The Biggest Property Gains and Losses in Singapore's Resales

The two extremes, up front, because that is what everyone comes for.

• Biggest gain: an Anderson Road condominium, 4,316 sqft, bought for $6.56M in 2007 and sold for $52.25M in 2025 — a $45.69M gross gain (+697%) after an 18-year hold.
• Biggest loss: a Mount Rosie Road detached house, 30,659 sqft, bought for $43.80M and sold five years later for $19.80M — a $24.00M loss (-55%).

Both are drawn from 31,374 matched private resale pairs — the same unit bought, then later sold — that transacted in the 730 days ending 23 June 2026. And both share a trait that runs down the entire list: they are ultra-prime homes. Almost every name at the top of either leaderboard is a large landed property in a prime district or a big prime-district condo, where the quantums are so large that a routine percentage move becomes an eye-watering dollar figure.

That is the whole point of reading these tables correctly. They show you how wide the spread gets at the edges — not what happens to an ordinary home. A $45.69M gain is not a scaled-up version of a normal outcome any more than a lottery jackpot is a scaled-up salary. To judge your own unit you need the base rate, not the record: across the full 267,641-pair history, 85.3% of private resales sold above their purchase price — that is the number to anchor on, and the full picture is in how to tell if your property will be profitable.

A leaderboard of extremes is only trustworthy if you know what sits behind each row, so here is the method.

• Matched pairs, one unit at a time. We take a private home with a recorded purchase and a later sale and compare its own buy price to its own sell price. Every figure here is a single transaction — one specific unit — not an average of a project or a district.
• A recent two-year window. These are pairs whose sale fell in the 730 days ending 23 June 2026 — a fresh window, so the names are current. Across it there were 31,374 resales.
• Gross, not net. "Gain" means the sale price beat the purchase price, full stop — the dollar figure is sell minus buy only, before agent commission, stamp duties, any Seller's Stamp Duty, legal fees or years of interest. On a multi-million-dollar landed deal those costs are substantial, so read every gain as a gross ceiling, not take-home.
• "Held" is ownership time — how long the owner owned the home between buying and selling, not how many days it sat on the market.
• Unit numbers dropped. These are public URA-style caveats, identified by project and size only.

One honest limit before the tables: because this is a recent window, the newest sales are still being lodged, so the freshest deals may not all be captured yet. That matters most for the headline share of profitable sales, which we tackle head-on below; the tables of named extremes are exactly what the caveats record.

Here is the winners' table exactly as the data has it — the five largest gross gains among resales in the window.

Two patterns explain almost everything here. First, scale: four of the five are large detached houses of 10,000 sqft and up, in the prime freehold belt around Bukit Timah, Gallop and Holland — homes bought for tens of millions, where even a moderate percentage rise prints a gain in the tens of millions. Second, the outright winner is different in kind: the Anderson Road condo's +697% is by far the biggest percentage move on the board, from the longest hold (18 years), bought at a pre-Global-Financial-Crisis price and sold into a very different prime-condo market. It is the one row where the percentage, not just the quantum, is doing the work.

None of these rows is a template. They are the far right tail of a distribution — the handful of ultra-prime owners with the capital, the land and the time for a routine move to compound into a headline. The winners teach you the shape of the spread, not a strategy to copy. The more repeatable question — which condo developments delivered the best median gains across all their sales, not one lucky unit — is covered in the most profitable condos in Singapore.

The same window produces a losers' table — the five largest gross losses, reproduced in full.

Notice the symmetry with the winners: these are the same kind of homes — big prime landed and luxury prime condos — because the same large quantums that make the gains huge make the losses huge. A 55% fall on a $43.80M house is a $24.00M hole; the identical percentage on a suburban unit would be a fraction of the dollars. Mount Rosie Road is the starkest case: bought for $43.80M near a cyclical high in prime landed, sold five years later for $19.80M into a softer market for that segment.

The holds tell the rest. The two shortest — Clifton Vale (3 years) and Mount Rosie Road (5 years) — show how fast a prime entry price can go underwater when the timing is wrong; the two long holds (St Thomas Suites at 14 years, Cliveden At Grange at 17) are luxury condos bought at rich pre-crisis prices that even a long hold didn't rescue. It is the mirror image of the winners: the same ultra-prime segment, just as unrepresentative of an ordinary home. The project-level counterpart — which developments most often left owners behind, and why — is in the condos that lost money in Singapore.

This is the section the headlines never write, and it's the most important one.

A $45.69M gain and a $24.00M loss are not two ends of your range — they are two ends of the ultra-prime range, produced by homes with the biggest quantums in Singapore. Extrapolating from either to a normal condo or a mass-market landed house is a category error. The tables tell you how wild the extremes get; they say nothing about the middle.

