For sale · Fourplex · 3-Storey
29 Winchester Street.
Cabbagetown-South St. James Town, Toronto, ON M4X 1A6
Balanced market
House market in Cabbagetown-South St. James Town. Sales and new listings are roughly in step, so neither side has a clear edge. Homes here sell in about 38 days. Market data
Sales-to-new-listings ratio, last 3 months: 41%
Months of supply: 4.7
What it means
- Balanced market in Cabbagetown-South St. James Town: houses take about 38 days to sell.
- About 4.7 months of houses for sale in Cabbagetown-South St. James Town at the current pace of sales.
At a glance
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.
Home details
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The homeproperty type, style, size, heating
- Property type
- Fourplex
- Style
- 3-Storey
- Size
- 3,000–3,500 sq ft
- Heating
- Baseboard
- Cooling
- Wall Unit(s)
- Basement
- Apartment
- Year built
- 100+
- Lot size
- 28.47 × 132.73 feet
- Possession
- Tbd
Parking and storageparking, garage
- Parking
- 4
- Garage
- None
Fees and taxesproperty taxes, price per sq ft
- Property taxes
- $12,354 (2026)
- Price per sq ft
- $892
Rooms15 rooms with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Bedroom | Second | 4.01 × 2.95 m | hardwood floor · closet · window |
| Kitchen | Main | 4.37 × 2.16 m | pass through · tile floor · w/o to balcony |
| Family Room | Lower | 4.98 × 2.97 m | w/o to yard · tile floor |
| Family Room | Second | 4.98 × 2.97 m | laminate · window · pass through |
| Bedroom | Third | 4.8 × 3.28 m | laminate · window · closet |
| Living Room | Third | 5.05 × 3.91 m | w/o to terrace · hardwood floor · combined w/dining |
| Kitchen | Third | 4.75 × 1.68 m | laminate · eat-in kitchen · window |
| Kitchen | Second | 2.37 × 2.16 m | laminate · w/o to balcony · window |
| Living Room | Lower | 7.04 × 4.7 m | laminate · window · combined w/dining |
| Living Room | Second | 7.09 × 4.65 m | laminate · bay window · combined w/dining |
| Family Room | Main | 4.98 × 2.97 m | hardwood floor · window |
| Bedroom | Lower | 4.11 × 3.05 m | broadloom · window · closet |
| Living Room | Main | 7.04 × 4.7 m | bay window · hardwood floor · combined w/dining |
| Bedroom | Main | 4.04 × 4.65 m | broadloom · window · double closet |
| Kitchen | Lower | 3.96 × 2.13 m | open concept · window · tile floor |
What is includedAppliances and fixtures
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.
What it could cost each month
— a month, estimated
With 20% down. Includes property tax. Estimate only.
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- Mortgage—
- Mortgage insurance (added to loan)—
- Property tax—
Down payment —. Estimate only, using Canadian semi-annual compounding; your lender's numbers will differ.
Sale and listing history
Past sales at this address are for members
A free account shows past sale prices and dates, sold prices nearby, and alerts when similar homes list.
The area
Listing brokerage · MLS® C14111438Royal Lepage Terrequity Sw RealtyData last updated Oct 27, 2026 5:43 pm.
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