Toronto’s Priciest Condos on the Market: Penthouse to Penthouse
From a $22.5M penthouse over Wellington Street to sky-high Yorkville penthouses and Rosedale estates-in-the-sky — these are the 25 priciest condos on the Toronto market right now. Which one would you take?
| # | Neighbourhood | List Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|---|
1. 4602/03 – 183 Wellington St W | Waterfront Communities C1 | $22,500,000 | 3 | 5 | 5000 + |
2. 5202 – 50 Yorkville Ave | Annex | $18,800,000 | 3 | 4 | 4750-4999 |
3. PH1 – 7 Dale Ave | Rosedale-Moore Park | $16,500,000 | 3 | 5 | 3750-3999 |
4. 3802 – 200 Cumberland St | Annex | $15,800,000 | 3 | 4 | 3750-3999 |
5. 1301 – 287 Davenport Rd | Annex | $10,499,900 | 3 | 5 | 3500-3749 |
6. SPH1 – 155 Merchants’ Wharf | Waterfront Communities C8 | $10,250,000 | 3 | 4 | 4750-4999 |
7. PH – 1 Chestnut Park | Rosedale-Moore Park | $9,795,000 | 4 | 4 | 4000-4249 |
8. 703 – 118 Yorkville Ave | Annex | $9,700,000 | 3 | 5 | 5000 + |
9. 401 – 321 Davenport Rd | Annex | $8,875,990 | 3 | 4 | 3750-3999 |
10. 101 – 33 Chatsworth Dr | Lawrence Park South | $8,600,000 | 3 | 4 | 4000-4249 |
11. 4001 – 50 Yorkville Ave | Annex | $8,595,000 | 2 | 4 | 2750-2999 |
12. 302 – 33 Chatsworth Dr | Lawrence Park South | $7,900,000 | 2 | 3 | 3250-3499 |
13. 1501 – 206 Bloor St W | Annex | $7,680,000 | 3 | 3 | 4250-4499 |
14. 4801 – 99 John St | Waterfront Communities C1 | $7,000,000 | 4 | 4 | 3250-3499 |
15. 205 – 7 Dale Ave | Rosedale-Moore Park | $6,890,000 | 2 | 3 | 2500-2749 |
16. 501 – 287 Davenport Rd | Annex | $6,799,900 | 3 | 4 | 2500-2749 |
17. 300 – 468 Wellington St W | Waterfront Communities C1 | $6,750,000 | 3 | 3 | 4750-4999 |
18. 302 – 7 Dale Ave | Rosedale-Moore Park | $6,749,000 | 2 | 3 | 2750-2999 |
19. 1102 – 89 Avenue Rd | Annex | $6,657,600 | 2 | 3 | 1600-1799 |
20. 304 – 7 Dale Ave | Rosedale-Moore Park | $6,499,000 | 2 | 3 | 2500-2749 |
21. 3203 – 50 Yorkville Ave | Annex | $6,399,000 | 2 | 3 | 2250-2499 |
22. 205 – 77 Clarendon Ave | Casa Loma | $6,350,000 | 2 | 3 | 2250-2499 |
23. 304 – 200 Russell Hill Rd | Casa Loma | $6,350,000 | 3 | 3 | 2250-2499 |
24. 4802 – 99 John St | Waterfront Communities C1 | $6,000,000 | 3 | 3 | 2750-2999 |
25. 1603 – 77 Charles St W | Bay Street Corridor | $5,900,000 | 3 | 4 | 2750-2999 |
Key Market Trends for Luxury Condo Buyers & Investors
Toronto’s luxury condo tier is holding firm: penthouse inventory across Yorkville, the Annex, Rosedale and the Waterfront is scarce, and the top end of the market continues to attract global buyers. Values sit where supply is thinnest — full-floor and penthouse units in boutique buildings command the highest per-square-foot premiums.
Private Showings & Portfolio Advisory
Every listing above is live and available for private showing. Whether you’re acquiring a trophy penthouse or building a luxury portfolio, I’ll walk you through the numbers — and the negotiation — like it’s my own deal.
About Yossi Kaplan, MBA
Toronto condos and preconstruction, Costa Rica beachfront — and the straight answers on the numbers that matter. Whether you’re buying your first condo, adding an investment unit, or looking at Guanacaste, I work the deal like it’s my own.