208 Roxborough Drive, Toronto, ON M4W 1X8, Toronto C09, ON
Bed 5
Bath 5
Set on one of Rosedale's most coveted streets, 208 Roxborough Drive is a 1928 Tudor Revival residence of landmark stature, designed by the prize-winning architect Harold Richard Watson. The composition is grounded in stone, with tracery, a sweeping bay, and a procession of steps to a carved entrance. Inside, the entrance hall is crowned by a coffered plaster ceiling, and light pours through original leaded glass. Wood panelling lines the principal rooms, concealing built-in cabinetry and adorned with fine scrollwork rare in both quality and extent. Original fireplaces ground the rooms, and a hand-crafted staircase rises through the heart of the home. The living room spans the full width of the house, scaled for an era that built for permanence. Above grade, the residence offers more than 5,000 square feet, with over 2,300 more on the lower level. The primary suite includes a private office, walk-in closets, and an ensuite, with four additional bedrooms completing the second floor. Beyond the house is the land itself: the lot extends over 88 feet wide by 408 feet deep, descending into the ravine, a depth almost unheard of in Rosedale. Included in the sale are approved plans and permits for an addition and renovation by Taylor Smyth Architects, with landscape design by Cecconi Simone, a striking contemporary statement uniting irreplaceable historic character with modern convenience inside and out. The rear garden becomes a private landscape, a patio above a swimming pool overlooking the ravine; the primary becomes a jewel box framed by tree views; and the garage is shifted for privacy yet kept for convenience. 208 Roxborough Drive is a true landmark, and an opportunity to become part of its story.
Property Highlights
For Sale
MLS NO.
C13476730
Type
Residential Freehold
Sub Type
Detached
Bedrooms
5
Bathrooms
5
Parking
8.0
Garage
Yes
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Active
Contract Status
Available
MLS® Number
C13476730
Living Area Range
5000 +
Total Bedrooms
5
Bedrooms Above Grade
5
Total Bathrooms
5
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
13
Rooms Below Grade
1
Interior Features
Carpet Free, Sump Pump, Water Heater
Fireplace
Yes
Fireplace Features
Wood
Central Vacuum Yn
No
Construction
Stone, Stucco (Plaster)
Roof
Tile
Lot Width
88.5
Parking Features
Private
Parking Total
8.0
Covered Spaces
2.0
Garage Type
Detached
Garage
Yes
Pool
None
Direction Facing
East
Cooling
Central Air
Heat Source
Gas
Heat Type
Water
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
208 Roxborough Drive, Toronto, ON M4W 1X8
City
Toronto C09
Neighbourhood
Rosedale-Moore Park
County / Region
Toronto
Province / State
ON
Postal Code
M4W 1X8
Cross Street
Glen Road and Whitney Drive
Directions
East of Glen Road, South of Summerhill Avenue
Country
CA
List Price
$8,950,000
Annual Taxes
$45,578
Tax Year
2026
Legal Description
LT 100 PL 344E TORONTO; PT LT D PL 344E TORONTO AS IN CA516179; CITY OF TORONTO
Possession Type
Flexible
Possession Details
Flexible
Listing Office
ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
Board
Toronto Regional Real Estate Board
Original Entry
2026-06-22T22:03:16Z
Media Updated
2026-06-24T12:32:14Z
Photos Updated
2026-06-24T12:32:14Z
Last Modified
2026-06-29T21:14:35Z
System Modified
2026-07-06T21:40:51.09107Z
MLS Status
New
Architectural Style
2-Storey
Basement
Partially Finished
Co List Office Name
ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
Ddfyn
Yes
Expiration Date
2026-11-20
Foundation Details
Unknown
Heat Source Multi
Gas
Heat Type Multi
Water
Hstapplication
Included In
Link Yn
No
Occupant Type
Vacant
Originating System Id
A00001796
Parcel Number
103940152
Parking Spaces
6
Property Features
Greenbelt/Conservation, Wooded/Treed, River/Stream, Ravine, Place Of Worship, Park
Public Remarks
Set on one of Rosedale's most coveted streets, 208 Roxborough Drive is a 1928 Tudor Revival residence of landmark stature, designed by the prize-winning architect Harold Richard Watson. The composition is grounded in stone, with tracery, a sweeping bay, and a procession of steps to a carved entrance. Inside, the entrance hall is crowned by a coffered plaster ceiling, and light pours through original leaded glass. Wood panelling lines the principal rooms, concealing built-in cabinetry and adorned with fine scrollwork rare in both quality and extent. Original fireplaces ground the rooms, and a hand-crafted staircase rises through the heart of the home. The living room spans the full width of the house, scaled for an era that built for permanence. Above grade, the residence offers more than 5,000 square feet, with over 2,300 more on the lower level. The primary suite includes a private office, walk-in closets, and an ensuite, with four additional bedrooms completing the second floor. Beyond the house is the land itself: the lot extends over 88 feet wide by 408 feet deep, descending into the ravine, a depth almost unheard of in Rosedale. Included in the sale are approved plans and permits for an addition and renovation by Taylor Smyth Architects, with landscape design by Cecconi Simone, a striking contemporary statement uniting irreplaceable historic character with modern convenience inside and out. The rear garden becomes a private landscape, a patio above a swimming pool overlooking the ravine; the primary becomes a jewel box framed by tree views; and the garage is shifted for privacy yet kept for convenience. 208 Roxborough Drive is a true landmark, and an opportunity to become part of its story.