Here is where the recent window itself has to be read carefully. Across these 31,374 resales, 96.2% sold above the purchase price — a startlingly high figure, and a tempting one to quote as "the odds of profit." Don't. Two things inflate it:

• Recent-seller skew. A two-year window over-represents owners who chose to sell now — and people are far readier to sell into a gain than to crystallise a loss. Quick winners are over-counted; would-be losers quietly hold and never enter the window.
• Under-lodging. As noted above, the freshest sales are still being lodged, so the most recent (and more marginal) deals aren't all captured yet.

So 96.2% is best read as "the share of this recent, still-settling window that happened to profit" — not the base rate. The dependable number comes from the full history, not a two-year slice: across 267,641 matched pairs spanning many market cycles, 85.3% of private resales sold above their purchase price — and even that is a base rate, not a promise. That is the figure to plan around. The complete method is in how to tell if your property will be profitable, and you can pressure-test a specific unit with the Profitability model. Read the tails for range; read the base rate for odds.

It's no coincidence that the same handful of segments dominates both leaderboards — two forces stack on top of each other.

• Quantum magnifies the dollars. A gain or loss in dollars is a percentage times the purchase price. When the price is $43.80M, a 55% move is a $24.00M loss; when it's $6.56M compounding over 18 years, a 697% move is a $45.69M gain. Ultra-prime homes carry the largest quantums in the market, so they own the extremes at both ends almost by arithmetic. Prime and luxury are also the most volatile segments — most exposed to foreign demand, cooling measures and the top-end cycle — which widens the percentage spread on top of the dollar magnification. It is no accident that these names cluster in the prime central and freehold belt, the very segment that had the lowest base-rate odds of profit across the whole market (see where owners profited most, CCR vs RCR vs OCR).
• Entry timing sorts the winners from the losers. Look at the dates. The winners were bought cheaply and early — Anderson Road in 2007, the Joan Road and Namly Grove houses in 2010 — or held long enough to ride a full cycle. The losers were bought near a top: Mount Rosie Road and Clifton Vale in 2021–2023, at prime-landed highs, then sold into a softer market. Same segment, opposite timing, opposite tail.

So the records are a story about scale and timing at the very top of the market, not a signal for a normal purchase — and a reminder that the biggest quantums carry the biggest two-way risk. When you bought mattered enormously across the whole market too, not just at the extremes: that is did when you bought matter more than what you bought.

What is the biggest profit ever made on a Singapore property resale? In the two years to 23 June 2026, the biggest single gain in the matched-pairs data was an Anderson Road condominium: bought for $6.56M in 2007 and sold for $52.25M in 2025, a $45.69M gross gain (+697%) over an 18-year hold. It is the largest in this recent window rather than an all-time record, and it is an ultra-prime outlier — the gain is gross, before commission, duties and interest.

Can you actually lose millions on a Singapore property? Yes. In the same window, a Mount Rosie Road detached house bought for $43.80M in 2021 sold for $19.80M in 2026 — a $24.00M loss (-55%) after five years. Large prime homes carry the biggest quantums, so a bad entry price and weak timing can produce losses in the millions. It is the exception, not the rule: across the full 267,641-pair history, 85.3% of private resales still sold above their purchase price.

Do these numbers mean most Singapore properties make (or lose) a fortune? No. They are the extreme tails, concentrated in ultra-prime landed and luxury condos where the quantums are largest. The 96.2% profitable share in this recent window is inflated by recent-seller skew and under-lodging, so it is not the true base rate; the dependable long-run figure is 85.3%. Read the leaderboards as the range at the edges, and the base rate as your odds.

What we counted. Matched private resale pairs from URA-style private caveats (public.resale_pairs_mv), where a "pair" is one unit with a recorded purchase and a later sale, so we compare the same home's own buy and sell price. This article is scoped to pairs whose sale fell in the 730 days ending 23 June 2026 — 31,374 resales — and ranks the five largest gross gains and the five largest gross losses within it. Project names come from condo_projects; unit numbers are dropped, so homes are identified by project and size only. The two named leaderboards are reproduced exactly from that cut.

What we did not claim. That any single row is typical — every named gain and loss is an ultra-prime outlier, the far tail of the spread, not a normal outcome. That the recent-window profitable share (96.2%) is your odds — it is inflated by recent-seller skew (owners are readier to sell into a gain than a loss) and by under-lodging (the newest sales are still being recorded), so we report the dependable long-run base rate of 85.3% (from 267,641 matched pairs across many cycles) as the number to plan around, and even that is a base rate, not a guarantee. That gross equals net — every figure is sell price minus buy price only, before agent commission, buyer's and seller's stamp duties, any Seller's Stamp Duty, legal fees and loan interest. That "held" is days-on-market — it is the ownership period, not marketing time. This is general information, not financial advice. To assess a specific unit, use the Profitability model.