29 Winchester Street, Toronto, ON
Cabbagetown-South St. James Town, Toronto · MLS® C13578164
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. 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. Building financials available upon request. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.
Key facts
- Property type
- Other, 3-Storey
- MLS®
- C13578164
- Bedrooms
- 4 (3 + 1)
- Bathrooms
- 4
- Size
- 3000-3500
- Lot
- 28.47 × 142 ft
- Cross streets
- Winchester & Parliament
- Parking
- 4 parking
- Driveway
- Lane, Private, Reserved/Assigned
- Basement
- Apartment
- Kitchens
- 4 (3 + 1)
- Heating
- Baseboard
- A/C
- Wall Unit(s)
- Exterior
- Brick
- Foundation
- Unknown
- Roof
- Unknown
- Sewer
- Sewer
- Property tax
- $12,354 / 2026
- Listing brokerage
- ROYAL LEPAGE TERREQUITY SW REALTY
Rooms
laminate · eat-in kitchen · window
hardwood floor · closet · window
w/o to terrace · hardwood floor · combined w/dining
broadloom · window · closet
laminate · bay window · combined w/dining
laminate · window · combined w/dining
laminate · window · pass through
laminate · window · closet
open concept · window · tile floor
broadloom · window · double closet
bay window · hardwood floor · combined w/dining
hardwood floor · window
w/o to yard · tile floor
pass through · tile floor · w/o to balcony
laminate · w/o to balcony · window
Listed at $3,400,000, this home is tracking about 23% above a wider set of listings, though close matches were thin, so treat this as a rough read until I run a precise CMA. The number above is my independent estimate of value, not the asking price.
There are only a few closely comparable homes right here, so this is a broad read from wider listings in the area. Ask me for a precise CMA before relying on it.
Based on 8 similar homes nearby, adjusted for size, beds, and baths.Median of 8 comparable active listings, adjusted for size, beds, and baths. The city (MPAC) assessment points to about $2.63M, a close match.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, listed at $2.30M
- Size difference +$423K
- Adjusts to $2.72M
That comparable adjusts to $2.72M; the $2.76M estimate above is the median of all 8 comparables, which is steadier than any single home.This uses comparable active listings, not sold prices. Lot, condition, and finishes are my in-person call, and I can run a full CMA with recent solds.
The assigned public school is Lord Dufferin Junior and Senior Public School. EQAO is only one input, and families here also look at French Immersion, boundary, and private options, the full breakdown is below.
On location, this is a very walkable address with everyday errands close by. Parliament St at Winchester St is about a 1-minute walk away. Walkable, transit-friendly spots tend to hold value and widen your resale pool.
Total price vs nearby homes. Fair value about $2.76M, median of 8 comparables.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Renovated / rebuilt: recent work can mean fewer upfront costs, worth confirming the scope, quality, and that permits were pulled.
- Addition / added square footage: more space lifts value when it is permitted and well integrated, verify the permits.
- Tall ceilings: they transform how a home feels, worth confirming the actual heights room to room.
- Hardwood floors: quality hardwood is durable and broadly desirable.
- Transit / schools nearby: convenience and resale support, verify the exact distances and school catchment.
- Value driver
- Worth verifying
- Lifestyle
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 4 closest active listings nearby.
See all comparable homesThis home lists 13% above the area average of $926/sqft.
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
Cabbagetown-South St. James Town, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
Getting around
Very WalkableA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Most daily errands can be done on foot.
🚉 Nearest transit: Parliament St at Winchester St, about 91 m away
Within a 15-minute (1.5 km) walk.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 3.99% via Ratehub.ca (as of July 17, 2026); conventional rates run a little higher.
Mortgage amount $2,720,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $14,515
- Property tax
- $1,030
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $15,544
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $71,475
- Toronto municipal land transfer tax
- $75,475
- Estimated closing costs
- $146,950
Plus your down payment of $680,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $870,896
- Principal paid down
- $346,393
- Interest paid
- $524,503
- Balance remaining
- $2,373,607
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Income potential: the basement has a separate entrance, which often supports a rentable in-law or second suite. That can lift real rent well above the figure above and help carry the mortgage. Ask us about permitted use in this area.
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of ROYAL LEPAGE TERREQUITY SW REALTY. MLS®/PropTx.