MLS® listing
29 Winchester Street: fourplex for sale
$3,400,000
From the listing brokerage
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.
Facts on the listing
| Square feet | 3000-3500 |
|---|---|
| Approximate age | 100+ |
| Style | 3-Storey |
| Basement | Apartment |
| Lot width | 28.47 |
| Lot depth | 142 |
| Lot measured in | Feet |
| Faces | South |
| Parking spaces | 4 |
| Garage | None |
| Heating | Baseboard |
| Cooling | Wall Unit(s) |
| Kitchens | 4 |
| Property tax | $12,354 |
| Tax year | 2026 |
| Parking | Lane, Private, Reserved/Assigned |
| Interior features | None |
| Features | Library, Park, Place Of Worship, Public Transit, School |
Listing courtesy of ROYAL LEPAGE TERREQUITY SW REALTY. MLS® C13578164.
About this fourplex
29 Winchester Street is a 4 bedroom fourplex in TRREB's Cabbagetown-South St. James Town community in Toronto, listed for sale at $3,400,000. The listing shows 4 bathrooms and 3000-3500 square feet. The style is given as 3-storey. The lot is listed as 28.47 by 142 feet. The listing gives the basement as apartment. It comes with 4 parking spaces according to the listing. The nearest main intersection given is Winchester & Parliament. The age is listed as 100+ years.
These details come from the listing brokerage through TRREB's MLS® System. Room sizes, the lot, the taxes and what is included in the sale should all be confirmed before an offer is firm.
What it costs to buy 29 Winchester Street
At the asking price of $3,400,000, a buyer pays two land transfer taxes on closing: the Ontario tax and the City of Toronto's municipal tax. Both apply to every home inside the City.
| Asking price | $3,400,000 |
|---|---|
| Ontario land transfer tax | $71,475 |
| Toronto municipal land transfer tax | $79,075 |
| Both taxes | $150,550 |
| First-time buyer relief, if you qualify | up to $8,475 |
| Minimum down payment | $680,000 |
The down payment figure is the federal minimum: 20 percent, because a home at $1.5 million or more cannot carry mortgage default insurance. A lender can ask for more. These figures use the asking price, so they change if you pay more or less. The rates above $2,000,000 used here are the ones for a home with one or two single family residences. A property with more units is taxed differently. Legal fees, title insurance and adjustments are extra: ask your lawyer for a written quote. This is general information, not legal or tax advice. Confirm the figures with a lawyer or accountant. You can change the price in our land transfer tax calculator and our mortgage calculator.
What it costs to own each month
| Property tax (2026) | $12,354 a year, about $1,029 a month |
|---|
That is before a mortgage payment, home insurance and utilities. The listing shows no monthly maintenance fee, so upkeep of the building and the lot is the owner's own cost.
What to check before you make an offer
- Book a home inspection. An inspector looks at the roof, foundation, wiring, plumbing and heating. The listing gives the heating as baseboard.
- Have a lawyer search the title. A title search shows mortgages, liens and easements registered against the property. Ask whether a survey exists and whether it matches the lot on the listing, 28.47 by 142 feet.
- Ask about permits. Ask which renovations had building permits and whether those permits were closed. The listing shows 4 kitchens. If there is a second unit, ask whether it meets the municipality's rules for one.
- Confirm what is included. Appliances, light fixtures and window coverings are included only if the agreement says so. Ask whether the water heater or furnace is rented.
- Get your financing in writing. A lender looks at the property tax and heating costs as well as the price.
- See it in person. The listing has a virtual tour, but photos do not show noise, light at different hours or the state of the street and the homes beside it.
Our first-time home buyer guide and our page for buyers walk through each step. This is general information, not legal advice. Confirm the details with a lawyer.
Toronto neighbourhoods and prices
Our neighbourhood guides set out TRREB prices by home type, transit and the housing in each area we cover.
Toronto neighbourhood guides · Toronto house prices · All Toronto homes for sale
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Questions about 29 Winchester Street
How much is land transfer tax on 29 Winchester Street?
At the asking price of $3,400,000 the Ontario tax is $71,475 and the Toronto tax is $79,075, $150,550 in total. A first-time buyer who qualifies can get up to $8,475 back. Confirm the final figures with your lawyer.
What is the minimum down payment for 29 Winchester Street?
$680,000 at the asking price of $3,400,000, under the federal minimum down payment rules. A lender may require more.
How much is the property tax on 29 Winchester Street?
The listing shows $12,354 a year for 2026, about $1,029 a month.
How do I book a showing for 29 Winchester Street?
Use the form on this page or call us. Quote MLS® C13578164. We will confirm the listing is still available and arrange a time with the listing brokerage.
Is 29 Winchester Street still for sale?
This page is refreshed from TRREB's MLS® System through the day. If the listing sells or is withdrawn the page says so. Contact us to confirm before you make plans.
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