Trinity Square | Downtown Yonge | Old Toronto |
| Farr House | 1847 | | | 905 Queen Street West | Niagara | Old Toronto |
| 254 King Street East | 1847 | | | 254 King Street East | Old Town | Old Toronto |
| I. A. Smith House | 1847 | | | 70 Gerrard Street East | Garden District | Old Toronto |
| Morley Cottage | 1847 | | | 60 Rosemount Avenue | Weston | York |
| William Noble's Tavern | 1847 | | Second Empire | 252 King Street East | Old Town | Old Toronto |
| 51 Yonge Street | 1847 | A.V. Brown (John Howard, architect) | Second Empire | 51 Yonge Street | St. Lawrence | Old Toronto |
| Church of St. Jude | 1848 | | Carpenter Gothic | 10 Howarth Avenue | Wexford | Scarborough |
| Edward Guardhouse Residence | 1848 | | | 1755 Steeles Avenue West (Connaught Laboratories) | Westminster–Branson | North York |
| Enoch Turner School | 1848 | Enoch Turner | | 106 Trinity Street | Corktown | Old Toronto |
| 97 Granby Street | 1848 | | | 97 Granby Street | Garden District | Old Toronto |
| Hoover House | 1848 | Abraham Hoover | | 10 Hoover Road | York University Heights | North York |
| Oakham House | 1848 | William Thomas | Gothic Revival | 322 Church Street | Garden District | Old Toronto |
| St. Michael's Cathedral Basilica | 1848 | William Thomas | English Gothic | 65 Bond Street | Garden District | Old Toronto |
| Toronto House of Industry | 1848 | William Thomas | | 110 Edward Street | Discovery District | Old Toronto |
| St. Andrew's Presbyterian Church | 1849 | | | 115 St. Andrews Road | Bendale | Scarborough |
| Half Way House Inn | 1849 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York |
| The Wheat Sheaf | 1849 | | | 667 King Street West | Niagara | Old Toronto |

### 1850 to 1859

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| 80 Church Street | 1850 | | | 80 Church Street | St. Lawrence | Old Toronto | |
| Bake Oven | 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | 6 |
| Charles Irvine Weaver Shop | 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Devonsleigh House | 1850 | | | 4125 Steeles Avenue East | Steeles | Scarborough | 14 |
| Elgin Building | 1850 | | | 118 Yonge Street | Financial District | Old Toronto | |
| St. Lawrence Hall | 1850 | William Thomas | Renaissance Revival | 157 King Street East | St. Lawrence | Old Toronto | |
| St. Lawrence Galleries | 1850 | | Georgian Revival | 142 King Street East | Old Town | Old Toronto | |
| Snider Drive Shed | 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | 6 |
| Temperance Hall (later Printing Shop) | 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Toronto Baptist Seminary (Samuel Platt House) | 1850 | | | 337 Jarvis Street | Garden District | Old Toronto | |
| Apple Storage Cellar | c. 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Fire House | c. 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Mackenzie Farm | c. 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Taylor's Cooperage | c. 1850 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Tinsmith Shop and Masonic Lodge | c. 1850 | | Gablefront | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| William Goodwin House | c. 1850 | | | 355 Lesmill Road | Graydon Hall | North York | |
| William Gray Second House | c. 1850 | | | 1413 Don Mills Road | Don Mills | North York | 18 |
| 151 King Street East | 1851 | | | 151 King Street East | St. Lawrence | Old Toronto | |
| 231 King Street East | 1851 | | | 231 King Street East | St. Lawrence | Old Toronto | |
| Forest Home | 1851 | | | 42–44 Macklingate Court | Agincourt | Scarborough | 8 |
| Gibson House | 1851 | David Gibson | | 5172 Yonge Street | Willowdale | North York | W |
| LaRose House | 1851 | Daniel LaRose | | 322 La Rose Avenue | Richview | Etobicoke | |
| Melville Church | 1851 | | | 70 Old Kingston Road | West Hill | Scarborough | 18 |
| Richard and Lucy Newborn Farm | 1851 | | Farmhouse | 28 Daisy Avenue | Long Branch | Etobicoke | |
| 191–197 Church Street | 1852 | | Georgian Revival | 191–197 Church Street | Garden District | Old Toronto | 8 |
| Adelaide Street Court House | 1852 | Frederick William Cumberland and Thomas Ridout | Greek Revival | 57 Adelaide Street East | St. Lawrence | Old Toronto | |
| Consumers' Gas Building | 1852 | Frederick William Cumberland and Thomas Ridout | Renaissance Revival | 17–25 Toronto Street | St. Lawrence | Old Toronto | |
| Herod & Mary Noble's Market Garden | 1852 | | | 35 Daniels Street | The Queensway – Humber Bay | Etobicoke | |
| Jacob P. Ross House | 1852 | Jacob P. Ross | | 108 Stayner Avenue | Glen Park | North York | |
| Moore House | 1852 | John Moore | | 18 Great Oak Drive | Princess Gardens | Etobicoke | |
| Neurologic Rehabilitation Institute of Ontario | 1852 | | Georgian Revival (front portico and siding added after 1939) | 59 Beaver Bend Crescent | Eringate – Centennial – West Deane | Etobicoke | 3 |
| 185 Adelaide Street East | 1853 | | | 185 Adelaide Street East | Old Town | Old Toronto | |
| 106 King Street East | 1853 | | | 106 King Street East | St. Lawrence | Old Toronto | |
| Benjamin Parker House | 1853 | | | 66 George Street | Mimico | Etobicoke | |
| William Galbraith House | 1853 | | | 37 Maitland Street | Church and Wellesley | Old Toronto | 18 |
| William Hannah House | 1853 | | | 36 Metcalfe Street | Cabbagetown | Old Toronto | 18 |
| Little Trinity Church Rectory | 1853 | | | 417 King Street East | Corktown | Old Toronto | 18 |
| Alexander Muirhead Farm House | 1853 | | Farm house | 179 Old Sheppard Avenue | Pleasant View | North York | |
| Thomson Manse | 1853 | | | St. Andrews Road | Bendale | Scarborough | 14 |
| Toronto Street Post Office | 1853 | Frederick William Cumberland and Thomas Ridout | Greek Revival | 10 Toronto Street | St. Lawrence | Old Toronto | |
| 39 Colborne Street | 1854 | | | 39 Colborne Street | St. Lawrence | Old Toronto | |
| Ashbridge Estate | 1854 | | | 1444 Queen Street East | Leslieville | Old Toronto | 18 |
| Clairville Tollhouse | 1854 | | | 2095 Codlin Crescent | Clairville | Etobicoke | |
| Jacob Stong House | 1854 | Jacob Strong | Victorian | 4700 Keele Street | York University Heights | North York | 18, |
| Jacob Stong Barn | 1854 | Jacob Strong | | 4700 Keele Street | York University Heights | North York | 18, |
| Paul Kane House | 1854 | Paul Kane | | 56 Wellesley Street East | Church and Wellesley | Old Toronto | 6, 18 |
| Thomas Clark House | 1854 | | Upright and Wing | 9 Barberry Place | Bayview Village | North York | 6 |
| 5 Old Yonge Street | 1854 | | | 5 Old Yonge Street | York Mills | North York | |
| 62–66 Gerrard St. East | 1854 | | Georgian Revival | 62–66 Gerrard St. East | Garden District | Old Toronto | 9 |
| 399–403 King Street East | 1854 | | | 399–403 King Street East | Corktown | Old Toronto | |
| Esten House | 1854 | James Grand | | 106 Beverley Street | Grange Park | Old Toronto | 18 |
| Hutchison Building | 1854 | | | 36–42 Wellington Street East | St. Lawrence | Old Toronto | |
| O'Keefe House | 1854 | | | 137 Bond Street | Garden District | Old Toronto | |
| The Warehouse | 1854 | | | 11 Wellington Street East | Financial District | Old Toronto | 6 |
| Emporium and Post Office | 1855 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Harness Shop and Saddlery | 1855 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| 181–183 King Street East | 1855 | | Georgian Revival | 181–183 King Street East | Old Town | Old Toronto | |
| Rowland Burr House | 1855 | | | 56 King Street | Weston | Etobicoke | |
| Shaw House | 1855 | | | 8 William Street | Weston | Etobicoke | |
| Samuel Stong House | c. 1855 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| 64–66 Shuter Street | 1856 | | | 64–66 Shuter Street | Garden District | Old Toronto | 18 |
| 68–70 Shuter Street | 1856 | | | 68–70 Shuter Street | Garden District | Old Toronto | 18 |
| Allandale | 1856 | Enoch Turner | | 241 Sherbourne Street | Cabbagetown | Old Toronto | 8 |
| Fisherville Church | 1856 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | H |
| William Wall House | 1856 | | | 77 Seaton Street | Cabbagetown | Old Toronto | 15 |
| Auberge du Pommier Restaurant (formerly Hogg's Hollow Cottage) | 1856 | | | 4150 Yonge Street | Armour Heights | North York | 6 |
| Northfield Estate (presently a part of Canada's National Ballet School) | 1856 | Joseph Sheard | | 372 Jarvis Street | Church and Wellesley | Old Toronto | 6, 18 |
| St. Basil's Church | 1856 | William Hay | | 50 St Joseph Street | Discovery District | Old Toronto | |
| University of St. Michael's College | 1856 | William Hay | | 50 Saint Joseph Street | Discovery District | Old Toronto | 2 |
| St. Michael's Mortuary Vault | 1856 | | | 1414 Yonge Street (St. Michael's Cemetery | Deer Park | Old Toronto | 6, 18 |
| Salvation Army Rest Home (former) | 1856 | | | 297 George Street | Garden District | Old Toronto | |
| Weston CNR bridge | 1856 | Sir Cazimir Gzowski for Grand Trunk Railway | | Over the Humber River (west of Weston Road and St. Phillips Street) | | | |
| Rose Blacksmith Shop | c. 1856 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| 85 Winchester Street | 1857 | | Georgian Revival | 85 Winchester Street | Cabbagetown | Old Toronto | 18 |
| Davis House (also Geary House "Caverhill") | 1857 | James Boyd Davis | | 124 Park Road | Rosedale | Old Toronto | 8, 18 |
| William Devenish House | 1857 | | | 1355 Victoria Park Avenue | Clairlea | Scarborough | |
| Mackenzie House | 1857 | William Roger | | 82 Bond Street | Garden District | Old Toronto | 3 |
| Miller Tavern | 1857 | | | 3885 Yonge Street | York Mills | North York | W |
| John B. Reid House | 1857 | John Tully | Greek Revival | 24 Mercer Street | Entertainment District | Old Toronto | 18 |
| Ritchie/Forneri House | 1857 | | | 283–285 Sherbourne Street | Cabbagetown | Old Toronto | 9 |
| Henry Scadding House | 1857 | | | 6 Trinity Square | Downtown Yonge | Old Toronto | 18 |
| James Small House | 1857 | | | 281–283 Sherbourne Street | Cabbagetown | Old Toronto | 18 |
| Toronto Magnetic and Meteorological Observatory | 1857 | Frederick William Cumberland and William George Storm | | 12 Hart House Circle | Discovery District | Old Toronto | W, 15, 18 |
| Tin and Copper Smith Building | 1857 | Joseph Sheard | | 83 Yonge Street | St. Lawrence | Old Toronto | 18 |
| Peter Hutty House | 1857 | | | 69 John Street | Weston | York | |
| Armoury Hotel | 1858 | William Cayley | | 10–12 Market Street | St. Lawrence | Old Toronto | |
| Daniel Stong's Piggery | 1858 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Felix Kent House | 1858 | | | 51 Royal York Road | Mimico | Etobicoke | |
| Mary Curts House | 1858 | | | 58 Royal York Road | Mimico | Etobicoke | |
| Rev. Samuel Boddy House | 1858 | | | 21 Winchester Street | Cabbagetown | Old Toronto | 18 |
| Thomas Clarkson Building/John Hallam Building | 1858 | | Renaissance Revival | 85 Front Street East | St. Lawrence | Old Toronto | |
| Cornell House | 1858 | | Upright and Wing | 1007 Brimley Road (Thomson Memorial Park) | Bendale | Scarborough | 6 |
| Culloden | 1858 | | | 291 Sherbourne Street | Cabbagetown | Old Toronto | 9, 18 |
| Flynn House | 1858 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Francey Barn | 1858 | | | 201 Winchester Street (Riverdale Farm) | Cabbagetown | Old Toronto | 18 |
| Green House | 1858 | | Georgian Revival | 78–80 Gerrard Street East | Garden District | Old Toronto | 9 |
| Thomas Helliwell Block | 1858 | | Georgian Revival | 81 Front Street East | St. Lawrence | Old Toronto | |
| Hughes Terrace | 1858 | | | 319–325 King Street West | Entertainment District | Old Toronto | 18 |
| John Kestevan House | 1858 | | | 56 Rose Avenue | Cabbagetown | Old Toronto | 18 |
| Edward Leadlay Company | 1858 | | Georgian Revival | 87 Front Street East | St. Lawrence | Old Toronto | |
