29 Winchester Street, Toronto, ON M4X 1A6
- Property tax
- $12,354 / year
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.
- MLS number
- C13578164
- Type
- Fourplex
- Status
- Active
- Bedrooms
- 4
- Bathrooms
- 4
- Postal code
- M4X 1A6
- Photos
- 50
- Laundry
- Not in the unit
This listing’s own days on market are shown above. How long the property has been for sale across every earlier listing is drawn from records the board releases only to registered users — a free account opens it, along with the sale history below.
Rooms
15 rooms as the listing brokerage filed them, with measurements.
Main
| Room | Size | Features |
|---|---|---|
| Living Room | 7.04 × 4.70 m | Bay Window · Hardwood Floor · Combined w/Dining |
| Kitchen | 4.37 × 2.16 m | Pass Through · Tile Floor · W/O To Balcony |
| Family Room | 4.98 × 2.97 m | Hardwood Floor · Window |
| Bedroom | 4.04 × 4.65 m | Broadloom · Window · Double Closet |
Second
| Room | Size | Features |
|---|---|---|
| Living Room | 7.09 × 4.65 m | Laminate · Bay Window · Combined w/Dining |
| Kitchen | 2.37 × 2.16 m | Laminate · W/O To Balcony · Window |
| Family Room | 4.98 × 2.97 m | Laminate · Window · Pass Through |
| Bedroom | 4.01 × 2.95 m | Hardwood Floor · Closet · Window |
Third
| Room | Size | Features |
|---|---|---|
| Living Room | 5.05 × 3.91 m | W/O To Terrace · Hardwood Floor · Combined w/Dining |
| Kitchen | 4.75 × 1.68 m | Laminate · Eat-in Kitchen · Window |
| Bedroom | 4.80 × 3.28 m | Laminate · Window · Closet |
Lower
| Room | Size | Features |
|---|---|---|
| Living Room | 7.04 × 4.70 m | Laminate · Window · Combined w/Dining |
| Kitchen | 3.96 × 2.13 m | Open Concept · Window · Tile Floor |
| Family Room | 4.98 × 2.97 m | W/O To Yard · Tile Floor |
| Bedroom | 4.11 × 3.05 m | Broadloom · Window · Closet |
Property details
As filed by the listing brokerage. Anything the board left blank is left out rather than shown as unknown — and none of it is guaranteed accurate by PropTx, so verify what you rely on.
Property
- Type
- Fourplex
- Style
- 3-Storey
- Class
- Residential Freehold
- Age
- 100+
- Fronting on
- South
- Community
- Cabbagetown-South St. James Town
- Municipality
- Toronto C08
- Cross street
- Winchester & Parliament
Inside
- Bedrooms
- 4
- Bedrooms above grade
- 3
- Bathrooms
- 4
- Washrooms
- 1 on the basement floor · 1 on the second floor · 1 on the third floor
- Kitchens
- 4
- Rooms above grade
- 15
- Family room
- Yes
- Fireplace
- Yes
- Basement
- Apartment
- Size
- 3000-3500
Building
- Construction
- Brick
- Roof
- Unknown
- Foundation
- Unknown
- Other structures
- None
Parking
- Covered spaces
- 0
- Driveway spaces
- 4
- Total parking
- 4
- Features
- Lane, Private, Reserved/Assigned
Land
- Lot
- 28.47 × 142 feet
- Pool
- None
Heating, cooling and services
- Heating
- Baseboard
- Heat source
- Electric
- Cooling
- Wall Unit(s)
- Water
- Municipal
- Sewer
- Sewer
Features
- Property
- Library, Park, Place Of Worship, Public Transit, School
- Interior
- None
Listing
- MLS number
- C13578164
- Status
- New
- Previous status
- Draft
- Listed on
- 2026-07-17
- Expires
- 2026-12-31
- Taxes
- $12,354 (2026)
- Board
- Toronto Regional Real Estate Board
Listing history
No previous listings found for this address.
Where this property is
Pick a school to see the boundary it is inside. Boards redraw these — confirm with the board.
Matched to a published address point for this address.
Schools
The school boundaries this address is inside, and the schools nearest it. Boards redraw boundaries and cap programs — confirm with the board before this affects a decision.
School boundaries this address is inside
Where these boundaries come from, and what they are worth
A school boundary is the area a board draws around a school. An address inside several of them is normal — boards publish a separate boundary per program, so regular track, French immersion and specialist programs each have their own.
Toronto. Read from the TDSB’s own School Search Map, one school at a time. The board states that the lines on that map are approximate and that the schools serving an individual address must be confirmed against its own address lookup — so the outline here shows you roughly where a boundary runs, and the board answers whether a particular house is in it. The map covers home schools only: French Immersion, gifted and the other optional programs have their own boundaries and their own admission rules, and are not shown.
Homula cannot tell you which school a child will attend. Boards move boundaries, hold students at capacity, cap programs and grant exceptions, and none of that is in any published file. The board is the only authority: TDSB Find Your School.
