Kaija Pitt
Direct: 416-371-9447
Office: 416-960-9995
Sotheby’s Canada
1867 Yonge Street, Suite 100
Toronto ON M4S 1Y5 CA

The Annex

The Annex is one of Toronto’s premier neighbourhoods. Located between Dupont and Bloor Street, west to Bathurst and east to Avenue Road, this heterogeneous community is made up of successful business people, prominent artists and University of Toronto students and faculty. The neighbourhood is full of restaurants, bookstores and independently owned shops.


The Annex is a great neighbourhood for those who appreciate architecture and detail. The residential tree-lined streets are filled with Victorian, Queen Anne, Edwardian and Richardsonian Romanesque homes and mansions, built between 1880 and the early 1900s. Between the 1950s and 1960s, mid-rise and high-rise apartment buildings began popping up to meet the needs of the eclectic community. The exterior facades of the homes are decorated with plum and pink Credit River sandstone, red brick, and terracotta clay tiles. The detail is among the finest – and most varied – in the city, with pyramidal roofs, turrets, grand archways and wooden spindled porches.


The Annex is an exciting and colourful neighbourhood. It has an active nightlife along Bloor Street for those who enjoy a night on the town after a long week. Plenty of green spaces make the Annex feel more residential than commercial, including nearby Christie Pits park which includes soccer, baseball and a weekly outdoor movie night in the summer, and tobogganing and outdoor skating in the winter.

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55 Madison Avenue
Annex Toronto M5R 2S3

$4,495,000 /For Sale
Commercial

Main Photo: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 1: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 2: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 3: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 4: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 5: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 6: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 7: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 8: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 9: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 10: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 11: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 12: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 13: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 14: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Photo 15: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
Status:
Active
Prop. Type:
Commercial
MLS® Num:
C14032390
Exceptional investment opportunity in Toronto's highly desirable Annex neighbourhood! Located at 55 Madison Avenue, this 15-unit multi-residential property offers investors a rare opportunity to acquire an income-producing asset in one of Toronto's most sought-after rental markets. Situated on a generous 50 x126 ft lot, the property features approximately 6,496 sq. ft. of existing building area across four levels, including the basement, along with a detached five-car garage offering five usable parking spaces - avaluable amenity in this prime urban location. Ideally situated steps from Bloor Street, the University of Toronto, Yorkville, TTC subway access, restaurants, shopping and everyday amenities. This central location supports strong long-term rental appeal and convenient access to major employment, educational and entertainment destinations. An outstanding opportunity for investors seeking a well-located multi-residential asset with long-term holding potential and future upside. *For Additional Property Details Click The Brochure Icon Below*
Property Type:
Commercial
Property Sub Type:
Investment
Freestanding:
Yes
Total Area:
5096 sq. ft. Sq Ft Divisible
Total Area:
5,096 sq. ft.
Lot Depth:
126'
Lot Frontage:
50'
Water supply:
Municipal
Zoning:
Residential
Heating type:
Radiant
Clear Height:
8'
Garage:
Outside/Surface
Possession Details:
Anytime
HST Applicable To Sale Price:
Not Subject to HST
Type Taxes:
N/A
Taxes:
$23,063.75 / 2026
Assessment:
$- / -
Toronto
Toronto C02
Annex
Yes
Existing appliances, light fixtures, and building equipment owned by the seller, in their current condition,excluding tenant-owned items.
All tenant-owned appliances, furniture, personal belongings, fixtures and equipment not owned by the seller.
None
No
Utilities:
Yes
Sewers:
Storm
Air Conditioning:
No
Seller Property Info Statement:
No
Category:
Apartment
Date Listed:
Oct 14, 2026
Original Price:
Previous Price:
  • Photo 1: 55 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02)  : MLS®# C14032390
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Listed by ICI SOURCE REAL ASSET SERVICES INC.
Data was last updated October 24, 2026 at 04:15 PM (UTC)
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