| St. James The Less Chapel | 1858 | Frederick William Cumberland and William George Storm | Gothic Revival | 635 Parliament Street | Cabbagetown | Old Toronto | 6 |
| St. Stephen-in-the-Fields | 1858 | | | 103 Bellevue Avenue | Kensington Market | Old Toronto | 18 |
| H. S. Strathy House | 1858 | | Second Empire | 342 Adelaide Street West | Entertainment District | Old Toronto | 18 |
| Wilmot Township Hall | 1858 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | T |
| Daniel Flynn Boot and Shoe Shop | c. 1858 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Bain House | 1859 | Robert Sargant | | 14 Dingwall Avenue | Riverdale | Old Toronto | 8 |
| Brick House | 1859 | | | 64 King Street | Weston | York | |
| Cherry Street Hotel | 1859 | Joseph Sheard | | 409 Front Street East | West Don Lands | Old Toronto | 6, 18 |
| Thomas Meredith House | 1859 | | | 305 George Street | Garden District | Old Toronto | 18 |
| Robertson Cottages | 1859 | | | 703–705,711–721 Richmond Street West | Niagara | Old Toronto | 6, 18 |
| University College Main Building | 1859 | Frederick William Cumberland and William George Storm; David Dick (1892) | Norman Romanesque Revival | 15 King's College Circle (University College) | Discovery District | Old Toronto | 6 |
| University College Croft House | 1859 | Frederick William Cumberland | | 15 King's College Circle (University College) | Discovery District | Old Toronto | 6 |
| Workers' Cottages | 1859 | | | 7–9 Government Road | The Kingsway | Etobicoke | |
| Applewood, The Shaver Homestead | c. 1850s | | | 450 The West Mall | Eatonville | Etobicoke | 14 |
| Newtonbrook Store | c. 1850s | | | 5926 Yonge Street | Newtonbrook | North York | 14 |
| 191–197 Church Street | c. 1850s | John Tully | | 191–197 Church Street | Garden District | Old Toronto | |

### 1860 to 1869

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| 72–74 Gerrard Street | 1860 | | | 72–74 Gerrard Street East | Garden District | Old Toronto | 18 |
| 136–140 Seaton Street | 1860 | | | 136–140 Seaton Street | Cabbagetown | Old Toronto | 18 |
| Ardenvohr | 1860 | | | 177 Balmoral Avenue | South Hill | Old Toronto | 18 |
| Burwick Stable | 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | 6 |
| Church Drive Shed | 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | D |
| St. Paul's, Bloor Street | 1860 | Edward and George Radford | | 227 Bloor Street East | Church and Wellesley | Old Toronto | 18 |
| Thos. Bonner house | 1860 | | | 47 Granby Street | Garden District | Old Toronto | 6 |
| Dempsey Store | 1860 | | | 250 Beecroft Road | Willowdale | North York | 6 |
| Drive Shed | 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | 6 |
| Edgeley Slaughter House | 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | 6 |
| Edgeley Mennonite Meeting House Drive Shed | 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | 6 |
| Garbutt-Gardhouse Residence | 1860 | | | 105 Elmhurst Drive | Humberwood | Etobicoke | |
| Garibaldi House | 1860 | | | 302 King Street East | Old Town | Old Toronto | |
| Neilson Park Fieldhouse | 1860 | | | 1555 Neilson Road (Neilson Park) | Malvern | Scarborough | 6 |
| Oaklands | 1860 | William Hay (architect) | Gothic Revival | 131 Farnham Avenue (De La Salle College) | Summerhill | Old Toronto | 8 |
| John Richardson House | 1860 | | | 27 Old Kingston Road | West Hill | Scarborough | 18 |
| Jared Sessions House | 1860 | | | 34 Isabella Street | Church and Wellesley | Old Toronto | 18 |
| Spring Bank (Archibald & Mary Thompson House) | 1860 | | Regency | 7 Meadowcrest Road | The Queensway – Humber Bay | Etobicoke | |
| William Kent House | 1860 | | | 54 Royal York Road | Mimico | Etobicoke | |
| Josiah Parker House | 1860 | | | 25 Queens Drive | Weston | York | |
| Lambton House | 1860 | | | 4066 Old Dundas Street West | Lambton | York | |
| Cumberland House | 1860 | John W. Cumberland | | 33 St. George Street | Discovery District | Old Toronto | |
| Chicken House | c. 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Dominion Carriage Works and Cabinet Shop | c. 1860 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Alexander Smith Block | 1861 | | | 77 Front Street East | St. Lawrence | Old Toronto | |
| Charles MacKay House | 1861 | | | 35 Spruce Street | Cabbagetown | Old Toronto | 18 |
| Dickson Hill School | 1861 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | D |
| Francis & Susan Daniels House | 1861 | | | 82 Daniels Street | The Queensway – Humber Bay | Etobicoke | |
| Gooderham and Worts Distillery Stone Distillery | 1861 | | Victorian | 28–36 Distillery Lane | Distillery District | Old Toronto | 1, 6, 18 |
| Holy Trinity Rectory | 1861 | William Hay | | 10 Trinity Square | Downtown Yonge | Old Toronto | 6 |
| James Weir House | 1861 | | | 1021 Tapscott Road | Amadale | Scarborough | 18 |
| Queen's Wharf Lighthouse | 1861 | | | — | Fort York | Old Toronto | W |
| St. Patrick Church | 1861 | | | 131 McCaul Street | Grange Park | Old Toronto | 18 |
| William Stonehouse House | 1861 | | | 5951 Steeles Avenue East | Armadale | Scarborough |
| Chapel of Ease, St. John's Anglican Church | 1861 | | | 2152 Weston Road | Weston | York | |
| 240 King Street East | 1862 | | | 240 King Street East | Old Town | Old Toronto | |
| Henry Scadding Home | 1862 | Henry Scadding | | 6 Trinity Square | Downtown Yonge | Old Toronto | |
| Heyroyd | 1862 | | Georgian Revival | 35 Sherbourne Street North | Rosedale | Old Toronto | 18 |
| Piper/Birnie House | 1862 | | Georgian Revival | 110–112 Bond Street | Garden District | Old Toronto | |
| Alfred Walton Stores | 1862 | | | 374 Yonge Street | Downtown Yonge | Old Toronto | 18 |
| Frederick Bell-Smith House | 1863 | | | 336 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| 440–444 Sackville Street | 1863 | | | 440–444 Sackville Street | Cabbagetown | Old Toronto | 18 |
| George Arthur House | 1863 | | | 433–435 Sackville Street | Cabbagetown | Old Toronto | 18 |
| John Kerr House and Store | 1863 | | | 324–326 Queen Street West | Grange Park | Old Toronto | 18 |
| Rev. William McClure House | 1863 | | | 306 Seaton Street | Cabbagetown | Old Toronto | 18 |
| Betty Oliphant Theatre (formerly Blaikie/Alexander House) | 1863 | Thomas Gundry | | 404 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| Snarr's Terrace | 1863 | Thomas Snarr | | 215—219 Jarvis Street | Cabbagetown | Old Toronto | 8, 18, |
| 230–232 Carlton Street | 1864 | | | 230–232 Carlton Street | Cabbagetown | Old Toronto | 18 |
| Don Jail | 1864 | William Thomas | Italianate | 550 Gerrard Street East | Riverdale | Old Toronto | W |
| Elderslie | 1864 | | | 1575 Neilson Road | Malvern | Scarborough | 8 |
| Gooderham & Worts Distillery Brick Malthouse | 1864 | | | 55 Mill Street | Distillery District | Old Toronto | 6, 18 |
| John Wanless Building | 1864 | | | 372 Yonge Street | Downtown Yonge | Old Toronto | 18 |
| Joshua J. Williams Stores | 1864 | | | 328–330 Queen Street West | Grange Park | Old Toronto | 18 |
| John McBean Building | 1864 | | | 376 Yonge Street | Downtown Yonge | Old Toronto | 18 |
| Bolton Shop | 1865 | | | 1000 Murray Ross Parkway (The Village at Black Creek) | York University Heights | North York | |
| Davis House | 1865 | | | 66 Milwood Road | Davisville Village | Old Toronto | 18 |
| David Duncan House | 1865 | | | 125 Moatfield Drive | Graydon Hall | North York | 6 |
| Edward Scarlett House | 1865 | | | 1 Heritage Place | Humber Heights – Westmount | Etobicoke | |
| Forsyth House | 1865 | | | 17 Queens Drive | Weston | York | |
| Milne House | 1865 | Alexander Milne | | 1185 Lawrence Avenue East | Victoria Village | North York | 6 |
| 320–322 Queen Street West | 1865 | | | 320–322 Queen Street West | Grange Park | Old Toronto | 18 |
| Rectory of St. George the Martyr | 1865 | | | 205 John Street | Grange Park | Old Toronto | 18 |
| 91 Seaton Street | 1865 | | | 91 Seaton Street | Cabbagetown | Old Toronto | 18 |
| Sheard House | 1865 | | | 314 Jarvis Street | Garden District | Old Toronto | 18 |
| Summer Hill Coach House | 1865 | | | 36 Summerhill Gardens | Summerhill | Old Toronto | 6 |
| St. Stephen-in-the-Fields Anglican Church | 1865 | Henry Langley | | 103 Bellevue Avenue | Kensington Market | Old Toronto | 6, |
| Weston Presbyterian Church | 1865 | | | 11 Cross Street | Weston | York | 18 |
| William Jamieson House | 1865 | | | 185 Carleton Street | Cabbagetown | Old Toronto | 18 |
| 502–504 Yonge Street | 1865 | | | 502–504 Yonge Street | Discovery District | Old Toronto | 18 |
| 506–508 Yonge Street | 1865 | | | 506–508 Yonge Street | Discovery District | Old Toronto | 18 |
| 526–528 Yonge Street | 1865 | | | 526–528 Yonge Street | Discovery District | Old Toronto | 18 |
| 634–644 Yonge Street | 1865 | | | 634–644 Yonge Street | Discovery District | Old Toronto | 18 |
| 8–12 Gloucester Street | 1866 | | | 8–12 Gloucester Street | Church and Wellesley | Old Toronto | 18 |
| Glen Hurst | 1866 | | | 2 Elm Avenue | Rosedale | Old Toronto | 18 |
| St. Peter's Anglican Church | 1866 | Grundy and Henry Langley | | 188 Carlton Street | Cabbagetown | Old Toronto | 6 |
| Spadina House | 1866 | James Austin | | 285 Spadina Road | Casa Loma | Old Toronto | 18 |
| The Witch's House | 1866 | | | 384 Sumach Street | Cabbagetown | Old Toronto | 18 |
| Daniel Lamb House | 1867 | | | 156 Winchester Street | Cabbagetown | Old Toronto | 18 |
| 358–362 Dundas Street East | 1867 | | | 358–362 Dundas Street East | Cabbagetown | Old Toronto | |
| 68–70 Gerrard Street | 1867 | | | 68–70 Gerrard Street West | Discovery District | Old Toronto | 18 |
| John and Louise Harrison's House | 1867 | | | 11 Yorkleigh Avenue | Humber Heights – Westmount | Etobicoke | |
| John Daniels House | 1867 | | | 77 Yorkville Avenue | Yorkville | Old Toronto | W |
| Jubilee Terrace | 1867 | | | 328–332 Sackville Street | Cabbagetown | Old Toronto | 18 |
| W. Davies and Company Pork Packing (later J. & J. Taylor Safeworks) | 1867 | | | 145 Front Street East | St. Lawrence | Old Toronto | |
| 251 King Street East | 1868 | | | 251 King Street East | St. Lawrence | Old Toronto | |
| Barberian's Steak House | 1868 | | | 7 Elm Street | Downtown Yonge | Old Toronto | 18 |
| 61 Hayden Street | 1868 | | Georgian Revival | 61 Hayden Street | Church and Wellesley | Old Toronto | 18 |
| John William Drummond Stores | 1868 | | | 253 Yonge Street | Garden District | Old Toronto | 18 |
| Euclid Hall (now Keg Mansion) | 1868 | Arthur McMaster | | 515 Jarvis Street | Church and Wellesley | Old Toronto | W |
| 65 Front Street East | 1869 | | | 65 Front Street East | St. Lawrence | Old Toronto | |
| 76 Church Street | 1869 | | | 76 Church Street | St. Lawrence | Old Toronto | |
| 242 King Street East | 1869 | | | 242 King Street East | Old Town | Old Toronto | |
| Factory Theatre | 1869 | | | 125 Bathurst Street | Fashion District | Old Toronto | 18 |
| 37 Gloucester Street | 1869 | | | 37 Gloucester Street | Church and Wellesley | Old Toronto | 18 |
| James Pearse Barn | 1869 | | | 1755 Meadowvale Road | Rouge | Scarborough |
| Richard West Houses | 1869 | Richard West | | 104–106 John Street | Entertainment District | Old Toronto | 6, 18 |
| Rouge Valley Conservation Centre | 1869 | James Pearse Jr. | | 1749 Meadowvale Road | Rouge | Scarborough | 6, 18 |
| 231 Seaton Street | 1869 | | | 231 Seaton Street | Cabbagetown | Old Toronto | 18 |
| Zion Schoolhouse | 1869 | | | 1091 Finch Avenue East | Don Valley Village | North York | 6 |

### 1870 to 1879

| Building | Image | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| Albert Harward Drug Store | | 1870 | | | 318 Queen Street West | Grange Park | Old Toronto | 18 |
| Andrew McFarren Building | | 1870 | | | 237 Queen Street East | Old Town | Old Toronto | 6 |
| Collin's Block | | 1870 | | | 456–458 Queen Street West | Alexandra Park | Old Toronto | 18 |
| Downsview United Church | | 1870 | | | 2822 Keele Street | Downsview | North York | 6 |
