| Name | Address | Coordinates | Government recognition (CRHP №) |  | Image |
| 1929 clubhouse of the Toronto Hunt Club | 1107 Avenue Road
Toronto ON | 43°44′34″N 79°24′47″W / 43.7428°N 79.4131°W / 43.7428; -79.4131 (1929 clubhouse of the Toronto Hunt Club) | Federal (11502) | | 
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| 47 Front Street East | 47 Front Street East
Toronto ON | 43°38′53″N 79°22′28″W / 43.6481°N 79.3745°W / 43.6481; -79.3745 (47 Front Street East) | Ontario (8837) | | 
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| 49 Front Street East (Dixon Building) | 49 Front Street East
Toronto ON | 43°38′54″N 79°22′28″W / 43.6482°N 79.3745°W / 43.6482; -79.3745 (49 Front Street East (Dixon Building)) | Ontario (8838),
Toronto municipality (1451) | |
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| Annesley Hall at the University of Toronto | 95 Queen's Park Crescent
Toronto ON | 43°40′4″N 79°23′35″W / 43.66778°N 79.39306°W / 43.66778; -79.39306 (Annesley Hall University of Toronto) | Federal (1155) | Q4769020 | 
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| Armour Heights College | 215 Yonge Boulevard
Toronto ON | 43°44′30″N 79°24′53″W / 43.7418°N 79.4148°W / 43.7418; -79.4148 (Armour Heights College) | Federal (7518) | | 
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| Jesse Ashbridge House | 1444 Queen Street
Toronto ON | 43°39′56″N 79°19′18″W / 43.6656°N 79.3218°W / 43.6656; -79.3218 (Jesse Ashbridge House) | Ontario (8869) | | 
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| Balmoral Fire Hall | Balmoral Avenue
Toronto ON | 43°41′08″N 79°23′41″W / 43.6855°N 79.3946°W / 43.6855; -79.3946 (Balmoral Fire Hall) | Federal (7371) | | 
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| Bank of Toronto | 205 Yonge Street
Toronto ON | 43°39′13″N 79°22′47″W / 43.6535°N 79.3797°W / 43.6535; -79.3797 (Bank of Toronto) | Ontario (8843),
Toronto municipality (19828) | | 
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| Bank of Upper Canada Building | 252 Adelaide Street East
Toronto ON | 43°39′06″N 79°22′15″W / 43.6518°N 79.3709°W / 43.6518; -79.3709 (Bank of Upper Canada Building) | Federal (1776) | | 
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| Bead Hill National Historic Site of Canada | Hill west of the confluence of Rouge River and Little Rouge Creek
Toronto (Scarborough) ON | 43°48′20″N 79°08′10″W / 43.8056°N 79.1360°W / 43.8056; -79.1360 (Bead Hill National Historic Site of Canada) | Federal (16783) | |
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| Birkbeck Building | 8-10 Adelaide Street East
Toronto ON | 43°39′03″N 79°22′40″W / 43.6507°N 79.3779°W / 43.6507; -79.3779 (Birkbeck Building) | Federal (7555),
Ontario (19809) | | 
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| Chapel of St. James-the-Less | 635 Parliament Street
Toronto ON | 43°40′11″N 79°22′10″W / 43.6696°N 79.3694°W / 43.6696; -79.3694 (Chapel of St. James-the-Less) | Federal (7487) | | 
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| Dominion Public Building | 1 Front Street West
Toronto ON | 43°38′46″N 79°22′41″W / 43.6462°N 79.3781°W / 43.6462; -79.3781 (Dominion Public Building) | Federal (18075) | | 
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| Don Brewery | 27-39 Old Brewery Lane | 43°39′28″N 79°21′25″W / 43.65778°N 79.35694°W / 43.65778; -79.35694 (Don Brewery) | Toronto municipality (1321) | Q17104966 | 
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| Don Valley Brick Works | 550 Bayview Avenue
Toronto ON | 43°41′11″N 79°21′46″W / 43.6863°N 79.3628°W / 43.6863; -79.3628 (Don Valley Brick Works) | Ontario (15361) | | 
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| Eaton's 7th Floor Auditorium and Round Room | 2 College Street
Toronto ON | 43°39′41″N 79°23′01″W / 43.6614°N 79.3835°W / 43.6614; -79.3835 (Eaton's 7th Floor Auditorium and Round Room) | Federal (7413) | | 
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| Eglinton Theatre | 400 Eglinton Avenue West
Toronto ON | 43°42′15″N 79°24′38″W / 43.7043°N 79.4105°W / 43.7043; -79.4105 (Eglinton Theatre) | Federal (12689) | | 
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| Elgin and Winter Garden Theatres | 189 Yonge Street
Toronto ON | 43°39′11″N 79°22′45″W / 43.6531°N 79.3793°W / 43.6531; -79.3793 (Elgin and Winter Garden Theatres) | Federal (11960),
Ontario (9622) | | 
