Cabbagetown-South St. James Town · C08 · M4X 1A6
$3,400,000
$1,133 / sq ft1 months on market
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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.
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What this home costs beyond the asking price, and how that price compares to what else is on the market.
This home is priced above most comparable listings — about 95% of comparable multiplex listings in Toronto are asking less.
Based on 96 comparable active multiplex listings in Toronto. These are asking prices, not sale prices.
Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.
Payable on closing, on top of the purchase price.
An estimate on the asking price of $3,400,000. 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.