| Duke of York Inn | | 1870 | | | 1225 Queen Street East | Leslieville | Old Toronto | 18 |
| 37–39 Elm Street | | 1870 | | | 37–39 Elm Street | Downtown Yonge | Old Toronto | 18 |
| 41 Elm Street | | 1870 | | | 41 Elm Street | Downtown Yonge | Old Toronto | 18 |
| 43 Elm Street | | 1870 | | | 43 Elm Street | Downtown Yonge | Old Toronto | 18 |
| 30 Government Road | | 1870 | | | 30 Government Road | The Kingsway | Etobicoke | 18 |
| Robertson Brothers Confections | | 1870 | | | 105–109 Queen Street East | Old Town | Old Toronto | 18 |
| Rueter House | | 1870 | | | 270 Drewry Avenue | Newtonbrook | North York | 18 |
| 590–596 Yonge Street | | 1870 | | | 590–596 Yonge Street | Discovery District | Old Toronto | 18 |
| 826–828 Yonge Street | | 1870 | | | 826–828 Yonge Street | Yorkville | Old Toronto | 18 |
| 838–844 Yonge Street | | 1870 | | | 838–844 Yonge Street | Yorkville | Old Toronto | 18 |
| 189 Burnhamthorpe Road | | c. 1870 | | | 189 Burnhamthorpe Road | Eatonville | Etobicoke | 18 |
| 132–142 Adelaide Street East | | c. 1870–1884 | | | 132–142 Adelaide Street East | Old Town | Old Toronto | |
| 9-15 Palmerston Avenue (11 & 11.5 illegal demo 2021) | https://www.acotoronto.ca/building.php?ID=13099 | 1871 | | Workmen's Cottages | 9-15 Palmerston Avenue | Trinity Bellwoods | Old Toronto | |
| 15 Prince Arthur Avenue | | 1871 | | | 15 Prince Arthur Avenue | The Annex | Old Toronto | 18 |
| 33–35 Elm Street | | 1871 | | | 33–35 Elm Street | Downtown Yonge | Old Toronto | 18 |
| 41 Spruce Street | | 1871 | | | 41 Spruce Street | Cabbagetown | Old Toronto | 18 |
| 55–79 Berkeley Street | | 1871 | | Worksmen's cottages | 55–79 Berkeley Street | Old Town | Old Toronto | 18, |
| 89–91 Ossington Avenue | | 1871 | | | 89–91 Ossington Avenue | Trinity-Bellwoods | Old Toronto | |
| 89–91 Gloucester Street | | 1871 | | | 89–91 Gloucester Street | Church and Wellesley | Old Toronto | 18 |
| 95 Scollard Street | | 1871 | | | 95 Scollard Street | Yorkville | Old Toronto | 18 |
| 122–124 Peter Street | | 1871 | | | 122–124 Peter Street | Entertainment District | Old Toronto | 18 |
| 144–152 Shuter Street | | 1871 | | | 144–152 Shuter Street | Garden District | Old Toronto | 18 |
| 230 Sherbourne Street | | 1871 | | | 230 Sherbourne Street | Garden District | Old Toronto | 18 |
| 256 Adelaide Street East | | 1871 | | | 256 Adelaide Street East | Old Town | Old Toronto | |
| 338–340 Jarvis Street | | 1871 | | | 338–340 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| 588 Yonge Street | | 1871 | | | 588 Yonge Street | Downtown Yonge | Old Toronto | 18 |
| Berkeley Castle | | 1871 | Joseph Simpson | | 2 Berkeley Street | St. Lawrence | Old Toronto | |
| James D. Bridgland House | | 1871 | | | 80 Yorkville Avenue | Yorkville | Old Toronto | 18 |
| Alexander Crombie House | | 1871 | | | 113 Maitland Street | Church and Wellesley | Old Toronto | 18 |
| De La Salle Institute | | 1871 | | | 253 Adelaide Street East | Old Town | Old Toronto | 18 |
| George M. Evans House | | 1871 | | | 69 Grange Avenue | Grange Park | Old Toronto | 18 |
| Oliver Goodwin House | | 1871 | | | 27 Rosedale Road | Rosedale | Old Toronto | 18 |
| Henry Howson House | | 1871 | | | 516 Wellington Street West | Fashion District | Old Toronto | 18 |
| Rev. Hoyes Lloyd House | | 1871 | | | 422 Sherbourne Street | Church and Wellesley | Old Toronto | 18 |
| Charles Moore and Co. | | 1871 | | | 5–9 Wellington Street West | Financial District | Old Toronto | 6 |
| National Casket Company Factories | | 1871 | | | 101–109 Niagara Street | Niagara | Old Toronto | 18 |
| Sherbourne Street Methodist Church | | 1871 | | | 355 Sherbourne Street | Cabbagetown | Old Toronto | 18 |
| Stonehouse-Lawrence House | | 1871 | | | 63 Delburn Drive | Agincourt | Scarborough | 18 |
| 40–42 Sullivan Street | | 1872 | | | 40–42 Sullivan Street | Grange Park | Old Toronto | 18 |
| 61–75 Jarvis Street | | 1872 | | | 61–75 Jarvis Street | Old Town | Old Toronto | |
| 105 Maitland Street | | 1872 | | | 105 Maitland Street | Church and Wellesley | Old Toronto | 18 |
| 105 Scollard Street | | 1872 | | | 105 Scollard Street | Yorkville | Old Toronto | 18 |
| 209–211 Carlton Street | | 1872 | | | 209–211 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 219 Carlton Street | | 1872 | | | 219 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 229–231 Carlton Street | | 1872 | | | 229–231 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 272–274 Queen Street West | | 1872 | | Georgian Revival | 272–274 Queen Street West | Grange Park | Old Toronto | 18 |
| 282–286 Queen Street West | | 1872 | | Georgian Revival | 282–286 Queen Street West | Grange Park | Old Toronto | 18 |
| Beardmore Building | | 1872 | | | 35 Front Street East | St. Lawrence | Old Toronto | |
| Berkeley St. Wesleyan Methodist Church | | 1872 | Smith & Gemell | | 315–317 Queen Street East | Old Town | Old Toronto | 6 |
| Samuel R. Briggs House | | 1872 | Henry Langley | Italianate | 467–469 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| Edward Burch House | | 1872 | | | 47 Gloucester Street | Church and Wellesley | Old Toronto | 18 |
| David Cornell House | | 1872 | | | 56 Spruce Street | Cabbagetown | Old Toronto | 18 |
| E.C. Gurney & Co. Stove Foundry | | 1872 | | | 500 Queen Street West | Entertainment District | Old Toronto | 18 |
| T Griffith Block | | 1872 | | | 35 Front Street East | St. Lawrence | Old Toronto | 6 |
| Hillside Outdoor Education Centre | | 1872 | | | 2259 Meadowvale Road | Rouge | Scarborough | 6, 10 |
| Italian Consulate | | 1872 | | | 136 Beverley Street | Grange Park | Old Toronto | 9 |
| Henry Jefferies House | | 1872 | | | 403 Sackville Street | Cabbagetown | Old Toronto | 18 |
| John Johnson House | | 1872 | | | 19 Amelia Street | Cabbagetown | Old Toronto | 18 |
| Knox United Church | | 1872 | | | 2569 Midland Avenue | Agincourt | Scarborough | 14 |
| MacDonald-Mowat House | | 1872 | | | 63 St. George Street | Discovery District | Old Toronto | 2, 18 |
| Patrick McBrine House | | 1872 | | | 103 Maitland Street | Church and Wellesley | Old Toronto | 18 |
| Metropolitan United Church | | 1872 | Henry Langley | French Gothic | 56 Queen St East | Garden District | Old Toronto | W |
| John Young Reid House | | 1872 | | | 87 Pembroke Street | Garden District | Old Toronto | 18 |
| Toronto Fire Department Fire Hall #3 (tower) | | 1872 | | | 486 Yonge St | Downtown Yonge | Old Toronto | 6 |
| Toronto Necropolis Chapel | | 1872 | | | 200 Winchester Street (Toronto Necropolis) | Cabbagetown | Old Toronto | 6, 18 |
| Toronto Necropolis Superintendent's Lodge | | 1872 | | | 200 Winchester Street (Toronto Necropolis) | Cabbagetown | Old Toronto | 18 |
| 45–49 Front Street East | | 1873 | W. R. Strickland | Commercial/industrial | 45–49 Front Street East | St. Lawrence | Old Toronto | |
| 106 Huron Street | | 1873 | | | 106 Huron Street | Grange Park | Old Toronto | 18 |
| 123–125 Baldwin Street | | 1873 | | | 123–125 Baldwin Street | Grange Park | Old Toronto | 18 |
| 646–662 Yonge Street | | 1873 | | | 646–662 Yonge Street | Discovery District | Old Toronto | 18 |
| 219–223 Parliament Street | | 1873 | | | 219–223 Parliament Street | Trefann Court | Old Toronto | 6 |
| 481–483 Ontario Street | | 1873 | | | 481–483 Ontario Street | Cabbagetown | Old Toronto | 18 |
| 484–490 Ontario Street | | 1873 | | | 484–490 Ontario Street | Cabbagetown | Old Toronto | 18 |
| 497–503 Ontario Street | | 1873 | | | 497–503 Ontario Street | Cabbagetown | Old Toronto | 18 |
| 505–511 Ontario Street | | 1873 | | | 505–511 Ontario Street | Cabbagetown | Old Toronto | 18 |
| Amelia Cottages | | 1873 | | | 36–40 Amelia Street | Cabbagetown | Old Toronto | 18 |
| Bank of British North America | | 1873 | John George Howard | | 49 Yonge Street | St. Lawrence | Old Toronto | 6, 18 |
| F.G. Perkins Block | | 1873 | | | 41 Front Street East | St. Lawrence | Old Toronto | |
| Joseph Bickerstaff Block | | 1873 | | | 401–403 Yonge Street | Downtown Yonge | Old Toronto | 18 |
| Gooderham & Worts The Cannery | | 1873 | | Victorian industrial | Case Goods Lane | Distillery District | Old Toronto | 18 |
| Gooderham & Worts Pure Spirits Building | | 1873 | | Victorian industrial | Trinity Street | Distillery District | Old Toronto | 18 |
| George H. Haymes House | | 1873 | | | 300 Sherbourne Street | Garden District | Old Toronto | 18 |
| William Hill House | | 1873 | | | 424 Ontario Street | Cabbagetown | Old Toronto | 18 |
| Bernard B. Hughes House | | 1873 | | | 104 Pembrooke Street | Garden District | Old Toronto | 18 |
| John Irwin House | | 1873 | | | 21 Grenville Street | Discovery District | Old Toronto | 18 |
| Thomas Jackson House | | 1873 | | | 10 Euclid Avenue | Trinity–Bellwoods | Old Toronto | 18 |
| Alex Leslie House | | 1873 | | | 10 Prince Arthur Avenue | The Annex | Old Toronto | 18 |
| Maple Cottage | | 1873 | | | 62 Laing Street (Maple Leaf Forever Park) | Leslieville | Old Toronto | 6 |
| St. Andrew's Manse | | 1873 | | | 73 Simcoe Street | Entertainment District | Old Toronto | 18 |
| St. Mary's Rectory | | 1873 | | | 589 Adelaide Street West | Niagara | Old Toronto | 18 |
| Somerset House | | 1873 | | | 27 Wellesley Street East | Church and Wellesley | Old Toronto | 18 |
| John Thomson and Andrew Woodcock House | | 1873 | | | 296–298 Sherbourne Street | Garden District | Old Toronto | 18 |
| St. Michael's College | | 1873 | William Irving | | Saint Joseph Street | Discovery District | Old Toronto | |
| John Ward House | | 1873 | | | 401 Sackville Street | Cabbagetown | Old Toronto | 18 |
| Zion Church | | 1873 | | | 1650 Finch Avenue East | Don Valley Village | North York | 6 |
| Winchester Junior and Senior Public School | | 1874 | | | 15 Prospect Street | Cabbagetown | Old Toronto | 18 |
| 95 Wellesley Street East | | 1874 | | | 95 Wellesley Street East | Church and Wellesley | Old Toronto | 18 |
| 101 Scollard Street | | 1874 | | | 101 Scollard Street | Yorkville | Old Toronto | 18 |
| 111 D'Arcy Street | | 1874 | | | 111 D'Arcy Street | Grange Park | Old Toronto | 18 |
| 362–368 King Street East | | 1874 | | | 362–368 King Street East | Corktown | Old Toronto | 18 |
| 538–544 Yonge Street | | 1874 | | | 538–544 Yonge Street | Discovery District | Old Toronto | 18 |
| All Saints Church and School | | 1874 | | | 223 Sherbourne Street | Garden District | Old Toronto | 18 |
| Peter Carroll House | | 1874 | | | 62 Metcalfe Street | Cabbagetown | Old Toronto | 18 |
| Cawthra House | | 1874 | | | 152 Beverley Street | Grange Park | Old Toronto | 9 |
| Christie, Brown & Company Factory | | 1874 | | | 200 King Street East (George Brown College St. James Campus) | Old Town | Old Toronto | |
| Cathedral Church of St. James | | 1874 | Frederick William Cumberland and Thomas Ridout | Gothic Revival | 65 Church Street | Old Town | Old Toronto | 2 |
| Elderslie | | 1874 | | | 471 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| Lambton CPR bridge | | 1874 | Credit Valley Railway | | North of Dundas Street West at the Humber River | | | TRCA |
| Phillipe Grandjean House | | 1874 | | | 41 Boswell Avenue | The Annex | Old Toronto | 18 |
| Sait Luke's United Church | | 1874 | Henry Langley and Edmund Burke | | 353 Sherbourne Street | Cabbagetown | Old Toronto | 6 |
| John Ward House | | 1874 | | Georgian Revival | 3904 Bloor Street West | Eatonville | Etobicoke | 3 |
| 1 Spadina Crescent | | 1875 | Smith & Gemell | Gothic Revival | 1 Spadina Crescent | Discovery District | Old Toronto | W |
| 21–23 Howard Street | | 1875 | | | 21–23 Howard Street | St. James Town | Old Toronto | 18 |
| 25–27 Howard Street | | 1875 | | | 25–27 Howard Street | St. James Town | Old Toronto | 18 |
| 25–29 Lowther Avenue | | 1875 | | | 25–29 Lowther Avenue | The Annex | Old Toronto | 18 |
| 36 Toronto Street | | 1875 | | | 36 Toronto Street | St. Lawrence | Old Toronto | |
