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 $10M Edenbridge-Humber Valley pool estate with open houses today and Sunday to a $13.5M Forest Hill South home on Dunvegan Road and a brand-new Bedford Park three-storey with eleven bathrooms. Neighbourhoods covered include Edenbridge-Humber Valley, Forest Hill South, Forest Hill North, Banbury-Don Mills, Bridle Path, Bedford Park, Trinity-Bellwoods, Rosedale, and Yorkville. Prices range from $3.2M to $13.5M.
25 North Drive, Edenbridge-Humber Valley
$10,000,000 · Luxury 3-Storey · Edenbridge-Humber Valley · 5 bed · 7 bath · 5000+ sqft · 8 parking · Open House Today 3–5pm · Sun Sep 13 6–8pm · Virtual Tour
Just listed yesterday — five bedrooms, seven bathrooms, a pool, eight parking spots, and over 5,000 square feet on North Drive in Edenbridge-Humber Valley. North Drive runs through one of the west end's most private estate pockets, along the Humber River ravine. There's an open house today from 3 to 5pm and again Sunday from 6 to 8pm — the virtual tour is also available if you want a preview first. At $10M this is the top-scored listing this week and the most active in terms of access. The west-end estate to see this weekend.
105 Dunvegan Road, Forest Hill South
$13,500,000 · Luxury 2-Storey · Forest Hill South · 5 bed · 7 bath · 5000+ sqft · 8 parking
Five bedrooms, seven bathrooms, a pool, eight parking spots, and over 5,000 square feet on Dunvegan Road — one of Forest Hill South's most coveted addresses. Dunvegan is a wide, tree-lined boulevard with some of the neighbourhood's most architecturally significant homes, and properties here rarely surface twice. At $13.5M this is the top-priced freehold on this week's list. No virtual tour listed — at this level, a private introduction is the standard process. The Forest Hill South listing to watch this week.
27 Penwood Crescent, Banbury-Don Mills
$11,499,000 · Luxury 2-Storey · Banbury-Don Mills · 8 bed · 11 bath · 5000+ sqft · 6 parking
Eight bedrooms, eleven bathrooms, a pool, an elevator, and over 5,000 square feet on Penwood Crescent in Banbury-Don Mills — one of the most fully-specified estate homes to hit the market this week. Eleven bathrooms across eight bedrooms signals meticulous suite-level coverage throughout, and the elevator adds long-term flexibility rare in a freehold at this scale. Banbury-Don Mills borders Edwards Gardens and the Bridle Path, with the private-lot character that estate buyers look for. No virtual tour listed. A serious contender for buyers who need maximum bedroom count at the $11M+ level.
18 Suncrest Drive, Bridle Path-Sunnybrook-York Mills
$9,499,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 5 bed · 6 bath · 5000+ sqft · 9 parking
Five bedrooms, six bathrooms, nine parking spots, and over 5,000 square feet on Suncrest Drive — a quiet Bridle Path-adjacent street known for its generous lots and natural privacy. At $9,499,000 it sits just below the $10M mark, which makes it a useful benchmark for buyers comparing across the corridor. No virtual tour or open house listed — a private showing is the way in. For buyers who've been watching the Bridle Path market and want 5,000+ square feet with serious parking under $10M, this is worth prioritising.
117 Yonge Boulevard, Bedford Park-Nortown
$7,998,888 · Luxury 3-Storey (New) · Bedford Park-Nortown · 6 bed · 11 bath · 5000+ sqft · 8 parking
Brand-new construction on Yonge Boulevard in Bedford Park — six bedrooms, eleven bathrooms, a pool, an elevator, eight parking spots, and over 5,000 square feet. Eleven bathrooms in a new build is exceptional and points to a home specified for complete ensuite and powder room coverage throughout. Bedford Park draws buyers for its school catchments and quieter pace along the Avenue Road and Yonge corridors, and new construction here moves consistently. No virtual tour listed yet. One of the most comprehensively specified new builds on this week's list.
22 Foxley Street, Trinity-Bellwoods
$5,995,000 · Luxury 3-Storey (New) · Trinity-Bellwoods · 5 bed · 7 bath · 3000–3500 sqft · 2 parking · Virtual Tour
A brand-new three-storey on Foxley Street in Trinity-Bellwoods — five bedrooms, seven bathrooms, a pool, and just under 3,500 square feet. Trinity-Bellwoods is the most unusual neighbourhood on this week's list for a luxury property: a culturally rich, walkable west-end community with a strong independent retail and restaurant scene, right next to the park. New builds at this price point here are genuinely rare. The virtual tour is live. A distinctive choice for buyers who want luxury finishes and a pool in a neighbourhood with real character rather than a traditional estate address.
150 Douglas Drive, Rosedale-Moore Park
$5,995,000 · Luxury 3-Storey · Rosedale-Moore Park · 7 bed · 5 bath · 3500–5000 sqft · 2 parking · Virtual Tour
Seven bedrooms and a pool on Douglas Drive in Rosedale-Moore Park — the highest bedroom count among the freeholds in this price range this week. Douglas Drive is a well-regarded Rosedale address, and a seven-bedroom three-storey with a pool at $5,995,000 is a competitive offer for the neighbourhood. Five bathrooms across seven bedrooms is on the leaner side, so the floor plan is worth walking carefully to understand the suite configuration. The virtual tour is available. A strong option for large families who want a Rosedale address and a pool without pushing past $6M.
615 Briar Hill Avenue, Forest Hill North
$5,795,000 · Luxury 3-Storey (New) · Forest Hill North · 7 bed · 8 bath · 3500–5000 sqft · 7 parking
Brand-new on Briar Hill Avenue in Forest Hill North — seven bedrooms, eight bathrooms, a pool, and seven parking spots across up to 5,000 square feet. Forest Hill North offers the Forest Hill name and school catchments at a more accessible price point than the south side, and new construction here with seven bedrooms and a pool is unusual at this price. At $5,795,000 it's one of the stronger new-build value propositions on this week's list. No virtual tour listed. A practical family purchase for buyers who want the Forest Hill address without the Forest Hill South price tier.
19 Saintfield Avenue, Bridle Path-Sunnybrook-York Mills
$5,219,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 6 bed · 4 bath · 3000–3500 sqft · 6 parking · Virtual Tour
Six bedrooms, four bathrooms, a pool, and six parking spots on Saintfield Avenue in the Bridle Path corridor — just listed yesterday. At $5,219,000 it's the most accessible Bridle Path freehold on this week's list, and the four bathrooms across six bedrooms signals an older home with larger rooms rather than a recently renovated or new-build layout. The virtual tour is available. Buyers who want a Bridle Path address and a pool at a relative entry price for the neighbourhood will want to load the virtual tour and assess the suite configuration before booking a showing.
80 Yorkville Avenue 902, Yorkville (80 & 100 Yorkville)
$3,188,000 · Luxury Apartment · Yorkville · 2 bed · 2 bath · 1400–1599 sqft · 2 parking
The entry point on this week's list — a ninth-floor suite at 80 & 100 Yorkville Residences, two bedrooms, two bathrooms, a balcony, and two parking spots at $3,188,000. Just listed yesterday, this is one of the most central Yorkville addresses available right now. At 1,400–1,599 square feet it's the most compact suite on this week's list, but the address, the building's reputation, and the two parking spots make it a strong lock-and-leave option. No virtual tour listed. An efficient entry into Yorkville condo ownership for buyers who prioritise address and simplicity over square footage.
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.
