29 Winchester Street

Cabbagetown-South St. James Town, Toronto, M4X 1A6

$3,400,000

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  • 3+1 bedrooms
  • 4 bathrooms
  • 4 parking
  • 3000-3500 sq ft

Listed 95 days ago · MLS® C13578164

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. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.

Details

Type
Fourplex
Style
3-Storey
Age
100+ years
Size
3000-3500 sq ft
Lot
28.47 × 142 ft
Basement
Apartment
Garage
None
Kitchens
4
Property tax
$12,354 (2026)
Neighbourhood
Cabbagetown-South St. James Town
Municipality
Toronto C08

Interior

Bedrooms
3 above ground + 1 below
Bathrooms
1 × 4-piece (basement), 1 × 3-piece (second), 1 × 3-piece (third), 1 × 4-piece (main)
Kitchens
4 (1 below ground)
Rooms
15 above ground
Family room or den
Yes
Fireplace
Yes

Heating, cooling and services

Heating
Baseboard, Electric
Air conditioning
Wall Unit(s)
Water and sewer
Sewer

Building and exterior

Style
3-Storey
Exterior
Brick
Age
100+
Faces
South

Parking

Total parking
4
Driveway and parking
Lane, Private, Reserved/Assigned

Lot

Size
28.47 × 142 ft

More

Possession
TBD
Nearby
Library, Park, Place Of Worship, Public Transit, School
Cross street
Winchester & Parliament

Rooms

RoomLevelSizeFeatures
Living RoomMain7.04 × 4.7 m (23'1" × 15'5")Bay Window, Hardwood Floor, Combined w/Dining
KitchenMain4.37 × 2.16 m (14'4" × 7'1")Pass Through, Tile Floor, W/O To Balcony
Family RoomMain4.98 × 2.97 m (16'4" × 9'9")Hardwood Floor, Window
BedroomMain4.04 × 4.65 m (13'3" × 15'3")Broadloom, Window, Double Closet
Living RoomSecond7.09 × 4.65 m (23'3" × 15'3")Laminate, Bay Window, Combined w/Dining
KitchenSecond2.37 × 2.16 m (7'9" × 7'1")Laminate, W/O To Balcony, Window
Family RoomSecond4.98 × 2.97 m (16'4" × 9'9")Laminate, Window, Pass Through
BedroomSecond4.01 × 2.95 m (13'2" × 9'8")Hardwood Floor, Closet, Window
Living RoomThird5.05 × 3.91 m (16'7" × 12'10")W/O To Terrace, Hardwood Floor, Combined w/Dining
KitchenThird4.75 × 1.68 m (15'7" × 5'6")Laminate, Eat-in Kitchen, Window
BedroomThird4.8 × 3.28 m (15'9" × 10'9")Laminate, Window, Closet
Living RoomLower7.04 × 4.7 m (23'1" × 15'5")Laminate, Window, Combined w/Dining
KitchenLower3.96 × 2.13 m (13' × 7')Open Concept, Window, Tile Floor
Family RoomLower4.98 × 2.97 m (16'4" × 9'9")W/O To Yard, Tile Floor
BedroomLower4.11 × 3.05 m (13'6" × 10')Broadloom, Window, Closet

Location

Location is approximate. See nearby homes on the map

Recent sales nearby

See what similar homes within 1 km sold for in the last year. Create a free account or sign in to see them.

The neighbourhood

Getting around Very walkable

  • 🚇 Castle Frank Subway14 min walk
  • 🚇 Sherbourne Subway15 min walk
  • 🚆 Toronto Union Station GO2.5 km

Within a 10-minute walk: 18 grocery stores, 117 cafés and restaurants, 18 parks, 24 pharmacies. Nearest grocery: Fairway Market Variety & Grocery (100 m). Nearest park: Winchester Park (150 m).

Schools nearby

Elementary

  • Winchester Junior and Senior Public School
    EQAO: Gr 6 reading 89%, math 57%
    2 min walk
  • Our Lady of Lourdes Catholic School Catholic
    EQAO: Gr 6 reading 80%, math 43%
    6 min walk
  • Sprucecourt Junior Public School
    EQAO: Gr 6 reading 85%, math 25%
    8 min walk
  • Rose Avenue Junior Public School
    EQAO: Gr 6 reading 67%, math 14%
    9 min walk

Secondary

  • Jarvis Collegiate Institute
    EQAO: Gr 9 math 34%, literacy test 80%
    9 min walk
  • Collège français French11 min walk
  • Msgr Fraser College - Isabella Campus Catholic12 min walk

EQAO: share of students meeting the provincial standard (2024–25). Ontario average: Gr 6 reading 86%, math 51%; Gr 9 math 55%; literacy test 83%.

Closest schools, not school zones. Check which school serves this address with the school board before relying on it.

Who lives here postal area M4X

Owners / renters
15% / 85%
Median household income
$58,800
Average age
41
Children under 15
12%
Homes
1% detached, 81% high-rise
Commute by transit
44%
Population
19,896

Languages spoken most at home besides English: Tagalog (Pilipino, Filipino) 5.2%, Tamil 2.7%, Spanish 1.6%, Mandarin 1.3%.