| 44–46 Elm Avenue | | 1875 | | | 44–46 Elm Avenue | Rosedale | Old Toronto | 18 |
| 49–51 Hazelton Avenue | | 1875 | | | 49–51 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 49–51 Boswell Avenue | | 1875 | | | 49–51 Boswell Avenue | The Annex | Old Toronto | 18 |
| 57–59 Hazelton Avenue | | 1875 | | | 57–59 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 64 South Drive | | 1875 | | | 64 South Drive | Rosedale | Old Toronto | 18 |
| 82 Huron Street | | 1875 | | | 82 Huron Street | Grange Park | Old Toronto | 18 |
| 84 Gerrard Street West | | 1875 | | | 84 Gerrard Street West | Discovery District | Old Toronto | 18 |
| 159 Stanley Avenue | | 1875 | | | 159 Stanley Avenue | Mimico | Etobicoke | 18 |
| 162 Major Street | | 1875 | | | 162 Major Street | Harbord Village | Old Toronto | 18 |
| 207 McCaul Street | | 1875 | | | 207 McCaul Street | Grange Park | Old Toronto | 18 |
| 317–327 Carlton Street | | 1875 | | | 317–327 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 342–344 Jarvis Street | | 1875 | | | 342–344 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| 364–368 Dundas Street East | | 1875 | | | 364–368 Dundas Street East | Cabbagetown | Old Toronto | 18 |
| 370 Dundas Street East | | 1875 | | | 370 Dundas Street East | Cabbagetown | Old Toronto | 18 |
| 432 Sherbourne Street | | 1875 | | | 432 Sherbourne Street | Church and Wellesley | Old Toronto | 18 |
| Crooker's Block | | 1875 | | | 506–514 Queen Street West | Alexandra Park | Old Toronto | 18 |
| 37 Metcalfe Street | | 1875 | | | 37 Metcalfe Street | Cabbagetown | Old Toronto | 18 |
| George S. Garden Building | | 1875 | | | 291–293 King Street West | Entertainment District | Old Toronto | 18 |
| Thomas Hogarth House | | 1875 | | | 58 Hogarth Avenue | Riverdale | Old Toronto | 18 |
| 237 Gerrard Street East | | 1875 | | | 237 Gerrard Street East | Cabbagetown | Old Toronto | 18 |
| H. J. C. Ireton House | | 1875 | | | 70 Lonsdale Road | Deer Park | Old Toronto | 18 |
| Jarvis Street Baptist Church | | 1875 | | | 130 Gerrard St East | Garden District | Old Toronto | 6 |
| William R. Johnston House | | 1875 | | | 571 Jarvis Street | Church and Wellesley | Old Toronto | 18 |
| Christopher Lean House/Alfred Ingram House | | 1875 | | | 397–399 Sackville Street | Cabbagetown | Old Toronto | 18 |
| James Logie House and Daniel J. Slade House | | 1875 | | | 419–421 Wellesley Street East | Cabbagetown | Old Toronto | 18 |
| Alexander McLean House | | 1875 | | | 395 Sackville Street | Cabbagetown | Old Toronto | 18 |
| James McMurray Building | | 1875 | | | 228 Brunswick Avenue | Harbord Village | Old Toronto | 18 |
| William Mullins House | | 1875 | | | 306 College Street | Harbord Village | Old Toronto | 18 |
| Playter Farmhouse | | 1875 | | | 28 Playter Crescent | Playter Estates | Old Toronto | 18 |
| Richardson House (later the Spadina Hotel) | | 1875 | | | 460 King Street West | Fashion District | Old Toronto | 6 |
| St. Andrew's Church | | 1875 | William George Storm | | 73 Simcoe Street | Entertainment District | Old Toronto | 18 |
| "Seven Oaks" Wilkie House | | 1875 | | | 432 Sherbourne Street | Church and Wellesley | Old Toronto | 6 |
| 10–16 Wellesley Street West | | 1876 | | | 10–16 Wellesley Street West | Discovery District | Old Toronto | 18 |
| 16 Elgin Avenue | | 1876 | | | 16 Elgin Avenue | The Annex | Old Toronto | 18 |
| 20 Elgin Avenue | | 1876 | | | 20 Elgin Avenue | The Annex | Old Toronto | 18 |
| 45–47 Elgin Avenue | | 1876 | | | 45–47 Elgin Avenue | The Annex | Old Toronto | 18 |
| 21–23 Pembroke Street | | 1876 | | | 21–23 Pembroke Street | Garden District | Old Toronto | 18 |
| 48 South Drive | | 1876 | | | 48 South Drive | Rosedale | Old Toronto | 18 |
| 53–55 Hazelton Avenue | | 1876 | | | 53–55 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 61–63 Hazelton Avenue | | 1876 | | | 61–63 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 62–64 Hazelton Avenue | | 1876 | | | 62–64 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 127–135 Amelia Street | | 1876 | | | 127–135 Amelia Street | Cabbagetown | Old Toronto | 18 |
| 195 Carlton Street | | 1876 | | | 195 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 265–271 Wellesley Street East | | 1876 | | Rowhouse | 265–271 Wellesley Street East | Cabbagetown | Old Toronto | 18 |
| 375–377 Church Street | | 1876 | | | 375–377 Church Street | Garden District | Old Toronto | 18 |
| 589–593 Church Street | | 1876 | | | 589–593 Church Street | Church and Wellesley | Old Toronto | 18 |
| Richard Bigley Building | | 1876 | | | 98 Queen Street East | Garden District | Old Toronto | 6 |
| Brougham Terrace | | 1876 | | | 549–563 Parliament Street | Cabbagetown | Old Toronto | 18 |
| George Brown House | | 1876 | William Irving | Second Empire | 186 Beverley Street | Grange Park | Old Toronto | 3 |
| Brunswick House | | 1876 | | | 481 Bloor Street West | Harbord Village | Old Toronto | W |
| Chamberlain Terrace | | 1876 | | | 568–582 Parliament Street | Cabbagetown | Old Toronto | 18 |
| Rev. William Darling House | | 1876 | | | 57 Benlamond Avenue | Upper Beaches | Old Toronto | 18 |
| Denbrae | | 1876 | | | 3 Elm Street | Rosedale | Old Toronto | 18 |
| John Ferguson Residence/Rev. Archibald Gross Residence | | 1876 | | | 17–19 Elgin Avenue | The Annex | Old Toronto | 18 |
| Edward Leadlay House | | 1876 | | | 25 Augusta Avenue | Alexandra Park | Old Toronto | 18 |
| Albert Locke House | | 1876 | | | 9 Lowther Avenue | The Annex | Old Toronto | 18 |
| Lorne Hall | | 1876 | | | 3 Meredith Crescent | Rosedale | Old Toronto | 18 |
| James McGee Building | | 1876 | | | 295–299 King Street West | Entertainment District | Old Toronto | 18 |
| Ritchie and Stratton Block | | 1876 | | | 440–450 Queen Street West | Alexandra Park | Old Toronto | 18 |
| Francis Shields House | | 1876 | | | 377 Sackville Street | Cabbagetown | Old Toronto | 18 |
| S. S. #3 School | | 1876 | | | 5810 Finch Avenue East | Malvern | Scarborough | 18 |
| Olivet Congregational Church (presently Heliconian Hall) | | 1876 | | | 35 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 28–30 Bernard Avenue | | 1877 | | | 28–30 Bernard Avenue | The Annex | Old Toronto | 18 |
| 133–141 Beverley Street | | 1877 | | | 133–141 Beverley Street | Grange Park | Old Toronto | 9 |
| 218 Carlton Street | | 1877 | | | 218 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 220 Carlton Street | | 1877 | | | 220 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 222–224 Carlton Street | | 1877 | | | 222–224 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 320 Carlton Street | | 1877 | | | 320 Carlton Street | Cabbagetown | Old Toronto | 18 |
| 370 Dundas St West | | 1877 | | | 370 Dundas St West | Garden District | Old Toronto | 18 |
| 67 Front Street East | | 1877 | | | 67 Front Street East | St. Lawrence | Old Toronto | |
| 65 Hazelton Avenue | | 1877 | | | 65 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| 29–31 Howard Street | | 1877 | | | 29–31 Howard Street | St. James Town | Old Toronto | 18 |
| 33–35 Howard Street | | 1877 | | | 33–35 Howard Street | St. James Town | Old Toronto | 18 |
| 86–90 Lewis Street | | 1877 | | | 86–90 Lewis Street | Riverdale | Old Toronto | 18 |
| 76–78 Huron Street | | 1877 | | | 76–78 Huron Street | Grange Park | Old Toronto | 18 |
| 11–13 Lowther Avenue | | 1877 | | | 11–13 Lowther Avenue | The Annex | Old Toronto | 18 |
| 23 Lowther Avenue | | 1877 | | | 23 Lowther Avenue | The Annex | Old Toronto | 18 |
| 31 Lowther Avenue | | 1877 | | | 31 Lowther Avenue | The Annex | Old Toronto | 18 |
| 33 Lowther Avenue | | 1877 | | | 33 Lowther Avenue | The Annex | Old Toronto | 18 |
| 122–136 Shuter Street | | 1877 | | | 122–136 Shuter Street | Garden District | Old Toronto | 18 |
| 45–47 Rose Avenue | | 1877 | | | 45–47 Rose Avenue | Cabbagetown | Old Toronto | 18 |
| Braemore | | 1877 | | | 22 Wychwood Park | Bracondale Hill | Old Toronto | 18 |
| Edwin Coleman House | | 1877 | | | 340 Dundas Street West | Grange Park | Old Toronto | 18 |
| Darling Terrace | | 1877 | | | 562–566 Parliament Street | Cabbagetown | Old Toronto | 18 |
| Davies Terrace | | 1877 | | | 467–477 Queen Street East | Corktown | Old Toronto | 18 |
| Don Brewery T. Davies & Bro Malt House | | 1877 | | | 27–39 Old Brewery Lane | Trefann Court | Old Toronto | 6 |
| Gate Lodge of Dale | | 1877 | | | 15 Dale Avenue | Rosedale | Old Toronto | 18 |
| Hillside Church | | 1877 | | | 361 Old Finch Avenue | Rouge | Scarborough | 6 |
| Old St. Mary's Separate School | | 1877 | | | 9 Portugal Square | Niagara | Old Toronto | 18 |
| Mary Perram House | | 1877 | | | 4 Wellesley Place | Church and Wellesley | Old Toronto | 18 |
| Rev. Alex Sutherland House | | 1877 | | | 437 Sherbourne Street | Cabbagetown | Old Toronto | 18 |
| Toronto Central Prison Chapel | | 1877 | | | 70 East Liberty Street (Liberty Village Park) | Liberty Village | Old Toronto | |
| Toronto Cold Storage Building | | 1877 | | | 9–11 Church Street | St. Lawrence | Old Toronto | |
| Zion Wexford Church | | 1877 | | | 2102 Lawrence Avenue East | Wexford | Scarborough | 18 |
| 126–128 Amelia Street | | 1878 | | | 126–128 Amelia Street | Cabbagetown | Old Toronto | 18 |
| 19–21 Baldwin Street | | 1878 | | | 19–21 Baldwin Street | Grange Park | Old Toronto | 18 |
| 10 Bernard Avenue | | 1878 | | | 10 Bernard Avenue | The Annex | Old Toronto | 18 |
| 24–26 Bernard Avenue | | 1878 | | | 24–26 Bernard Avenue | The Annex | Old Toronto | 18 |
| 145–147 Beverley Street | | 1878 | | | 145–147 Beverley Street | Grange Park | Old Toronto | 9 |
| 181–183 Carleton Street | | 1878 | | | 181–183 Carleton Street | Cabbagetown | Old Toronto | 18 |
| Chamberlin Block | | 1878 | | | 165–179 Carleton Street | Cabbagetown | Old Toronto | 18 |
| 187–189 Carleton Street | | 1878 | | | 187–189 Carleton Street | Cabbagetown | Old Toronto | 18 |
| 511–513 Church Street | | 1878 | | | 511–513 Church Street | Church and Wellesley | Old Toronto | 18 |
| 551–555 Church Street | | 1878 | | | 551–555 Church Street | Church and Wellesley | Old Toronto | 18 |
| 580–582 Church Street | | 1878 | | | 580–582 Church Street | Church and Wellesley | Old Toronto | 18 |
| 595 Church Street | | 1878 | | | 595 Church Street | Church and Wellesley | Old Toronto | 18 |
| 634–636 Church Street | | 1878 | | | 634–636 Church Street | Church and Wellesley | Old Toronto | 18 |
| 336 Dundas Street West | | 1878 | | | 336 Dundas Street West | Grange Park | Old Toronto | 18 |
| 4160 Dundas Street West | | 1878 | | | 4160 Dundas Street West | Humber Valley Village | Etobicoke | 18 |
| 68 Elm Grove Avenue | | 1878 | | | 68 Elm Grove Avenue | Parkdale | Old Toronto | 18 |
| 74 Elm Grove Avenue | | 1878 | | | 74 Elm Grove Avenue | Parkdale | Old Toronto | 18 |
| 205–207 Gerrard Street East | | 1878 | | | 205–207 Gerrard Street East | Cabbagetown | Old Toronto | 18 |
| 241–243 King Street East | | 1878 | | | 241–243 King Street East | Old Town | Old Toronto | |
| 73 Lonsdale Road | | 1878 | | | 73 Lonsdale Road | Deer Park | Old Toronto | 18 |
| 1 Old Yonge Street | | 1878 | | | 1 Old Yonge Street | York Mills | North York | 18 |
| 38 Prospect Street | | 1878 | | | 38 Prospect Street | Cabbagetown | Old Toronto | 18 |
| 284 Sherbourne Street | | 1878 | | | 284 Sherbourne Street | Garden District | Old Toronto | 18 |
| Toronto Fire Services Station 315 | | 1878 | | | 132 Bellevue Avenue | Kensington Market | Old Toronto | 18 |
| 257–263 Wellesley Street East | | 1878 | | | 257–263 Wellesley Street East | Cabbagetown | Old Toronto | 18 |
| 17–19 Winchester Street | | 1878 | | | 17–19 Winchester Street | Cabbagetown | Old Toronto | 18 |
| 620–632 Yonge Street | | 1878 | | | 620–632 Yonge Street | Discovery District | Old Toronto | 18 |
| Dr. Joseph Adams House | | 1878 | | | 318 Dundas Street West | Grange Park | Old Toronto | 18 |
