29 Winchester Street, Toronto, ON
Property Highlights
Welcome to this remarkable 3-Storey fourplex located in the coveted neighborhood of Cabbagetown-South St. James Town. Expertly crafted featuring premium brick construction, this residence presents an exceptional opportunity offered at $2,900,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.
- 4 Bedrooms and 4 Bathrooms with 4 functional kitchens
- Generous living space spanning 3000-3500 sqft on a premium 28.47 x 132.73 ft lot
- Features a apartment basement, adding superb versatility for recreation, a home gym, or extra storage
- Ample parking with 0.0 garage spaces (4.0 total parking spaces)
- Notable attributes: None
- equipped with wall unit(s) central cooling and highly efficient baseboard heating via electric
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. 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.
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Property Summary
This fourplex located at 29 Winchester Street, Toronto is currently for sale and has been available for 2 days. This property is listed at $2,900,000 with an estimated mortgage of $9,653* per month. It has 4 beds, 4 bathrooms, and is 3000-3500 square feet. 29 Winchester Street, Toronto is in the Cabbagetown-South St. James Town neighborhood.
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* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.Yes! Featuring 4 bedrooms and 4 bathrooms, this home offers ample space and comfort for growing families in Cabbagetown-South St. James Town, Toronto.
- •4 spacious bedroom layout offering versatile living space
- •4 well-appointed bathrooms
- •3000-3500 sqft of generous functional square footage
Growing families needing multi-bedroom flexibility and space in Cabbagetown-South St. James Town, Toronto.
Key Features
Additional Details
Property Details
Parking & Garage
Heating & Cooling
Features
Property Features
- Library
- Park
- Place Of Worship
- Public Transit
- School
Interior Features
- None
Security Features
- None
Community Features
None listed
Property History
No historical data available for this property.
This could be the first listing for this address.
Looking to Buy a Home in Toronto?
If you are looking for a house in Toronto or researching Toronto real estate for sale, this 4-bedroom fourplex at 29 Winchester Street, Toronto, ON offers an exceptional opportunity to buy a home in Toronto, Ontario. Whether you are a first-time Toronto home buyer or comparing active Toronto MLS® homes for sale, working with a dedicated Toronto buyer agent ensures you receive priority showing access, unrepresented buyer protection, and aggressive price negotiation.
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Under Ontario REBBA/TRESA regulations, the listing brokerage is legally bound to the seller's financial interests. Work with an experienced Toronto realtor & real estate broker who represents you 100%—at zero cost to you as a buyer.
Toronto Buyer Budget & Costs
Estimated mortgage: $9,653*/month*. Estimated Ontario Land Transfer Tax: $117,950. First-time Toronto home buyers may qualify for up to $8,475 in rebates.
Frequently Asked Questions: Buying a Home in Toronto
Frequently Asked Questions about 29 Winchester Street, Toronto, ON
Q.What is the asking price for 29 Winchester Street, Toronto, ON ?
The current listing price for 29 Winchester Street, Toronto, ON in Cabbagetown-South St. James Town, Toronto is $2,900,000.
Q.How many bedrooms and bathrooms does this property have?
This property features 4 bedrooms and 4 bathrooms across approximately 3000-3500 sqft.
Q.What property type and architectural style is 29 Winchester Street, Toronto, ON ?
29 Winchester Street, Toronto, ON is a Fourplex (3-Storey) featuring a Apartment basement.
Q.What key property features does 29 Winchester Street, Toronto, ON offer?
Key property features include: Library, Park, Place Of Worship, Public Transit, School.
Q.What interior features are included in this home?
Interior highlights include: None.
Q.What security features are installed at 29 Winchester Street, Toronto, ON ?
Security features include: None.
Q.Is parking available at this property?
Yes, this property offers parking space for 4.0 vehicles (None).
Q.What heating and cooling systems are installed?
Heating is provided via Electric and cooling via Wall Unit(s).
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Location
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Open in Google MapsNeighborhood Safety & Crime Analytics
Cabbagetown-South St. James Town, Toronto
161 assaults (45.0/100k)
43 B&E (40.0/100k)
60 thefts (45.0/100k)
Improving vs previous year
Formula: (Annual Occurrences / Population) Ă— 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.
Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.
Pricing & Value Insights
Data-driven valuation for 29 Winchester Street, Toronto, ON M4X 1A6
Based on 0 recent similar sales in the pocket.
Properties in this area are selling at a steady pace.
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About Purchasing a Home in Toronto, ON
For a property listed at $2,900,000 in Toronto, the legal minimum down payment is $580,000 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.
Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $58,975 for this transaction. Since the property is located in Toronto, a municipal land transfer tax of $58,975 also applies, bringing the total estimated land transfer taxes to $117,950.
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Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.
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