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37 Madison Avenue
Annex Toronto M5R 2S2

$4,988,888
Residential Freehold beds: 1 baths: 4.0

Main Photo: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 1: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 2: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 3: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 4: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 5: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 6: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 7: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 8: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 9: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 10: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 11: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 12: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 13: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 14: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 15: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 16: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 17: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 18: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 19: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 20: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 21: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Photo 22: 37 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12259630
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12259630
Bedrooms:
1
Bathrooms:
4
Step into history at 37 Madison Avenue, an architectural masterpiece by Edward James Lennox, famed for landmarks like Casa Loma and Old City Hall. Completed in 1891, this rare heritage home blends Gothic, Romantic Revival, Queen Anne, and Edwardian influences with striking presence and timeless elegance. Located between Yorkville and the Annex, the home features a distinctive façade, soaring ceilings, original woodwork, and expansive windows throughout approx. 6,000 sq. ft. of living space. A unique opportunity to restore or reimagine a landmark residence in one of Toronto's most coveted neighbourhoods. Enjoy unmatched access to world-class dining, boutique shopping, cultural institutions, top schools, and two subway lines, all just steps from your front door
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
3-Storey
Total Approx Floor Area:
5000 +
Depth:
126'
Frontage:
44'2"
Direction Faces:
East
Bedrooms:
1
Bathrooms:
4.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
12
Zoning:
Mixed Zoning, Commercial
Heating type:
Forced Air
Heating Fuel:
Gas
Foundation:
Stone
Roof:
Shingles
Basement:
Full
Fireplace Features:
Wood
Fireplace/Stove:
Yes
Garage:
None
Garage Spaces:
0.0
Parking Spaces:
8
Total Parking Spaces:
8.0
Family Room:
Yes
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Assessment Year:
2024
Taxes:
$65,662.54 / 2024
Assessment:
$- / 2024
Toronto C02
Annex
Toronto
None
Brick
Special Designation:
Heritage
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Date Listed:
Jul 03, 2025
Original Price:
Previous Price:
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Listed by RE/MAX REALTRON REALTY INC.
Data was last updated July 5, 2025 at 06:15 AM (UTC)
Area Statistics
Listings on market:
10
Avg list price:
$3,795,000
Min list price:
$1,799,000
Max list price:
$8,998,000
Avg days on market:
53
Min days on market:
2
Max days on market:
96
These statistics are generated based on the current listing's property type and located in Annex. Average values are derived using median calculations.
DARYL  KING
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