Skip to main content
Sell Your Home
Shortlisted Properties
  • New Homes
  • For Sale
  • For Rent
Danger! Indicates a dangerous or potentially negative action.
Error

Maximum 4 project can be compared at one go.

Last Updated : 9 Days ago
29 Winchester Street, Toronto, ON, Cabbagetown-South St. James Town
Photo Gallery
+ 50 Photos

29 Winchester Street, Toronto MLS Number: C14111438

Cabbagetown-South St. James Town, Toronto, ON, M4X 1A6

$2,900,000

Status: For Sale

  • 3+1 Beds
  • 4 Baths
  • Area : 3000-3500 sqft
  • Property Type: Residential Freehold (Fourplex)
  • Property Taxes : $12353.71 (Tax Year:2026)
  • Listing Courtesy : Royal Lepage Terrequity Sw Realty

29 Winchester Street Property Description

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.

Read More

29 Winchester Street Property Facts

Property Type :Residential Freehold
MLS Number :C14111438
Listing Type :Sale
Property Age :100+ Years
Possession Date :
know more link icon
Last Updated :27 Oct, 2026 (9 Days ago)
Source :Toronto Regional Real Estate Board
Area :Toronto
Postal Code : M4X 1A6
property detail community link icon

29 Winchester Street Property Price & Tax Insights

Price : $2,900,000
Property Taxes :$12353.71
Tax Year :2026

29 Winchester Street, Toronto Property Details

Bedrooms :3 + 1
No. of Rooms :15
Air Conditioning :Wall Unit(s)
Heating :Baseboard
Place of Worship :Yes
Cross Street :Winchester & Parliament
Bathrooms :4
Fuel :Electric
Approx Square Footage :3000-3500 sqft
Fireplace/Stove :No
Virtual Tour
Dimensions 12
Bedroom :4.01 m x 2.95 m
Family Room :4.98 m x 2.97 m
Bedroom :4.8 m x 3.28 m
Kitchen :4.75 m x 1.68 m
Living Room :7.04 m x 4.7 m
Family Room :4.98 m x 2.97 m
Kitchen :4.37 m x 2.16 m
Family Room :4.98 m x 2.97 m
Living Room :5.05 m x 3.91 m
Kitchen :2.37 m x 2.16 m
Living Room :7.09 m x 4.65 m
Bedroom :4.11 m x 3.05 m

Exterior Information

Exterior Finish :Brick
Parking Space :4
Basement :Apartment
Park :Park
Library :Library

29 Winchester Street, Toronto - Price History

2026-10

23 Oct, 2026

TREB #C14111438

Listed

$2900000.0

property sold history blur background
View More

Sign in to view full price history of this property

  • 0
  • 400k
  • 800k
  • 1.2M
  • 1.6M
  • 2M+
  • 0
  • 6
  • 12
  • 18
  • 24
  • 30+
  • 0
  • 6
  • 12
  • 18
  • 24
  • 30+

