43.6654° N · 79.3696° W — Cabbagetown-South St. James Town, Toronto — MLS® #C14111438
29 Winchester St
$2,900,000
Cabbagetown-South St. James Town, Toronto, Ontario M4X 1A6
- 3+1
- BedroomsBeds
- 4
- BathroomsBaths
- 3000-3500 sqft3000-3500
- SizeSq ft
- 28.47 x 132.73 ft
- Lot sizeLot
Inquire about this listing
In short · from the listing record
29 Winchester St is a 3+1-bedroom, 4-bathroom fourplex in Cabbagetown-South St. James Town, Toronto, listed for sale at an asking price of $2,900,000 (MLS® C14111438).
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. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.
Listing readings
How it measures up
Scores from the listing record and the market around it.
78Good
Condition score
2 documented update signals
Listing age, structured features and disclosed update language; not an inspection.
5Shortfall
Cash flow quality
−$10,310/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Median of 405 homes with 4 bedrooms for lease in Toronto right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The data table
Every fact
Everything the board publishes for this home.
- Tax
- $12,354 / 2026
- MLS® number
- C14111438
- Board
- TRREB MLS®
- Property Type
- Fourplex
- Building Age
- 100+
- Time on market
- Size
- 3000-3500 sqft
- Lot Size
- 28.47 x 132.73 ft
- Listed on
- Parking
- None, 4 Parking
Listing history
Listing activity for 29 Winchester St, Toronto, Ontario
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $2,900,000 | N/A | For Sale | C14111438 |
Inside
Room by room
From the listing.
- Living4.7 × 7.04 mBay Window, hardwood floor, Combined W/Dining
- Kitchen2.16 × 4.37 mPass Through, Tile Floor, W/O To Balcony
- Family2.97 × 4.98 mhardwood floor, Window
- Br4.65 × 4.04 mBroadloom, Window, Double Closet
- Living4.7 × 7.04 mLaminate, Window, Combined W/Dining
- Kitchen2.13 × 3.96 mOpen Concept, Window, Tile Floor
- Family2.97 × 4.98 mW/O To Yard, Tile Floor
- Br3.05 × 4.11 mBroadloom, Window, Closet
- Living4.65 × 7.09 mLaminate, Bay Window, Combined W/Dining
- Kitchen2.16 × 2.37 mLaminate, W/O To Balcony, Window
- Family2.97 × 4.98 mLaminate, Window, Pass Through
- Br2.95 × 4.01 mhardwood floor, Closet, Window
- Living3.91 × 5.05 mW/O To Terrace, hardwood floor, Combined W/Dining
- Kitchen1.68 × 4.75 mLaminate, Eat-In Kitchen, Window
- Br3.28 × 4.8 mLaminate, Window, Closet
Property
- Property Type
- Fourplex
- Style
- 3-Storey
- Community
- Cabbagetown-South St. James Town
- Municipality
- Toronto
Building
- Size
- 3000-3500 sqft
- Building Age
- 100+
- Construction
- Brick
Inside
- Bedrooms
- 3+1
- Bathrooms
- 4
- Bathroom Details
- 1 × 4pc Bsmt, 1 × 3pc 2nd, 1 × 3pc 3rd, 1 × 4pc Main
- Basement Type
- Apartment
- Kitchens
- 3
Parking
- Driveway
- Lane, Private
- Garage Type
- None
- Additional Parking
- 4
- Total Parking
- 4
Utilities
- Water
- Municipal
- Cooling
- Wall Unit
- Heating Type
- Baseboard
Land
- Sewer
- Sewers
- Frontage
- 28.47 ft
- Depth
- 132.73 ft
- Lot Size
- 28.47 x 132.73 ft
Where it sits
The street and the area
Asking prices on the map.
Map and tour
Transit nearby
| Station | Lines | Distance |
|---|---|---|
| Sherbourne Station | TTC subway: Line 2 Bloor-Danforth | 900 m |
| Castle Frank Station | TTC subway: Line 2 Bloor-Danforth | 950 m |
| Wellesley Station | TTC subway: Line 1 Yonge-University | 1.1 km |
| Union Station | TTC subway: Line 1 Yonge-UniversityGO Transit train: Barrie, Kitchener, Lakeshore East, Lakeshore West, Milton, Richmond Hill, StouffvilleUP Express train | 2.4 km |
| Eglinton Station | TTC subway: Line 1 Yonge-UniversityTTC light rail: Line 5 Eglinton | 5 km |
The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: TTC schedule data (GTFS) from the Toronto Transit Commission under the Open Government Licence – Toronto; GO Transit and UP Express schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx, downloaded October 18, 2026. Contains information licensed under the Open Government Licence – Toronto. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx.
Site report
What the record says
What the City and the conservation authority have on file for this address.
- Heritage and ravineAppliesOn the Heritage Register — Part V, by-law 325-2008
- Heritage and ravineAppliesIn the Cabbagetown Northwest Heritage Conservation District, by-law 325-2008
- Heritage and ravineNone foundNot in the mapped ravine protection area
- ZoningR (d1.0) (x881)Residential zone (R) · Chapter 10, section 10.10 of By-law 569-2013 · Exception 900.2.10(881)
- PermitsNone on fileNo building permits on file at this address.
