29 Winchester Street, Toronto, ON M4X 1A6
Cabbagetown-South St. James Town, Toronto · Near Winchester & Parliament · View map
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. 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.
The home
- Type
- Fourplex
- Style
- 3-Storey
- Square footage
- 3000-3500 sq ft
- Bedrooms
- 3
- Basement bedrooms
- 1
- Bathrooms
- 4
- Kitchens
- 4
- Rooms
- 15
- Basement
- Apartment
- Lot size
- 28.5 x 132.7 ft
- Faces
- South
- Approximate age
- 100+ years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Brick
Heating & cooling
- Heating fuel
- Electric
- Heating type
- Baseboard
- Air conditioning
- Wall Unit(s)
- Fireplace
- Yes
Garage & parking
- Driveway spaces
- 4
- Total parking
- 4
- Parking features
- Lane, Private
Taxes & other
- Property taxes
- $12,354/yr
- Tax year
- 2026
- Occupancy
- Tenant
- Possession
- TBD
- Cross street
- Winchester & Parliament
- Neighbourhood
- Cabbagetown-South St. James Town
More
- Price per sq ft
- ~$892 (at 3,250 sq ft)
- MLS® number
- C14111438
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The home and its surroundings
- Library
- Park
- Place Of Worship
- Public Transit
- School
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax and Toronto municipal land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
29 Winchester Street, Toronto, ON M4X 1A6
Cabbagetown-South St. James Town, Toronto · Near Winchester & Parliament
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Listing history for 29 Winchester Street
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 29 Winchester Street
Answers come straight from this home’s MLS® listing.
How much is 29 Winchester Street listed for, and what would it cost each month?
29 Winchester Street is listed for $2,900,000. With 20% down ($580,000), the mortgage payment would be roughly $11,698 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $12,727 a month, all in. That figure is an illustration, not a quote.
Is 29 Winchester Street freehold or a condo, and is there a monthly fee?
29 Winchester Street is a fourplex in Cabbagetown-South St. James Town, Toronto. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 29 Winchester Street have?
29 Winchester Street has 3 bedrooms, plus 1 more bedroom in the basement, and 4 bathrooms. The listing gives the style as 3-storey.
Does 29 Winchester Street have a garage and parking?
The listing does not show a garage. The driveway adds 4 spaces. In total the listing counts 4 parking spaces.
Does 29 Winchester Street have a finished basement?
The listing describes the basement as apartment. It counts 1 bedroom on that level. A listing description is not proof of a legal second unit, so confirm zoning and permits with the municipality before counting on rental income.
What style of home is 29 Winchester Street?
29 Winchester Street is a fourplex. A multiplex holds two or more separate units under one roof, often bought to live in one unit and rent the others.
How big is 29 Winchester Street, and what is the lot size?
The listing puts the home between 3,000 and 3,500 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 28.5 x 132.7 ft.
How is 29 Winchester Street heated and cooled?
Heating is baseboard (electric). Cooling is wall unit(s).
What are the property taxes for 29 Winchester Street?
Property taxes are $12,354 a year (2026), or about $1,029 a month.
Where is 29 Winchester Street?
29 Winchester Street is in the Cabbagetown-South St. James Town community of Toronto. The nearest main intersection is Winchester & Parliament. The postal code is M4X 1A6.
Is 29 Winchester Street still for sale?
Yes. It is an active listing (MLS® C14111438). Listings here update from the board through the day and come down once a home sells.
What are similar properties near 29 Winchester Street asking?
Similar properties for sale nearby right now include 34 Winchester Street at $2,299,000 (4+1 bed), 21 Rose Avenue at $2,898,000 (8 bed) and 214 Gerrard Street E at $2,300,000 (10 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 29 Winchester Street sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 29 Winchester Street?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar properties nearby
More properties for sale near Cabbagetown-South St. James Town, picked by style, size and price.
Multiplex$2,299,00034 Winchester Street, Toronto4+1 bed · 5 bath · Cabbagetown-South St. James TownCourtesy of: RE/MAX NOBLECORP REAL ESTATEView home →
Fourplex$2,898,00021 Rose Avenue, Toronto8 bed · 4 bath · Cabbagetown-South St. James TownCourtesy of: SOTHEBY'S INTERNATIONAL REALTY CANADAView home →
Fourplex$2,300,000214 Gerrard Street E, Toronto10 bed · 4 bath · Cabbagetown-South St. James TownCourtesy of: RE/MAX Professionals NorthView home →Courtesy of: ROYAL LEPAGE TERREQUITY SW REALTY
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.