Kaija Pitt
Direct: 416-371-9447
Office: 416-960-9995
Sotheby’s Canada
1867 Yonge Street, Suite 100
Toronto ON M4S 1Y5 CA

Wychwood

Wychwood is one of Toronto’s most intriguing neighbourhoods. The enclave, which was once a former gated community, sits just north of Davenport Road and west of Bathurst. This private community, with its private driveways and meandering creek, has its own council and is very strict about protecting the privacy of the neighbourhood. Which is why, no doubt, it remains a mysterious neighbourhood to the rest of Toronto.


In the 19th century, the neighbourhood was envisioned as an artists’ colony, which was to be home to an artistic community. Artist Marmaduke Matthews was the man behind the vision, and he named the enclave after his childhood home, Wychwood, in Oxfordshire. He and his friend Alexander Jardine jointly bought the land in 1891 and registered a plan of subdivision in what is now Wychwood.


The homes here compliment the landscape of the neighbourhood and are built in the Arts and Crafts style, and include a few contemporary homes as well. In terms of new-builds, there aren’t many. The council is quite strict on what is built so to preserve the cohesive feel of the neighbourhood.


Wychwood also contains a ravine area known as Taddle Creek Pond –created by damming Taddle Creek. Residents share an outdoor tennis court.


This private community is managed by an executive council and is committed to paying for its streets and amenities. In 1985, Wychwood was the first residential zone in Ontario to be granted heritage status.

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138 Winona Drive
Wychwood Toronto M6G 3S7

$849,000
Residential Freehold beds: 2+1 baths: 3.0

Main Photo: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 1: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 2: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 3: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 4: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 5: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 6: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 7: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 8: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 9: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 10: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 11: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 12: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 13: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 14: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 15: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 16: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 17: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 18: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 19: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 20: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 21: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 22: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 23: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 24: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 25: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 26: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 27: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 28: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 29: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 30: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Photo 31: 138 Winona Drive in Toronto: Wychwood House for sale (Toronto C02)  : MLS®# C12146469
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12146469
Bedrooms:
2+1
Bathrooms:
3
Set in the sought after neighbourhood of Hillcrest Village, this home is ready for its next chapter offering endless potential for any visionary buyer. While zoned as a single-family home, the house has been configured into three one-bedroom units with a separate entrance to the lower level. Renovated to keep as an income generating property just steps to St. Clair, or convert back to single family in this vibrant and family-centric neighbourhood. Being a corner lot, the home benefits from an added side yard with mature flowering trees and plenty of large unobstucted windows. A sliding-door walk-out from the main floor kitchen brings natural light into the main floor, and connects to a west-facing deck with garden views. The second floor can hold up to three bedrooms as a single family residence, or one bedroom with a large kitchen/eat-in area when used as a duplex. The lower level has a separate entrance from the rear of the home. A large private driveway at the rear of the lot with access from Benson provides convenient parking for up to two vehicles. Renovate to suit, this home is a blank canvas to step into this enviable Hillcrest community within one block from St. Clair Wests vibrant shops, minutes to Wychwood Barns, and direct access to the local top-rated schools.
Property Type:
Residential Freehold
Property Sub Type:
Semi-Detached
Home Style:
2-Storey
Total Approx Floor Area:
700-1100
Depth:
88'1"
Frontage:
14'10"
Direction Faces:
West
Bedrooms:
2+1
Bathrooms:
3.0
Water supply:
Municipal
Kitchens:
2
Bedrooms Above Grade:
2
Bedrooms Below Grade:
1
Kitchens Above Grade:
2
Rooms Above Grade:
6
Ensuite Laundry:
No
Heating type:
Forced Air
Heating Fuel:
Gas
Foundation:
Other
Roof:
Unknown
Basement:
Separate Entrance
Fireplace/Stove:
No
Garage:
None
Garage Spaces:
0.0
Parking Spaces:
2
Total Parking Spaces:
2.0
Family Room:
No
Possession Details:
To be arranged
Pool:
None
HST Applicable To Sale Price:
Included In
Assessment Year:
2024
Taxes:
$5,279 / 2024
Assessment:
$- / 2024
Toronto C02
Wychwood
Toronto
Other
Hot water tank and furnace.
See schedule B
See schedule B
Brick
Floor
Type
Size
Other
Main
Foyer
16'1" × 4'11"
Main
Bedroom
12'2" × 9'10"
Main
Dining Room
12'9½" × 10'10"
Main
Kitchen
13'5" × 8'2"
Second
Bedroom
13'5" × 9'6"
Second
Living Room
24'3" × 8'2"
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Date Listed:
May 14, 2025
Original Price:
$849,000
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Listed by CHESTNUT PARK REAL ESTATE LIMITED
Data was last updated May 19, 2025 at 04:15 AM (UTC)
Area Statistics
Listings on market:
39
Avg list price:
$2,099,000
Min list price:
$849,000
Max list price:
$8,380,000
Avg days on market:
30
Min days on market:
2
Max days on market:
573
These statistics are generated based on the current listing's property type and located in Toronto C02. Average values are derived using median calculations.
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.