| H. St. George Baldwin House | | 1878 | | | 50 Lowther Avenue | The Annex | Old Toronto | 18 |
| E.M. Chadwick House | | 1878 | | | 44 St. George Street | Discovery District | Old Toronto | 18 |
| Dominion Brewery | | 1878 | | | 468–478 Queen Street East | Trefann Court | Old Toronto | 18 |
| Joseph Goulding House/Howard Bryant House | | 1878 | | | 324–326 Dundas Street West | Grange Park | Old Toronto | 18 |
| William James House/Charles Luney House | | 1878 | | | 62–64 Amelia Street | Cabbagetown | Old Toronto | 18 |
| George M. Lee House | | 1878 | | | 68 Hazelton Avenue | Yorkville | Old Toronto | 18 |
| J S Lockie House "Melrose" | | 1878 | | | 32 Beaty Avenue | Parkdale | Old Toronto | 6 |
| Inglis Lough House | | 1878 | | | 322 Dundas Street West | Grange Park | Old Toronto | 18 |
| Maple Terrace | | 1878 | | | 519–527 Parliament Street | Cabbagetown | Old Toronto | 18 |
| Hugh Neilson House | | 1878 | | | 295 Carlton Street | Cabbagetown | Old Toronto | 18 |
| Robert Parker House | | 1878 | | | 26 Lowther Avenue | The Annex | Old Toronto | 18 |
| Rosar Morrison Funeral Home | | 1878 | | | 467 Sherbourne Street | Cabbagetown | Old Toronto | 18 |
| Schomburg Furniture | | 1878 | | | 647–649 Yonge Street | Church and Wellesley | Old Toronto | 18 |
| Grace Toronto Church | | 1878 | Henry Langley & Edmund Burke | Gothic Revival | 383 Jarvis Street | Garden | Old Toronto | 18 |
| Toronto Fire Services Station 312 (formerly Hose No. 8 and later Toronto Fire Department Station 10) | | 1878 | | Victorian Gothic | 34 Yorkville Avenue | Yorkville | Old Toronto | 6 |
| Toronto Fire Services Station 315 (formerly Toronto Fire Department Station 8) | | 1878 | | | 132 Bellevue Avenue | Kensington Market | Old Toronto | 18 |
| Toronto Western Hospital Men's Detox Centre | | 1878 | | | 16 Ossington Avenue | Trinity–Bellwoods | Old Toronto | 18 |
| Christopher Wilson House/Angus McColl House | | 1878 | | | 287–289 Carlton Street | Cabbagetown | Old Toronto | 18 |
| St. John's Rectory | | 1878 | "Mr. Fisher of Eglinton" (carpenter); Joseph Pennock (contractor) | | 174 Old Yonge Street | York Mills | Old Toronto | 18 |
| Windsor Terrace | | 1878 | | | 18–26 Earl Street | Church and Wellesley | Old Toronto | 18 |
| 130 Amelia Street | | 1879 | | | 130 Amelia Street | Cabbagetown | Old Toronto | 18 |
| 106 Front Street | | 1879 | | | 106 Front Street | St. Lawrence | Old Toronto | |
| 18–22 Bernard Avenue | | 1879 | | | 18–22 Bernard Avenue | The Annex | Old Toronto | 18 |
| 226–228 Carlton Street | | 1879 | | | 226–228 Carlton Street | Cabbageotown | Old Toronto | 18 |
| 237 King Street East | | 1879 | | 237 King Street East | Old Town | Old Toronto | |
| 21 Elgin Avenue | | 1879 | | | 21 Elgin Avenue | The Annex | Old Toronto | 18 |
| 24–26 Elgin Ave | | 1879 | | | 24–26 Elgin Ave | The Annex | Old Toronto | 18 |
| 25 Elgin Avenue | | 1879 | | | 25 Elgin Avenue | The Annex | Old Toronto | 18 |
| 4 Elm Avenue | | 1879 | | | 4 Elm Avenue | Rosedale | Old Toronto | 18 |
| 76 Gerrard Street East | | 1879 | | | 76 Gerrard Street East | Garden District | Old Toronto | 18 |
| 85–87 Gloucester Street | | 1879 | | | 85–87 Gloucester Street | Church and Wellesley | Old Toronto | 18 |
| 207–213 Jarvis Street | | 1879 | | | 207–213 Jarvis Street | Garden District | Old Toronto | 18 |
| 59 McGill Street | | 1879 | | | 59 McGill Street | Garden District | Old Toronto | 18 |
| 502–508 Parliament Street | | 1879 | | | 502–508 Parliament Street | Cabbagetown | Old Toronto | 18 |
| 21–23 Prince Arthur Avenue | | 1879 | | | 21–23 Prince Arthur Avenue | The Annex | Old Toronto | 18 |
| 484 Queen Street West | | 1879 | | | 484 Queen Street West | Alexandra Park | Old Toronto | 18 |
| 298 Sackville Street | | 1879 | | Worker's cottage | 298 Sackville Street | Cabbagetown | Old Toronto | |
| 280 Sherbourne Street | | 1879 | | | 280 Sherbourne Street | Garden District | Old Toronto | 18 |
| 6–14 St. Joseph Street | | 1879 | | | 6–14 St. Joseph Street | Discovery District | Old Toronto | 18 |
| 31 Sussex Avenue | | 1879 | | | 31 Sussex Avenue | Discovery District | Old Toronto | 18 |
| Church of the Redeemer | | 1879 | | | 162 Bloor Street West | Yorkville | Old Toronto | 18 |
| Clarence Terrace | | 1879 | | | 5–16 Clarence Square | Entertainment District | Old Toronto | 18 |
| William Copeland Buildings | | 1879 | | | 245–247 King Street East | Old Town | Old Toronto | |
| Davis Villa | | 1879 | | | 309 Davisville Avenue | Davisville Village | Old Toronto | 18 |
| Earl Court | | 1879 | | | 38 Earl Street | Church and Wellesley | Old Toronto | 18 |
| Gooderham & Worts Paints Shop | | 1879 | | | 21 Tank House Lane | Distillery District | Old Toronto | 18 |
| Hollydene | | 1879 | | | 10 Elm Avenue | Rosedale | Old Toronto | 18 |
| Mason and Risch Piano Manufactory | | 1879 | | | 642 King Street West | Entertainment District | Old Toronto | 18 |
| Samuel T. Scilly House | | 1879 | | | 283–285 Carlton Street | Cabbagetown | Old Toronto | 18 |
| Jane Pillow House | | 1879 | | | 291 Carlton Street | Cabbagetown | Old Toronto | 18 |
| St.Stanislaus Kostka Church (original West Presbyterian Church) | | 1879 | | | 12 Denison Avenue | Alexandra Park | Old Toronto | 18 |
| Stables for Little York Inn | | 1879 | | | 67 George Street | Old Town | Old Toronto | |
| James Travers House | | 1879 | | | 312–314 Dundas Street West | Grange Park | Old Toronto | 18 |
| Winchester Block | | 1879 | | | 1–11 Rose Avenue | Cabbagetown | Old Toronto | 18 |

### 1880 to 1889

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| 169 King Street East | 1880 | | | 169 King Street East | Old Town | Old Toronto | 6 |
| Armadale Free Methodist Church | 1880 | Volunteer labourers | | 400 Passmore Avenue | Armadale | Scarborough | 6 |
| Cadillac Lounge | 1880 | | | 1296–1298 Queen Street West | Parkdale | Old Toronto | 18 |
| Donalda Barn | c. 1880 | | | 1413 Don Mills Road | Don Mills | North York | 18 |
| Little York Inn | 1880 | | Second Empire | 187 King Street East | Old Town | Old Toronto | |
| Little York Inn stables | 1880 | | | 65 George Street | Old Town | Old Toronto | |
| Musson House | 1880 | | | 4884 Dundas Street West | Islington-City Centre West | Etobicoke | |
| William Barber Building | 1880 | | | 289 King Street West | Entertainment District | Old Toronto | 6 |
| 11–13 Draper Street | 1881 | | | 11–13 Draper Street | Fashion District | Old Toronto | 18 |
| 15–17 Draper Street | 1881 | | | 15–17 Draper Street | Fashion District | Old Toronto | 18 |
| 23–25 Draper Street | 1881 | | | 23–25 Draper Street | Fashion District | Old Toronto | 18 |
| 29 Draper Street | 1881 | | | 29 Draper Street | Fashion District | Old Toronto | 18 |
| 280 Queen Street West | 1881 | | Queen Anne | 280 Queen Street West | Grange Park | Old Toronto | |
| 1312–1320 Queen Street West | 1881 | | | 1312–1320 Queen Street West | Parkdale | Old Toronto | 18 |
| McMaster Hall | 1881 | Henry Langley & Edmund Burke | | 273 Bloor Street West | Discovery District | Old Toronto | 2 |
| James Cooper House | 1881 | | Second Empire | 582 Sherbourne Street | St. James Town | Old Toronto | 6, 18 |
| 3–5 Draper Street | 1882 | | | 3–5 Draper Street | Fashion District | Old Toronto | 18 |
| 4–6 Draper Street | 1882 | | | 4–6 Draper Street | Fashion District | Old Toronto | 18 |
| 7–9 Draper Street | 1882 | | | 7–9 Draper Street | Fashion District | Old Toronto | 18 |
| 8–10 Draper Street | 1882 | | | 8–10 Draper Street | Fashion District | Old Toronto | 18 |
| 12–14 Draper Street | 1882 | | | 12–14 Draper Street | Fashion District | Old Toronto | 18 |
| 16–18 Draper Street | 1882 | | | 16–18 Draper Street | Fashion District | Old Toronto | 18 |
| 70 The Esplanade | 1882 | | | 70 The Esplanade | St. Lawrence | Old Toronto | |
| 82 Church Street | 1882 | | | 82 Church Street | St. Lawrence | Old Toronto | |
| Brockton Town Hall | 1882 | | | 1617 Dundas Street West | Brockton Village | Old Toronto | 6 |
| Standard Woolen Mill | 1882 | | | 227 Front Street East | St. Lawrence | Old Toronto | |
| Charles H. Gooderham House | 1882 | David Roberts Jr. | Queen Anne | 592 Sherbourne Street | St. James Town | Old Toronto | 18 |
| 187-189 Soudan | 1883 | Unknown | Bay-and-gable | 187-189 Soudan Ave. | Davisville Village | North York | 18 |
| Doyle House | 1884 | | | 77 Granby Street | Garden District | Old Toronto | 6 |
| Fee's Terrace | 1884 | | | 524–534 Queen Street East | Trefann Court | Old Toronto | 6 |
| St. Andrew-by-the-Lake Church and Bishop's Cottage | 1884 | A. R. Dennison; (church windows by Robert McCausland) | | Cibola Avenue | Toronto Islands | Old Toronto | 6 |
| 630–634 Wellington Street West | 1884 | | Row housing | 630–634 Wellington Street West | Niagara | Old Toronto | |
| Toronto Metropolitan University Centre for Urban Innovation (formerly the Ontario College of Pharmacy Building) | 1885 | | | 46 Gerrard Street East | Garden District | Old Toronto | 18 |
| 74 Gerrard Street East | 1885 | | Queen Anne | 74 Gerrard Street East | Garden District | Old Toronto | 9 |
| Townhouses Sumach Street | 1885 | | | 83-89 Sumach Street | Trefann Court | Old Toronto | 11 |
| 219 Front Street East | 1885 | | | 219 Front Street East | St. Lawrence | Old Toronto | |
| Hockey Hall of Fame (formerly the Bank of Montreal) | 1885 | Frank Darling & S. George Curry | | 30 Yonge Street | Financial District | Old Toronto | W |
| Massey Harris Office building | 1885, (additions 1899 and prior to World War I) | E. J. Lennox George M. Miller (south addition) | | 915 King Street West | Liberty Village | Old Toronto | |
| Poulton Block | 1885 | Kennedy, Gaviller & Holland | Gothic Revival | 798 Queen Street East | Riverdale | Old Toronto | W |
| Scholes Hotel (later Ocean Hotel) | 1885 | | Second Empire | 1633–1647 Queen Street West | Parkdale | Old Toronto | 6, 18 |
| St. Mary's Church | 1885 | Joseph Connolly (spire by A. W. Holmes) | | 588 Adelaide Street West | Niagara | Old Toronto | 6 |
| 1 Draper Street | 1886 | | | 1 Draper Street | Fashion District | Old Toronto | 18 |
| 50 King Street East | 1886 | | | 50 King Street East | St. Lawrence | Old Toronto | |
| Eden Court | 1886 | | Romanesque Revival | 515 Royal York Road | The Queensway – Humber Bay | Etobicoke | 18 |
| George S. Pratt House | 1886 | | | 17 Mill Street | York Mills | North York | 6, 18 |
| John E. Thompson Block | 1886 | | | 221 Yonge Street | Garden District | Old Toronto | 18 |
| Lombard Street Fire Hall | 1886 | | | 110 Lombard Street | Old Town | Old Toronto | 18 |
| 491–497 Queen Street East | 1886 | | Row housing | 491–497 Queen Street East | Corktown | Old Toronto | 6 |
| Toronto Chinese Baptist Church (formerly Beverley Street Baptist Church) | 1886 | Henry Langley & Edmund Burke | | 72 Beverley Street | Grange Park | Old Toronto | 6 |
| Upper Canada Bible & Tract Societies Building | 1886 | | | 102 Yonge Street | Financial District | Old Toronto | 18 |
| 251 Front Street East | 1887 | | | 251 Front Street East | St. Lawrence | Old Toronto | |
| Inglenook Community High School | 1887 | | | 19 Sackville Street | Corktown | Old Toronto | 18 |
| Ontario College of Pharmacy | 1887 | | | 44 Gerard Street East | Garden District | Old Toronto | |
| Robert Armstrong House | 1887 | | Second Empire | 309–311 George Street | Garden District | Old Toronto | |
| Toronto Free Theatre (originally Consumer's Gas Co.) | 1887 | | | 26 Berkeley Street | St. Lawrence | Old Toronto | |
| Chester D. Massey House | 1887 (later altered) | E. J. Lennox | Queen Anne Revival | 519 Jarvis Street | Church and Wellesley | Old Toronto | 6 |
| Central United Church | 1887 | | | 1 King Street | Weston | York | |
| 133–135 King Street | 1888 | | | 133–135 King Street East | St. Lawrence | Old Toronto | |
| 236 King Street East | 1888 | | | 236 King Street East | Old Town | Old Toronto | |
