Toronto’s luxury real estate market represents some of North America’s finest residential architecture, private acreage, and engineering feats. From private two-acre gated châteaus on The Bridle Path to subterranean 10-car collector garages in exclusive enclaves and Mies van der Rohe-inspired modernism in Lawrence Park, the tier between $3,000,000 and $27,500,000 offers unprecedented opportunity for discerning buyers and institutional portfolios.
Below is a curated benchmark analysis of the 25 most expensive homes currently available for sale in Toronto across The Bridle Path, St. Andrew-Windfields, York Mills, Lawrence Park, and Bedford Park.
Toronto’s 25 Most Expensive Homes For Sale:
| Address | Neighbourhood | List Price | Beds / Baths | Parking | Standout Architectural Highlight |
|---|---|---|---|---|---|
| 85 The Bridle Path | The Bridle Path | $27,500,000 | 8+1 / 11 | 35 (5-Car Gar) | 2-Acre Gated Château by Joe Brennan, 20,000+ sf |
| 45 Park Lane Circle | The Bridle Path | $22,800,000 | 5+1 / 9 | 28 (4-Car Gar) | 302′ Frontage LA-Style Modern Bungalow, Pool |
| 90 Arjay Crescent | Bridle Path Enclave | $13,680,000 | 5+1 / 9 | 26 | 10-Car Subterranean Collector Garage, Ravine Lot |
| 92 Arjay Crescent | Bridle Path Enclave | $11,500,000 | 5+1 / 8 | 22 | 9-Car Subterranean Garage, Salt Pool, Richard Wengle |
| 50 Teddington Park Ave | Lawrence Park North | $10,795,000 | 4+1 / 8 | 6 | “Infinity House” Mies van der Rohe modernism, Bronze |
| 17 Bayview Ridge | Bridle Path-York Mills | $9,280,000 | 7+1 / 7 | 11 (3-Car Gar) | Corner Ravine Estate Overlooking Rosedale Golf Club |
| 370 Glengrove Ave W | Lawrence Park South | $8,499,000 | 7+1 / 10 | 5 | 50′ x 170′ Lot, Backlit Absolute Marble Feature Wall |
| 24 Strathallan Blvd | Lawrence Park South | $7,590,000 | 4+1 / 7 | 4 | Concrete Sub-floors, 8-Zone Radiant, Snow-Melt Drive |
| 21 Fifeshire Road | St. Andrew-Windfields | $6,995,000 | 5+1 / 8 | 16 | 121′ Manicured Lot, ~8,300 sf Living, Imported Marble |
| 46 Wimpole Drive | St. Andrew-Windfields | $6,799,000 | 6+2 / 10 | 14 (4-Car Gar) | Vaulted Ceilings, Skylights, 10-Car Circular Drive |
| 105 Arjay Crescent | Bridle Path Enclave | $6,580,000 | 5+1 / 8 | 8 | Leaded-Glass Dome Foyer, Heated Driveway, Elevator |
| 230 Hillhurst Blvd | Bedford Park-Nortown | $6,218,000 | 5+1 / 6 | 6 | Lorne Rose Design, Ravine Lot on Cortleigh Parkette |
| 363 Bedford Park Ave | Bedford Park-Nortown | $5,695,000 | 4+1 / 8 | 8 | SAAZE Building Group Custom Build, Limestone Facade |
| 17 Heathcote Avenue | St. Andrew-Windfields | $5,199,000 | 8+2 / 9 | 21 (5-Car Gar) | 100′ Frontage, 1,300 sf Garage, 10,870 sf Living Area |
| 235 Hillhurst Blvd | Bedford Park-Nortown | $4,995,000 | 5+2 / 7 | 8 | Richard Wengle Classic Stone Front, South Garden |
| 75 Bannockburn Ave | Bedford Park-Nortown | $4,988,000 | 4+1 / 5 | 8 | Oakland Custom Homes, Lauren Rose Architecture |
| 159 Cortleigh Blvd | Lawrence Park South | $4,899,000 | 4+1 / 5 | 3 | Sustainable Indiana Limestone Eco-Luxury, Heat Pump |
| 38 Fifeshire Road | St. Andrew-Windfields | $4,549,999 | 4+1 / 5 | 14 | 0.5-Acre Ravine Estate Lot (118′ x 200′), Mature Trees |
| 15 Aldershot Crescent | St. Andrew-Windfields | $4,499,000 | 4+1 / 7 | 6 | Brand New 7,620 sf Total Living, South-Facing Lot |
| 15 Alexandra Wood | Bedford Park-Nortown | $4,450,000 | 4+1 / 5 | 12 | Georgian English Estate, 8-Car Courtyard, Gardens |
| 436 Glengarry Ave | Bedford Park-Nortown | $3,995,000 | 4+2 / 6 | 8 | Danieli Developments, Wine Cellar, Executive Study |
| 11 Mead Court | St. Andrew-Windfields | $3,895,000 | 3+1 / 5 | 8 | Ranch-Style Bungalow on Cul-de-Sac, Cathedral Ceilings |
| 178 Blythwood Road | Lawrence Park South | $3,800,000 | 3 / 2 | 8 | 70′ x 200′ Lot w/ CoA Approval for 7,842 sf Luxury Build |
| 59 Burncrest Drive | Bedford Park-Nortown | $3,495,000 | 4+1 / 5 | 7 | Contempo Studio Architecture, Marisa Carmen Interiors |
| 339 Broadway Avenue | Bridle Path-Sunnybrook | $3,288,000 | 4+1 / 5 | 4 | Custom Vapour Fireplace, Integrated Built-In Audio |
Key Market Trends for Luxury Buyers & Investors
- Subterranean Collector Garages: Properties such as 90 Arjay ($13.68M) and 92 Arjay ($11.5M) feature specialized 9-to-10 car underground garages designed specifically for automotive collectors and private multi-vehicle storage.
- Whole-Building Performance & Concrete Framing: High-end buyers in Lawrence Park and Lytton Park are prioritizing structural silence and efficiency. Notable examples include 24 Strathallan ($7.59M) with solid 1.5-inch concrete radiant sub-flooring and 159 Cortleigh ($4.89M) clad in solid Indiana limestone.
- Acreage & Privacy: Landmark parcels in The Bridle Path (such as 85 The Bridle Path and 45 Park Lane Circle) command substantial premiums due to irreplaceable 2-acre footprints and 300+ foot frontages.
Private Showings & Portfolio Advisory
Navigating off-market luxury acquisitions or finding the right architectural match requires financial rigor, valuation acumen, and discretion.
Yossi Kaplan, MBA
Realtor® | Right At Home Realty
Direct: 437-848-3077
Toronto Luxury Real Estate & Portfolio Advisory
Disclaimer: Not intended to solicit buyers or sellers currently under contract with a brokerage. Listing data sourced via TRREB MLS® System for informational purposes.
The information may change at any time, c,please ontact us for current updates.