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For sale · Fourplex · 3-Storey

29 Winchester Street.

Cabbagetown-South St. James Town, Toronto, ON M4X 1A6

On the market6 days
MLS® C14111438Courtesy of Royal Lepage Terrequity Sw Realty
Bedrooms3+1Plus 1 more
Bathrooms4
Lot28.47 x 132.73 ftFrontage by depth, as listed
Parking4None

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

Property taxes$12,354 / year
BasementApartment
Approximate age100+ years
Size3,000–3,500 sq ft

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
RoomLevelSizeFeatures
BedroomSecond4.01 × 2.95 mhardwood floor · closet · window
KitchenMain4.37 × 2.16 mpass through · tile floor · w/o to balcony
Family RoomLower4.98 × 2.97 mw/o to yard · tile floor
Family RoomSecond4.98 × 2.97 mlaminate · window · pass through
BedroomThird4.8 × 3.28 mlaminate · window · closet
Living RoomThird5.05 × 3.91 mw/o to terrace · hardwood floor · combined w/dining
KitchenThird4.75 × 1.68 mlaminate · eat-in kitchen · window
KitchenSecond2.37 × 2.16 mlaminate · w/o to balcony · window
Living RoomLower7.04 × 4.7 mlaminate · window · combined w/dining
Living RoomSecond7.09 × 4.65 mlaminate · bay window · combined w/dining
Family RoomMain4.98 × 2.97 mhardwood floor · window
BedroomLower4.11 × 3.05 mbroadloom · window · closet
Living RoomMain7.04 × 4.7 mbay window · hardwood floor · combined w/dining
BedroomMain4.04 × 4.65 mbroadloom · window · double closet
KitchenLower3.96 × 2.13 mopen 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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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

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The area

Listing brokerage · MLS® C14111438Royal Lepage Terrequity Sw RealtyData last updated Oct 27, 2026 5:43 pm.

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The information provided herein is deemed reliable but is not guaranteed accurate by TRREB or its members. It is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. 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. Used under licence.

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