| Bathurst Street Theatre (formerly Bathurst Street Methodist Church) | 1888 | | | 736 Bathurst Street | Palmerston–Little Italy | Old Toronto | W |
| Campbell Block | 1888 | | | 2856 Dundas Street West | The Junction | Old Toronto | |
| 2–36 Monteith Street | 1888 | | Second Empire | 2–36 Monteith Street | Church and Wellesley | Old Toronto | |
| McLeish-Powell Houses | 1888 | Robert Crabbe | | 422-424 Wellington Street West | Fashion District | Old Toronto | |
| Nealon House | 1888 | | | 197 King Street East | Old Town | Old Toronto | |
| Parkdale Hotel | 1888 | | | 1302 Queen Street West | Parkdale | Old Toronto | 6, 18 |
| Robert Edey House | 1888 | Robert Edey | | 222 Garden Avenue | Roncesvalles | Old Toronto | 6 |
| The Toronto Club | 1888 | Frank Darling & S. George Curry | Palladian, Renaissance Revival, Richardsonian Romanesque | 107–109 Wellington Street West | Financial District | Old Toronto | 6 |
| Winchester Hotel (formerly Lakeview Hotel) | 1888 | | | 531 Parliament Street | Cabbagetown | Old Toronto | 6, W |
| Young People's Theatre (formerly Toronto Street Railway stables) | 1888 | H.G. Salisbury | | 165 Front Street East | St. Lawrence | Old Toronto | |
| 17 Leader Lane | 1889 | | | 17 Leader Lane | St. Lawrence | Old Toronto | |
| 41 Colborne Street | 1889 | | | 41 Colborne Street | St. Lawrence | Old Toronto | |
| St. Paul's Basilica | 1889 | Joseph Connolly | Romanesque Revival | 83 Power Street | Corktown | Old Toronto | 6 |
| 100 Adelaide Street East | 1889 | | | 100 Adelaide Street East | Old Town | Old Toronto | |
| 189–191 King Street East | 1889 | | | 189–191 King Street East | Old Town | Old Toronto | |
| A. C. Thompson Block | 1889 | | | 2845–2853 Dundas Street West; 363–367 Keele Street | The Junction | Old Toronto | 6 |
| Avenue Hotel | 1889 | | | 340 High Park Avenue | The Junction | Old Toronto | 6 |
| Bloor Street United Church | 1889 | | | 300 Bloor Street West | The Annex | Old Toronto | 6 |
| College Street Baptist Church | 1889 | | | 506 College Street | Palmerston–Little Italy | Old Toronto | |
| Dominion Hotel | 1889 | | | 498 Queen Street East | Trefann Court | Old Toronto | |
| Dr William McCormick Sanitorium | 1889 | | | 32 Gothic Avenue | High Park North | Old Toronto | , 6, 18 |
| Ernest Smith and F.W. Hutt Stores | 1889 | | | 1408–1410 Queen Street West | Parkdale | Old Toronto | 6, 18 |
| Fairbank United Church | 1889 | | | 2750 Dufferin Street | Glen Park | North York | 6 |
| Gladstone Hotel | 1889 | | Romanesque Revival | 1214 Queen Street West | Little Portugal | Old Toronto | 6, W |
| The Great Hall | 1889 | Gordon & Helliwell | Victorian | 1087 Queen Street West | Niagara | Old Toronto | 6, 18 |
| Heintzman House | 1889 | Knox, Elliot & Jarvis | | 288 Annette Street | The Junction | Old Toronto | 6 |
| Lakeshore Psychiatric Hospital Administration Building | 1889 | Kivas Tully | | 17 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 18 |
| 1–7 Melbourne Place | 1889 | | Georgian Revival row housing | 1–7 Melbourne Place | Parkdale | Old Toronto | 6, 18 |
| Milburn Building | 1889 | E. J. Lennox | | 47 Colborne Street | St. Lawrence | Old Toronto | |
| 216–232 Queen Street East | 1889 | | | 216–232 Queen Street East | Moss Park | Old Toronto | 6 |
| Rupert Simpson House | 1889 | | Richardsonian Romanesque | 2 Wellesley Place | Church and Wellesley | Old Toronto | 18 |
| Toronto Hydro Dynamo House | 1889 | | | 532 Bay Street | Downtown Yonge | Old Toronto | |
| Trinity-St. Paul's United Church | 1889 | Henry Langley & Edmund Burke | | 427 Bloor Street West | Harbord Village | Old Toronto | 6 |
| W. H. Ives Tailor Building | 1889 | William James | | 2959 Dundas Street West | The Junction | Old Toronto | 18 |

### 1890 to 1899

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| 20–24 Draper Street | 1890 | | | 20–24 Draper Street | Fashion District | Old Toronto | 18 |
| 26–28 Draper Street | 1890 | | | 26–28 Draper Street | Fashion District | Old Toronto | 18 |
| Don Valley Brick Works | 1890 | | Victorian industrial | 550 Bayview Avenue | Rosedale | Old Toronto | 6 |
| Drake Hotel | 1890 | | | 1150 Queen Street West | Little Portugal | Old Toronto | W, 18 |
| Fashion Institute (Humber College) | 1890 | | | 3166 Lake Shore Boulevard West | New Toronto | Etobicoke | 18 |
| G. H. Gooderham House | 1890 | David Roberts Jr. | Richardsonian Romanesque | 504 Jarvis Street | Church and Wellesley | Old Toronto | 6, 18 |
| Palace Arms Hotel | 1890 | Frederick Henry Herbert | | 950 King Street West | Niagara | Old Toronto | , 6 |
| Peacock Hotel | 1890 | | | 2760–2762 Dundas Street West | The Junction | Old Toronto | 18 |
| R.G. McLean Company Building and Barclay, Clark and Company Building | 1890 | | | 20–26 Lombard Street | St. Lawrence | Old Toronto | 18 |
| Rotman's Men's Shop | 1890 | William George Storm | | 350–358 Spadina Avenue | Chinatown | Old Toronto | |
| Sunlight Soap/Lever Brothers Works Factory | 1890 | | | 2 Don Roadway | Leslieville | Old Toronto | |
| Swansea Public School | 1890 | | Romanesque Revival | 207 Windermere Avenue | Swansea | Old Toronto | |
| University of St. Michael's College Elmsley Place Houses | 1890 | | | Elmsley Place | Discovery District | Old Toronto | |
| Dr. Anderson Ruffin Abbott House | 1890 | | | 119 Dowling Avenue | Parkdale | Old Toronto | 18 |
| 256 King Street East | 1891 | | | 256 King Street East | Old Town | Old Toronto | |
| Athenaeum Club | 1891 | Denison and King | Moorish Revival | 167 Church Street | Church and Wellesley | Old Toronto | 18 |
| A.W. Dingman Shops | 1891 | | | 704 Queen Street East | Riverdale | Old Toronto | 6 |
| Crocker Building | 1891 | | | 652–672 Queen Street West | Trinity-Bellwoods | Old Toronto | 6, 18 |
| Dennis Avenue Community School | 1891 | James Augustus Ellis | | 17 Dennis Avenue | Mount Dennis | York | 18 |
| Heydon House Hotel | 1891 | James A. Ellis | | 1834 St. Clair Avenue West | Earlscourt | Old Toronto | 18 |
| Independent Order of Odd Fellows Hall | 1891 | Norman Dick & Frank Wickson | | College Street and Yonge Street | Discovery District | Old Toronto | |
| Boxer Building | 1891 | | Richardsonian Romanesque | 222 Islington Avenue | New Toronto | Etobicoke | 18 |
| J. Morrish General Store | 1891 | | | 6282 Kingston Road | Highland Creek | Scarborough | 6 |
| 2–6 Melbourne Street | 1891 | Alvary Beecroft | Row houses | 2–6 Melbourne Street | Parkdale | Old Toronto | 6 |
| Ryrie Building | 1891 | Langley & Burke | Palazzo style | 229 Yonge Street | Garden District | Old Toronto | |
| St. George's Hall (now Arts and Letters Club) | 1891 | Edwards & Webster | Gothic Revival | 14 Elm Street | Downtown Yonge | Old Toronto | 6, 18 |
| Wycliffe College | 1891 | | | 5 Hoskin Avenue | Discovery District | Old Toronto | |
| Underwood House | 1891 | | | 5933 Steeles Avenue East | Armadale | Scarborough | 6 |
| 266–270 Adelaide Street West | 1892 | Robert Brown | Row housing | 266–270 Adelaide Street West | Entertainment District | Old Toronto | 6 |
| Berry House | 1892 | | | 125 Kingsway Crescent | The Kingsway | Etobicoke | |
| Densmore and Company Building | 1892 | | | 271 Queen Street West | Entertainment District | Old Toronto | 6 |
| George Gooderham House (now York Club) | 1892 | David Roberts Jr. | Romanesque Revival | 135 St. George Street | The Annex | Old Toronto | 6, 18 |
| Gooderham Building | 1892 | David Roberts Jr. | Romanesque Revival | 49 Wellington Street East | St. Lawrence | Old Toronto | |
| Lakeshore Psychiatric Hospital Carriage House | 1892 | Robert Brown | | 21 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| MacMillan Storage Company Moving and Storage | 1892 | | | 1291 Queen Street West | Parkdale | Old Toronto | 6, 18 |
| Reid & Co. Lumber | 1892 | | | 359 King Street East | Old Town | Old Toronto | |
| Victoria Hospital for Sick Children | 1892 | Frank Darling & S. George Curry | Romanesque Revival | 67 College St | Discovery District | Old Toronto | W, 3 |
| Harbord Collegiate Institute | 1892 | | | 286 Harbord Street | Palmerston–Little Italy | Old Toronto | W, 10 |
| Confederation Life Building | 1892 | Knox & Elliot | Romanesque Revival | 20 Richmond Street East | St. Lawrence | Old Toronto | W |
| 345-347 Wellesley Street East | 1892 | David J. Carlyle | Bay and Gable | 345-347 Wellesley Street East | Cabbagetown | Old Toronto | 6 |
| Broadview Hotel (formerly Dingman's Hall) | 1893 | Archibald Dingman | Romanesque Revival | 106 Broadview Avenue | Riverdale | Old Toronto | W |
| Carlyle Block | 1893 | David and William Carlyle | | 234–242 Queen Street East | Moss Park | Old Toronto | 6 |
| Lakeshore Psychiatric Hospital Gatehouse | 1893 | Kivas Tully | | 3101 Lake Shore Boulevard West | New Toronto | Etobicoke | 6 |
| Maple Hurst | 1893 | | | 89 Rosemount Avenue | Weston | York | 18 |
| Ontario Legislative Building | 1893 | Richard A. Waite | Richardsonian Romanesque | 111 Wellesley Street West | Discovery District | Old Toronto | W |
| 1075–1085 Queen Street West | 1893 | | | 1075–1085 Queen Street West | Niagara | Old Toronto | 6, 18 |
| St John the Baptist (Norway) Anglican Church | 1893 | C. J. Gibson | | 470 Woodbine Avenue | Upper Beaches | Old Toronto | |
| 18 Fern Avenue | 1894 | | | 18 Fern Avenue | Weston | York | 18 |
| Davisville General Store and Post Office | 1894 | | | 1909 Yonge Street | Davisville Village | Old Toronto | |
| Fern Avenue Public School | 1894 | | | 128 Fern Avenue | Roncesvalles | Old Toronto | |
| Havergal College | 1894 | | | 1451 Avenue Road | Lytton Park | Old Toronto | W |
| Humberside Collegiate Institute | 1894 | | | 280 Quebec Ave | High Park North | Old Toronto | |
| Massey Hall | 1894 | Sidney Badgley | Palladian exterior, Moorish Revival interior | 178 Victoria Street | Garden District | Old Toronto | W |
| 1–3 Queens Drive | 1894 | | Second Empire | 1–3 Queens Drive | Weston | York | 18 |
| 125 Rosemount Avenue | 1894 | | Second Empire | 125 Rosemount Avenue | Weston | York | 18 |
| St. Phillip's Anglican Church | 1894 | | | 31 St Phillips Road | Humber Heights – Westmount | Etobicoke | 6 |
| Toronto Athletic Club | 1894 | | | 149 College Street | Grange Park | Old Toronto | |
| Eastern Gap Lighthouses | 1895 | | 19th century lighthouse | 2225 Lake Shore Boulevard West (Humber Bay Park West) | The Queensway – Humber Bay | Etobicoke | |
| F. W. Woolworth Building | 1895 | | | 220 Yonge Street | Downtown Yonge | Old Toronto | W |
| Robert Simpson Co. (now Hudson's Bay Queen Street) | 1895 | Burke and Horwood | Romanesque Revival | 176 Yonge Street | Financial District | Old Toronto | 18 |
| Roncesvalles Carhouse | 1895 | | | 20 The Queensway | Roncesvalles | Old Toronto | W |
| St. George's Greek Orthodox Church (formerly Holy Blossom Temple) | 1895 | John Wilson Siddall | | 115 Bond Street | Garden District | Old Toronto | 6 |
| Victory Life Church | 1895 | | | 691 Scarlett Road | Humber Heights – Westmount | Etobicoke | 18 |
| Baird House | 1896 | | | 261–263 Keele Street | High Park North | Old Toronto | 6, 18 |
| Don CPR railway station | 1896 | | | 255 Bremner Blvd (Roundhouse Park) | South Core | Old Toronto | |
| George Jackson House | 1896 | | | 2950 Keele Street | Downsview | North York | 18 |
| Cumberland House | 1896 | | | 3131 Lake Shore Boulevard West | New Toronto | Etobicoke | 6 |
| Royal Canadian Yacht Club | 1896 | Dick & Wickson | | 2 Chippewa Avenue | Toronto Islands | Old Toronto | W |
| Scarboro Centennial Memorial Library | 1896 | | | 115 St. Andrews Road | Bendale | Scarborough | |
| Victoria University | 1896 | | | 73 Queen Park's Crescent | Discovery District | Old Toronto | W |
| Dineen Building | 1897 | | | 2 Temperance Street | Financial District | Old Toronto | |
| George Gray House | 1897 | | | 1299 Don Mills Road | Don Mills | North York | 18 |
| Kormann House Hotel | 1897 | | | 229 Queen Street East | Old Town | Old Toronto | 6 |
