









































$929,000 - 288 Greenwood Avenue, Leslieville
Semi-Detached for Sale in Leslieville
New — Listed yesterday- MLS Number
- E13450234
- Property Type
- Semi-Detached
- Status
- active
- Days on Site
- 1
- Bedrooms
- 5
- Bathrooms
- 3
- Square Feet
- 1,500 - 1,999 sqft
- Neighbourhood
- Riverdale / Leslieville
- Listing Brokerage
- REAL ESTATE HOMEWARD
Located in Toronto's vibrant Leslieville/South Riverdale neighbourhood, 288 Greenwood Avenue is a charming 21/2 storey solid brick semi-detached home. Rich in period character and thoughtfully configured for flexibility,. The property offers a unique opportunity for multi-generational living, owner-occupancy with supplementary rental income, or investment purposes through its three self-contained residential units.The home features a beautifully renovated upper owner's suite with three bedrooms, an updated modern kitchen and bathroom, exposed brick walls and private laundry facilities. The main floor includes a separate one-bedroom unit with high ceilings, eat in kitchen, exposed brick and a walkout to a beautifully landscaped backyard, while the lower level provides additional self-contained living space. Original architectural details, solid brick construction, a welcoming front porch, and strong curb appeal contribute to the home's enduring appeal. Situated just north of Gerrard Street East, the home enjoys excellent access to transit, local shops, restaurants, cafés, and community amenities, contributing to the area's reputation as one of Toronto's most dynamic east-end communities. The location offers a highly walkable urban lifestyle with convenient access to schools, parks, and downtown Toronto.
Estimate your monthly payments for this property
Estimated Payment
$4,766.25/mo
Includes CMHC insurance ($25,919)
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 Riverdale / Leslieville
Riverdale / Leslieville 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 Riverdale / Leslieville
- •Convenient location in Riverdale / Leslieville
- •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
Riverdale / Leslieville 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.
288 Greenwood Avenue, Riverdale / Leslieville
Open in Google MapsUse the map controls to zoom, pan, and switch between map and satellite views. Drag to explore the neighbourhood.
Rental income estimator & ROI calculator
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
Competitive Pricing
At $619/sqft, this is priced below the area average. This could represent genuine value, but let's investigate why. In my experience, underpriced homes often have deferred maintenance, unfavourable layouts, or motivated sellers. I'll help you determine which it is.
Just Listed - Act Strategically
This property hit the market within the last week. In Leslieville's current market, desirable homes often receive multiple offers within 5-7 days. If you're seriously interested, I recommend booking a showing immediately. However, never let urgency override due diligence - we'll still do proper inspections.
Detached Home Advantages
Detached homes in Leslieville are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.
Excellent Flexibility
With 5 bedrooms, you have genuine flexibility. Beyond the master and kids' rooms, you can have a dedicated home office, guest room, hobby space, or even rental income potential. In today's work-from-home era, extra bedrooms add significant value. Properties with 5+ bedrooms are relatively rare in Leslieville.
Bathroom Count Matters
With 3 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.
Investment Perspective
Looking at this as an investment: Leslieville properties have averaged 5-7% annual appreciation over the past decade. Your estimated monthly carrying costs would be around $3,871 (mortgage, taxes, insurance). Consider whether you're comfortable with this as both a home and a financial commitment.