The past 12 months have seen remarkable resilience at the very pinnacle of the Toronto luxury market. While broader sales volumes navigated shifting interest rate cycles and inventory adjustments, ultra-luxury buyers continued transacting in the city’s most prestigious enclaves — from heritage estates in Rosedale and manicured grounds in Forest Hill to the rolling acreage of The Bridle Path. Here are the Top 25 most expensive homes sold in Toronto over the past 12 months, verified directly through Toronto MLS sold records — complete with final sold prices, original list prices, beds, baths, and square footage.
The Top 25 Most Expensive Home Sales
Ranked by final confirmed sold price on the Toronto Regional Real Estate Board (TRREB) MLS system over the past 12 months (October 2025 – September 2026).
| # | Property | Neighbourhood | Sold Price | List Price | Beds / Baths | Sq Ft |
|---|---|---|---|---|---|---|
| 1 |
 211 Dunvegan Rd MLS® C13653822 · Detached · 3-Storey |
Forest Hill South | $23,500,000 | $22,000,000 | 5 bd / 8 ba | 5000 + |
| 2 |
 19 Country Lane MLS® C12870578 · Detached · 2-Storey |
Bridle Path-Sunnybrook-York Mills | $16,300,000 | $18,800,000 | 5 bd / 11 ba | 5000 + |
| 3 |
 76 Binscarth Rd MLS® C13211736 · Detached · 3-Storey |
Rosedale-Moore Park | $15,500,000 | $17,000,000 | 6 bd / 7 ba | 5000 + |
| 4 |
 101 Old Colony Rd MLS® C12354716 · Detached · 2-Storey |
St. Andrew-Windfields | $14,200,000 | $17,500,000 | 5 bd / 10 ba | 5000 + |
| 5 |
 1 Edmund Gate MLS® C12685978 · Detached · 2-Storey |
Casa Loma | $13,550,001 | $13,250,000 | 6 bd / 5 ba | 5000 + |
| 6 |
 7 Appleby Crt MLS® W13152672 · Detached · 2-Storey |
Islington-City Centre West | $12,350,000 | $13,950,000 | 6 bd / 9 ba | 5000 + |
| 7 |
 18 Chestnut Park Rd MLS® C12410500 · Detached · 3-Storey |
Rosedale-Moore Park | $12,200,000 | $13,995,000 | 5 bd / 7 ba | 5000 + |
| 8 |
 100 Bayview Rdge MLS® C12487614 · Detached · 2-Storey |
Bridle Path-Sunnybrook-York Mills | $12,000,000 | $15,888,888 | 6 bd / 12 ba | 5000 + |
| 9 |
 123 Glenayr Rd MLS® C13527176 · Detached · 3-Storey |
Forest Hill South | $11,600,000 | $12,800,000 | 5 bd / 10 ba | 5000 + |
| 10 |
 31 South Dr MLS® C12793900 · Detached · 2 1/2 Storey |
Rosedale-Moore Park | $10,675,000 | $12,250,000 | 6 bd / 7 ba | 5000 + |
| 11 |
 170 Roxborough Dr MLS® C13461906 · Detached · 3-Storey |
Rosedale-Moore Park | $10,500,000 | $11,500,000 | 5 bd / 9 ba | 5000 + |
| 12 |
 106 Glenayr Rd MLS® C13581614 · Detached · 3-Storey |
Forest Hill South | $10,500,000 | $12,800,000 | 5 bd / 8 ba | 5000 + |
| 13 |
 5 Brookfield Rd MLS® C13086380 · Detached · 2-Storey |
Bridle Path-Sunnybrook-York Mills | $10,200,000 | $11,498,000 | 4 bd / 7 ba | 5000 + |
| 14 |
 135 Crescent Rd MLS® C12224644 · Detached · 3-Storey |
Rosedale-Moore Park | $9,622,500 | $9,995,000 | 7 bd / 6 ba | 5000 + |
| 15 |
 33 Bayview Wood MLS® C13138064 · Detached · 2-Storey |
Bridle Path-Sunnybrook-York Mills | $8,900,000 | $9,550,000 | 5 bd / 8 ba | 5000 + |
| 16 |
 1 Suncrest Dr MLS® C12861138 · Detached · 2-Storey |
Bridle Path-Sunnybrook-York Mills | $8,800,000 | $9,980,000 | 5 bd / 9 ba | 5000 + |
| 17 |
 76 Arjay Cres MLS® C13477906 · Detached · 2-Storey |
Bridle Path-Sunnybrook-York Mills | $8,650,000 | $8,998,000 | 5 bd / 10 ba | 5000 + |