Sources: TDSB School Search Map — the board states these lines are approximate and that individual addresses must be confirmed against its own lookup.
Other schools nearby
By distance from this address, not school boundary — a school 400 m away can be in another school’s attendance area.
| School | Level | Distance | Rating |
|---|---|---|---|
| Winchester Junior and Senior Public School Toronto DSB | Elementary | 120 m | / 10 76% met the standard · 4 of 6 measures |
| Our Lady of Lourdes Catholic School Toronto CDSB | Elementary | 394 m | / 10 64% met the standard |
| St Martin Catholic School(OL of Lourdes Toronto CDSB | Elementary | 427 m | Not reported |
| St Martin Catholic School (St.Martin) Toronto CDSB | Secondary | 479 m | Not reported |
| Rose Avenue Junior Public School Toronto DSB | Elementary | 583 m | / 10 46% met the standard |
How the rating is calculated
EQAO — Ontario’s testing agency — publishes, for each school, the percentage of students meeting the provincial standard in Grade 3 and Grade 6 reading, writing and mathematics. The rating is the average of those percentages divided by ten. A school where 72% of students met the standard rates 7.2 out of 10.
Nothing is weighted or adjusted, and schools are not ranked against each other. Where EQAO withholds a result to protect the privacy of a small group of students, that measure is left out rather than counted as zero — so a rating built on fewer than six measures says so.
What it does not measure. It is one year of standardised testing in three subjects. It says nothing about teaching, programs, or whether a school suits a particular child, and it tracks neighbourhood household income closely enough that it partly measures the neighbourhood rather than the school. Treat it as one figure among many.
Source: Ontario Ministry of Education, School Information and Student Demographics (2024–25), Open Government Licence – Ontario.
H-Value
What an H-Value is and how it is calculated — the method and our measured error, no account needed.
This neighbourhood
Statistics Canada 2021 Census, for the surrounding few blocks — about 445 people.
The neighbourhood, by the census
Statistics Canada 2021 Census for dissemination area 35204275 — the few blocks around this address, home to 445 people. It describes the area, not this property.
Percentages are of the 310 responses in this category. Statistics Canada rounds counts and withholds small ones to keep individuals unidentifiable, so categories with too few people to publish are absent rather than shown as zero.
Source: Statistics Canada, 2021 Census of Population. Contains information licensed under the Open Government Licence – Canada.
Work out the numbers
Everything below is calculated in your browser from figures you can change. Nothing is sent anywhere.
If you rented it out
How this is calculated, and what it leaves out
Canadian fixed-rate mortgages compound semi-annually, not monthly, so the monthly rate here is (1 + rate/2)1/6 − 1. Most calculators use rate ÷ 12, which is the American convention and overstates the payment by tens of dollars a month.
Below 20% down, default insurance is mandatory and is added to the loan rather than paid at closing: 2.80% at 85% loan-to-value, 3.10% at 90%, 4.00% at 95%. It is unavailable at or above $1.5M, which is why 20% is a hard floor there.
Not included: vacancy, property management, capital repairs, income tax, and the fact that a lender qualifies you at a stress-test rate rather than the one you are quoted. This is arithmetic on the numbers above, not a mortgage approval or an opinion of what you can afford.
What’s being built nearby
Planning applications within 500 m — 6 still in progress.
Zoning By-law Amednement for a 41-storey infill mixed-use building while maintaining the existing 24-storey rental apartment building on site.…
City planning file →Draft Plan of Subdivision to establish two development blocks with pedestrian and vehicular connections into and through the subject site.…
City planning file →Site Plan Approval application to permit three new buildings on the lands, comprising a 47-storey mixed-use building with 5,770 square metres of non-residential uses in the lower floors and 620 dwelling units, a 21-storey building with 300 dwelling units, and …
City planning file →*** Proposed Draft Plan of Condominium for a 39-storey mixed-use building containing 456 residential units.
City planning file →Site Plan Approval Application for a 42-storey mixed-use building having a non-residential gross floor area of 240 square metres and a residential gross floor area of 31,273 square metres.
City planning file →Official Plan and Zoning By-law Amendment applications to permit three new buildings on the lands, comprising a 58-storey mixed-use condominium building with 4,060 square metres of non-residential uses in the lower floors and 741 dwelling units, a 21-storey pu…
City planning file →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 388 square metres of non-residential gross floor area and a landscaped mid-block connection between S…
City planning file →The 2025 Proposal consists of a single building articulated as two towers, rising to 26 and 35 storeys on a two-storey podium.…
City planning file →What these are
These are applications made to the City — a proposal to build something, not a decision that it will be built. Many are refused, withdrawn, reduced, or approved and then left for years. The status shown is the one the City last recorded, and each entry links to the City’s own file, which is the authoritative record.
Whether a nearby development is welcome depends on what you want from a street, so this panel reports what has been applied for and leaves the judgement to you.
Contains information licensed under the Open Government Licence – Toronto. Toronto only for now; other municipalities publish this differently or not at all.