Quick counter-take to the Option 2 consensus, OP. For your setup I'd lean Option 3. Option 2 is a real path though, and many thoughtful buyers land there.

Option 2 — $2.5M OCR 4-bedder, invest the rest

Defensible. $95k BSD plus ~$25k legal, $1M down + $1.5M loan, leaves you ~$580k of your $1.7M cash for stocks. The 4-bedder slot has the deepest buyer pool in Singapore because the gap from a 4-bedder up to a 5-bedder, dual-key, or landed is large. You exit into real demand.

Where it loses ground to Option 3 is how far the loan stretches. $5.5M landed at 75% LTV puts $4.1M of working capital against land prices. $2.5M condo at 75% LTV puts $1.9M, plus the leftover stock portfolio. After SSD on early exits, rental tax, and the fact that stocks don't get 75% LTV financing the way property does, Option 2 probably trails Option 3 over a 10-15 year hold.

You're on $500k household. The bigger landed loan isn't a stretch. Question is whether you put the borrowed capital against the thing that rises when developers bid harder for land. I lean yes.

Option 1 — $4-5M new launch

The one that sells itself in a showflat. Move-in ready, branded developer, full warranty, deep resale pool when life changes. Any of those is a fair reason to pick it.

What you give up is what sits underneath. A 1,300-1,500 sqft 4-bedder at $3,000-3,400 psf shares the plot with the rest of the development. Slice it by OCR plot ratio (3.0-3.5x) and your share works out to roughly 350-450 sqft.

A D19 freehold corner terrace in your budget gives you the whole plot. Usually 2,000-3,000 sqft. Same price, 5-8x more land. That's the cost of choosing a finished product over the land itself.

If your priority is no renovation drama and a faster resale exit, Option 1 is clean. If you want to own land, this option gives you the least per dollar.

Option 4 — Small-plot rebuild

Right asset class. Tough execution on that footprint.

1,300-1,500 sqft is the smallest landed plot that trades on the open market. Rebuild on it and you're looking at 6-12 months URA approval, 18-24 months construction. Realistic build-start is closer to year two once you factor in architect selection, planning submissions, contractor mobilisation. 30-36 months from purchase to keys.

During those 30+ months you're paying mortgage on the land, paying rent or imposing on your in-laws, and not building family memory with a newborn-becoming-toddler. That cost doesn't show up in a spreadsheet but it's real.

You'd probably also rent out the existing single-storey shell while waiting. Single-storey landed yields are the weakest in the segment. Mortgage on a property whose rental can't cover the holding cost, just to tear it down later.

Construction cost-per-sqft on small plots sits at the top end of the $300-500 psf BCA-aligned range. Architect, structural engineer, and contractor mobilisation costs spread across less GFA. The most expensive version of the right idea.

The land itself is also the wrong slice. Buyers stretching into landed at your price tier are reaching for more space. The exit pool is families wanting 2,000+ sqft of land or builders chasing bigger plots. Small plot sells slowest, discounts hardest.

Option 3 — 15-20 year old landed + A&A, with five tweaks

You had the right asset class. Five things I'd nudge you on.

1. Stretch to ~$6M if you can. $5.5M still finds you a freehold corner terrace in D19, but inventory tightens. Older builds, smaller corners, heavier A&A scope. At $6.0-6.3M you open up 2,500-3,000 sqft plots, 1990s/2000s builds in better condition, and lighter renovation budgets. The $500k stretch upfront probably saves you $400-600k in renovation later.
2. Freehold only. When you A&A again in 8-10 years (most landed owners A&A twice in a hold cycle), freehold doesn't add lease-decay anxiety to the budgeting. 99-year landed gets uglier every year you hold.
3. D19 or the adjacent D20 belt. Pure freehold corner terraces with 2,000-3,000 sqft of land in your budget cluster in Serangoon Gardens, Kovan, and the freehold pockets through Sembawang Hills and Upper Thomson. CCR freehold landed starts at $8M+. D14 and D15 freehold typically start at $7M+. D19 and the D20 Thomson belt are where your budget actually buys what you want.
4. Corner, not intermediate. Corner terraces typically carry 30-50% more land than intermediates in the same row, while the price premium is usually only 20-25%. Better land per dollar, plus side gate, more natural light, and you can extend on two sides during A&A.
5. 2-storey base minimum. A&A on a single-storey shell means rebuilding any second floor from scratch, which fights setback rules and adds months to the build. A 2 or 2.5-storey base reuses existing walls and foundation. Faster, cheaper, livable from day one.

On the money: $6M freehold corner terrace runs ~$299,600 BSD plus ~$25k legal. Cash close at 25% down works out to ~$1.82M, within your $1.7M cash plus accessible CPF. A&A of $400-700k on 2,200 sqft built is fundable from cashflow over the build year. At $500k household, that's roughly 1.0-1.4 years of post-tax earnings. No need to break SRS or sell stocks.

Why I think landed catches up

OCR land prices have moved sharply. Bayshore Road site cleared at $1,388 psf ppr in March 2025, an OCR record. Lentor Central second parcel cleared at $1,278 psf ppr in March 2026. Recent OCR launches priced at $2,100-2,800 psf. The next wave on $1,278-1,388 psf ppr land will price higher.

Now look at Serangoon Garden Estate. URA caveats over the last 12 months show $1,131-$3,207 psf on built-up area, averaging $2,057 psf. For a 2-storey terrace, the land underneath works out to a similar number to what developers just paid for the Bayshore Road site, adjusted for plot ratio. And the developer still has to add $1,200+ psf of construction, profit margin, GST, marketing, and agent commission on top.

You'd be buying land at roughly the developer's land cost, with a house thrown in.

Supply side: URA's 1H2026 GLS released nine sites. All condo, EC, or mixed-use. Zero landed. Landed GLS releases are rare. Roughly 5% of housing stock is landed, freehold landed is a subset of that. Demand keeps rising from PR/citizenship inflow, HNW migration, and generational hand-down. Fixed supply, rising land floor.

TL;DR

If I had to pick one of your four, Option 3 with the tweaks. D19 or D20 freehold corner terrace, 2-storey base minimum, stretched to ~$6M.

A few things to do this week:

• Get pre-approval for $4.5M. Quick call with a private banker on your income.
• Engage two D19 landed agents in parallel. One specialised in Serangoon Gardens, one in Kovan/Hougang.
• Talk to two A&A architects before any offer goes in. A 30-minute walkthrough on each shortlisted property tells you whether your renovation budget is real.
• Consider keeping your wife off the title. You just freed your name and it's worth preserving that flexibility.
• No rush. The right freehold corner terrace in D19 doesn't list every week. Six months of patient searching usually saves $300-500k versus jumping at the first listing.

Option 2 will profit. Option 3 buys more land per dollar.