29 Winchester Street
Cabbagetown-South St. James Town · Toronto, ON M4X 1A6
Listing brokerage: ROYAL LEPAGE TERREQUITY SW REALTY
Asking price
$2,900,000
Key facts
- MultiplexProperty type
- 4Bedrooms
- 4Bathrooms
- 4 spacesParking
- 3,250 sq ftLiving space
- 28.47 ftLot frontage
- Oct 23, 2026Listed
- 17 daysOn market
- C14111438MLS® number
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.
Price history
- Listed$2,900,000
Location
29 Winchester Street, Toronto
Schools & transit
School locations and boards shown from open data. We do not publish rankings; any future scores will be sourced, dated and shown factually.
Nearby schools
- Winchester Junior and Senior Public SchoolToronto DSB · Elementary · 139 m in a straight lineBoundary data unavailable for this board — we don't guess catchment lines.
- Our Lady of Lourdes Catholic SchoolToronto CDSB · Elementary · 412 m in a straight lineBoundary data unavailable for this board — we don't guess catchment lines.
- St Martin Catholic School (St.Martin)Toronto CDSB · Secondary · 460 m in a straight lineBoundary data unavailable for this board — we don't guess catchment lines.
Nearby transit
Lines nearby: 65, 94, 306, 365, 506
- Parliament St at Winchester StTTC · 89 m in a straight line · about 1 min walk (estimate) · 65, 94, 365
- Parliament St at Carlton StTTC · 175 m in a straight line · about 2 min walk (estimate) · 65, 306, 365, 506
- Carlton St at Ontario StTTC · 193 m in a straight line · about 2 min walk (estimate) · 94, 306, 506
Estimated commute
- Downtown Mississauga (Square One)~91 minestimate
- Downtown Toronto (Union Station)~17 minestimate
- Toronto Pearson Airport~81 minestimate
How is the commute estimated?
Estimate only. A coarse model from straight-line distance and an average transit speed — not a live routed trip. Actual times vary with schedules, transfers and traffic.
Sources
- Contains information licensed under the Open Government Licence – Ontario. Source: Ontario Ministry of Education.
- Contains information licensed under the Open Government Licence – Toronto.
MLS® #C14111438
Last updated Oct 27, 2026
MLS®, Multiple Listing Service®, and the associated logos are owned by The Canadian Real Estate Association (CREA)/the applicable board and identify the quality of services provided by real estate professionals who are members.
Listing data is provided under licence by the Toronto Regional Real Estate Board and is deemed reliable but not guaranteed accurate.