Ten properties across the city this week, from a waterfront suite at Bayside to a Rosedale apartment with over 3,000 square feet, and a pool-and-elevator estate in St. Andrew-Windfields. Neighbourhoods covered include Casa Loma, Leaside, the Annex, Bridle Path, and Edenbridge. Prices range from $3.5M to $8.25M.
1 Forest Hill Road 701, Casa Loma
$5,399,000 · Luxury Apartment · Casa Loma · 3 bed · 3 bath · 2500–2749 sqft · 2 parking · Virtual Tour
Perched on the seventh floor of a brand-new building at the foot of Forest Hill, this 3-bedroom suite sits in one of Toronto's most storied neighbourhoods — quiet streets, ravine-adjacent, and minutes from some of the city's best private schools. At 2,500+ square feet, it's one of the larger luxury condos you'll find anywhere in the city. The virtual tour is worth loading before you do anything else. For buyers who want genuine square footage without the upkeep of a freehold, this is a compelling case.
7 Dale Avenue 106, Rosedale-Moore Park
$8,250,000 · Luxury Apartment · Rosedale-Moore Park · 2 bed · 3 bath · 3250–3499 sqft · 1 parking · Virtual Tour
The top price point on this list, and the square footage tells you why — over 3,250 square feet in Rosedale, one of the most prestigious addresses in the country. Two bedrooms with three bathrooms suggests serious principal suite space and likely a layout built around entertaining. Dale Avenue is a quiet, tree-lined street tucked off the main Rosedale network, with the ravine trail system close at hand. The virtual tour is available if you want to get a feel before booking. Buyers at this level know what they're looking for — this one rewards a closer look.
36 Birch Avenue 309, Yonge-St. Clair
$4,875,000 · Luxury 2-Storey · Yonge-St. Clair · 2 bed · 3 bath · 2500–2749 sqft · 2 parking · Virtual Tour
A two-storey suite inside a luxury building — closer to a townhouse experience than a standard condo — in the heart of Yonge and St. Clair. That's a walkable, well-served midtown pocket with great restaurants, quick subway access, and a residential feel that's hard to find this close to the core. Just under $4.9M for a 2,500+ square foot two-level layout with two parking spots is a notable package for this neighbourhood. The virtual tour is available. Worth a look for buyers who want vertical living space without a standalone house.
155 Merchants' Wharf 912, Waterfront Communities
$3,500,000 · Luxury Apartment (Aqualuna – Bayside Toronto) · Waterfront Communities C8 · 2 bed · 3 bath · 2250–2499 sqft · 2 parking · Virtual Tour
Aqualuna at Bayside is one of the more architecturally distinctive waterfront buildings in Toronto — and this ninth-floor suite comes in as the most accessible price on this list at $3.5M. Over 2,250 square feet with two parking spots, right on the lake. The Bayside neighbourhood has matured well, with the Martin Goodman Trail, Sugar Beach, and Corktown all nearby. The virtual tour is live. For buyers who want a landmark waterfront address without reaching into the $5M+ range, this is the one to start with.
134 Rykert Crescent, Leaside
$6,750,000 · Luxury 2-Storey · Leaside · 6 bed · 7 bath · 5000+ sqft · 3 parking · Virtual Tour
Six bedrooms, seven bathrooms, a pool, and over 5,000 square feet on one of Leaside's most sought-after crescents. Leaside has long been a top family neighbourhood — excellent schools, tight community, tree-lined streets — and properties of this scale rarely surface here. At 6–15 years old, the house is past the new-build premium but well within a well-maintained window. The virtual tour gives a solid first impression of the layout. Families upgrading to their forever home in Toronto's east end should put this on the shortlist.
