Set on one of Rosedale's most coveted and quietly prestigious streets, 74 Chestnut Park Road represents a once-in-a-generation opportunity to reimagine a grand family home in Toronto's most storied neighbourhood. Built in 1903 by well-known architects Langley & Langley, this stately residence rests on an expansive +8,000 sq.ft. corner lot, offering remarkable width, privacy, and presence. With gracious proportions, high ceilings, and enduring architectural integrity, the home provides a rare canvas for those with the vision to restore, renew, or completely reimagine a landmark property. Extensive front and back gardens and a bricked patio lie behind a century old brick wall and large detached double car garage and private driveway. Its character and scale evoke an era of craftsmanship seldom replicated today, while its setting, just moments from Yonge Street, top schools, parks, and ravines, anchors it among Rosedale's finest addresses. A truly exceptional opportunity, properties of this calibre and potential are increasingly scarce. Prompt viewing is recommended.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
3-Storey
Total Approx Floor Area:
3500-5000
Lot Depth:
145'44.2 m
Lot Frontage:
53'10"16.4 m
Lot Shape:
Irregular
Topography:
Flat
Direction Faces:
North
Bedrooms:
7
Bathrooms:
5.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
7
Kitchens Above Grade:
1
Rooms Above Grade:
13
Rooms Below Grade:
5
Heating type:
Water
Heating Fuel:
Gas
Foundation:
Unknown
Roof:
Unknown
Basement:
Unfinished
Fireplace/Stove:
Yes
Garage:
Detached
Garage Spaces:
2.0
Parking Features:
Private Double
Parking Spaces:
1
Total Parking Spaces:
3.0
Family Room:
Yes
Possession Details:
60 Days/TBA
Lot Irregularities:
rear width 68.83ft, east depth 149.17ft
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$21,039.03 /
2025
Assessment:
$- /
-
Toronto
Toronto C09
Rosedale-Moore Park
Fenced Yard, Ravine, River/Stream, School, Public Transit, Park
None
Hot Water Tank
All electric light fixtures (except those excluded), all existing window coverings, 2nd floor family room built-in wall unit, existing kitchen appliances, washer, dryer, (all as-is), mailbox, natural gas generator, fireplace grates, hardware in basement (door knobs, window locks, hinges, hooks etc), storage units in garage.
Fireplace Screens Main Floor, Electric Light Fixtures: Dining Room Chandelier, Family Room Chandelier, 3rd Floor East Bedroom Ceiling Light, Brass Eagle Wall Sconces Landing to 2nd Floor, Main Floor Wall Sconces, Kitchen panel with family height measurements, Various plants in garden.
Data was last updated October 17, 2025 at 04:15 PM (UTC)
Area Statistics
Listings on market:
49
Avg list price:
$5,895,000
Min list price:
$1,499,000
Max list price:
$18,500,000
Avg days on market:
25
Min days on market:
1
Max days on market:
206
These statistics are generated based on the current listing's property type
and located in
Rosedale-Moore Park. Average values are
derived using median calculations. This data is not produced by the MLS® system.
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.