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Detached for sale at 39 Rockingham Drive, Toronto W08 - 4 bedroom, 5 bathroom - Photo 1 of 50
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Detached for sale at 39 Rockingham Drive, Toronto W08 - 4 bedroom, 5 bathroom - Photo 12 of 50
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$2,798,000

39 Rockingham Dr

Toronto W08, ON M9A 1P5

39 Rockingham Dr, Toronto W08Listed at $2,798,000. 4 bedroom, 5 bathroom 2-Storey Detached. MLS® W13797384.

Just listed — 3 days ago

Possession · seller's timeline

30-59 days

4Beds
5Baths
3000-3500sqft
Detached
2-Storey
5Parking
$12,767Taxes/yr · 2025

What's this home worth?

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Description

Welcome to 39 Rockingham Drive, an exceptional custom-built residence situated on one of Islington Heights' most coveted streets. Thoughtfully updated and impeccably maintained, this elegant four-bedroom, five-bathroom home offers a refined balance of luxurious everyday living and effortless entertaining. The main level is beautifully appointed with a spacious family room anchored by a wood burning fireplace, flowing seamlessly into the newly renovated kitchen featuring custom cabinetry, a generous breakfast bar, and direct walkout to the new deck and beautifully landscaped backyard. A private hot tub and tranquil outdoor setting create an inviting retreat for relaxing or entertaining. An elegant formal living room with its own gas fireplace and a sophisticated dining room provide gracious spaces for hosting family and friends. A dedicated main-floor office offers an ideal work-from-home environment, while the convenient garage entrance leads to a generous mudroom and laundry area, thoughtfully designed with abundant storage. Upstairs, the luxurious primary suite offers a true private retreat, complete with a spa-inspired, state-of-the-art ensuite and walk-in closet. A generously proportioned second bedroom enjoys its own three-piece ensuite, while two additional bedrooms share a beautifully appointed five-piece family bathroom. The fully finished lower level extends the living and entertaining space with an impressive temperature-controlled wine cellar and tasting room, spacious home gym, large recreation room, and additional bathroom-perfectly suited for entertaining. Ideally located just steps from the shops and amenities of Thorncrest Plaza, the highly sought-after Rosethorn Junior School, and Rosethorn Tennis Club, this exceptional family friendly neighbourhood offers convenient access to major highways and transit.A rare opportunity to enjoy turnkey living in one of Islington Heights' most desirable communities.

Property Details

Property TypeDetached
Style2-Storey
CommunityPrincess-Rosethorn
Rooms5+3
Kitchens1
Washrooms5
Square Feet3000-3500 sqft
Lot Dimensions65 × 120 ft
Fronting OnSouth
Dir/Cross StIslington & Rathburn
Garage TypeBuilt-In
Garage Parking Spaces2
DrivePrivate
Parking Drive Spaces3
Total Parking Spaces5
ExteriorBrick
RoofAsphalt Shingle
FoundationBlock
BasementFinished
Fireplace FeaturesWood, Natural Gas
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2025)$12,767
HSTIncluded In
SecurityAlarm System
Listed Date9/17/2026
Days on Market3 days
PossessionTBD

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Listing Courtesy of: ROYAL LEPAGE REAL ESTATE SERVICES LTD.

MLS® #W13797384

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: 39 Rockingham Drive

This detached (2-Storey) is located in the Princess-Rosethorn neighbourhood of Toronto.

The home offers 4 bedrooms, 5 bathrooms.

Features include a finished basement, 5 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 65 × 120 feet.

Listed at $2,798,000 CAD with annual property taxes of $12,767 (2025).

About Toronto Real Estate

This Detached is located in the Princess-Rosethorn 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 →