29 Winchester Street, Toronto

29 Winchester Street
29 Winchester Street
29 Winchester Street
+47
3+1
 bed
4
 bath
4
 parking
3000 - 3500
 sqft
Fourplex
$2,900,000
For Sale
1 day
 on site
$2,900,000
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Size
-
Lot size
3778 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$829 - $967
Taxes
$12,353.71 (2026)
Parking Type
-
Style
3-Storey
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Description
The finest 4-plex in Cabbagetown has returned to market for the first time in a generation! This impeccably maintained and professionally updated income property has been meticulously renovated and represents a rare opportunity to acquire a best-in-class asset of this stature in one of Toronto's most storied neighbourhoods. With over 4200+ sq ft of living space (each unit is over 1000+ sq. ft in size), 29 Winchester offers a spacious and gracious living environment, complimented with multiple walk-out balconies, large windows, private decks and terraces, all overlooking lush rear grounds under a densely treed canopy. The building is home to a high-quality tenant base, and each suite enjoys dedicated climate controls. The building has been curated to appeal to professionals and offers living spaces that are ideal for both entertaining and relaxing in a quiet environment. Fine interior finishes include hardwood floors, updated bathrooms, updated kitchens, high ceilings, and ensuite laundry in each unit. Parking is accessed via a private rear laneway (4 parking spaces at present including 1 tandem space, and the possibility to expand up to 6 car parking on site). Highly desirable and strongly appealing to tenants in any market. This premium location is steps to restos and shopping along Parliament Street, and accessible to multiple TTC options (including the Carlton Street Car) or a short walk to Castle Frank Station TTC Subway. Tenants can enjoy Winchester Park at their doorstep, or stroll to Riverdale farm. Mere minutes to the downtown core and Distillery District / St Lawrence Market. Building financials available upon request. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.
Broker: ROYAL LEPAGE TERREQUITY SW REALTY
MLS®#: C14111438
Property details
Parking:
4
Parking type:
-
Property type:
Fourplex
Heating type:
Baseboard
Style:
3-Storey
MLS Size:
3000-3500 sqft
Lot front:
28 Ft
Lot depth:
132 Ft
Listed on:
Oct 23, 2026
Show all details
Rooms
LevelNameSizeFeatures
Second
Bedroom
13.2 x 9.7 ft
Main
Kitchen
14.3 x 7.1 ft
Lower
Family Room
16.3 x 9.7 ft
Show all
Instant estimate:
orto view instant estimate
$153,648
lower than listed price
i
High
$2,844,294
Mid
$2,746,352
Low
$2,608,166
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About 29 Winchester Street

Located at 29 Winchester Street, this Toronto fourplex is available for sale. It was listed at $2900000 in October 2026 and has 3+1 beds and 4 bathrooms. 29 Winchester Street, Toronto is situated in Cabbagetown, with nearby neighbourhoods in St. James Town, Church St. Corridor, Regent Park and Moss Park.

Some good places to grab a bite are St Jamestown Steak & Chops, Kingyo Izakaya or Kibo Sushi House. Venture a little further for a meal at one of Cabbagetown neighbourhood's restaurants. If you love coffee, you're not too far from Tim Hortons located at 581 Parliament St. For groceries there is Fairway Variety which is only steps away.

If you are looking for transit, don't fear, 29 Winchester St, Toronto has a public transit Bus Stop (Parliament St / Winchester St) only steps away. It also has route Parliament, and route Parliament close by. For drivers, the closest highway is Don Valley Parkway and is within a 4-minute drive from 29 Winchester St, making it easier to get into and out of the city