74 Chestnut Park Road
Rosedale-Moore Park Toronto M4W 1W9

$7,250,000
Residential Freehold beds: 7 baths: 5.0

Main Photo: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 1: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 2: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 3: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 4: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 5: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 6: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 7: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 8: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 9: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 10: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 11: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 12: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 13: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 14: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 15: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 16: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 17: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 18: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 19: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 20: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 21: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 22: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 23: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 24: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 25: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 26: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 27: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 28: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 29: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 30: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 31: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 32: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 33: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Photo 34: 74 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12466955
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12466955
Bedrooms:
7
Bathrooms:
5
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'
Lot Frontage:
53'10"
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.
Brick
Floor
Type
Size
Other
Main
Foyer
7'6" × 6'9"
Hardwood Floor, Separate Room, Wainscoting
Main
Common Room
16'8" × 14'8"
Scarlet OHara Stairs, Hardwood Floor, Closet
Main
Living Room
25'11" × 17'7"
Bay Window, Fireplace, Stained Glass
Main
Dining Room
17'7" × 14'8"
Hardwood Floor, Bay Window, Moulded Ceiling
Main
Family Room
17'5½" × 15'9¾"
Bay Window, Fireplace, Hardwood Floor
In Between
Mud Room
10'6" × 6'6¾"
W/O To Yard
Main
Kitchen
16'4½" × 12'7"
Centre Island, Large Window, Pantry
Main
Breakfast
10'1" × 8'4"
Wood, B/I Shelves, Beamed Ceilings
Second
Primary Bedroom
20'1¾" × 15'10"
Bay Window, Fireplace, Semi Ensuite
Second
Bedroom 2
13'8" × 12'8"
Semi Ensuite, Window
Second
Great Room
25'11" × 16'1"
Fireplace, Bay Window, French Doors
Second
Bedroom 4
17'6¼" × 14'8"
Wood, Bay Window, Overlooks Backyard
Third
Bedroom 5
12'6" × 9'3"
Hardwood Floor, Window, Closet
Third
Bedroom
11'5" × 10'8"
Combined w/Kitchen, Closet, Window
Third
Bedroom
14'5" × 10'5"
Hardwood Floor, Window, Closet
Third
Bedroom
16'10" × 11'9"
Hardwood Floor, Window, Closet
Basement
Recreation
25'11" × 17'8¼"
Concrete Floor, Above Grade Window
Basement
Workshop
17'6¼" × 12'8"
Concrete Floor, Above Grade Window
Basement
Laundry
16'4½" × 12'7"
Laundry Sink, Above Grade Window, Ensuite Bath
Basement
Other
17'11¾" × 10'3"
B/I Closet, Above Grade Window
Basement
Utility Room
25'2¾" × 15'7¾"
Above Grade Window
Special Designation:
Heritage
Sewers:
Sewer
Air Conditioning:
None
Central Vacuum:
No
Seller Property Info Statement:
No
Ensuite Laundry:
No
Date Listed:
Oct 16, 2025
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Virtual Tour

Listed by FREEMAN REAL ESTATE LTD.
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.