Space
Finished area and layout
- Square Feet
- 3,000-3,500 sqft
- Bedrooms
- 4
- Bathrooms
- 4





Property Snapshot
Finished area and layout
Type, style and structure
This 4-bedroom, 4-bathroom fourplex in Toronto offers 3,000-3,500 sqft of square feet on a 28.5 x 142 FT lot. 3 storeys. The home features wall unit(s), a apartment basement, a fireplace. Highlights include a none pool.
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. 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.
We can help you find properties matching your criteria, including exclusive listings not yet on the market.
Save favorites, track showings, view sold data & get market alerts — Free account — 100% free
Land, frontage and setting
Price, taxes and monthly charges
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.
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.
Winchester & Parliament
Listed by ROYAL LEPAGE TERREQUITY SW REALTY
The listing data displayed is deemed reliable but is not guaranteed accurate by the Canadian Real Estate Association (CREA). The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. 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.
Not A Dream Realty Inc., Brokerage is a member of CREA and the Toronto Regional Real Estate Board. All information should be independently verified. © 2026 Not A Dream Realty Inc., Brokerage. All rights reserved.
Important notice: This website provides free general real estate information for consumer convenience. Listing data, maps, photos, descriptions, measurements, room sizes, lot sizes, taxes, prices, availability, school/market information, estimates, and other property details may be incomplete, delayed, approximate, generated from third-party sources, or changed without notice. We do not warrant that any information is complete, current, or error-free, and we have not independently verified all information shown. Do not rely on this website alone when making a purchase, sale, lease, financing, investment, tax, legal, valuation, or insurance decision. Verify all material facts directly with the listing brokerage, real estate board, municipality, lender, insurer, lawyer, inspector, surveyor, or other qualified professional, as applicable. Nothing on this website is an appraisal, market valuation, price opinion, professional recommendation, or legal, financial, tax, engineering, inspection, or investment advice. To the fullest extent permitted by law, the website operator, brokerage, and their representatives are not responsible for losses or damages arising from errors, omissions, delays, changes, or reliance on information displayed here.
Connect with a local real estate professional for a private showing or more details.
Listed by ROYAL LEPAGE TERREQUITY SW REALTY · MLS# C14111438
Configured mortgage defaults and jurisdiction rules are required before property payment estimates can be calculated.
Disclaimer: The mortgage estimates and monthly cost calculations shown above are for illustrative purposes only and should not be relied upon as financial advice. Actual mortgage rates, terms, and eligibility depend on your personal financial situation, credit history, and current market conditions. Please consult a licensed mortgage broker, financial advisor, or your bank to determine your actual affordability and mortgage costs before making any purchasing decisions.
Calculating…
Estimate from the jurisdiction's published transfer-tax rates. Consult your lawyer for exact amounts.