For Sale: 29 Winchester Street, Toronto, ON - REW
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$3,400,000
4 bd 4 ba 3000 - 3499 sf Multifamily

29 Winchester StreetToronto, ON, M4X 1A6

Cabbagetown-South St. Jamestown
  • 4 Bed
  • 4 Bath
  • 3000 - 3499 Sqft
  • Multifamily

About this home

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. Over 4200+ sq ft of living space, complimented with multiple walk-out exterior spaces including 2x large private decks, a rear walk-out patio at grade, and a stunning oversized south facing rooftop terrace on the upper level 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 large windows. Each unit has dedicated ensuite laundry. Parking is accessed via a private rear laneway off of Aberdeen Ave, including 4 parking spaces at present (of which 1 is a tandem parking space,) and the possibility exists to expand up to 6 car parking on site). 29 Winchester has been assembled to remain highly desireable 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. (id:63626)
Listed by: LISA SHIRRIFF, Salesperson, ROYAL LEPAGE TERREQUITY SW REALTY

Home facts and features

Price details
List Price
Gross Taxes for 2026
$12,354
Home facts
Bedrooms
4
Full Bathrooms
4
Parking Spaces
4
Parking Details
No Garage
Property Type
Multifamily
Depth
142 feet
Frontage
28.6 feet
Exterior Finish
Brick
Heating Type
Baseboard heaters, Forced air, Electric, Natural gas
Cooling
Wall unit
Basement Details
Apartment in basement,
Features
Lane
Appliances
Dishwasher, Refrigerator, Stove
Community
Agent details
Primary Agent
LISA SHIRRIFF
Primary Broker
ROYAL LEPAGE TERREQUITY SW REALTY
Secondary Agent
Secondary Broker
ROYAL LEPAGE TERREQUITY SW REALTY
Listing details
Days on REW
1 Day
MLS® Number
C13578164
Source
Canadian Real Estate Association
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Building Information

29 Winchester Street, Multifamily in Cabbagetown-South St. Jamestown
Units:
n/a
Floors:
3
Built in:
0
Active Listings:
1

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Estimated Payments
Purchase Price
Mortgage Total
Down Payment
Amortization
25 Years
Interest Rate
3.99%

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Property Insights

Winchester Junior & Senior Public School
  • Public
  • JK - 8
Our Lady of Lourdes Catholic School
  • Catholic
  • JK - 8
Sprucecourt Junior Public School
  • Public
  • JK - 8
Rose Avenue Junior Public School
  • Public
  • JK - 6
Lord Dufferin Junior & Senior Public School
  • Public
  • JK - 8
Canada's National Ballet
  • Private
  • 6 - 12
Jarvis Collegiate Institute
  • Public
  • 9 - 12
Collège français
  • Public
  • 7 - 12
ÉÉC du Sacré-Coeur-Toronto
  • Catholic
  • JK - 6
TAIE International Institute
  • Private
  • 10 - 12
School catchments and distances are intended to be used as reference only. To verify enrolment eligibility for a property, contact the school directly.Report Incorrect Info
Listing data is subject to copyright, disclaimer, and additional requirements from the data provider. See our Terms of Use for terms applicable to this listing. Listing data was last updated on 2026-07-17.