| First Evangelical Lutheran Church | 1898 | | Gothic Revival | 116 Bond Street | Garden District | Old Toronto | 18 |
| Lakeshore Psychiatric Hospital Assembly Hall | 1898 | | | 1 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6 |
| MacFarlane's Hotel | 1898 | | | 99 Jarvis Street | Old Town | Old Toronto | |
| Masaryk-Cowan Community Recreation Centre | 1898 | Frank Darling and John Pearson | | 220 Cowan Avenue | Parkdale | Old Toronto | 6 |
| Toronto Police Service 51 Division (former Consumer's Gas Co. Station A) | 1898 | Bond & Smith | | 51 Parliament Street | Corktown | Old Toronto | |
| 366 Adelaide Street East | 1899 | | | 366 Adelaide Street East | Old Town | Old Toronto | |
| Don Station | 1899 | | | 255 Bremner Blvd (Roundhouse Park) | South Core | Old Toronto | W, 15 |
| Fetherstonhaugh Estate Gardener's Cottage | 1899 | Henry Sproatt | Queen Anne | 2669–2673 Lake Shore Boulevard West | Mimico | Etobicoke |
| John Gibson House | 1899 | | | 227 A Crawford Street | Trinity-Bellwoods | Old Toronto | 6, 18 |
| Melville Manse | 1899 | | | 476 Manse Road | Bendale | Scarborough | 18 |
| Old City Hall | 1899 | E. J. Lennox | Romanesque Revival | 60 Queen Street West | Downtown Yonge | Old Toronto | W |
| Parkdale Telephone Exchange Building | 1899 | | | 207 Cowan Avenue | Parkdale | Old Toronto | |

### 1900 to 1909

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| John Hallam Warehouse | 1900 | A. R. Denison | | 8 Market Street | St. Lawrence | Old Toronto | 6 |
| Lakeshore Psychiatric Hospital Building C | 1900 | Kivas Tully | | 7 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building D | 1900 | Kivas Tully | | 9 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building E | 1900 | Kivas Tully | | 11 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building F | 1900 | Kivas Tully | | 15 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building H | 1900 | Kivas Tully | | 23 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building I | 1900 | Kivas Tully | | 25 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building J | 1900 | Kivas Tully | | 27 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Lakeshore Psychiatric Hospital Building K | 1900 | Kivas Tully | | 29 Colonel Samuel Smith Park Drive | New Toronto | Etobicoke | 6, 18 |
| Dixon Homestead | c. 1900 | | | 1671 Kipling Avenue | Richview | Etobicoke | |
| La Rose Homestead | c. 1900 | | | 322 La Rose Avenue | Richview | Etobicoke | 6 |
| T.W. Mulholland House | c. 1900 | | | 7 Wendy Crescent | Armour Heights | North York | 18 |
| Neil Family Cottage | c. 1900 | | | 12 Alexis Boulevard | Clanton Park | North York | 18 |
| A. M. Orpen House | 1900 | Henry Simpson | | 380 Sherbourne Street | Garden District | Old Toronto | 6, 18 |
| Castle Memorial Hall (now Ettore Mazzoleni Hall) | 1901 | Burke and Harwood | | 273 Bloor Street West | Discovery District | Old Toronto | |
| Wymilwood (now Falconer Hall) | 1901 | Sproatt & Rolph | | 84 Queen's Park Crescent | Discovery District | Old Toronto | 6, 18 |
| Holwood House (now Flavelle House) | 1901 | Darling and Pearson | Georgian Revival | 78 Queen's Park Crescent West | Discovery District | Old Toronto | |
| Free Reformed Church of Toronto | 1901 | | | 1130 Finch Avenue West | York University Heights | North York | 18 |
| General Services Building | 1901 (original section) (numerous additions) | | | 2 Manitoba Drive | Exhibition Place | Old Toronto | |
| Gates of Philosopher's Walk | 1901 | | | Queen's Park Crescent | Discovery District | Old Toronto | |
| 214 King Street East | 1901–1911 | | | 214 King Street East | Old Town | Old Toronto | |
| Kew Gardens Gardener's Cottage | 1902 | | | 30 Lee Avenue | The Beaches | Old Toronto | |
| Bank of Hamilton | 1902 | G. W. Gouinlock | | 165 Spadina Avenue | Chinatown | Old Toronto | 6 |
| St. Lawrence Market South | 1902 | John William Siddall | | 92 Front Street East | St. Lawrence | Old Toronto | |
| Adams Brothers Harness Manufacturing Company Ltd. | 1903 | | | 185 Frederick Street | Old Town | Old Toronto | 6 |
| Annesley Hall | 1903 | | Queen Anne Revival | 95 Queen's Park Crescent | Discovery District | Old Toronto | 18 |
| J.F. Brown Building (Heintzman Hall) | 1903 | | Chicago School | 193 Yonge Street | Garden District | Old Toronto | |
| Kimberley Junior Public School | 1903 | | | 50 Swanwick Avenue | Upper Beaches | Old Toronto | 6, 10 |
| King Edward Hotel | 1903 | E. J. Lennox | | 37 King Street East | St. Lawrence | Old Toronto | |
| Poor Alex Theatre | 1903 | | | 296 Brunswick Avenue | Harbord Village | Old Toronto | 6 |
| Scarborough Bluffs Refreshment Room | 1903 | | | 171 Midland Avenue | Cliffside | Scarborough | 18 |
| Trinity College Gates | 1903 | Frank Darling | | 790 Queen Street West (Trinity Bellwoods Park) | Trinity–Bellwoods | Old Toronto | |
| Lassonde Mining Building | 1904 | Francis R. Heakes | | 170 College Street | Discovery District | Old Toronto | |
| Ontario Hydro Bridgman Transformer Station | 1904 | | | 391 Davenport Road | South Hill | Old Toronto | |
| Richardson-Corson House | 1904 | | | 21 Old Kingston Road | West Hill | Scarborough | 18 |
| 197 Yonge Street | 1905 | | | 197 Yonge Street | Garden District | Old Toronto | 18 |
| Alumnae Theatre | 1905 | | | 70 Berkeley Street | Old Town | Old Toronto | |
| Casa Loma Stables | 1905 | E. J. Lennox | Gothic Revival | 330 Walmer Road | Casa Loma | Old Toronto | 18 |
| CNE Press Building | 1905 | George W. Gouinlock | | | Exhibition Place | Old Toronto | 6, W |
| Trader's Bank Building | 1905 | Carrère and Hastings | | 67 Yonge Street | St. Lawrence | Old Toronto | |
| Crescent School (formerly Frank Porter Wood Home) | 1906 | William Adams Delano | | 2365 Bayview Avenue | Bridle Path | North York | W |
| Christie, Brown & Co. stables | 1906 | | | 95 Berkeley Street | Old Town | Old Toronto | |
| Convocation Hall | 1906 | Darling and Pearson | | 31 Kings College Circle | Discovery District | Old Toronto | W |
| Malvern Collegiate Institute | 1906 | | | 55 Malvern Avenue | Upper Beaches | Old Toronto | 10 |
| National Club | 1906 | Curry, Sproat & Rolph | Georgian Revival | 303 Bay Street | Financial District | Old Toronto | 18 |
| 1975–1975A Queen Street East | 1906 | | Queen Anne Revival | 1975–1975A Queen Street Eas | The Beaches | Old Toronto | |
| St. Margaret in-the-Pines Church | 1906 | | | 4130 Lawrence Avenue East | West Hill | Scarborough | |
| Spadina Gardens | 1906 | Edwardian apartments | A. R. Denison | 41,45 Spadina Road | The Annex | Old Toronto | |
| Toronto Fire Services Station 227 | 1906 | | Amsterdam School | 1904 Queen Street East | The Beaches | Old Toronto | |
| Toronto Water High Level Pumping Station | 1906 | | | 235 Cottingham Street | South Hill | Old Toronto | |
| 205 Yonge Street | 1906 | E. J. Lennox | Neoclassical | 205 Yonge Street | Garden District | Old Toronto | 18 |
| 197 King Street East | 1907 | | | 197 King Street East | Old Town | Old Toronto | |
| Antique Carousel | 1907 | | | Centreville Amusement Park | Toronto Islands | Old Toronto | |
| Bank of Commerce | 1907 | Darling and Pearson | Neoclassical | 144 King Street East | Old Town | Old Toronto | |
| Burroughes Building | 1907 | | | 639 Queen Street West | Fashion District | Old Toronto | 18 |
| CNE Music Building | 1907 | George W. Gouinlock | Beaux-Arts | 285 Manitoba Drive | Exhibition Place | Old Toronto | 6, 15, W |
| Fred Victor Centre Women's Hostel (formerly City Morgue) | 1907 | Robert McCallum | | 86 Lombard Street | Old Town | Old Toronto | 6 |
| Sanford Fleming Building | 1907 | Darling and Pearson | | 10 King's College Road | Discovery District | Old Toronto | |
| Sigmund Samuel Building | 1907 | Darling and Pearson | | 7 King's College Road | Discovery District | Old Toronto | |
| Riverdale Collegiate Institute | 1907 | | | 1094 Gerrard Street East | Leslieville | Old Toronto | |
| Darling Building | 1907 | | | 96 Spadina Avenue | Fashion District | Old Toronto | 6 |
| Horticulture Building | 1907 | George W. Gouinlock | | 15 Saskatchewan Road | Exhibition Place | Old Toronto | 15, W |
| Royal Alexandra Theatre | 1907 | John M. Lyle | Beaux-Arts | 300 King Street West | Entertainment District | Old Toronto | W |
| Toronto Public Library Yorkville branch | 1907 | | | 22 Yorkville Avenue | Yorkville | Old Toronto | |
| Alfred Baker House | 1908 | Albert Baker | | 58 Wheatfield Road | Mimico | Etobicoke | 18 |
| Aluminum & Crown Stopper Company | 1908 | Frederick H. Herbert & Henry Simpson | | 334 King Street East | Corktown | Old Toronto | 18 |
| 41 Binscarth Road | 1908 | G. M. Miller & Co. | | 41 Binscarth Road | Rosedale | Old Toronto | |
| Birkbeck Building | 1908 | G.W. Gouinlock | | 10 Adelaide Street East | St. Lawrence | Old Toronto | 9, 15, 18 |
| Glendoveer | 1908 | | Georgian Revival | 120 Inglewood Drive | Moore Park | Old Toronto | 6, 18 |
| Queen City Vinegar Company Factory | 1908 | J. Francis Brown | | 19 River Street | Trefann Court | Old Toronto | |
| Samuel Building | 1908 | | Chicago School | 431 King Street West | Fashion District | Old Toronto | |
| St. Anne's Anglican Church | 1908 | | | 270 Gladstone Avenue | Dufferin Grove | Old Toronto | 6, |
| St. Matthews Lawn Bowling Club | 1908 | Robert McCallum | Arts and Crafts | 450 Broadview Avenue | Riverdale | Old Toronto | 18 |
| St. Patrick's Church | 1908 | | Romanesque Revival | 131 McCaul Street | Grange Park | Old Toronto | |
| Toronto Hydro Defoe Station (formerly Toronto Electric Light Company Substation) | 1908 | | | 660 Adelaide Street West | Niagara | Old Toronto | |
| Union Building | 1908 | Darling and Pearson | | 212 King Street West | Entertainment District | Old Toronto | |
| 33 Sherbourne Street | 1909 | | | 33 Sherbourne Street | Old Town | Old Toronto | |
| 125 Adelaide Street East | 1909 | | | 125 Adelaide Street East | Old Town | Old Toronto | |
| 176 Front Street East | 1909 | | | 176 Front Street East | St. Lawrence | Old Toronto | |
| City Dairy Stables | 1909 | G. M. Miller | | 563 Spadina Crescent | Discovery District | Old Toronto | 6 |
| Hotel Victoria | 1909 | Frederick Mossop | | 56 Yonge Street | Financial District | Old Toronto | |
| Kilgour Farms Barn | 1909 | | | 1132 Leslie Street (Sunnybrook Park) | Leaside | East York | |
| Knox Presbyterian Church | 1909 | James Wilson Grey | | 630 Spadina Avenue | Harbord Village | Old Toronto | 6 |
| Koffler Student Services Centre | 1909 | Neoclassical | Wickson & Gregg and A.H. Chapman; Chapman & Oxley (1928 additions) | 214 College Street | Discovery District | Old Toronto | 18 |
| The Opera House | 1909 | | | 735 Queen Street East | Riverdale | Old Toronto | 18 |
| Toronto Public Library Annette branch | 1909 | Ellis and Connery (architects); Eagle and Son (contractors) | | 145 Annette Street | High Park North | Old Toronto | 6 |

### 1910 to 1919

| Building | Year completed | Builder | Style | Address | Neighbourhood | District | Source |
| Chapman Bros. Ltd. Jewellers | 1910 | Benjamin Chapman | | 261 Yonge Street | Garden District | Old Toronto | 18 |
| Dixon Hall-School House Hostel (formerly Allan Public School) | 1910 | C. H. Bishop | | 349 George Street | Garden District | Old Toronto | 6 |
| Merchandise Building | 1910 | Max Dunning of Burke, Horwood and White | | 155 Dalhousie Street | Garden District | Old Toronto | |
| Palm House | 1910 | Robert McCallum, Mathers and Haldenby, Lord and Burnham Company, and Nexus Architects | | 160 Gerrard Street East (Allan Gardens) | Garden District | Old Toronto | |
| South African War Memorial | 1910 | Walter Seymour Allward | | Queen Street and University Avenue | | Old Toronto | |
| Toronto Fire Services Station 226 | 1910 | | Amsterdam School | 87 Main Street | Upper Beaches | Old Toronto | |
| Toronto Hydro Substation D | 1910 | | | 29 Nelson Street | Entertainment District | Old Toronto | |
