Forgot password Extend Verify Contact

29 Winchester Street
Cabbagetown-South St. James Town Toronto M4X 1A6

$2,900,000
Residential Freehold beds: 3+1 baths: 4.0

Main Photo: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 1: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 2: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 3: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 4: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 5: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 6: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 7: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 8: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 9: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 10: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 11: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 12: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 13: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 14: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 15: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 16: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 17: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 18: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 19: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 20: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 21: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 22: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 23: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 24: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 25: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 26: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 27: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 28: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 29: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 30: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 31: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 32: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 33: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 34: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 35: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 36: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 37: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 38: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 39: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 40: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 41: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 42: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 43: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 44: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 45: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 46: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 47: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 48: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 49: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Photo 50: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C14111438
Bedrooms:
3+1
Bathrooms:
4
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.
Under Contract:
Hot Water Tank-Electric
Property Type:
Residential Freehold
Property Sub Type:
Fourplex
Home Style:
3-Storey
Approx. Age:
100+
Total Approx Floor Area:
3000-3500
Lot Depth:
132'8¾"
Lot Frontage:
28'6"
Lot Shape:
Irregular
Direction Faces:
South
Bedrooms:
3+1
Bathrooms:
4.0
Water supply:
Municipal
Kitchens:
4
Kitchens in Basement:
1
Bedrooms Above Grade:
3
Bedrooms Below Grade:
1
Kitchens Above Grade:
3
Rooms Above Grade:
15
Heating type:
Baseboard
Heating Fuel:
Electric
Foundation:
Unknown
Roof:
Asphalt Shingle, Metal
Basement:
Apartment
Fireplace/Stove:
Yes
Garage:
None
Garage Spaces:
0.0
Other Structures:
None
Parking Features:
Lane, Private
Parking Spaces:
4
Total Parking Spaces:
4.0
Family Room:
Yes
Possession Details:
TBD
Pool:
None
HST Applicable To Sale Price:
Not Subject to HST
Taxes:
$12,353.71 / 2026
Assessment:
$- / -
Toronto
Toronto C08
Cabbagetown-South St. James Town
Library, Park, Place Of Worship, Public Transit, School
None
None
HWT 34.52/month
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.
Brick
No
None
Floor
Type
Size
Other
Main
Living Room
23'1" × 15'5"
Bay Window, Hardwood Floor, Combined w/Dining
Main
Kitchen
14'4" × 7'1"
Pass Through, Tile Floor, W/O To Balcony
Main
Family Room
16'4" × 9'9"
Hardwood Floor, Window
Main
Bedroom
15'3" × 13'3"
Broadloom, Window, Double Closet
Second
Living Room
23'3" × 15'3"
Laminate, Bay Window, Combined w/Dining
Second
Kitchen
7'9" × 7'1"
Laminate, W/O To Balcony, Window
Second
Family Room
16'4" × 9'9"
Laminate, Window, Pass Through
Second
Bedroom
13'2" × 9'8"
Hardwood Floor, Closet, Window
Third
Living Room
16'7" × 12'10"
W/O To Terrace, Hardwood Floor, Combined w/Dining
Third
Kitchen
15'7" × 5'6"
Laminate, Eat-in Kitchen, Window
Third
Bedroom
15'9" × 10'9"
Laminate, Window, Closet
Lower
Living Room
23'1" × 15'5"
Laminate, Window, Combined w/Dining
Lower
Kitchen
13' × 7'
Open Concept, Window, Tile Floor
Lower
Family Room
16'4" × 9'9"
W/O To Yard, Tile Floor
Lower
Bedroom
13'6" × 10'
Broadloom, Window, Closet
UFFI:
No
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Wall Unit(s)
Central Vacuum:
No
Seller Property Info Statement:
No
Date Listed:
Oct 23, 2026
Original Price:
Previous Price:
  • Photo 1: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 1 of 50
  • Photo 2: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 2 of 50
  • Photo 3: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 3 of 50
  • Photo 4: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 4 of 50
  • Photo 5: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 5 of 50
  • Photo 6: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 6 of 50
  • Photo 7: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 7 of 50
  • Photo 8: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 8 of 50
  • Photo 9: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 9 of 50
  • Photo 10: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 10 of 50
  • Photo 11: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 11 of 50
  • Photo 12: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 12 of 50
  • Photo 13: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 13 of 50
  • Photo 14: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 14 of 50
  • Photo 15: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 15 of 50
  • Photo 16: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 16 of 50
  • Photo 17: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 17 of 50
  • Photo 18: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 18 of 50
  • Photo 19: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 19 of 50
  • Photo 20: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 20 of 50
  • Photo 21: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 21 of 50
  • Photo 22: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 22 of 50
  • Photo 23: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 23 of 50
  • Photo 24: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 24 of 50
  • Photo 25: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 25 of 50
  • Photo 26: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 26 of 50
  • Photo 27: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 27 of 50
  • Photo 28: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 28 of 50
  • Photo 29: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 29 of 50
  • Photo 30: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 30 of 50
  • Photo 31: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 31 of 50
  • Photo 32: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 32 of 50
  • Photo 33: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 33 of 50
  • Photo 34: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 34 of 50
  • Photo 35: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 35 of 50
  • Photo 36: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 36 of 50
  • Photo 37: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 37 of 50
  • Photo 38: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 38 of 50
  • Photo 39: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 39 of 50
  • Photo 40: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 40 of 50
  • Photo 41: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 41 of 50
  • Photo 42: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 42 of 50
  • Photo 43: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 43 of 50
  • Photo 44: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 44 of 50
  • Photo 45: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 45 of 50
  • Photo 46: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 46 of 50
  • Photo 47: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 47 of 50
  • Photo 48: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 48 of 50
  • Photo 49: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 49 of 50
  • Photo 50: 29 Winchester Street in Toronto: Cabbagetown-South St. James Town House for sale (Toronto C08)  : MLS®# C14111438
    Photo 50 of 50
Listed by ROYAL LEPAGE TERREQUITY SW REALTY
Data was last updated October 24, 2026 at 04:15 AM (UTC)
JARROD  ARMSTRONG
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.