- Signals nearby6 to note509 PARLIAMENT ST, Official plan or zoning amendment, 130 m away · 505 PARLIAMENT ST, Official plan or zoning amendment, 140 m away · 405 SHERBOURNE ST, Site plan, 320 m away · 383 SHERBOURNE ST, Site plan, 320 m away · 240 WELLESLEY ST E, Site plan, 330 m away · 240 WELLESLEY ST E, Plan of subdivision, 330 m away
- ca regulatedNone in rangeNot in Toronto and Region Conservation Authority’s mapped regulated area
- provincial plansNone in rangeOutside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areas
- wetlandNone in rangeNo mapped wetland within 120 m
- aggregateNone in rangeNo licensed pit or quarry within 2 km
- wellsNone in rangeNo recorded oil, gas or salt well within 250 m
- railOn recordNearest rail line: 940 m
- trailOn recordA trail on the Ontario trail network within 1 km
- permitsOn record69 building permits issued within 250 m in the last 2 years
- devappsOn record2 open development applications within 250 m An application is a proposal: it may change, be refused or never be built.
- airportOn recordNearest airport: 3.9 km
- parcelOn recordMapped parcel: about 4,050 sq ft Measured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.
- water wellsNone in rangeNo water-supply well recorded within 250 m 41 test or monitoring holes also recorded.
- groundwaterOn recordGroundwater recorded about 12.4 m below ground nearby The middle water level in the well records within 500 m (180 records). It changes with the season and from spot to spot.
- npriNone in rangeNo facility within 1 km reports pollutant releases to Environment Canada The nearest is Enwave Energy Corporation — Walton Street Steam Plant, 1.5 km away. Only facilities above the inventory’s reporting thresholds are listed.
- fcsiNone in rangeNo federal contaminated site within 1 km The federal inventory covers federal land only; it says nothing about provincial or private sites.
- electricityOn recordElectricity is distributed here by Toronto Hydro-Electric System Limited
- internet speedOn recordWired internet 50/10 Mbps or faster is listed at this location Fixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (10 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.
- broadbandOn recordAcross the surrounding area: fibre to the home, cable, DSL internet listed Fibre to the home: Beanfield Metroconnect, Bell, CIK Telecom, Dotto One, FibreStream, Rally, Rogers. Cable: Rogers. DSL: Bell. Fixed wireless: Rogers, Routcom, SkyChoice Communications. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.
Changes outside the house, and tree removal, may need the City’s review on top of the usual permits. Ask the City before you plan work.
Each record is the map at the home’s location, not an inspection. Confirm anything that matters with the municipality, Toronto and Region Conservation Authority or the record’s publisher.
City of Toronto Open Data and zoning map, read at this address. Contains information licensed under the Open Government Licence – Toronto. City of Toronto Open Data — Development Applications and Building Permits (cleared permits since 2017). An application is a proposal: it may change, be refused or never be built. Contains information licensed under the Open Government Licence – Toronto. Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Toronto. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.
Lot
- Street frontage
- 28.47 ft8.7 m
- Depth
- 132.73 ft40.5 m
The record marks this lot irregular, so its area is not the frontage multiplied by the depth. It is not given here. Confirm with a survey before you buy.
Source: the MLS® listing record.
Land transfer tax on this home
- Ontario land transfer tax
- $58,975
- Toronto municipal land transfer tax
- $58,975
- Total land transfer tax
- $117,950
- First-time buyer rebates (Ontario up to $4,000 + Toronto up to $4,475)
- −$8,475
- Total for first-time buyers
- $109,475
See how this is worked out
- 0.5% on the first $55,000
- $275
- 1.0% from $55,000 to $250,000
- $1,950
- 1.5% from $250,000 to $400,000
- $2,250
- 2.0% from $400,000 to $2,000,000
- $32,000
- 2.5% from $2,000,000 to $2,900,000
- $22,500
- Ontario total
- $58,975
Toronto’s municipal tax uses the same brackets at this price, so it adds another $58,975.
An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.
Schools
Nearest schools
Straight-line distances. Check catchments with the board.
ElementaryEQAO average 2024–25
- Winchester Junior and Senior Public SchoolToronto DSBPublic · grades JK–8 · French Immersion77%Grade 6 average150 m
- Our Lady of Lourdes Catholic SchoolToronto CDSBCatholic · grades JK–866%Grade 6 average400 m
- Sprucecourt Junior Public SchoolToronto DSBPublic · grades JK–858%Grade 6 average500 m
- École élémentaire Gabrielle-RoyConseil scolaire ViamondeFrench-language public · grades JK–696%Grade 6 average1 km
SecondaryGrade 9 math 2024–25
- St Martin Catholic School (St.Martin)Toronto CDSBCatholic · grades 9–12—500 m
- Jarvis Collegiate InstituteToronto DSBPublic · grades 9–1234%Grade 9 math600 m
- Collège français secondaireConseil scolaire ViamondeFrench-language public · grades 9–1286%Grade 9 math700 m
- Msgr Fraser College (Isabella Campus)Toronto CDSBCatholic · grades 9–12—750 m
EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.
Searches this home is in
Keep looking
The ledger
What it costs to own
Worked out for this home. Change any number.
A month, all in
$14,260
- Mortgage$13,231
- Property tax$1,029
A planning figure, not a quote.
Land transfer tax
$117,950
$109,475 for first-time buyers; Toronto adds its own tax.
Rent, similar homes
$3,950
a month, median asking rent of 405 similar homes in Toronto.
Community
Who lives around it
Similar homes
You might also like
For sale nearby at a similar price.
Shemeer AhmadVALERY REAL ESTATE INC.
Want to see it this week?
Ask me anything about this home, or what fair looks like nearby.