| University Of Toronto President's Estate (formerly Dunlap Estate) | 1910 | Wickson and Gregg | | 93 Highland Avenue | Rosedale | Old Toronto | |
| University of Toronto Schools | 1910 | | | 371 Bloor Street West | Discovery District | Old Toronto | |
| Victoria University | 1910 | Henry Sproatt | | 73 Queens Park Crescent | Discovery District | Old Toronto | 6, W |
| Bedford Park Public School | 1911 | | | 81 Ranleigh Avenue | Bedford Park | Old Toronto | 18 |
| Birge-Carnegie Library | 1911 | Sproatt and Rolph | Gothic Revival | 75 Queen's Park Crescent | Discovery District | Old Toronto | 18 |
| High Park Club | 1911 | Gemmell and W. R. Gregg | | 100 Indian Road | Roncesvalles | Old Toronto | |
| House for Home Smith | 1911 | | | 1 Baby Point Road | Baby Point | York | 18 |
| Miller Lash House | 1911 | Edward Brodhead Green | American Craftsman | 130 Old Kingston Road | West Hill | Scarborough | 6 |
| Oakwood Collegiate Institute | 1911 | | | 991 St. Clair Avenue West | Regal Heights | Old Toronto | 10 |
| St. Alphonsus Catholic Church (formerly St. Columba United Church) | 1911 | | | 540 St. Clair Avenue West | Humewood–Cedarvale | York | |
| St. Margaret's Church | 1911 | | | 156 Sixth Street | New Toronto | Etobicoke | 18 |
| Toronto Fire Services Station 344 | 1911 | | Victorian and Queen Anne | 240 Howland Avenue | The Annex | Old Toronto | 18 |
| Toronto Hunt Club Clubhouse | 1911 | | | 1355 Kingston Road | Birch Cliff | Scarborough | 18 |
| Toronto Fire Services Station 311 | 1911 | | Richardsonian Romanesque and Amsterdam School | 20 Balmoral Avenue | Deer Park | Old Toronto | |
| Toronto Hydro High Level Sub-Station | 1911 | | | 290 MacPherson Avenue | South Hill | Old Toronto | |
| Toronto Hydro Junction Substation | 1911 | | | 30 Edwin Avenue | Junction Triangle | Old Toronto | |
| Toronto West End YMCA | 1911 | | | 931 College Street | Little Italy | Old Toronto | |
| 95 King Street East | 1914 | | | 95 King Street East | St. Lawrence | Old Toronto | |
| 215 King Street East | 1914 | | | 215 King Street East | Old Town | Old Toronto | |
| Centre for Medieval Studies (formerly Lillian Massey Department of Household Science building) | 1912 | | | 125 Queen's Park | Discovery District | Old Toronto | |
| Island Water Treatment Plant | 1912 | | | 446 Lakeshore Avenue | Toronto Islands | Old Toronto | |
| Government Building | 1912 | George W. Gouinlook | | 10 Dufferin Street | Exhibition Place | Old Toronto | 6, W |
| Lakeshore Psychiatric Hospital Pumphouse | 1912 | | | 65 Colonel Samuel Smith Park Drive | New Toronto | Old Toronto | 6 |
| Lillian Massey Building | 1912 | George Martell Miller | Neoclassical | 125 Queen's Park | Discovery District | Old Toronto | 18, W |
| Manitou Road bridge | 1912 | | | Avenue of the Island | Toronto Islands | Old Toronto | |
| Revue Cinema | 1912 | Kaplan & Sprachman | Art Deco, Edwardian | 400 Roncesvalles Avenue | Roncesvalles | Old Toronto | |
| St. Patrick's Market | 1912 | | | 238 Queen Street West | Grange Park | Old Toronto | |
| Toronto Fire Services Station 346 | 1912 | George W. Gouinlook | Gothic Revival | 90 Quebec Street | Exhibition Place | Old Toronto | 15, W |
| Bala Avenue Community School | 1913 | | | 6 Bala Avenue | Mount Dennis | York | 18 |
| Barton Street Stables | 1913 | | | 1755 Steeles Avenue West (Connaught Laboratories) | Westminster–Branson | North York | 18 |
| Burwash Hall | 1913 | Sproatt and Rolph | Gothic Revival | 89 Charles Street West | Discovery District | Old Toronto | 18 |
| Canadian Pacific Building | 1913 | | Edwardian | 69 Yonge Street | St. Lawrence | Old Toronto | |
| Central Technical School | 1913 | Ross and Macdonald | Collegiate Gothic | 725 Bathurst Street | Harbord Village | Old Toronto | |
| Elgin and Winter Garden Theatres | 1913 | Thomas W. Lamb and Stanley Makepeace | |
| Gallanough Block | 1913 | | Georgian Revival | 483-499 Bloor Street West | The Annex | City of Toronto | |
| 189 Yonge Street | 1913 | | | 189 Yonge Street | Downtown Yonge | Old Toronto | 18 |
| Graphic Arts Building | 1913 | | | 73 Richmond Street West | Financial District | Old Toronto | 18 |
| Kiever Synagogue | 1913 | B. Swartz | Byzantine Revival | 25 Bellevue Avenue | Kensington Market | Old Toronto | 6 |
| Kilgour Estates Gatehouse | 1913 | | | 510 Sutherland Drive | Leaside | East York | 18 |
| Labour Lyceum | 1913 | | | 346 Spadina Avenue | Chinatown | Old Toronto | |
| MaRS Discovery District (formerly Toronto General Hospital College Wing) | 1913 | Darling and Pearson | | 101 College Street | Discovery District | Old Toronto | |
| Miller Lash Estate Carriage House | 1913 | | American Craftsman | 130 Old Kingston Road | West Hill | Scarborough | 18 |
| Rosedale United Church | 1913 | | | 159 Roxborough Drive | Rosedale | Old Toronto | 18 |
| Russell Carhouse | 1913 | | | 1411 Queen Street East | Leslieville | Old Toronto | 6, W |
| St. Paul's Anglican Church | 1913 | | | 404 Willard Avenue | Runnymede | Old Toronto | 6 |
| New St. Paul's Bloor Street | 1913 | E. J. Lennox | | 227 Bloor Street East | Church and Wellesley | Old Toronto | 6 |
| St. Augustine's Seminary | 1913 | Arthur W. Holmes | Beaux Arts | 2661 Kingston Road | Cliffside | Scarborough | 6, W |
| Toronto Public Library Bloor/Gladstone branch | 1913 | Howard V. Walker and Howard D. Chapman | Beaux-Arts | 1101 Bloor Street West | Dufferin Grove | Old Toronto | 18 |
| Toronto Public Library Queen/Saulter branch | 1913 | E. J. Lennox | Neoclassical | 765 Queen Street East | Riverdale | Old Toronto | 18 |
| Wychwood Barns (formerly St. Clair Carhouse) | 1913 | | | 601 Christie Street | Bracondale Hill | Old Toronto | |
| 3 Church Street | 1914 | | | 3 Church Street | St. Lawrence | Old Toronto | |
| Broadview Lofts | 1914 | | | 68 Broadview Avenue | Riverdale | Old Toronto | 18 |
| Casa Loma | 1914 | E. J. Lennox | Gothic Revival | 1 Austin Terrace | Casa Loma | Old Toronto | W |
| Dominion Bank Building | 1914 | Darling and Pearson | Renaissance Revival | 1 King Street West | Financial District | Old Toronto | 18 |
| Guild Inn | 1914 | | | 201 Guildwood Parkway (Guild Park and Gardens) | Guildwood | Scarborough | W |
| Luella Massey Studio Theatre | 1914 | | | 4 Glen Morris Street | Discovery District | Old Toronto | 18 |
| Old Mill Toronto | 1914 | | | 9 Old Mill Road | Old Mill | Etobicoke | W |
| Olympic Island bridge | 1914 | | | — | Toronto Islands | Old Toronto | |
| 299 Queen Street West | 1914 | Burke, Horwood and White | Gothic Revival | 299 Queen Street West | Entertainment District | Old Toronto | W |
| The Redwood Theatre (formerly Classic Theatre) | 1914 | | | 1300 Gerrard Street East | Leslieville | Old Toronto | 11 |
| Royal Ontario Museum | 1914 | Darling and Pearson | | 100 Queen's Park | Discovery District | Old Toronto | 18 |
| Studio Building | 1914 | Eden Smith | | 25 Severn Street | Yorkville | Old Toronto | |
| Timothy Eaton Memorial Church | 1914 | Frank Wickson and Alfred Holden Gregg | | 230 St Clair Avenue West | Forest Hill | Old Toronto | 6 |
| Toronto Public Library Weston branch | 1914 | Peter White Lindsay | Arts and Crafts | 2 King Street | Weston | York | 18 |
| William Burgess Elementary School | 1914 | Lindsay, Brydon and Greig | Art Deco | 100 Torrens Avenue | Old East York | East York | 18 |
| 164 Princess Street | 1915 | | | 164 Princess Street | Old Town | Old Toronto | |
| Agincourt Junior Public School | 1915 | | Colonial Revival and Georgian Revival | 29 Lockie Avenue | Agincourt | Scarborough | 10 |
| Bishop Strachan School | 1915 | | | 298 Lonsdale Road | Forest Hill, Toronto | Old Toronto | |
| Danforth Carhouse | 1915 | | | 1627 Danforth Avenue | East Danforth | Old Toronto | |
| Hart House | 1915 | Henry Sproatt, Ernest Rolph | Gothic Collegiate | 7 Hart House Circle | Discovery District | Old Toronto | 6, W |
| Humbercrest Public School | 1915 | | | 14 Saint Marks Road | Lambton | York | 18 |
| Knox College | 1915 | Chapman and McGiggin | Collegiate Gothic | 59 St. George Street | Discovery District | Old Toronto | 15, W |
| Old Administration Building | 1915 | | | 263 McCaul Street | Grange Park | Old Toronto | |
| Royal Bank Building | 1915 | | | 2 King Street East | St. Lawrence | Old Toronto | 18 |
| Toronto Fire Services Station 342 | 1915 | | Tudor Revival | 106 Ascot Avenue | Fairbank | York | |
| Toronto Water Island Pumping Station | 1915 | Allen Hazen | | 446 Lakeshore Avenue | Toronto Island | Old Toronto | |
| Union Station | 1915 | Ross and Macdonald, John M. Lyle | Beaux Arts | 65 Front Street West | South Core | Old Toronto | W |
| Birch Cliff Public School | 1916 | | Neoclassical | 1650 Kingston Road | Birch Cliff | Scarborough | 18 |
| Central Toronto Academy | 1916 | | | 570 Shaw Street | Palmerston–Little Italy | Old Toronto | |
| Cherry Street Strauss Trunnion Bascule Bridge | 1916 | Joseph Strauss (architect); Dominion Bridge Company (builder) | Bascule and truss bridge | Cherry Street | Port Lands | Old Toronto | |
| Connaught Laboratories House | 1916 | | | 1755 Steeles Avenue West | Westminster–Branson | North York | 18 |
| Mimico Railway Station | 1916 | | | 15 Judson Street (Mimico Coronation Park) | Mimico | Etobicoke | 18 |
| North Toronto station | 1916 | Darling and Pearson, and Goldsmith Borgal & Co. | | 1109 Yonge Street | Rosedale | Old Toronto | 18 |
| Toronto Fire Services Station 343 | 1916 | | Queen Anne | 65 Hendrick Avenue | Bracondale Hill | Old Toronto | |
| Toronto Hydro Electric System Building | 1916 | | | 369 Carlaw Avenue | Leslieville | Old Toronto | |
| Toronto Public Library Beaches branch | 1916 | Eden Smith & Sons | Collegiate Gothic | 2161 Queen Street East | The Beaches | Old Toronto | |
| Toronto Public Library High Park branch | 1916 | | Gothic Revival | 228 Roncesvalles Avenue | Roncesvalles | Old Toronto | 6 |
| Albert Building | 1917 | | Palladian | 15 Shuter Street | Garden District | Old Toronto | |
| General Services Building | 1917 | | | 2 Manitoba Drive | Exhibition Place | Old Toronto | 15, W |
| New Toronto Hydro Substation | 1917 | E. J. Lennox | Edwardian Revival | 140 Birmingham Street | New Toronto | Etobicoke | 18 |
| St. Clement's School | 1917 | | | 21 St Clements Avenue | Yonge–Eglinton | Old Toronto | |
| Dominion Wheel & Foundries Limited | 1917 | unknown | | 153-185 Eastern Avenue | West Don Lands | Old Toronto | |
| Toronto Harbour Commission Building | 1917 | Chapman and Oxley | | 60 Harbour Street | Harbourfront | Old Toronto | 6, W |
| Highland Creek Public School | 1918 | James, Laudon and Hertzberg | | 1410 Military Trail | Highland Creek | Scarborough | |
| Masonic Temple | 1918 | William F. Sparling & Co. | | 888 Yonge Street | Yorkville | Old Toronto | 18 |
| 314 Adelaide Street East | 1919 | | | 314 Adelaide Street East | Old Town | Old Toronto | |
| 383 Adelaide Street East | 1919 | | | 383 Adelaide Street East | Old Town | Old Toronto | |
| Beach Mall (formerly Allen Beach Theatre) | 1919 | C. Howard Crane | | 1971 Queen Street East | The Beaches | Old Toronto | |
| Canadian Northern Railway Eastern Lines Locomotive Shop | 1919 | | | 93 Laird Drive | Thorncliffe Park | East York | 18 |
| Danforth Music Hall | 1919 | Hymes, Feldman and Watson | | 147 Danforth Avenue | Riverdale | Old Toronto | 18 |
| Ferriers Block | 1919 | | | 526–536 Danforth Avenue | Greektown | Old Toronto | 18 |
| George Davis House | 1919 | | Tudor Revival | 40 Kingswood Road | The Beaches | Old Toronto | W |
| Hart House Theatre | 1919 | Henry Sproatt (architect); Ernst Rolph (engineer) | Collegiate Gothic | 7 Hart House Circle (Hart House | Discovery District | Old Toronto | 6, W |
| Prince Edward Viaduct | 1919 | Edmund Burke | Truss arch bridge | Bloor Street East | | Old Toronto | |
| Tower Automotive Building | 1919 | J.W. Schreiber | Art Deco | 158 Sterling Road | Junction Triangle | Old Toronto | |