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 new Bayside penthouse with four open house dates to a $12.3M Forest Hill South estate with pool and elevator. Neighbourhoods covered include Rosedale, the Annex, St. Andrew-Windfields, Bridle Path, Banbury-Don Mills, Bedford Park, and Lawrence Park North. Prices range from $3.8M to $12.3M.
155 Merchants' Wharf LPH22, Waterfront Communities
$3,800,000 · Luxury Penthouse (New) · Waterfront Communities C8 · 3 bed · 3 bath · 2250–2499 sqft · 2 parking · Open House Tue Jun 24 · Fri Jun 26 · Sat Jun 27 · Sun Jun 28, all 6–9pm · Virtual Tour
A lower penthouse at Aqualuna Bayside — brand new, three bedrooms, 2,250+ square feet, a balcony, and two parking spots right on the Toronto waterfront. At $3.8M it's the entry point on this week's list, and for a new penthouse in this location that's a competitive number. There are four open house sessions this week: Tuesday, Friday, Saturday and Sunday from 6 to 9pm — more access than most luxury listings offer. The virtual tour is also available. A strong option for waterfront buyers who want new construction without crossing the $4M threshold.
7 Dale Avenue 106, Rosedale-Moore Park
$8,250,000 · Luxury Apartment · Rosedale-Moore Park · 2 bed · 3 bath · 3250–3499 sqft · 1 parking · Open House Tue Jun 24, 9–11pm · Virtual Tour
Over 3,250 square feet on Dale Avenue — one of Rosedale's quietest streets — with two bedrooms, three bathrooms, and a balcony. The suite is sized more like a large freehold than a typical condo, with a floor plan that suggests a principal suite of significant scale. There's an open house this Tuesday from 9 to 11pm if you want to walk through before the weekend. The virtual tour is available now. A top-tier Rosedale address for buyers who want the neighbourhood's prestige without freehold maintenance.
15 Aldershot Crescent, St. Andrew-Windfields
$5,270,000 · Luxury 2-Storey (New) · St. Andrew-Windfields · 5 bed · 7 bath · 5000+ sqft · 4 parking · Open House Sat Jun 27, 6–8:30pm · Virtual Tour
Brand-new construction in St. Andrew-Windfields — five bedrooms, seven bathrooms, and over 5,000 square feet at a price that sits well below most comparable new builds in the Bridle Path corridor next door. Seven bathrooms in a five-bedroom home indicates strong suite separation and likely a dedicated guest or in-law configuration. There's an open house Saturday from 6 to 8:30pm, with a virtual tour also available. A well-priced new-build entry into one of Toronto's most established north-east estate neighbourhoods.
140 Bedford Road, Annex
$6,500,000 · Luxury 3-Storey · Annex · 4 bed · 5 bath · 3500–5000 sqft · 3 parking · Open House Sat & Sun Jun 27–28, 6–8pm · Virtual Tour
A 100+ year old three-storey on Bedford Road in the Annex — with a pool, four bedrooms, five bathrooms, and up to 5,000 square feet of living space. Heritage homes of this scale in the Annex don't surface often, and Bedford Road is one of the street's most desirable stretches, steps from Yorkville and the ROM. Open houses run Saturday and Sunday from 6 to 8pm, with a virtual tour already available. Buyers who want genuine Annex character and architectural history at a freehold scale should put this on the list.
6 Penwood Crescent S, Banbury-Don Mills
$5,998,000 · Luxury 2-Storey · Banbury-Don Mills · 8 bed · 7 bath · 5000+ sqft · 8 parking · Open House Sat & Sun Jun 27–28, 6–8pm · Virtual Tour
Eight bedrooms, seven bathrooms, eight parking spots, a pool, and over 5,000 square feet in Banbury-Don Mills — at under $6M, this is one of the stronger value propositions on this week's list for sheer volume of space and land. The neighbourhood borders Edwards Gardens and the Bridle Path, with the large-lot, private-feel character that estate buyers look for. Open houses run Saturday and Sunday from 6 to 8pm, with a virtual tour available as well. A practical choice for large or multi-generational families who need serious room to spread out.