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| Enoch Turner Schoolhouse | 106 Trinity Street
Toronto ON | 43°39′11″N 79°21′41″W / 43.6530°N 79.3613°W / 43.6530; -79.3613 (Enoch Turner Schoolhouse) | Ontario (19803) | | 
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| Fourth York Post Office | 260 Adelaide Street East
Toronto ON | 43°39′06″N 79°22′13″W / 43.6518°N 79.3704°W / 43.6518; -79.3704 (Fourth York Post Office) | Federal (12726) | | 
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| Fort York Heritage Conservation District | 100 Garrison Road
Toronto ON | 43°38′21″N 79°24′10″W / 43.6391°N 79.4029°W / 43.6391; -79.4029 (Fort York Heritage Conservation District) | Toronto municipality (3567) | |  |
| Fort York Armoury | 700 Fleet Street
Toronto ON | 43°38′13″N 79°24′29″W / 43.637°N 79.408°W / 43.637; -79.408 (Fort York Armoury) | Federal (9693) | | 
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| Fort York | 100 Garrison Road
Toronto ON | 43°38′18″N 79°24′21″W / 43.6383°N 79.4057°W / 43.6383; -79.4057 (Fort York) | Federal (3677) | |
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| George Brown House | 186 Beverley Street
Toronto ON | 43°39′21″N 79°23′41″W / 43.6559°N 79.3948°W / 43.6559; -79.3948 (George Brown House) | Federal (9182),
Ontario (8868) | | 
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| Gooderham and Worts Distillery | Trinity Street
Toronto ON | 43°39′01″N 79°21′33″W / 43.6504°N 79.3592°W / 43.6504; -79.3592 (Gooderham and Worts Distillery) | Federal (1195) | | 
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| Gooderham Building | 49 Wellington Street East
Toronto ON | 43°38′54″N 79°22′28″W / 43.6483°N 79.3745°W / 43.6483; -79.3745 (Gooderham Building) | Ontario (8311) | | 
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| Gouinlock Buildings / Early Exhibition Buildings National Historic Site of Canada |
Toronto ON | 43°37′43″N 79°24′42″W / 43.6285°N 79.4118°W / 43.6285; -79.4118 (Gouinlock Buildings / Early Exhibition Buildings National Historic Site of Canada) | Federal (10470) | | 
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| Heliconian Hall | 35 Hazelton Avenue
Toronto ON | 43°40′18″N 79°23′36″W / 43.6717°N 79.3934°W / 43.6717; -79.3934 (Heliconian Hall) | Federal (13819) | | 
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| John Street Roundhouse | 255 Bremner Boulevard
Toronto ON | 43°38′28″N 79°23′10″W / 43.641°N 79.386°W / 43.641; -79.386 (John Street Roundhouse) | Federal (12781) | | 
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| Joseph Sheppard Building | 4900 Yonge Street
Toronto ON | 43°45′47″N 79°24′47″W / 43.763°N 79.413°W / 43.763; -79.413 (Joseph Sheppard Building) | Federal (10230) | | 
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| Kensington Market | Dundas West, Bellevue, Spadina, College Streets
Toronto ON | 43°39′15″N 79°24′04″W / 43.6542°N 79.4011°W / 43.6542; -79.4011 (Kensington Market) | Federal (14463) | | 
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| Maple Leaf Gardens | 60 Carleton Street
Toronto ON | 43°39′44″N 79°22′49″W / 43.6621°N 79.3804°W / 43.6621; -79.3804 (Maple Leaf Gardens) | Federal (13397) | | 
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| Mary Perram House | 4 Wellesley Place
Toronto ON | 43°40′02″N 79°22′37″W / 43.6671°N 79.3770°W / 43.6671; -79.3770 (Mary Perram House) | Toronto municipality (1439) | | 
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| Masaryk Hall | 220 Cowan Avenue
Toronto ON | 43°38′28″N 79°25′58″W / 43.6411°N 79.4329°W / 43.6411; -79.4329 (Masaryk Hall) | Ontario (10512) | | 
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| Massey Hall | 178 Victoria Street
Toronto ON | 43°39′15″N 79°22′45″W / 43.6543°N 79.3791°W / 43.6543; -79.3791 (Massey Hall) | Federal (9369) | | 
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| Montgomery's Tavern | 2384 Yonge Street
Toronto ON | 43°42′34″N 79°23′57″W / 43.7094°N 79.3992°W / 43.7094; -79.3992 (Montgomery's Tavern) | Federal (14414) | |  |
| Mount Pleasant Cemetery | 375 Mount Pleasant Road
Toronto ON | 43°41′46″N 79°23′03″W / 43.696°N 79.3843°W / 43.696; -79.3843 (Mount Pleasant Cemetery) | Federal (9514) | | 
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| Newman Centre | 89 St.George Street
Toronto ON | 43°39′51″N 79°23′54″W / 43.6642°N 79.3983°W / 43.6642; -79.3983 (Newman Centre) | Ontario (10539) | | 
