29 Winchester St
Cabbagetown-South St. James Town, Toronto, Ontario M4X 1A6
- Bedrooms
- 3+1
- Bathrooms
- 4
- Size
- 3,000–3,500sq ft
- Per sq ft
- $892at the range’s middle
- Lot
- 28.47 x 132.73 ft
- Tax a year
- $12,3542026 tax year
- Built
- 100+
- Parking
- 4none
- Days on market
- Members
The brief
About 29 Winchester St
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.
Insights
Condition Score
Good78/1002 documented update signals
Source: Listing age, structured features and disclosed update language; not an inspection.
Cashflow Quality
Shortfall5/100−$10,310/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Source: Median of 404 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 home
Key facts
- Tax
- $12,354 / 2026
- MLS® number
- C14111438
- Board
- TRREB MLS®
- Property Type
- Fourplex
- Building Age
- 100+
- Days on market
- Size
- 3000-3500 sqft
- Lot Size
- 28.47 x 132.73 ft
- Listed on
- Parking
- None, 4 Parking
Property details
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
Additional
- Roof
- Asphalt Shingle, Metal
- Fireplace
- Yes
- Pool
- None
- Den
- Yes
- Family room
- Yes
- Extras
- Sale includes all existing appliances and fixtures, excluding tenants personal effects. 4x fridges, 4 stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical(owned), HWT (rental), 4 fireplaces (as-is), 4x dishwashers). Full list of renovations / improvements included with attachments.
Rooms
| Room | Size | Features | Level |
|---|---|---|---|
| Living | 4.7 × 7.04 m | Bay Window, hardwood floor, Combined W/Dining | Main |
| Kitchen | 2.16 × 4.37 m | Pass Through, Tile Floor, W/O To Balcony | Main |
| Family | 2.97 × 4.98 m | hardwood floor, Window | Main |
| Br | 4.65 × 4.04 m | Broadloom, Window, Double Closet | Main |
| Living | 4.65 × 7.09 m | Laminate, Bay Window, Combined W/Dining | 2nd |
| Kitchen | 2.16 × 2.37 m | Laminate, W/O To Balcony, Window | 2nd |
| Family | 2.97 × 4.98 m | Laminate, Window, Pass Through | 2nd |
| Br | 2.95 × 4.01 m | hardwood floor, Closet, Window | 2nd |
| Living | 3.91 × 5.05 m | W/O To Terrace, hardwood floor, Combined W/Dining | 3rd |
| Kitchen | 1.68 × 4.75 m | Laminate, Eat-In Kitchen, Window | 3rd |
| Br | 3.28 × 4.8 m | Laminate, Window, Closet | 3rd |
| Living | 4.7 × 7.04 m | Laminate, Window, Combined W/Dining | Lower |
| Kitchen | 2.13 × 3.96 m | Open Concept, Window, Tile Floor | Lower |
| Family | 2.97 × 4.98 m | W/O To Yard, Tile Floor | Lower |
| Br | 3.05 × 4.11 m | Broadloom, Window, Closet | Lower |
Listing history
Buy/sell history for 29 Winchester St, Toronto, Ontario
Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $2,900,000 | N/A | For Sale | C14111438 |
Members see the full history. Prices are hidden from signed-out visitors.
The numbers
Mortgage Calculator
Plan with the current asking price
CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.
Mortgage Details
4.8% · 5-year term · 25-year amortization · 20% down
- Total down payment
- $580,000
- Total mortgage amount
- $2,320,000
- Total interest payment
- $1,649,300
- Total purchase cost
- $4,549,300
- Mortgage payment
- $13,231/mo
Cash Flow Analysis
If you rented this home out at 20% down
Break-even down payment
82%Monthly carrying cost
$14,260- Rent $3,950
- Shortfall $10,310
Rental income opens at $3,950, the median asking rent of 404 comparable homes for lease in Toronto. Type over it with the rent you expect. This is a planning tool, not advice.
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.
Estimate
Estimated value requires sign in
Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.
The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Yossi Kaplan, MBA, Salesperson for a full comparative market analysis.
Comparable sales
Comparable sales require sign in
Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.
The land
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 and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
Water and conservation4
- Not in Toronto and Region Conservation Authority’s mapped regulated areaAt the address
- No mapped wetland within 120 m120 m
- No water-supply well recorded within 250 m41 test or monitoring holes also recorded.250 m
- Groundwater recorded about 12.4 m below ground nearbyThe middle water level in the well records within 500 m (180 records). It changes with the season and from spot to spot.500 m
Toronto and Region Conservation Authority · Province of Ontario open data
Planning and building activity5
- Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasAt the address
- 69 building permits issued within 250 m in the last 2 years250 m
- 2 open development applications within 250 mAn application is a proposal: it may change, be refused or never be built.250 m
- Nearest airport: 3.9 km3.9 km
- Mapped parcel: about 4,050 sq ftMeasured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.At the address
Province of Ontario open data · Municipal building permits · Municipal development applications · toronto.parcels
Around the home2
- Nearest rail line: 940 m940 m
- A trail on the Ontario trail network within 1 km1 km
Province of Ontario open data
Environmental records4
- No licensed pit or quarry within 2 km2 km
- No recorded oil, gas or salt well within 250 m250 m
- No facility within 1 km reports pollutant releases to Environment CanadaThe nearest is Enwave Energy Corporation — Walton Street Steam Plant, 1.5 km away. Only facilities above the inventory’s reporting thresholds are listed.1 km
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km
Province of Ontario open data · Government of Canada open data
Power and internet3
- Electricity is distributed here by Toronto Hydro-Electric System LimitedAt the address
- Wired internet 50/10 Mbps or faster is listed at this locationFixed 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.At the address
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre 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.Area-wide
Ontario Energy Board · Innovation, Science and Economic Development Canada
Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Toronto and Region Conservation Authorityor the record’s publisher.