43 Hillholm Road, Forest Hill South
$12,295,000 · Luxury 2-Storey · Forest Hill South · 4 bed · 6 bath · 5000+ sqft · 6 parking · Open House Tue Jun 24, 4–5pm
The top price on this week's list — $12.3M in Forest Hill South, one of Toronto's most coveted freehold addresses. Four bedrooms with six bathrooms and over 5,000 square feet, with a pool and elevator, on Hillholm Road. Forest Hill South commands this kind of pricing for a reason: the street presence, lot depth, and neighbourhood cachet are in a category of their own. There's a private open house this Tuesday from 4 to 5pm — a tight window that reflects how these properties typically trade. No virtual tour listed; in-person is the way to see it.
223 Hillhurst Boulevard, Bedford Park-Nortown
$5,495,000 · Luxury 2-Storey · Bedford Park-Nortown · 5 bed · 6 bath · 3500–5000 sqft · 8 parking · Open House Sat & Sun Jun 27–28, 6–9pm · Virtual Tour
Eight parking spots on Hillhurst Boulevard — a clear signal about lot depth in a neighbourhood not known for oversized lots. Five bedrooms and six bathrooms across up to 5,000 square feet, in one of north midtown's most family-focused streets. Bedford Park draws buyers for the school catchments and quieter pace, and Hillhurst in particular has seen strong demand for larger homes. Open houses run Saturday and Sunday from 6 to 9pm, with a virtual tour available ahead of time. A practical family-scale option at a price that makes sense for the area.
135 Buckingham Avenue, Bridle Path-Sunnybrook-York Mills
$6,500,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 5 bed · 5 bath · 3500–5000 sqft · 6 parking · Open House Sat & Sun Jun 27–28, 6–8pm · Virtual Tour
Five bedrooms, five bathrooms, a pool, and six parking spots on Buckingham Avenue in the Bridle Path corridor. The Sunnybrook-York Mills stretch of this neighbourhood offers the prestige of the Bridle Path address at a slightly more approachable price point, and Buckingham in particular is a well-regarded street with established estate homes. Open houses are Saturday and Sunday from 6 to 8pm — the virtual tour is also ready if you want a preview first. A solid mid-range Bridle Path option for buyers comparing across the corridor.
12 York Road, Bridle Path-Sunnybrook-York Mills
$5,880,000 · Luxury 2-Storey · Bridle Path-Sunnybrook-York Mills · 5 bed · 5 bath · 3500–5000 sqft · 6 parking · Open House Sat & Sun Jun 27–28, 6–8pm
Five bedrooms, five bathrooms, and six parking spots on York Road — a quiet Bridle Path-adjacent street with the kind of privacy and green surroundings that draw estate buyers to this corridor. At $5.88M it sits just below the Buckingham Avenue listing nearby, making for an interesting direct comparison if you're touring the area this weekend. Open houses are Saturday and Sunday from 6 to 8pm. No virtual tour listed, so the open house is your best first look. Worth pairing with a Buckingham Avenue visit for a side-by-side read on value.
95 Riverview Drive, Lawrence Park North
$7,890,000 · Luxury 2-Storey · Lawrence Park North · 5 bed · 5 bath · 3500–5000 sqft · 6 parking · Virtual Tour
Riverview Drive is one of Lawrence Park North's most desirable streets, running along the Chatsworth Ravine — and this freshly listed home brings five bedrooms, five bathrooms, six parking spots, and up to 5,000 square feet to a setting that's hard to beat for mature trees and ravine proximity. Just listed on June 20, it's the newest addition to this week's list. The virtual tour is available now. Buyers who toured the 130 Riverview Drive listing from last week will want to compare these two directly — similar street, different scale and price point.
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.