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| Old Toronto City Hall and York County Court House | 60 Queen Street West
Toronto ON | 43°39′09″N 79°22′55″W / 43.6526°N 79.382°W / 43.6526; -79.382 (Old Toronto City Hall and York County Court House) | Federal (4255) | | 
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| Osgoode Hall | 130 Queen Street West
Toronto ON | 43°39′07″N 79°23′08″W / 43.6519°N 79.3856°W / 43.6519; -79.3856 (Osgoode Hall) | Federal (4258) | | 
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| St. Anne's Anglican Church | 270 Gladstone Avenue
Toronto ON | 43°39′02″N 79°25′51″W / 43.6505°N 79.4307°W / 43.6505; -79.4307 (St. Anne's Anglican Church) | Federal (12681),
Ontario (8901) | | 
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| Postal Station "D" | 328 Keele Street
Toronto ON | 43°39′50″N 79°27′50″W / 43.664°N 79.464°W / 43.664; -79.464 (Postal Station "D") | Federal (4686) | | 
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| Royal Alexandra Theatre | 260 King Street West
Toronto ON | 43°38′50″N 79°23′15″W / 43.6471°N 79.3876°W / 43.6471; -79.3876 (Royal Alexandra Theatre) | Federal (1137) | | 
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| Rupert Simpson House and Stable | 2 Wellesley Place
Toronto ON | | Toronto municipality (1291) | | 
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| St. George's Hall (Arts and Letters Club) | 14 Elm Street
Toronto ON | 43°39′28″N 79°22′57″W / 43.6578°N 79.3825°W / 43.6578; -79.3825 (St. George's Hall (Arts and Letters Club)) | Federal (12139) | | 
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| St. Lawrence Hall | 157 King Street East
Toronto ON | 43°39′00″N 79°22′20″W / 43.6501°N 79.3722°W / 43.6501; -79.3722 (St. Lawrence Hall) | Federal (7527) | | 
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| The Studio Building | 25 Severn Street
Toronto ON | 43°40′24″N 79°23′10″W / 43.6732°N 79.3861°W / 43.6732; -79.3861 (The Studio Building) | Federal (9521) | | 
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| The Grange | 317 Dundas Street West
Toronto ON | 43°39′14″N 79°23′37″W / 43.6538°N 79.3935°W / 43.6538; -79.3935 (The Grange) | Federal (7529) | | 
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| The Royal Conservatory of Music | 273 Bloor Street West
Toronto ON | 43°40′05″N 79°23′46″W / 43.668°N 79.3962°W / 43.668; -79.3962 (The Royal Conservatory of Music) | Federal (12044) | | 
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| Toronto Island Airport Terminal Building |
Toronto ON | 43°37′58″N 79°23′43″W / 43.6327°N 79.3953°W / 43.6327; -79.3953 (Toronto Island Airport Terminal Building) | Federal (7530) | | 
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| Toronto Street Post Office / Bank of Canada Building | 10 Toronto Street
Toronto ON | 43°38′59″N 79°22′34″W / 43.6498°N 79.3762°W / 43.6498; -79.3762 (Toronto Street Post Office / Bank of Canada Building) | Federal (9933) | | 
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| Union Station (Canadian Pacific Railway and Grand Trunk Railway) | 65-71 Front Street West
Toronto ON | 43°38′44″N 79°22′51″W / 43.6455°N 79.3808°W / 43.6455; -79.3808 (Union Station (Canadian Pacific Railway and Grand Trunk Railway)) | Federal (6299, (6492) | | 
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| University College, Toronto | 15 King's College Circle, St. George campus of the University of Toronto
Toronto ON | 43°39′45″N 79°23′43″W / 43.6625°N 79.3954°W / 43.6625; -79.3954 (University College, Toronto) | Federal (9520) | | 
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| Wesley Building | 299 Queen Street West
Toronto ON | 43°38′52″N 79°23′28″W / 43.6479°N 79.391°W / 43.6479; -79.391 (Wesley Building) | Toronto municipality (4921) | | 
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| Winchester Hotel and Winchester Hall | 531 Parliament St
Toronto ON | 43°39′56″N 79°22′06″W / 43.6656°N 79.3682°W / 43.6656; -79.3682 (Winchester Hotel and Winchester Hall) | Toronto municipality (3631) | | 
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| Women's College Hospital | Grenville Street
Toronto ON | 43°39′42″N 79°23′15″W / 43.6617°N 79.3874°W / 43.6617; -79.3874 (Women's College Hospital) | Federal (7738) | | 
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