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Detached for sale at 208 Roxborough Drive, Toronto C09 - 5 bedroom, 5 bathroom - Photo 1 of 49
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Active

$8,950,000

208 Roxborough Dr

Toronto C09, ON M4W 1X8

208 Roxborough Dr, Toronto C09Listed at $8,950,000. 5 bedroom, 5 bathroom 2-Storey. MLS® C13476730.

5Beds
5Baths
5000 +sqft
2-Storey
8Parking
$45,578.27 (2026)

What's this home worth?

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Description

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 Details

Property TypeDetached
Style2-Storey
CommunityRosedale-Moore Park
Approximate Age51-99
Rooms13+1
Kitchens1
Washrooms5
Square Feet5000 + sqft
Lot Dimensions88.5 × 408.21 ft
Fronting OnEast
Dir/Cross StGlen Road and Whitney Drive
Garage TypeDetached
Garage Parking Spaces2
DrivePrivate
Parking Drive Spaces6
Total Parking Spaces8
ExteriorStone, Stucco (Plaster)
RoofTile
FoundationUnknown
BasementPartially Finished
Fireplace FeaturesWood
Heating TypeWater
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2026)$45,578.27
HSTIncluded In
Listed Date6/22/2026
Days on Market26 days
PossessionFlexible

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Listing Courtesy of: ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM

MLS® #C13476730

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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HouseIndex Take: 208 Roxborough Drive

This detached (2-Storey) is located in the Rosedale-Moore Park neighbourhood of Toronto.

The home offers 5 bedrooms, 5 bathrooms.

Features include a partially finished basement, 8 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 88.5 × 408.21 feet.

Listed at $8,950,000 CAD with annual property taxes of $45,578.27 (2026).

About Toronto Real Estate

This Detached is located in the Rosedale-Moore Park community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity. Detached homes in Toronto are in high demand among families seeking space, privacy, and long-term equity growth.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →