| 103 OLD COLONY ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2K3 | M2L | | $19,995,000 | 2/19/2025 | |
| 19 COUNTRY LANE, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1E1 | M2L | | $19,388,000 | 2/12/2025 | |
| 101 OLD COLONY ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2K3 | M2L | | $17,500,000 | 2/14/2025 | |
| 90 ARJAY CRESCENT, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1C7 | M2L | | $15,000,000 | 2/11/2025 | |
| 15 CHIEFTAIN CRESCENT, Toronto (St. Andrew-Windfields), Ontario M2L2H3 | M2L | | $13,380,000 | 2/4/2025 | |
| 11 DOON ROAD, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1M1 | M2L | | $11,900,000 | 2/11/2025 | |
| 28 BAYVIEW RIDGE, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1E5 | M2L | | $11,888,000 | 2/7/2025 | |
| 52 FIFESHIRE ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2G6 | M2L | | $11,288,000 | 2/25/2025 | |
| 4 FIFESHIRE ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2G5 | M2L | | $10,999,000 | 2/20/2025 | |
| 23 BAYVIEW RIDGE, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1E3 | M2L | | $10,998,000 | 3/4/2025 | |
| 49 ARJAY CRESCENT, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1C6 | M2L | | $9,800,000 | 2/6/2025 | |
| 48 THE BRIDLE PATH, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1C8 | M2L | | $7,980,000 | 2/24/2025 | |
| 20 WILKET ROAD, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1N6 | M2L | | $7,750,000 | 2/4/2025 | |
| 32 TRUMAN ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2L5 | M2L | | $6,500,000 | 2/27/2025 | |
| 8 COLVESTONE ROAD, Toronto (St. Andrew-Windfields), Ontario M2L1X3 | M2L | | $6,500,000 | 2/27/2025 | |
| 151 HIGHLAND CRESCENT, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1H2 | M2L | | $5,880,000 | 2/11/2025 | |
| 11 TUDOR GATE, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1N3 | M2L | | $5,688,000 | 2/2/2025 | |
| 106 HIGHLAND CRESCENT, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1H1 | M2L | | $5,600,000 | 2/6/2025 | |
| 18 OLD COLONY ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2J7 | M2L | | $5,150,000 | 2/5/2025 | |
| 78 GERALD STREET W, Toronto (St. Andrew-Windfields), Ontario M2L2M8 | M2L | | $5,000,000 | 2/27/2025 | |
| 53 YORK ROAD, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1H7 | M2L | | $4,995,000 | 3/11/2025 | |
| 1 WILKET ROAD, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1N5 | M2L | | $4,950,000 | 2/7/2025 | |
| 139 BEECHWOOD AVENUE, Toronto (Bridle Path-Sunnybrook-York Mills), Ontario M2L1J9 | M2L | | $4,588,000 | 3/5/2025 | |
| 36 CHIEFTAIN CRESCENT, Toronto (St. Andrew-Windfields), Ontario M2L2H4 | M2L | | $4,500,000 | 3/4/2025 | |
| 15 OLD COLONY ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2J7 | M2L | | $4,495,000 | 3/16/2025 | |
| 11 VERNHAM AVENUE, Toronto (St. Andrew-Windfields), Ontario M2L2B1 | M2L | | $4,480,000 | 3/18/2025 | |
| 8 MEAD COURT, Toronto (St. Andrew-Windfields), Ontario M2L2A6 | M2L | | $4,300,000 | 2/17/2025 | |
| 57 ROLLSCOURT DRIVE, Toronto (St. Andrew-Windfields), Ontario M2L1X6 | M2L | | $3,688,000 | 2/19/2025 | |
| 28 HARRISON ROAD, Toronto (St. Andrew-Windfields), Ontario M2L1V4 | M2L | | $3,520,000 | 2/10/2025 | |
| 236 YORK MILLS ROAD, Toronto (St. Andrew-Windfields), Ontario M2L1L1 | M2L | | $2,680,000 | 3/13/2025 | |
| 48 BANNATYNE DRIVE, Toronto (St. Andrew-Windfields), Ontario M2L2N9 | M2L | | $2,650,000 | 3/4/2025 | |
| 10 MELLOWOOD DRIVE, Toronto (St. Andrew-Windfields), Ontario M2L2E3 | M2L | | $2,599,000 | 3/13/2025 | |
| 36 BANNATYNE DRIVE, Toronto (St. Andrew-Windfields), Ontario M2L2N9 | M2L | | $2,588,000 | 2/8/2025 | |
| 371 WOODSWORTH ROAD, Toronto (St. Andrew-Windfields), Ontario M2L2T8 | M2L | | $2,380,000 | 3/6/2025 | |
| 39 DAVEAN DRIVE, Toronto (St. Andrew-Windfields), Ontario M2L2R6 | M2L | | $1,999,999 | 2/21/2025 | |
| 5 HOPPERTON DRIVE, Toronto (St. Andrew-Windfields), Ontario M2L2S5 | M2L | | $1,699,999 | 2/20/2025 | |