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 $12.7M Lansing-Westgate estate on Sandringham Drive to a new Leaside build with open houses this weekend and a Four Seasons Private Residence suite on Yorkville. Neighbourhoods covered include Leaside, Bridle Path, Rosedale, Lansing-Westgate, Lawrence Park South, St. Andrew-Windfields, Forest Hill South, and Yorkville. Prices range from $5.6M to $12.7M.
431 Heath Street E, Leaside
$5,949,000 · Luxury 2-Storey (New) · Leaside · 5 bed · 6 bath · 3500–5000 sqft · 4 parking · Open House Sat & Sun Sep 19–20, 6–8pm · Virtual Tour
Brand-new construction on Heath Street East in Leaside — five bedrooms, six bathrooms, up to 5,000 square feet, and four parking spots. Open houses run Saturday and Sunday from 6 to 8pm, with a virtual tour already available. Leaside is one of Toronto's most consistently strong family neighbourhoods, and new builds here move quickly. At $5,949,000 this is a practical new-build entry for buyers targeting the east end who don't want to cross the $6M threshold. One of the most accessible new freeholds on this week's list.
92 Arjay Crescent, Bridle Path-Sunnybrook-York Mills
$11,500,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 6 bed · 8 bath · 5000+ sqft · 13 parking · Open House Sun Sep 20, 6–8pm
Six bedrooms, eight bathrooms, a pool, an elevator, thirteen parking spots, and over 5,000 square feet on Arjay Crescent — one of the Bridle Path corridor's most prestigious addresses. At 0–5 years old this is a near-new estate in exceptional condition, built to the specification that the upper Bridle Path market demands. There's an open house Sunday from 6 to 8pm. No virtual tour listed, so the open house is the way to see it properly before booking a private showing. One of the top Bridle Path offerings on this week's list.
37 St Andrews Gardens, Rosedale-Moore Park
$5,600,000 · Luxury 2½-Storey · Rosedale-Moore Park · 6 bed · 5 bath · 2500–3000 sqft · 3 parking · Open House Today 3:30–5pm · Sat Sep 19, 6–8pm
A 100+ year old home on St Andrews Gardens — the architecturally distinctive Rosedale street with a landscaped central garden running its full length. Six bedrooms, five bathrooms, and a pool in one of the most characterful settings Toronto has to offer. There's an open house today from 3:30 to 5pm and again Saturday from 6 to 8pm. No virtual tour listed, so this weekend is the time to see it. Properties on St Andrews Gardens are genuinely rare, and the heritage character here is something newer builds on adjacent streets simply can't replicate.
149 Highland Crescent, Bridle Path-Sunnybrook-York Mills
$7,998,000 · Luxury 2-Storey (New) · Bridle Path-Sunnybrook-York Mills · 5 bed · 7 bath · 5000+ sqft · 6 parking · Open House Sun Sep 20, 6–8pm · Virtual Tour
Brand-new construction on Highland Crescent — five bedrooms, seven bathrooms, a pool, six parking spots, and over 5,000 square feet in the Bridle Path corridor. At $7,998,000 it sits between the two Arjay Crescent properties in price, and the new-build quality and warranty coverage set it apart from older estates in the same range. Open house Sunday from 6 to 8pm, with the virtual tour available now. A well-rounded new-build Bridle Path option for buyers who want pool and scale without crossing into the $10M+ tier.
132 Glen Road, Rosedale-Moore Park
$5,395,000 · Luxury 2½-Storey · Rosedale-Moore Park · 6 bed · 5 bath · 3500–5000 sqft · 6 parking · Open House Sun Sep 20, 6–8pm
Six bedrooms, five bathrooms, six parking spots, and up to 5,000 square feet on Glen Road — a heritage Rosedale address running along the ravine edge. At $5,395,000 this is the most accessible Rosedale freehold on this week's list, and six parking spots on a Rosedale street is genuinely unusual. Open house Sunday from 6 to 8pm. No virtual tour listed — the open house is the practical first step. For buyers who want a Rosedale address and serious parking at a relative entry price for the neighbourhood, this is the one to prioritise Sunday.
126 Sandringham Drive, Lansing-Westgate
$12,695,000 · Luxury 2-Storey · Lansing-Westgate · 6 bed · 10 bath · 5000+ sqft · 14 parking
Six bedrooms, ten bathrooms, a pool, an elevator, fourteen parking spots, and over 5,000 square feet on Sandringham Drive in Lansing-Westgate. Ten bathrooms and fourteen parking spots are exceptional by any standard — this is a property built to a specification that rivals anything in the Bridle Path or Forest Hill South at a price that still undercuts those corridors. The open house field is flagged but no dates are listed — contact the agent directly to arrange access. A remarkable estate for buyers who want maximum specification and land without the traditional luxury postal code premium.
370 Glengrove Avenue W, Lawrence Park South
$8,499,000 · Luxury 3-Storey (New) · Lawrence Park South · 8 bed · 10 bath · 5000+ sqft · 4 parking · Virtual Tour
Brand-new three-storey on Glengrove Avenue West in Lawrence Park South — eight bedrooms, ten bathrooms, a pool, an elevator, and over 5,000 square feet. Eight bedrooms is the highest count among the freeholds on this week's list, and the ten bathrooms signal a home built with full ensuite coverage throughout. Lawrence Park South draws buyers for its school catchments and ravine proximity, and new construction here at this scale is rare. The virtual tour is available. A serious family estate for buyers who need maximum bedroom count in one of Toronto's top school neighbourhoods.
17 Heathcote Avenue, St. Andrew-Windfields
$5,199,000 · Luxury 2½-Storey · St. Andrew-Windfields · 10 bed · 9 bath · 5000+ sqft · 16 parking · Virtual Tour
Ten bedrooms, nine bathrooms, sixteen parking spots, and over 5,000 square feet on Heathcote Avenue in St. Andrew-Windfields — at $5,199,000 this is the most unusual value proposition on this week's list. The scale here is exceptional for the price: a home of this bedroom count and parking capacity would command multiples of this figure in Bridle Path or Forest Hill. The virtual tour is available. Worth loading before anything else — the sheer volume of space at this price point makes it stand out regardless of neighbourhood tier preferences.
11 Ridgewood Road, Forest Hill South
$7,999,000 · Luxury 2-Storey · Forest Hill South · 5 bed · 7 bath · 5000+ sqft · 10 parking · Virtual Tour
Five bedrooms, seven bathrooms, ten parking spots, and over 5,000 square feet on Ridgewood Road in Forest Hill South. Ten parking spots on a Forest Hill South address is exceptional and signals a lot with serious depth and likely a private drive configuration that's rare in this neighbourhood. At just under $8M it sits in the accessible mid-tier for Forest Hill South. The virtual tour is available. A well-specified option for buyers who want the Forest Hill South address with serious parking and square footage without crossing the $10M mark.
50 Yorkville Avenue 3203, Yorkville (Four Seasons Private Residences)
$6,399,000 · Luxury Apartment · Yorkville · 3 bed · 3 bath · 2250–2499 sqft · 2 parking · Virtual Tour
A suite at the Four Seasons Private Residences on Yorkville Avenue — three bedrooms, three bathrooms, 2,250+ square feet, a balcony, elevator, and two parking spots with the full Four Seasons hotel services available. The building is 11–15 years old and well-established in the Yorkville luxury condo market. At $6,399,000 for this size and address with hotel-backed amenities, the proposition is clear for buyers who want the absolute centre of Yorkville with a service level that freehold ownership can't match. The virtual tour is available now.
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.
