$3,400,000 - 29 Winchester Street, Cabbagetown
Multi-Family for Sale in Cabbagetown
37 days on marketNeighbourhood: Cabbagetown-South St. James Town
- MLS Number
- C13578164
- Property Type
- Multi-Family
- Status
- active
- Days on Site
- 37
- Bedrooms
- 4
- Bathrooms
- 4
- Square Feet
- 3,000 - 3,499 sqft
- Neighbourhood
- Regent Park / Cabbagetown / St. James Town
- Listing Brokerage
- ROYAL LEPAGE TERREQUITY SW REALTY
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. Over 4200+ sq ft of living space, complimented with multiple walk-out exterior spaces including 2x large private decks, a rear walk-out patio at grade, and a stunning oversized south facing rooftop terrace on the upper level 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 large windows. Each unit has dedicated ensuite laundry. Parking is accessed via a private rear laneway off of Aberdeen Ave, including 4 parking spaces at present (of which 1 is a tandem parking space,) and the possibility exists to expand up to 6 car parking on site). 29 Winchester has been assembled to remain highly desireable 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.
Estimate your monthly payments for this property
Estimated Payment
$15,039.35/mo
5-yr fixed avg.
Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.
Discover Cabbagetown-South St. James Town
Cabbagetown-South St. James Town is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.
Why Live in Cabbagetown-South St. James Town
- •Convenient location in Regent Park / Cabbagetown / St. James Town
- •Access to local shops and dining
- •Good public transit connections
- •Community parks and green spaces
- •Well-maintained neighbourhoods
Nearby Schools
Transit & Commuting
- •MiWay bus routes throughout the area
- •GO Transit stations within driving distance
- •Easy highway access to 401/403/QEW
- •Walking distance to local amenities
Parks & Amenities
- •Local parks and recreational facilities
- •Community centres
- •Shopping plazas nearby
- •Restaurants and cafes
Lifestyle & Community
Cabbagetown-South St. James Town offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.
29 Winchester Street, Regent Park / Cabbagetown / St. James Town
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Monthly Cash Flow Breakdown
Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.
Joe's Thoughts
Honest perspective from 30+ years of GTA real estate experience
Fair Market Value
At $1133/sqft, this property is priced in line with current Cabbagetown market conditions. The pricing suggests the seller has done their homework. We may have modest room for negotiation, typically 2-4% in today's market.
Market Position
At 37 days on site, this property has had reasonable exposure. It hasn't sold immediately (which often indicates overpricing), but isn't languishing either. There's likely room for a 3-5% negotiation from asking price.
Larger Home Realities
At 3,000 sqft, this is a substantial home. Budget approximately $400-600/month more for utilities compared to an average-sized home. Maintenance costs scale with size too - roof, HVAC, and cleaning all cost more. That said, space is a luxury that's hard to add later, and larger homes often have better resale in family-oriented neighbourhoods.
Family-Friendly Layout
4 bedrooms hits the sweet spot for most families. You'll have room for 2-3 children plus a home office or guest room. This is the most sought-after configuration for families relocating to Cabbagetown. Good resale value as demand remains consistent.
Bathroom Count Matters
With 4 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.
About Cabbagetown-South St. James Town
I know Cabbagetown-South St. James Town well from working with many buyers and sellers here. Each pocket has its own character - let me share what I've learned about this specific street and block. During our showing, I'll point out local amenities, school catchments, and what similar homes have sold for recently.