29 Winchester Street - Location Map and Landmarks

  • Sherbourne Subway, Toronto 0.92 km
  • Castle Frank Subway, Toronto 0.94 km
  • Wellesley Subway, Toronto 1.15 km
  • College Subway, Toronto 1.18 km
  • Dundas Subway, Toronto 1.33 km
  • Bloor-Yonge Subway, Toronto 1.47 km
  • Broadview Subway, Toronto 1.56 km
  • Queen Subway, Toronto 1.65 km
  • Bay Subway, Toronto 1.74 km
  • Queen'S Park Subway, Toronto 1.79 km
  • Winchester Junior & Senior Public School, Toronto 0.16 km
  • Our Lady Of Lourdes Catholic Elementary School, Toronto 0.42 km
  • Apple Program And Safe Schools, Toronto 0.46 km
  • Sprucecourt Junior Public School, Toronto 0.47 km
  • Lord Dufferin Junior & Senior Public School, Toronto 0.55 km
  • Rose Avenue Junior Public School, Toronto 0.59 km
  • Jarvis Collegiate Institute, Toronto 0.65 km
  • Le College Francais - Carlton Campus, Toronto 0.74 km
  • Monsignor Fraser College - Isabella Campus, Toronto 0.76 km
  • Native Learning Centre, Toronto 0.8 km
  • Sunnybrook & Women'S Coll Orth&Arth Site, Toronto 1.03 km
  • Steadson Hospital, Toronto 1.05 km
  • Sinai Health System - Bridgepoint Active Healthcare, Toronto 1.15 km
  • Salvation Army Toronto Grace Hospital, Toronto 1.23 km
  • Toronto Grace Health Centre, Toronto 1.23 km
  • St Regis Hospital, Toronto 1.35 km
  • St. Michael's, Toronto 1.47 km
  • Women's College, Toronto 1.48 km
  • Beacon Health, Toronto 1.5 km
  • Sunnybrook & Women'S Coll W C Site, Toronto 1.5 km
  • Cabbage Town Organics, Toronto 0.15 km
  • Ambal Trading, Toronto 0.25 km
  • No Frills, Toronto 0.29 km
  • Jamestown Milk, Toronto 0.29 km
  • Harla Ethio Spice Market, Toronto 0.34 km
  • Sarker Groceries, Toronto 0.37 km
  • Fast Tech Cellular, Toronto 0.4 km
  • Food Basics, Toronto 0.4 km
  • Little Bee Supermarket, Toronto 0.52 km
  • Rob'S No Frills, Toronto 0.65 km
  • Parliament Street and Carlton Street, Toronto 0.18 km
  • Bleecker Street and Carlton Street, Toronto 0.3 km
  • Sherbourne Street and Carlton Street, Toronto 0.37 km
  • Parliament Street and Gerrard Street East, Toronto 0.44 km
  • Sherbourne Street and Wellesley Street East, Toronto 0.45 km
  • Carlton Street and Homewood Avenue, Toronto 0.47 km
  • Gerrard Street East and Sherbourne Street, Toronto 0.51 km
Last Updated : 5 Hours ago
3601 Lawrence Avenue E, Toronto, ON
Last Updated : 5 Hours ago
2855 Bloor Street W, Toronto, ON
Last Updated : 5 Hours ago
138 Downes Street, Toronto, ON
Last Updated : 5 Hours ago
105 George Street, Toronto, ON
$398000.0
  • 1 +1 Bd
  • 1 Ba
  • 500-599 sq-ft
Last Updated : 5 Hours ago
51 Bowmore Road, Toronto, ON
$999000.0
  • 3 +1 Bd
  • 2 Ba
  • 1100-1500 sq-ft
Last Updated : 5 Hours ago
52 Shrewsbury Square, Toronto, ON
Last Updated : 5 Hours ago
68 Corporate Drive, Toronto, ON
$499900.0
  • 2 Bd
  • 2 Ba
  • 800-899 sq-ft
Last Updated : 5 Hours ago
90 Trethewey Drive, Toronto, ON
$1350000.0
  • 8 +3 Bd
  • 6 Ba
  • 3500-5000 sq-ft
Last Updated : 5 Hours ago
227 Donlands Avenue, Toronto, ON
Last Updated : 5 Hours ago
2366 Queen Street E, Toronto, ON
$995000.0
  • 2 Bd
  • 2 Ba
  • 1400-1599 sq-ft
Last Updated : 5 Hours ago
451 The West Mall Drive, Toronto, ON
Last Updated : 5 Hours ago
2010 Bathurst Street, Toronto, ON
Last Updated : 5 Hours ago
18 Sorlyn Avenue, Toronto, ON
$999000.0
  • 3 Bd
  • 2 Ba
  • 1100-1500 sq-ft
Last Updated : 5 Hours ago
64 Cliveden Avenue, Toronto, ON
$1698000.0
  • 3 Bd
  • 2 Ba
  • 1100-1500 sq-ft
Last Updated : 5 Hours ago
33 Saint Hilda's Avenue, Toronto, ON
$4295000.0
  • 4 +1 Bd
  • 5 Ba
  • 2000-2500 sq-ft
Last Updated :38 Days ago
12 St. James Court, Toronto, ON
Last Updated :517 Days ago
40 Homewood Avenue, Toronto, ON
Last Updated :27 Days ago
150 Homewood Avenue, Toronto, ON
Last Updated :16 Days ago
411 Wellesley Street E, Toronto, ON
Last Updated :35 Days ago
201 Seaton Street, Toronto, ON
Last Updated :598 Days ago
225 Wellesley Street E, Toronto, ON
Last Updated :15 Days ago
16 St. James Court, Toronto, ON
Last Updated :36 Days ago
225 Wellesley Street E, Toronto, ON
Last Updated :89 Days ago
77 Maitland Place, Toronto, ON
Last Updated :28 Days ago
15 Maitland Place, Toronto, ON
Last Updated :52 Days ago
40 Homewood Avenue, Toronto, ON
Last Updated :12 Days ago
225 Wellesley Street E, Toronto, ON
Last Updated :21 Days ago
358 Sackville Street, Toronto, ON
Last Updated :42 Days ago
415 Jarvis Street, Toronto, ON
Recently Viewed

FAQs: 29 Winchester Street, Toronto

  • Q:What is the Area Size of the 29 Winchester Street In Sq.Ft and it's MLS No.?

    A: The project covers an area of approximately 3000-3500 sq. ft and is strategically located in Toronto. The MLS No of this project is C14111438 and the Project is located in ON, Canada
  • Q: Does this Project 29 Winchester Street available for Sale ?

    A: The project 29 Winchester Street is readily available for Sale and can be purchased at competitive prices today. You can schedule a tour or request a call back for knowing further.
  • Q: How far is this property from my workplace?

    A:You can calculate your travel time and see how this property is far from your Office, your spouse's workplace or your kid's school. You just need to tell us which places you commute to frequently and Square Yards will tell you how far they are from this property.
  • Q:What are the Key Features 29 Winchester Street is Offering?

    A:Square Yards is giving a Cashback of $14,500 if you buy this property from us, however there are several key features offered by the 29 Winchester Street. You get 3+1 Beds with 4 Bath, central air conditioning, parking space and garage along with a heating system, basement, gas fuel system and balcony.
  • Q:How many Parking Space available in this 29 Winchester Street?

    A: 29 Winchester Street in Toronto offers a total of 4 parking spaces for residents.
  • Q:How many Beds & Baths available in 29 Winchester Street, Toronto?

    A: 29 Winchester Street, Toronto comes with 3+1 Beds for maximum convenience and space. There are 4 baths available as well for when you have guests over or if you have a large family!
  • Q:How many Apartments and Condos are available for Sale in Toronto, On?

    A:Toronto, ON is one of the biggest real estate markets in Canada. There are several options available here pertaining to condos and apartments alike. There are approximately apartments and condos available currently for your perusal.
Related to your search
Nearby Postal Codes of Toronto

Tell us a Little about yourself!