“Can We Really Own a Property in Orchard?” — How One Couple Turned a Landed Upgrade Dream Into a $5M Net Worth Reality

Shermain and Kenneth are no strangers to strategic property moves.

Like many Singaporean couples, they started with a BTO. Years later, they upgraded to an Executive Condominium (EC) in the North — a decision that rewarded them handsomely when their property appreciated in value.

When their EC reached MOP, and their income had taken a significant leap, they came to us with what seemed like the natural next step:

"We want to sell our EC and upgrade to a landed."

They had their eyes on a cluster house — more space, privacy, and landed living, without the hassle of maintaining a garden. It felt like the perfect solution.

But during our conversation, something unexpected came up.

The Unspoken Fear

Beneath all the financial readiness, Shermain hesitated.

She shared a fear many don’t talk about openly:
Pests.

Yes — roaches, rats, lizards.
Stories of ground-floor or landed living came with warnings she couldn’t ignore.

And suddenly, the question became bigger than just upgrading.

“Is this move truly necessary?
What if the better move… is no move at all?”

What If… You Didn’t Have to Sell?

That’s when we asked a bold question:

“What if you could own two properties instead?
What if you could keep your EC… and invest in another?”

They paused.
And Shermain asked: “Wait, isn’t that only for the super-rich?”

That’s when we ran the numbers.

With Shermain holding onto the EC under her name, we assessed Kenneth’s profile for a second property. Based on their income, CPF, and loan eligibility — we proposed something they never considered possible:

A freehold, undervalued 2-bedder in the Core Central Region (CCR) — right in Cairnhill, just steps from Orchard.

The Result? Two Properties. One Smart Plan.

Today, Shermain and Kenneth are:

✅ Still living comfortably in their EC (under Shermain’s name)
✅ Proud owners of a prime CCR investment property under Kenneth’s name
✅ Enjoying 75% rental coverage of their monthly instalments
✅ Using Kenneth’s CPF to cover the rest of the instalments — with no cash outlay
✅ Sitting on an estimated net worth of $5 million for future retirement

No fear of pests.
No stress from landed upkeep.
No rush to sell a home they love.
And definitely — no regrets.

The Big Lesson?

Sometimes the next level isn’t about buying bigger, but buying smarter.

Don’t be limited by traditional thinking — that upgrading means you must sell, or that CCR properties are out of reach.

With the right guidance, strategic structuring, and proper risk planning, it’s possible to own premium assets, generate passive income, and build multi-million dollar net worth — all while living in a home you love.

Inspired by Shermain and Kenneth’s story?
Let’s explore what’s possible for you — no pressure, just possibilities.
– David & Audrie, The Real Estate Couple for Couples