95 Highbourne Road, Toronto, ON M5P 2J5, Toronto C03, ON
Bed 4
Bath 2
Offered for the first time in 47 years, 95 Highbourne Road presents a truly rare opportunity in the heart of Chaplin Estates. Situated on one of the neighbourhood's most desirable, quiet, tree-lined streets, this classic detached home sits among beautifully maintained residences on larger lots in a setting defined by low traffic and midtown Toronto charm. Set on a 39.5 x 130 ft lot, the home showcases its original character through spacious principal rooms and timeless architectural details. The living room, centred around a wood-burning fireplace, is enhanced by a large bow window that fills the space with natural light and flows seamlessly into the dining room, ideal for both everyday living and entertaining. At the rear, the kitchen and adjoining sitting room open directly to a quiet and private garden, creating a natural extension of the living space and a tranquil backdrop for outdoor living. A main floor powder room adds convenience. Upstairs, four well-sized bedrooms and a full family bathroom provide comfortable accommodation for growing families. Perfectly positioned just moments from Yonge & Eglinton, this location offers exceptional access to the subway and the new Eglinton LRT, along with an array of neighbourhood shops, cafés, and restaurants (Little Sister and Oretta!). Steps to Oriole Park and the Kay Gardner Beltline Trail, along with access to some of Toronto's most respected schools (UCC, BSS, Oriole Park JPS, Hodgson MS and North Toronto CI), further enhance the appeal. Whether reimagined, renovated or rebuilt, this is a remarkable opportunity to create a lasting home in one of midtown Toronto's most established and coveted communities.
Property Highlights
For Sale
MLS NO.
C12911866
Type
Residential Freehold
Sub Type
Detached
Bedrooms
4
Bathrooms
2
Parking
2.0
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Closed
Contract Status
Unavailable
MLS® Number
C12911866
Living Area Range
1500-2000
Total Bedrooms
4
Bedrooms Above Grade
4
Total Bathrooms
2
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
8
Interior Features
Carpet Free
Fireplace
Yes
Fireplace Features
Wood
Central Vacuum Yn
No
Construction
Brick
Roof
Asphalt Shingle
Lot Width
39.5
Parking Features
Private
Parking Total
2.0
Covered Spaces
0.0
Garage Type
None
Garage
No
Pool
None
Direction Facing
East
Cooling
Wall Unit(s)
Heat Source
Gas
Heat Type
Radiant
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
95 Highbourne Road, Toronto, ON M5P 2J5
City
Toronto C03
Neighbourhood
Yonge-Eglinton
County / Region
Toronto
Province / State
ON
Postal Code
M5P 2J5
Cross Street
Avenue Road & Chaplin Crescent
Directions
East of Avenue & North of Chaplin
Country
CA
List Price
$2,295,000
Annual Taxes
$12,163
Tax Year
2026
Legal Description
PT LT 106-107 PL 569E TORONTO AS IN CT388224; CITY OF TORONTO
Possession Type
Flexible
Possession Details
Flexible
Listing Office
SOTHEBY'S INTERNATIONAL REALTY CANADA
Board
Toronto Regional Real Estate Board
Original Entry
2026-03-23T20:40:20Z
Media Updated
2026-03-27T02:33:24Z
Photos Updated
2026-03-24T16:02:47Z
Last Modified
2026-03-30T14:15:24Z
System Modified
2026-03-30T14:15:49.765763Z
MLS Status
Sold
Architectural Style
2-Storey
Basement
Unfinished, Full
Co List Office Name
SOTHEBY'S INTERNATIONAL REALTY CANADA
Ddfyn
Yes
Expiration Date
2026-06-30
Foundation Details
Concrete
Heat Source Multi
Gas
Heat Type Multi
Radiant
Hstapplication
Included In
Link Yn
No
Occupant Type
Owner
Originating System Id
A00001796
Parking Spaces
2
Property Features
Public Transit, Rec./Commun.Centre, Park, Library, School, Fenced Yard
Public Remarks
Offered for the first time in 47 years, 95 Highbourne Road presents a truly rare opportunity in the heart of Chaplin Estates. Situated on one of the neighbourhood's most desirable, quiet, tree-lined streets, this classic detached home sits among beautifully maintained residences on larger lots in a setting defined by low traffic and midtown Toronto charm. Set on a 39.5 x 130 ft lot, the home showcases its original character through spacious principal rooms and timeless architectural details. The living room, centred around a wood-burning fireplace, is enhanced by a large bow window that fills the space with natural light and flows seamlessly into the dining room, ideal for both everyday living and entertaining. At the rear, the kitchen and adjoining sitting room open directly to a quiet and private garden, creating a natural extension of the living space and a tranquil backdrop for outdoor living. A main floor powder room adds convenience. Upstairs, four well-sized bedrooms and a full family bathroom provide comfortable accommodation for growing families. Perfectly positioned just moments from Yonge & Eglinton, this location offers exceptional access to the subway and the new Eglinton LRT, along with an array of neighbourhood shops, cafés, and restaurants (Little Sister and Oretta!). Steps to Oriole Park and the Kay Gardner Beltline Trail, along with access to some of Toronto's most respected schools (UCC, BSS, Oriole Park JPS, Hodgson MS and North Toronto CI), further enhance the appeal. Whether reimagined, renovated or rebuilt, this is a remarkable opportunity to create a lasting home in one of midtown Toronto's most established and coveted communities.