108 Cheltenham Avenue, Bridle Path-Sunnybrook-York Mills
$5,895,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 5 bed · 7 bath · 3500–5000 sqft · 6 parking · Virtual Tour
Six parking spots is the detail that stands out here — unusual even at this price point, and a strong signal about the lot and garage configuration. The Bridle Path corridor is Toronto's most prestigious freehold address, bordered by Sunnybrook Park and York Mills, with the kind of privacy and greenery you simply don't find elsewhere in the city. Five bedrooms and seven bathrooms across up to 5,000 square feet gives this home serious family credentials. The virtual tour is ready. For buyers targeting the Bridle Path area, this one is worth scheduling.
38 Edenbrook Hill, Edenbridge-Humber Valley
$6,499,999 · Luxury 2-Storey · Edenbridge-Humber Valley · 6 bed · 4 bath · 3500–5000 sqft · 20 parking · Virtual Tour
Twenty parking spots. That's not a typo — and it makes this west-end property genuinely unusual at any price. Set in Edenbridge-Humber Valley, a quietly prestigious neighbourhood running along the Humber River with ravine access and large private lots, this older estate-style home offers 6 bedrooms and up to 5,000 square feet of living space. Properties with this kind of land and parking capacity rarely appear even in the luxury segment. The virtual tour is available. Buyers looking for something with real estate character — and room for a serious collection — should take a look.
287 Davenport Road 804, Annex
$3,499,900 · Luxury Apartment (New) · Annex · 2 bed · 3 bath · 1600–1799 sqft · 2 parking · Elevator
Brand new, just listed, and sitting at the entry point for this week's luxury picks — $3,499,900 in the Annex for a new-build eighth-floor suite. The Annex is one of Toronto's most walkable and culturally rich neighbourhoods, with Yorkville steps away and the University of Toronto campus nearby. At 1,600–1,799 square feet, it's the more compact option on this list, but two bedrooms with three bathrooms in a new building with an elevator and two parking spots is a refined package. A strong choice for buyers who want a lock-and-leave lifestyle in a genuinely central location.
300 Bloor Street E 2701, Rosedale-Moore Park
$4,099,000 · Luxury Apartment · Rosedale-Moore Park · 3 bed · 3 bath · 3000–3249 sqft · 2 parking
The 27th floor on Bloor East at the edge of Rosedale — city views, a 3,000+ square foot layout, three bedrooms and three bathrooms, and two parking spots. For a building in the 16–30 year age range, that kind of floor plate is exceptional and reflects an era of construction that prioritised real living space. Rosedale-Moore Park is one of the most established luxury addresses in Toronto, with the ravine system, Summerhill, and Yorkville all within reach. At just over $4M for this much space and this address, it's worth running the numbers carefully.
29 Junewood Crescent, St. Andrew-Windfields
$5,780,000 · Luxury 2-Storey · St. Andrew-Windfields · 5 bed · 5 bath · 5000+ sqft · 10 parking · Virtual Tour
A pool, an elevator, ten parking spots, and over 5,000 square feet in St. Andrew-Windfields — one of Toronto's most quietly prestigious north-midtown neighbourhoods, bordering the Bridle Path and Bayview. Five bedrooms and five bathrooms gives this home genuine family scale, and the elevator makes it unusually flexible across different life stages. St. Andrew-Windfields draws buyers who want the privacy and lot size of the Bridle Path corridor without the highest price tier. The virtual tour is available. A strong option for buyers comparing this area against Lawrence Park or York Mills.
Listings sourced from roofup.ca. Property details are current as of the publish date and may change. Data is sourced from the Toronto Regional Real Estate Board and generated by AI — we do not guarantee accuracy or completeness. Verify all information directly with a licensed Real Estate Agent before making any decisions.
Note: These properties were automatically surfaced by AI from this week's Toronto listings on roofup.ca. Not paid placements or agent recommendations — just a data-driven snapshot of what's worth a look right now. Property data is sourced from the Toronto Regional Real Estate Board and generated by AI. We do not guarantee the accuracy or completeness of this information. Always verify all details directly with a licensed Real Estate Agent before making any decisions.
