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 — headlined by a 9-bedroom, 18-parking estate in St. Andrew-Windfields and a $8.9M Davenport Road penthouse in the Annex. Several homes have open houses running this weekend. Neighbourhoods covered include St. Andrew-Windfields, Bridle Path, Rosedale, the Annex, and High Park-Swansea. Prices range from $5.6M to $10.9M.
9 Fifeshire Road, St. Andrew-Windfields
$7,550,000 · Luxury 2-Storey · St. Andrew-Windfields · 7 bed · 7 bath · 5000+ sqft · 12 parking · Open House Sat & Sun 6–8pm · Virtual Tour
Seven bedrooms, seven bathrooms, twelve parking spots, and over 5,000 square feet on Fifeshire Road — a quiet pocket of St. Andrew-Windfields just off the Bridle Path. The scale here suggests a home built for hosting and multi-generational living in equal measure. There's an open house Saturday and Sunday from 6 to 8pm if you want to walk it in person, plus a virtual tour if you'd rather get a first look online. For buyers comparing estate properties in this price band, this is a strong one to see firsthand.
14 St Margarets Drive, Bridle Path-Sunnybrook-York Mills
$8,988,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 7 bed · 10 bath · 5000+ sqft · 7 parking · Open House Sat 6–9pm · Virtual Tour
Ten bathrooms across seven bedrooms is a ratio you rarely see, even in the Bridle Path corridor — and it points to a home designed around guest suites and entertaining at a serious scale. Add a pool and over 5,000 square feet, and this St. Margarets Drive estate is one of the most fully-loaded properties on this week's list. There's an open house Saturday from 6 to 9pm, with a virtual tour available beforehand. A clear must-see for buyers shopping the Bridle Path price tier.
148 Munro Boulevard, St. Andrew-Windfields
$6,295,000 · Luxury 2-Storey · St. Andrew-Windfields · 5 bed · 8 bath · 3500–5000 sqft · 8 parking · Open House Thu 4–5:30pm · Virtual Tour
Munro Boulevard sits in one of St. Andrew-Windfields' more private stretches, and this home backs that up with a pool, an elevator, and eight bathrooms across five bedrooms. Eight parking spots tells you the lot has real width to work with. There's an open house this Thursday from 4 to 5:30pm — a shorter window, so worth planning ahead if you want to see it in person, with a virtual tour as backup. A practical mid-range option for buyers in the St. Andrew-Windfields market.
101 Forest Heights Boulevard, St. Andrew-Windfields
$10,880,000 · Luxury 2-Storey · St. Andrew-Windfields · 9 bed · 11 bath · 5000+ sqft · 18 parking · Open House Sat & Sun 6–7pm · Virtual Tour
The top price on this week's list — nine bedrooms, eleven bathrooms, an elevator, and eighteen parking spots on Forest Heights Boulevard. This is estate-scale property in the truest sense, with enough bathroom and bedroom count to comfortably handle a large extended family or significant staff. There's an open house both Saturday and Sunday from 6 to 7pm, plus a virtual tour if you want a preview first. At nearly $11M, this is the headline property of the week for serious buyers in the St. Andrew-Windfields corridor.
55 Farnham Avenue, Yonge-St. Clair
$5,595,000 · Luxury 3-Storey · Yonge-St. Clair · 4 bed · 5 bath · 3000–3500 sqft · 2 parking · Open House Sat & Sun 6–8pm
A three-storey freehold on Farnham Avenue, tucked into one of Yonge-St. Clair's quieter residential streets just south of the subway line. Four bedrooms and five bathrooms across roughly 3,200 square feet is a comfortable family scale without tipping into estate territory. There's an open house Saturday and Sunday from 6 to 8pm — no virtual tour listed, so this weekend's showing is the way to see it. A solid option for buyers who want midtown walkability without the price tag of the Annex or Rosedale.
7 Dale Avenue 304, Rosedale-Moore Park
$6,499,000 · Luxury Apartment (New) · Rosedale-Moore Park · 4 bed · 3 bath · 2500–2749 sqft · 1 parking · Virtual Tour
A brand-new four-bedroom suite on Dale Avenue, one of Rosedale's quietest and most established streets. Four bedrooms in a condo this size is uncommon — most luxury buildings max out at two or three — making this a rare find for a family that wants Rosedale without a freehold-sized maintenance commitment. The virtual tour is available now. With the ravine trails and Summerhill both close by, this suits buyers who want established-neighbourhood prestige with condo simplicity.
33 Delisle Avenue 1004, Yonge-St. Clair
$5,775,000 · Luxury Apartment · Yonge-St. Clair · 4 bed · 7 bath · 5000+ sqft · 4 parking · Virtual Tour
Seven bathrooms and over 5,000 square feet in a condo is genuinely exceptional — this is closer to a sky mansion than a typical suite, with four bedrooms spread across a footprint most freeholds would envy. Delisle Avenue sits right at the heart of the Yonge-St. Clair node, walkable to the subway and a strong restaurant strip. The virtual tour is live. For buyers who want the full square footage of a luxury home but in a building with concierge and amenities, this is one of the more unusual options on the market right now.
30 Dacre Crescent, High Park-Swansea
$5,998,000 · Luxury 2-Storey (New) · High Park-Swansea · 4 bed · 5 bath · 3500–5000 sqft · 5 parking · Virtual Tour
Brand-new construction in High Park-Swansea, a west-end neighbourhood that's increasingly drawing luxury buyers priced out of Forest Hill or Rosedale but unwilling to compromise on green space. High Park itself is right there, along with the Bloor West Village strip for shopping and restaurants. Four bedrooms and five bathrooms across up to 5,000 square feet, with five parking spots, makes this a genuinely new and move-in-ready option. The virtual tour is available. Worth a look for buyers who want new-build quality at a relative discount to the city's established luxury corridors.
321 Davenport Road 401, Annex
$8,875,990 · Luxury Apartment (New) · Annex · 3 bed · 4 bath · 3750–3999 sqft · 2 parking
Brand new on Davenport Road in the Annex, this suite runs nearly 4,000 square feet — a footprint that puts it in direct competition with freehold properties twice its price elsewhere in the city. Three bedrooms and four bathrooms, with a balcony and two parking spots, in a building that's just hit the market. No virtual tour listed yet, so an in-person visit is the way to get a feel for the space. At $8,875,990, this is a statement purchase for buyers who want Annex prestige with brand-new construction.
335 Cortleigh Boulevard, Bedford Park-Nortown
$6,249,000 · Luxury 3-Storey · Bedford Park-Nortown · 7 bed · 6 bath · 3500–5000 sqft · 7 parking · Virtual Tour
Another three-storey property on Cortleigh Boulevard, a street that's quietly become one of Bedford Park's most active for new luxury construction. Seven bedrooms and six bathrooms across up to 5,000 square feet, with a pool and seven parking spots, gives this home serious capacity for a large family. Bedford Park continues to draw buyers for its school catchments and quieter pace relative to more central neighbourhoods. The virtual tour is live. A strong option for families needing more bedrooms than bathrooms in their next home.
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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.
