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.
Ten properties across the city this week — from a $34.5M Casa Loma estate on Ardwold Gate to a $17.2M Forest Hill South home on Russell Hill Road and a $12.45M riverside pool home in High Park-Swansea. Neighbourhoods covered include Casa Loma, Forest Hill South, High Park-Swansea, the Annex, Yorkville, Lawrence Park South, St. Andrew-Windfields, Banbury-Don Mills, and Waterfront Communities. Prices range from $4M to $34.5M.
17 Ardwold Gate, Casa Loma
$34,500,000 · Luxury 3-Storey · Casa Loma · 8 bed · 11 bath · 5000+ sqft · 20 parking
Just listed today — the most expensive residential listing in Toronto this week by a considerable margin. Eight bedrooms, eleven bathrooms, a pool, an elevator, and twenty parking spots on Ardwold Gate, one of Casa Loma's most private and storied addresses. Ardwold Gate sits on the escarpment above the neighbourhood, with the kind of lot depth, privacy, and city views that simply don't exist elsewhere in Toronto at this scale. No virtual tour listed — properties at this level trade through private introductions. The headline listing of the week.
474 Russell Hill Road, Forest Hill South
$17,200,000 · Luxury 2-Storey · Forest Hill South · 5 bed · 7 bath · 5000+ sqft · 5 parking
Five bedrooms, seven bathrooms, an elevator, and over 5,000 square feet on Russell Hill Road — one of Forest Hill South's most prestigious addresses. At $17.2M this sits in the rarefied tier of Toronto freehold real estate where the conversation is about lot position, architectural significance, and privacy as much as square footage. Russell Hill is a wide, tree-lined boulevard with some of the city's most architecturally distinguished homes. No virtual tour listed. For buyers operating at this level, a private showing introduction is the expected process.
23 Riverside Crescent, High Park-Swansea
$12,450,000 · Luxury 2-Storey · High Park-Swansea · 5 bed · 7 bath · 5000+ sqft · 8 parking · Virtual Tour
Five bedrooms, seven bathrooms, a pool, eight parking spots, and over 5,000 square feet on Riverside Crescent in High Park-Swansea — a rare address running directly along the Humber River with the kind of natural setting that's genuinely irreplaceable inside city limits. At $12.45M it's the third-highest price on this week's list and the most significant west-end estate available right now. The virtual tour is available. For buyers who want estate-scale living with ravine and waterway proximity, Riverside Crescent is in a category of its own in Toronto's west end.
118 Yorkville Avenue 703, Yorkville
$9,900,000 · Luxury Apartment (New) · Yorkville · 4 bed · 5 bath · 5000+ sqft · 4 parking
Four bedrooms, five bathrooms, over 5,000 square feet, and four parking spots in a brand-new building on Yorkville Avenue — the heart of Toronto's most prestigious retail and dining district. A 5,000+ square foot condo suite is exceptional by any standard; at this scale the product is closer to a private floor than a conventional apartment. Just listed yesterday. No virtual tour yet — an in-person visit will be the right introduction to a suite of this calibre. For buyers who want the absolute centre of Yorkville in a brand-new building, this is the one to watch.
128 Hazelton Avenue 802, Annex
$5,899,000 · Luxury Apartment (New) · Annex · 3 bed · 4 bath · 2750–2999 sqft · 2 parking · Virtual Tour
Just listed today — a brand-new eighth-floor suite at 128 Hazelton Avenue in the heart of Yorkville. Three bedrooms, four bathrooms, nearly 3,000 square feet, a balcony, elevator, and two parking spots. Hazelton Avenue is one of Yorkville's most boutique addresses, known for its low density and architectural character. At $5,899,000 it sits well below the Yorkville Avenue listing above but on the same street network — a useful comparison for buyers weighing price against floor size. The virtual tour is live now.
243 Dawlish Avenue, Lawrence Park South
$5,395,000 · Luxury 2-Storey · Lawrence Park South · 6 bed · 6 bath · 3500–5000 sqft · 6 parking · Virtual Tour
Six bedrooms, six bathrooms, a pool, and six parking spots on Dawlish Avenue in Lawrence Park South — one of Toronto's most consistently coveted family neighbourhoods, known for its school catchments, ravine proximity, and wide tree-lined streets. At $5,395,000 this is competitive for a pool home with this bedroom count and parking in Lawrence Park South. The virtual tour is available. A strong family-scale purchase for buyers targeting this corridor who want a pool included without pushing into the $7M+ range.
48 Wimpole Drive, St. Andrew-Windfields
$6,995,000 · Luxury 2-Storey · St. Andrew-Windfields · 7 bed · 9 bath · 5000+ sqft · 14 parking
Seven bedrooms, nine bathrooms, a pool, fourteen parking spots, and over 5,000 square feet on Wimpole Drive — one of St. Andrew-Windfields' most established addresses. Fourteen parking spots is a standout even for this neighbourhood and points to a significant private drive or garage configuration that's rare at any price. Just listed today. No virtual tour yet. At $6,995,000 for this scale and lot, it's one of the stronger value propositions in St. Andrew-Windfields this week for buyers who need serious bedroom and bathroom count.
27 Hurlingham Crescent, Banbury-Don Mills
$5,290,000 · Luxury 2-Storey (New) · Banbury-Don Mills · 7 bed · 9 bath · 5000+ sqft · 9 parking
Brand-new construction on Hurlingham Crescent — seven bedrooms, nine bathrooms, nine parking spots, and over 5,000 square feet in Banbury-Don Mills. At $5,290,000 this is among the most accessible prices on this week's list for a new-build home at this scale, and the bedroom-to-price ratio is hard to match anywhere else in Toronto's luxury market right now. Banbury-Don Mills borders Edwards Gardens and sits adjacent to the Bridle Path, with the large-lot and green-space character that estate buyers seek. No virtual tour listed yet. A standout value for buyers who need seven bedrooms in a new build.
36 Hazelton Avenue 4C, Annex (36 Hazelton)
$3,550,000 · Luxury Apartment · Annex · 2 bed · 2 bath · 1800–1999 sqft · 2 parking · Virtual Tour
36 Hazelton is one of Yorkville's most respected boutique luxury buildings — and this fourth-floor suite offers two bedrooms, two bathrooms, just under 2,000 square feet, a balcony, and two parking spots. Just listed today. At $3,550,000 it's the second-most accessible price on this week's list and the most accessible entry into the Hazelton Avenue address. The virtual tour is live. A strong lock-and-leave option for buyers who want a Yorkville condo in an established building without the new-construction price premium of 128 Hazelton nearby.
155 Merchants' Wharf LPH03, Waterfront Communities
$3,999,900 · Luxury Penthouse · Waterfront Communities C8 · 3 bed · 3 bath · 2250–2499 sqft · 1 parking
A lower penthouse at Aqualuna Bayside — three bedrooms, three bathrooms, 2,250+ square feet, and a balcony right on the Toronto waterfront. At just under $4M it's the entry point on this week's list and continues to represent one of the more competitive price points for a penthouse-level waterfront suite at this size. No virtual tour listed — an in-person visit to see the lake views is the obvious next step. The Bayside neighbourhood has matured well, with Sugar Beach, the Martin Goodman Trail, and Corktown all within easy reach.
Browse all Toronto luxury listings on roofup.ca.
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.
