"How much condo can I afford?" has a precise answer, and it is almost always lower than the headline figure a showflat agent quotes. Your ceiling is set by the lowest of three limits: what the bank will lend (TDSR), how much of the price a loan can cover (LTV), and how much cash + CPF you can put down.
Limit 1 — TDSR (how much a bank will lend)
Total Debt Servicing Ratio caps all your monthly debt repayments at 55% of gross monthly income. Crucially, the bank tests this at a 4.00% stress rate, not your actual promo rate. So if a couple earns S$14,000/month combined with no other debt:
At the 4% stress rate over a 30-year tenure, roughly S$7,700/month supports a loan of about S$1.6m. (Exact figure depends on tenure and age — the affordability calculator computes it.)

Limit 2 — LTV (how much of the price a loan can cover)
A first housing loan is capped at 75% of the property value or price, whichever is lower. So a S$1.6m loan implies a property of about S$2.13m — but only if you can fund the other 25%.
Limit 3 — cash + CPF (the downpayment and duties)
On a 25% downpayment, at least 5% must be paid in cash; the remaining 20% can be cash or CPF. On top of that you owe Buyer's Stamp Duty. For a S$2.13m home:
Your real budget is the lowest of these three ceilings. Most upgraders are limited not by the loan but by the cash-and-CPF gate — which is exactly why the proceeds from your HDB sale matter so much.
The one number people forget
When you eventually sell the condo, you must refund to CPF everything you used plus accrued interest. Factor this "CPF clawback" into your long-term sums so the paper gain on your next sale is not a surprise.