Listed for:Listed 4 days ago
$2,900,000

29 Winchester Street

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

Multiplex For Sale
Kim Karimi
Kim Karimi

Real Estate Broker

416-838-3031
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Sale & Price History for 29 Winchester Street, Toronto, Cabbagetown-South St. James Town

No listing history available

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*Sold prices and complete sale & price history are regulated data. Under the Trust in Real Estate Services Act, 2002 (TRESA) and the rules of the Real Estate Council of Ontario (RECO), and pursuant to the Multiple Listing Service® rules of the Canadian Real Estate Association (CREA) and the Toronto Regional Real Estate Board (TRREB), this information may be shown only to registered users who have agreed to the applicable terms of use (a Virtual Office Website, or "VOW," arrangement). HOMEH Inc., Brokerage therefore provides it to signed-in members only. Creating an account is free and takes under a minute.

About 29 Winchester Street, Toronto, Cabbagetown-South St. James Town

Summarized Description

  • Impeccably maintained 4-plex in Cabbagetown.
  • Over 4200 sq ft of living space.
  • Meticulously renovated with high-end finishes.
  • Multiple walk-out balconies and private terraces.
  • Strong tenant base with dedicated climate controls.
  • Steps from restaurants and shopping.
  • Close to public transit and downtown.
  • Ideal investment opportunity for high-caliber portfolio.

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.

Key Facts & Features

Property Costs

Annual Property Tax Amount
$12,354
Land Transfer Tax Fee
$117,950

Rental Items

Rental Equipment
HWT 34.52/month
Under Contract
Hot Water Tank-Electric

Basement Type
Apartment

Interior Features

Interior Extras
None
Security Features
None
Fireplace/Stove
Yes
Elevator
No

Exterior Features

Pool
None
Property Features
Library, Park, Place Of Worship, Public Transit, School
Accessibility Features
None
Other Structures
None

Building

Building Type
Multiplex
Building Style
3-Storey
Approx Age
100+

Construction

Exterior Finish
Brick
Roof
Asphalt Shingle, Metal
Foundation Details
Unknown
Special Designation
Unknown

Lot

Lot Front
28.47 ft
Lot Depth
132.73 ft
Lot Shape
Irregular

Inclusions

Inclusions
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.

Parking & Garages

Garage Type
None
Garage Spaces
0
Parking Spaces
4
Total Garage And Parking Spaces
4

Heating & Cooling

Heat Source
Electric
Heat Type
Baseboard
Air Conditioning
Wall Unit(s)
Water
Municipal
Sewers
Sewer

Bedrooms
3 + 1
Washrooms
4
Kitchens
4
Family / bonus room
Yes

Room sizes

  • Bedroom—
    Second level, Hardwood Floor, Closet, Window
  • Kitchen—
    Main level, Pass Through, Tile Floor, W/O To Balcony
  • Family Room—
    Lower level, W/O To Yard, Tile Floor
  • Family Room—
    Second level, Laminate, Window, Pass Through
  • Bedroom—
    Third level, Laminate, Window, Closet
  • Living Room—
    Third level, W/O To Terrace, Hardwood Floor, Combined w/Dining
  • Kitchen—
    Third level, Laminate, Eat-in Kitchen, Window
  • Kitchen—
    Second level, Laminate, W/O To Balcony, Window
  • Living Room—
    Lower level, Laminate, Window, Combined w/Dining
  • Living Room—
    Second level, Laminate, Bay Window, Combined w/Dining
  • Family Room—
    Main level, Hardwood Floor, Window
  • Bedroom—
    Lower level, Broadloom, Window, Closet
  • Living Room—
    Main level, Bay Window, Hardwood Floor, Combined w/Dining
  • Bedroom—
    Main level, Broadloom, Window, Double Closet
  • Kitchen—
    Lower level, Open Concept, Window, Tile Floor

Washrooms

  • 4-piece, Basement
  • 3-piece, Second
  • 3-piece, Third
  • 4-piece, Main

Municipality
Toronto
Neighbourhood
Cabbagetown-South St. James Town
Main cross streets
Winchester & Parliament
Directions
Winchester & Parliament

MLS® number
C14111438
Data source
Toronto Regional Real Estate Board
Listed on
2026-10-22
Updated on
2026-10-23
Days on market
4 days
Possession type
Flexible
Co-op commission
2.5%
Seller
Listed by
ROYAL LEPAGE TERREQUITY SW REALTY

Home Market Value

Current home valuation for 29 Winchester Street, Toronto, Cabbagetown-South St. James Town, Toronto, ON. Listed for $2,900,000

HOMEH Estimate

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Estimated Sales Range

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HOMEH Estimate for 29 Winchester Street, Toronto, Cabbagetown-South St. James Town

Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.

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Mortgage Payment Calculator

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Toronto, ON
Minimum Down Payment Required:20.0%

20% required for homes $1.5M or more

Minimum down payment

$580,000

Scenario 1 Scenario 2 Scenario 3 Scenario 4
−Down payment
%
$
%
$
%
$
%
$
+CMHC insurance
$0$0$0$0
=Total mortgage
$2,320,000$2,175,000$2,030,000$1,885,000
Amortization
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%
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%
Payment frequency
=Mortgage payment
$11,327monthly$10,619monthly$9,911monthly$9,204monthly
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Land Transfer Tax

Provincial

$58,975

Municipal (Toronto)

$58,975

Total Land Transfer Tax

$117,950

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