29 Winchester Street, Toronto, ON M4X 1A6
Cabbagetown-South St. James Town · C08 · M4X 1A6
$2,900,000
$967 / sq ft1 weeks on market
- Bedrooms
- 3+1
- Bathrooms
- 4
- Interior
- 3,000 sf
- Parking
- 4
- Lot
- 28.47 × 132.73 ft
- Age
- 100+ years
What's special
- 4 parking spaces
- Wall unit(s)
- Basement apartment
- Fireplace
About this property
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.
Rooms
15 rooms. Dimensions as published by the listing brokerage.
| Room | Level | Dimensions | Features |
|---|---|---|---|
| Living Room | Main | 7.04 × 4.70 m23.1 × 15.4 ft | Bay Window · Hardwood Floor · Combined w/Dining |
| Kitchen | Main | 4.37 × 2.16 m14.3 × 7.1 ft | Pass Through · Tile Floor · W/O To Balcony |
| Family Room | Main | 4.98 × 2.97 m16.3 × 9.7 ft | Hardwood Floor · Window |
| Bedroom | Main | 4.04 × 4.65 m13.3 × 15.3 ft | Broadloom · Window · Double Closet |
| Living Room | Second | 7.09 × 4.65 m23.3 × 15.3 ft | Laminate · Bay Window · Combined w/Dining |
| Kitchen | Second | 2.37 × 2.16 m7.8 × 7.1 ft | Laminate · W/O To Balcony · Window |
| Family Room | Second | 4.98 × 2.97 m16.3 × 9.7 ft | Laminate · Window · Pass Through |
| Bedroom | Second | 4.01 × 2.95 m13.2 × 9.7 ft | Hardwood Floor · Closet · Window |
| Living Room | Third | 5.05 × 3.91 m16.6 × 12.8 ft | W/O To Terrace · Hardwood Floor · Combined w/Dining |
| Kitchen | Third | 4.75 × 1.68 m15.6 × 5.5 ft | Laminate · Eat-in Kitchen · Window |
| Bedroom | Third | 4.80 × 3.28 m15.7 × 10.8 ft | Laminate · Window · Closet |
| Living Room | Lower | 7.04 × 4.70 m23.1 × 15.4 ft | Laminate · Window · Combined w/Dining |
| Kitchen | Lower | 3.96 × 2.13 m13.0 × 7.0 ft | Open Concept · Window · Tile Floor |
| Family Room | Lower | 4.98 × 2.97 m16.3 × 9.7 ft | W/O To Yard · Tile Floor |
| Bedroom | Lower | 4.11 × 3.05 m13.5 × 10.0 ft | Broadloom · Window · Closet |
Features
- None
Property details
Property
- Property type
- multiplex
- Bedrooms
- 3 + 1
- Bathrooms
- 4
- Interior size
- 3,000 sq ft
- Year built
- 100+
- Lot size
- 28.47 × 132.73 ft
- Possession
- TBD
Interior
- Basement
- Apartment
- Heating
- Baseboard · Electric
- Cooling
- Wall Unit(s)
- Fireplaces
- 1
- Exposure
- South
Exterior & services
- Construction
- Brick
- Parking spaces
- 4
- Sewer
- Sewer
Costs
- List price
- $2,900,000
- Property taxes
- $12,354 / year (2026)
- Price per sq ft
- $967
- Rental items
- HWT 34.52/month
Listing
- MLS® number
- C14111438
- Status
- For sale
- Listed
- October 23, 2026
- Days on market
- 12
- Last updated
- October 27, 2026
- Listing brokerage
- ROYAL LEPAGE TERREQUITY SW REALTY
Price & sale history
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Before you make an offer
What this home costs beyond the asking price, and how that price compares to what else is on the market.
How this price compares
This home is priced above most comparable listings — about 88% of comparable multiplex listings in Toronto are asking less.
- This home
- $967 / sq ft
- Comparable median
- $820 / sq ft
Based on 95 comparable active multiplex listings in Toronto. These are asking prices, not sale prices.
Mortgage estimate
- Principal & interest
- $12,827.68
- Property tax (est.)
- $1,029.48
- Estimated monthly
- $13,857
Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.
Land transfer tax
Payable on closing, on top of the purchase price.
- Ontario
- $58,975
- Toronto municipal
- $58,975
- Total due on closing
- $117,950
An estimate on the asking price of $2,900,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.
Listing courtesy of ROYAL LEPAGE TERREQUITY SW REALTY. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.
Comparable sales nearby
What similar homes in this area actually sold for.
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