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135 Madison Avenue
Annex Toronto M5R 2S3

$4,295,000
Residential Freehold beds: 6 baths: 5.0

Main Photo: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 1: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 2: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 3: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 4: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 5: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 6: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 7: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 8: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 9: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 10: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 11: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 12: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 13: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 14: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 15: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 16: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 17: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 18: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 19: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 20: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 21: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 22: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 23: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 24: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 25: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 26: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 27: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 28: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 29: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 30: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 31: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 32: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 33: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 34: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 35: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 36: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 37: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 38: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 39: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 40: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 41: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 42: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 43: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 44: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 45: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 46: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 47: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 48: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Photo 49: 135 Madison Avenue in Toronto: Annex House for sale (Toronto C02)  : MLS®# C12388547
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12388547
Bedrooms:
6
Bathrooms:
5
This grand dame home sits on the iconic Madison Avenue in the prime Annex. Circa 1905, 135 Madison Avenue is just under 4,000 square feet above grade and filled with original character including 4 fireplaces, original trim, wainscotting, crown moulding, and stained glass windows. The well proportioned house features 9.5" ceilings on the main floor, a large formal living and dining room as well as an oversized kitchen with a butlers pantry, and a beautiful main floor family room that leads out to the lush garden. On the second floor you will find a generous primary bedroom with a sitting area, fireplace and a three piece ensuite. There are an additional 2 large bedrooms on the second floor as well as 2 full washrooms, a dedicated laundry room, and a large sunny deck. The third floor would make a fabulous primary suite and currently includes a large living room, kitchen, two additional bedrooms and a large deck with skyline and treetop views. The basement is partially finished with 7 foot ceilings and features a separate entrance. This home has been used as single family for many years but has potential for many layouts and possibilities. Two car private drive parking and garden suite potential. The Annex speaks for its self with easy TTC, fabulous shops, restaurants, parks and schools. Floor plans attached to listing.
Under Contract:
Hot Water Heater
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
3-Storey
Approx. Age:
100+
Total Approx Floor Area:
3500-5000
Depth:
126'
Frontage:
33'4"
Direction Faces:
East
Bedrooms:
6
Bathrooms:
5.0
Water supply:
Municipal
Kitchens:
3
Bedrooms Above Grade:
6
Kitchens Above Grade:
3
Rooms Above Grade:
12
Rooms Below Grade:
1
Heating type:
Water
Heating Fuel:
Gas
Fireplaces:
4
Foundation:
Brick
Roof:
Asphalt Rolled, Shingles, Slate
Basement:
Partially Finished
Fireplace Features:
Living Room
Fireplace/Stove:
No
Garage:
None
Garage Spaces:
0.0
Parking Features:
Private
Parking Spaces:
2
Total Parking Spaces:
2.0
Family Room:
Yes
Possession Details:
90/TBD
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$18,814.47 / 2025
Assessment:
$- / -
Toronto C02
Annex
Toronto
Fenced Yard, Library, Park, Public Transit, Rec./Commun.Centre, School
Water Heater
Deck, Patio, Porch
Hot Water Tanks (2)
All Appliances, Boiler, All Light Fixtures & Window Coverings, Projector & Equipment. Full List in Schedule B.
All Artwork, Two Wine Fridges, Wall Mounted TV & Bracket in Living Room.
Brick
No
No
Floor
Type
Size
Other
Main
Living Room
21'6" × 12'
Stained Glass, Fireplace, B/I Bookcase
Main
Dining Room
16'9" × 14'4"
Window, Fireplace, Pocket Doors
Main
Kitchen
24'8½" × 12'8"
Centre Island, Fireplace, Pantry
Main
Family Room
12'3" × 10'
W/O To Garden, Hardwood Floor, 4 Pc Bath
Main
Bedroom
14'4" × 7'9"
Closet, Hardwood Floor, Pocket Doors
Second
Primary Bedroom
19'9" × 14'9"
3 Pc Ensuite, Fireplace, Bay Window
Second
Bedroom 3
17' × 16'4"
3 Pc Ensuite, B/I Closet, Window
Second
Bedroom 4
17' × 11'
Bay Window, B/I Shelves, W/O To Deck
Second
Laundry
7'8" × 7'4"
Laundry Sink, B/I Shelves, W/O To Deck
Third
Living Room
16'3" × 15'10"
Open Concept, B/I Shelves, Window
Third
Bedroom 5
17'9" × 10'
Closet, Broadloom, Window
Third
Bedroom
13' × 8'5"
Closet, East View, W/O To Deck
Utilities Cable:
Available
Utilities Telephone:
Available
Utilities Gas:
Yes
Utilities Hydro:
Yes
Utilities Water:
Yes
Sewers:
Yes
Special Designation:
Heritage
Sewers:
Sewer
Air Conditioning:
Window Unit(s)
Central Vacuum:
No
Seller Property Info Statement:
No
Physically Handicapped-Equipped:
No
Ensuite Laundry:
No
Laundry Level:
Upper Level
Date Listed:
Sep 08, 2025
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Listed by BOSLEY REAL ESTATE LTD.
Data was last updated September 9, 2025 at 06:15 AM (UTC)
Area Statistics
Listings on market:
14
Avg list price:
$3,824,950
Min list price:
$1,089,000
Max list price:
$8,998,000
Avg days on market:
61
Min days on market:
1
Max days on market:
155
These statistics are generated based on the current listing's property type and located in Annex. Average values are derived using median calculations. This data is not produced by the MLS® system.
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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.