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.
Heritage and ravine protection
- On the Heritage Register — Part V, by-law 325-2008
- In the Cabbagetown Northwest Heritage Conservation District, by-law 325-2008
- Not in the mapped ravine protection area
What this means: 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.
City of Toronto Heritage Register, Heritage Conservation Districts and the Ravine and Natural Feature Protection by-law, read at this address from the City’s maps. Contains information licensed under the Open Government Licence – Toronto.
Zoning
Zone
R (d1.0) (x881)By-law
569-2013Municipality
Toronto1 d1.0
Density: floor area is capped at 1.0 times the lot area.
2 x881
Site-specific exception 881: this site has rules of its own, written in the by-law.
3 Where this is written
Chapter 10, section 10.10 of By-law 569-2013 · Exception 900.2.10(881)
4 What that means in practice
These are the zone’s rules, not permission for this lot. What can be built also depends on the exceptions, overlays and setbacks that apply here. Confirm with the City before you plan.
City of Toronto Zoning By-law 569-2013, read at this address from the City’s zoning map. Open the City’s zoning map. Contains information licensed under the Open Government Licence – Toronto.
Permit history
No building permits on file at this address.
Signals around this home
Changing nearby. 6 open development applications within 800 m of this home.
509 PARLIAMENT STOfficial plan or zoning amendmentOMB Appeal
Zoning By-law Amendment law to permit the development of site for a 10-storey mixed-use building (38.6 metres) with retail at-grade (278 square metres) and 60 dwelling units. The western (Parliament Street) elevation of the existing 1½ storey listed heritage building at 509 Parliament Street is proposed to be retained. The proposal has been revised and removed the property at 505 Parliament Street from the original development proposal.
130 m away505 PARLIAMENT STOfficial plan or zoning amendmentOMB Appeal
Zoning By-law Amendment law to permit the development of site for a 10-storey mixed-use building (38.6 metres) with retail at-grade (278 square metres) and 60 dwelling units. The western (Parliament Street) elevation of the existing 1½ storey listed heritage building at 509 Parliament Street is proposed to be retained. The proposal has been revised and removed the property at 505 Parliament Street from the original development proposal.
140 m away405 SHERBOURNE STSite planApplication Received
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 Sherbourne and Bleecker Streets.
320 m away383 SHERBOURNE STSite planAppeal Received
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. incorporating 378 units, and 1,384 sq. m. of indoor and outdoor amenity space.
320 m away240 WELLESLEY ST ESite planUnder Review
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 a 9-storey building with 65 dwelling units, including 27 replacement rental units. A 2,209 square metre public park and enhanced open spaces with a range of programming across the site are proposed. A new public street, which would extend Rose Avenue through to the northern boundary of the site and a series of private streets across the site are proposed. The proposal includes modifications to the layout and uses within the existing buildings to create new amenity and non-residential spaces, which would result in the loss of 27 existing rental dwelling units that would be replaced in the new 9-storey building. The remaining 2,197 rental dwelling units are proposed to be retained, along with 2,986 square metres of existing non-residential space. The existing and proposed buildings would result in 3,182 dwelling units with a gross floor area of 224,675 square metres, and 8,756 square metres of non-residential gross floor area, for a total gross floor area of 233,431 square metres across the site.
330 m away240 WELLESLEY ST EPlan of subdivisionUnder Review
Draft Plan of Subdivision to establish two development blocks with pedestrian and vehicular connections into and through the subject site. A new public park and publicly-accessible open spaces, framed by the addition of new buildings to be incorporated enhance the pedestrian experience of St. James Town neighbourhood.
330 m away
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.
The market
Market area · filters apply to the charts below
The street
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.
Schools nearby
| Elementary | Type | Distance | EQAO average 2024–25 |
|---|---|---|---|
| Winchester Junior and Senior Public SchoolToronto DSB | Public · grades JK–8 · French Immersion | 150 m | 77%Grade 6 average |
| Our Lady of Lourdes Catholic SchoolToronto CDSB | Catholic · grades JK–8 | 400 m | 66%Grade 6 average |
| Sprucecourt Junior Public SchoolToronto DSB | Public · grades JK–8 | 500 m | 58%Grade 6 average |
| École élémentaire Gabrielle-RoyConseil scolaire Viamonde | French-language public · grades JK–6 | 1 km | 96%Grade 6 average |
| Secondary | Type | Distance | Grade 9 math 2024–25 |
|---|---|---|---|
| St Martin Catholic School (St.Martin)Toronto CDSB | Catholic · grades 9–12 | 500 m | — |
| Jarvis Collegiate InstituteToronto DSB | Public · grades 9–12 | 600 m | 34%Grade 9 math |
| Collège français secondaireConseil scolaire Viamonde | French-language public · grades 9–12 | 700 m | 86%Grade 9 math |
| Msgr Fraser College (Isabella Campus)Toronto CDSB | Catholic · 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.
The verdict
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