

















































$3,395,000 - 38 Annesley Avenue, Don Mills
Detached for Sale in Don Mills
66 days on market- MLS Number
- C12983738
- Property Type
- Detached
- Status
- active
- Days on Site
- 66
- Bedrooms
- 5
- Bathrooms
- 4
- Square Feet
- 2,500 - 2,999 sqft
- Neighbourhood
- Flemingdon Park / Don Mills
- Listing Brokerage
- CHESTNUT PARK REAL ESTATE LIMITED
This custom-built luxury residence in Leaside offers exceptional space and presence, set on a rare 36-foot frontage along a quiet enclave on one of North Toronto's most sought-after streets. Designed for modern family living & elegant entertaining, the main level features grand principal rooms adorned with exquisite wainscoting, creating a warm yet sophisticated atmosphere. At the heart of the home is a gourmet kitchen complete with a large island, marble countertops, pantry, B/I desk & eat-in dining area. The spacious family room w/ fireplace & custom built-ins, seamlessly walks out to a deck, patio & fully fenced private yard. A convenient 2-piece powder room, mudroom, side entrance & direct access to an attached garage complete the main floor. The second level w/ skylight offers four generously sized bedrooms, including a private & luxurious primary suite featuring a 5-piece marble ensuite, walk-in closet & its own balcony retreat. Three additional bedrooms, a 4-pc bathroom, a well-appointed upper-level laundry room & linen closet provide comfort & practicality for family living.The finished lower level w/ in-floor heating expands the living space w/ a large recreation room, an adjoining wine cellar, a 5th bedroom, a 3-pc bathroom & ample storage. A rare offering on an A+ street, this home totalling approx 4,000sf includes a one-car attached garage & private drive, along w/ high-end finishes throughout. Thoughtful extras such as the mudroom, main flr powder room, upstairs laundry & wine cellar enhance both convenience & functionality. Ideally located within walking distance to top schools including Northlea Public School (JK-Grade 8 & French immersion) & Leaside High School, as well as transit, including the new LRT. Enjoy close proximity to private schools, shops, restaurants & amenities along the Bayview & Laird corridors, Leaside SmartCentre, Sunnybrook Hospital & an abundance of parks, trails & recreational facilities including Serena Gundy & Sunnybrook Parks
Estimate your monthly payments for this property
Estimated Payment
$15,017.23/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 Flemingdon Park / Don Mills
Flemingdon Park / Don Mills 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 Flemingdon Park / Don Mills
- •Convenient location in Flemingdon Park / Don Mills
- •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
Flemingdon Park / Don Mills 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.
38 Annesley Avenue, Flemingdon Park / Don Mills
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
Premium Pricing
At $1358/sqft, this property is priced above the Don Mills average of $950/sqft. I'd want to see upgraded finishes, premium location, or recent renovations to justify this price point. During our showing, I'll point out exactly what you're paying extra for.
Negotiation Opportunity
At 66 days on site, this property has exceeded the typical selling timeline for Don Mills. This creates leverage for buyers. The seller may be motivated by carrying costs, life circumstances, or previous deals falling through. I'd recommend a strategic offer below asking with terms that favour you.
Detached Home Advantages
Detached homes in Don Mills 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 Don Mills.
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.
Investment Perspective
Looking at this as an investment: Don Mills properties have averaged 5-7% annual appreciation over the past decade. Your estimated monthly carrying costs would be around $14,146 (mortgage, taxes, insurance). Consider whether you're comfortable with this as both a home and a financial commitment.