| 18 |
 43 The Kingsway MLS® W12476896 · Detached · 2 1/2 Storey |
Kingsway South | $8,550,000 | $9,950,000 | 6 bd / 7 ba | 5000 + |
| 19 |
 52 Rosedale Rd MLS® C12709212 · Detached · 3-Storey |
Rosedale-Moore Park | $8,420,000 | $8,980,000 | 5 bd / 7 ba | 5000 + |
| 20 |
 133 Hudson Dr MLS® C13020764 · Detached · 2-Storey |
Rosedale-Moore Park | $8,350,000 | $8,995,000 | 5 bd / 4 ba | 3000-3500 |
| 21 |
 1 Glen Edyth Pl MLS® C13452154 · Detached · 2-Storey |
Casa Loma | $8,200,000 | $8,950,000 | 4 bd / 6 ba | 5000 + |
| 22 |
 64 Old Forest Hill Rd MLS® C13548782 · Detached · 3-Storey |
Forest Hill South | $8,200,000 | $8,890,000 | 6 bd / 7 ba | 5000 + |
| 23 |
 48 Old Forest Hill Rd MLS® C13047546 · Detached · 2-Storey |
Forest Hill South | $8,075,000 | $8,495,000 | 5 bd / 7 ba | 3500-5000 |
| 24 |
 112 Hazelton Ave MLS® C12072633 · Detached · 3-Storey |
Annex | $8,000,000 | $8,998,000 | 3 bd / 5 ba | 3500-5000 |
| 25 |
 148 Forest Hill Rd MLS® C13213388 · Detached · 3-Storey |
Forest Hill South | $7,750,148 | $8,495,000 | 5 bd / 6 ba | 3500-5000 |
Key Market Trends
What Toronto’s ultra-luxury sales data reveals about top-tier buyer behavior, pricing dynamics, and wealth preservation over the past 12 months:
1. The Pinnacle Commands Cash and Conviction
The #1 sale of the year — 211 Dunvegan Road in Forest Hill South — commanded an astounding $23,500,000, selling for $1.5M over its $22M asking price in just 7 days on market. When rare, turnkey architectural estates hit the market in AAA central pockets, trophy buyers move swiftly without hesitation.
2. Heritage Enclaves Dominate the Top 25
Over 80% of Toronto’s 25 highest residential sales occurred in just three legendary neighbourhoods: Rosedale-Moore Park (7 sales), Bridle Path-Sunnybrook-York Mills (6 sales), and Forest Hill South (6 sales). Casa Loma, The Annex, and South Kingsway accounted for the remainder, reaffirming that heritage location equity remains the ultimate store of real estate value.
3. Negotiation Room Returned for Broader Ultra-Luxury
Outside of select competitive situations like Dunvegan Rd and Edmund Gate, the majority of sales closed between 85% and 95% of initial list price. Luxury buyers exercised rigorous valuation discipline, leveraging market inventory to negotiate discounts averaging 7% to 12% off ambitious initial asking prices.
4. The 5,000+ Square Foot Threshold
Nearly every single estate in the Top 25 exceeded 5,000 square feet of above-grade living area, featuring multi-car subterranean garages, dedicated staff quarters, custom wine cellars, and resort-calibre grounds with private pools. In the ultra-luxury tier, scale combined with private outdoor acreage is non-negotiable.
Sources: Toronto Regional Real Estate Board (TRREB) MLS® residential sales data for the 12-month period ending September 30, 2026. Data covers verified closed transactions across the City of Toronto.
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Sales data sourced from the Toronto Regional Real Estate Board (TRREB) MLS® system for closed residential transactions over the past 12 months. All information deemed reliable but not guaranteed. Not intended to solicit buyers or sellers currently under contract with another brokerage. Yossi Kaplan, MBA · RECO #4727677.