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For saleMLS® C14111438

29 Winchester Street, Toronto, ON M4X 1A6

Cabbagetown-South St. James Town · C08 · M4X 1A6

$2,900,000

$967 / sq ft

1 weeks on market

Bedrooms
3+1
Bathrooms
4
Interior
3,000 sf
Parking
4
Lot
28.47 × 132.73 ft
Age
100+ years

What's special

  • 4 parking spaces
  • Wall unit(s)
  • Basement apartment
  • Fireplace

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About this property

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.

Rooms

15 rooms. Dimensions as published by the listing brokerage.

Room dimensions and features
RoomLevelDimensionsFeatures
Living RoomMain7.04 × 4.70 m23.1 × 15.4 ftBay Window · Hardwood Floor · Combined w/Dining
KitchenMain4.37 × 2.16 m14.3 × 7.1 ftPass Through · Tile Floor · W/O To Balcony
Family RoomMain4.98 × 2.97 m16.3 × 9.7 ftHardwood Floor · Window
BedroomMain4.04 × 4.65 m13.3 × 15.3 ftBroadloom · Window · Double Closet
Living RoomSecond7.09 × 4.65 m23.3 × 15.3 ftLaminate · Bay Window · Combined w/Dining
KitchenSecond2.37 × 2.16 m7.8 × 7.1 ftLaminate · W/O To Balcony · Window
Family RoomSecond4.98 × 2.97 m16.3 × 9.7 ftLaminate · Window · Pass Through
BedroomSecond4.01 × 2.95 m13.2 × 9.7 ftHardwood Floor · Closet · Window
Living RoomThird5.05 × 3.91 m16.6 × 12.8 ftW/O To Terrace · Hardwood Floor · Combined w/Dining
KitchenThird4.75 × 1.68 m15.6 × 5.5 ftLaminate · Eat-in Kitchen · Window
BedroomThird4.80 × 3.28 m15.7 × 10.8 ftLaminate · Window · Closet
Living RoomLower7.04 × 4.70 m23.1 × 15.4 ftLaminate · Window · Combined w/Dining
KitchenLower3.96 × 2.13 m13.0 × 7.0 ftOpen Concept · Window · Tile Floor
Family RoomLower4.98 × 2.97 m16.3 × 9.7 ftW/O To Yard · Tile Floor
BedroomLower4.11 × 3.05 m13.5 × 10.0 ftBroadloom · Window · Closet

Features

  • None

Property details

Property

Property type
multiplex
Bedrooms
3 + 1
Bathrooms
4
Interior size
3,000 sq ft
Year built
100+
Lot size
28.47 × 132.73 ft
Possession
TBD

Interior

Basement
Apartment
Heating
Baseboard · Electric
Cooling
Wall Unit(s)
Fireplaces
1
Exposure
South

Exterior & services

Construction
Brick
Parking spaces
4
Sewer
Sewer

Costs

List price
$2,900,000
Property taxes
$12,354 / year (2026)
Price per sq ft
$967
Rental items
HWT 34.52/month

Listing

MLS® number
C14111438
Status
For sale
Listed
October 23, 2026
Days on market
12
Last updated
October 27, 2026
Listing brokerage
ROYAL LEPAGE TERREQUITY SW REALTY

Price & sale history

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Before you make an offer

What this home costs beyond the asking price, and how that price compares to what else is on the market.

How this price compares

This home is priced above most comparable listings — about 88% of comparable multiplex listings in Toronto are asking less.

$977KMedian $1.74M$2.98M
This home
$967 / sq ft
Comparable median
$820 / sq ft

Based on 95 comparable active multiplex listings in Toronto. These are asking prices, not sale prices.

Mortgage estimate

Down payment20.0% · minimum $580,000
$580,000
Interest rate5-year fixed, illustrative only
4.49%
Amortization
Principal & interest
$12,827.68
Property tax (est.)
$1,029.48
Estimated monthly
$13,857

Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.

Land transfer tax

Payable on closing, on top of the purchase price.

Ontario
$58,975
Toronto municipal
$58,975
Total due on closing
$117,950

An estimate on the asking price of $2,900,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.

Listing courtesy of ROYAL LEPAGE TERREQUITY SW REALTY. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.

$2,900,000

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