29 WINCHESTER STREET

Toronto (Cabbagetown-South St. James Town), , M4X1A6, Canada

$2,900,000

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.

EXTRAS: Refrigerator, Dishwasher, Stove

Virtual Tour: https://www.winsold.com/tour/462753

Last updated on : Friday 23rd of October 2026 01:05:22 PM

ADDRESS

Street : 29 WINCHESTER STREET

City : Toronto (Cabbagetown-South St. James Town)

Country : Canada

Postal Code : M4X1A6

Open in Google Map

PROPERTY SUMMARY

Property ID : C14111438

Building Type : Fourplex

Property Type : Multi-family

Bedrooms : 3 + 1

Bathrooms : 4

Parking : 4

Parking Type: No Garage

Similar Properties

Multi-family

87 QUEEN STREET WEST WEST

Springwater (Elmvale), Ontario, L0L1P0

$675,000

Beds: 3Baths: 3

property Type: Duplex

type: Sale

AVA ALWARD
2 days ago

DETAILS

Multi-family

805 ROCKWAY DRIVE

Kitchener, Ontario, N2G3B6

$699,900

Beds: 3Baths: 2

property Type: Duplex

type: Sale

CINDY CODY
1 month ago

DETAILS

Multi-family

69 MAPLE STREET

Trent Hills (Campbellford), Ontario, K0L1L0

$449,000

Beds: 3Baths: 2

property Type: Duplex

type: Sale

Nicole Matthews
3 months ago

DETAILS

Multi-family

43 PORT STREET

Brantford, Ontario, N3S1Y3

$499,900

Beds: 3Baths: 3

property Type: Triplex

type: Sale

Penny Shurr
3 months ago

DETAILS

Multi-family

48 BROCK STREET

Barrie (Sanford), Ontario, L4N2L7

$599,000

Beds: 3Baths: 2

property Type: Duplex

type: Sale

PEGGY HILL
4 days ago

DETAILS

Inquire about this property