Flood and conservation No mapped hazard

Not inside a mapped flood plain or regulated area.

Screening maps only. Ask the conservation authority for a property inquiry before relying on this.

Safety

Major crime per resident in Cabbagetown-South St.James Town (2025): 26% above the Toronto average, down 8% from the year before.

  • Assault40% above average
  • Break and enter70% above average
  • Auto theft59% below average
  • Robbery85% above average
  • Theft from vehiclesabout average
  • Shootingsnone reported

Crime Severity Index for Toronto police: 60 vs 57 for Ontario (2025).

Police-reported figures for the whole neighbourhood, not this street. Rates use the area’s resident population.

Development nearby 12 active

  • 306 GERRARD ST E · 400 m
    Site Plan · Under Review · applied 2026
    Site Plan Approval for an 11-storey mixed-use building containing 228 market and affordable residential units, plus office and community program space.
    Application details
  • 405 SHERBOURNE ST · 300 m
    Site Plan · Application Received · applied 2026
    Site Plan Control Application for a 35-storey (112.6) metre building (excluding mechanical penthouse) 25,069 square metres of residential gross floor area and…
    Application details
  • 219 GERRARD ST E · 450 m
    Site Plan · Under Review · applied 2025
    Site Plan Approval for a 10-storey mixed use building with 60 purpose-built rental units and commercial uses at grade.
    Application details
  • 325 GERRARD ST E · 500 m
    Site Plan · NOAC Issued · applied 2025
    Building 4A Proposal to construct a 26-storey tower, 10 storey mid-rise podium TCHC social housing building with 271 units, retail at grade along Gerrard…
    Application details
  • 240 WELLESLEY ST E · 300 m
    Plan of Subdivision · Under Review · applied 2024
    Draft Plan of Subdivision to establish two development blocks with pedestrian and vehicular connections into and through the subject site. A new public park…
    Application details
  • 383 SHERBOURNE ST · 300 m
    Site Plan · Appeal Received · applied 2023
    The proposal will introduce a 39 storey residential building representing an F.S.I. of 13.58 and lot coverage of 69%. The total GFA will be 20,328 sq. m.…
    Application details

15 more within 500 m.

Rezoning, site plan, subdivision and condominium applications filed with the city.

Distances are approximate. Places © OpenStreetMap contributors. Neighbourhood figures: Statistics Canada, 2021 Census. School results: EQAO via Ontario Data Catalogue (Open Government Licence – Ontario). Neighbourhood crime: Toronto Police Service Public Safety Data Portal (Open Government Licence – Toronto Police Service). Crime Severity Index: Statistics Canada. Planning applications: City of Toronto open data.

Living here

Commute

To Union Station (downtown Toronto): 2 km. Transit times · Driving times

Coming transit

  • 🚧 Moss Park 1.2 km
  • 🚧 Distillery District 1.6 km
  • 🚧 Queen 1.6 km

Stations under construction or approved. Opening dates are the latest public estimates and often move.

Noise Nothing major nearby

No highway within 500 m, rail line within 300 m, or airport flight path nearby.

Distances from the map, not noise measurements. Visit at rush hour to judge for yourself.

What can be built R

Residential (with a site-specific exception).

  • ✅ Up to 6 homes on the lot (multiplex): a sixplex ward
  • ✅ Garden suite in the backyard
  • ✅ Laneway suite, if the lot backs onto a lane

From Toronto’s Zoning By-law 569-2013 map. Lot size, setbacks and trees decide what actually fits; check with a planner before you buy.

Full lot check · Run the numbers

Heritage Protected

This address is on Toronto’s Heritage Register: Heritage Conservation District (Part V) (2008). Changes to the outside (and sometimes inside) usually need a heritage permit, and demolition is restricted.

Heritage Register entry

Building permits

No building permits at this address since 2014.

4 permits on this block of the street in the last 2 years.

Permits filed with the City of Toronto. A permit doesn’t mean the work passed final inspection.

Trees

87 City street trees within 100 m. That’s more than the Toronto average of 42.

Trees on City boulevards only, not private yards or parks.

Internet High-speed

50/10 Mbps or faster available here by cable, fibre or DSL (the federal high-speed target).

From the federal broadband map. Check exact speeds and providers for the address.

Short-term rentals

Only in your principal residence (where you live). The entire home can be rented up to 180 nights a year; renting up to 3 bedrooms while you live there has no limit. Hosts register with the City and collect the 6% accommodation tax.

City rules

Zoning, heritage, building permits and street trees: City of Toronto open data (Open Government Licence – Toronto). Roads, rail, airports and planned stations © OpenStreetMap contributors. Internet: Innovation, Science and Economic Development Canada, National Broadband Data.

Listed by ROYAL LEPAGE TERREQUITY SW REALTY.

Listing information provided by PropTx Innovations Inc. and TRREB; deemed reliable but not guaranteed accurate by PropTx.

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