Your search results

The “Sell One, Buy Two” Strategy in 2025: Real Stories from Singaporean Homeowners

Posted by Jayson Ang on May 24, 2026

| 0

The “Sell One, Buy Two” strategy gained popularity in Singapore after the Additional Buyer’s Stamp Duty (ABSD) was introduced in 2011. This approach involves selling an existing property and using the proceeds to acquire two new properties under separate ownership (typically between spouses). The common goal is to secure a larger unit for the family and a smaller one for rental income, or vice-versa depending on space needs. But how has this strategy fared for those who implemented it? We spoke with several homeowners who adopted this method in previous years.

Rental Challenges, But No Major Regrets:

AB’s parents sold their terrace house in 2017 to purchase two condo units. Their decision was partly driven by the terrace house’s inaccessibility as they aged. They acquired a 3-bedroom unit in Simei (for their own use) and a 2-bedroom unit in Tanah Merah (initially for AB, who worked nearby). The original plan was to rent out the 2-bedroom unit after AB moved out.

AB recounts that the rental plan lasted only two years: “After I moved out they did try to rent it, but it was a headache. The property agent really didn’t care after he got his commission, and it was difficult for my parents because they don’t really know English.” AB, who was about to move abroad, found herself constantly mediating with tenants. Consequently, when she left Singapore, her parents ceased renting out the unit.

The 2-bedroom unit is now occupied by AB’s uncle, who maintains it in lieu of rent. AB plans to move into it when she returns to Singapore permanently in a couple of years. Despite the rental difficulties, AB’s parents express no significant regrets, though they acknowledge that managing tenants was far more challenging than their agent suggested. The primary benefit of the second property, ultimately, became providing accommodation for family members rather than generating consistent financial gain.

Good Rental Income, But Desire for More Space Persists:

In 2016, CD and his wife sold their maisonette and, in a “last-minute” decision, purchased a 2-bedroom and a 3-bedroom unit under separate names. Their initial intention was to buy a single, larger condo (over 1,600 sq ft) in the Katong area. This shift in strategy left them with an 800+ sq ft unit as their home and a 668 sq ft unit in Katong for rental.

CD chose not to disclose the location of their primary residence but states the 2-bedroom rental unit is a freehold apartment (without facilities like pools or gyms) in the desirable Joo Chiat area. This unit has seen minimal vacancies (only four months in 10+ years) and generates “high” rental income for the area.

Despite the strong rental performance, CD admits to some regret. When their second child arrived, their 800+ sq ft home felt too small. They also faced challenges selling the rental apartment: “Even though it is freehold, it is not so attractive because District 15 has a lot of condos that have a pool, BBQ, clubhouse, all those things.” The small, 12-unit development with infrequent sales further complicated a potential sale. CD advises others to “make an exit plan also” before committing to a second property, as the family’s options were limited by their choice of a smaller, less liquid asset.

Maximizing Gains by Living in the Smaller Unit:

EF and her husband purchased two properties in 2019 after moving out of a shared multi-generational home. They bought a 3-bedroom condo in the Geylang/Aljunied area and a 1+Study unit approximately 12 minutes’ walk away. Both were resale properties in good condition. The 1+Study unit was tenanted quickly after minor renovations. The 3-bedroom unit also had relatively recent renovations (less than five years old).

The couple was pleasantly surprised by the surge in rental demand during COVID-19. They retained their tenant in the 1+Study unit by not raising rent, securing a longer lease. When their child moved closer to the CBD in 2024, EF and her husband decided to move into the 1+Study unit themselves, finding it sufficiently spacious for their needs and conveniently located “just down the road” from their other unit. They then rented out the larger 3-bedroom unit, quickly securing a new tenant.

EF attributes their success to their deep familiarity with the Aljunied/Geylang area, having worked there for over two decades. She advises anyone considering a second rental unit to invest in an area they intimately understand. They have no regrets and also suggest that it can be practical to rent out the larger unit if one’s need for space is not immediate.

These experiences highlight the varied outcomes of the “Sell One, Buy Two” strategy, underscoring the importance of understanding rental market dynamics, potential space constraints, and the nuances of property liquidity, particularly for smaller or niche developments.

Should You Buy, Sell or Wait?

If you’re reading this, you must be trying to figure out the best course of action right now: is it the right time to buy or sell?

It’s difficult to give an exact answer since everyone’s situation is unique and what works for one person may not necessarily work for you.

I can bring you a wealth of on-the-ground experience and a data-driven approach to provide clarity and direction. From beginners to experienced investors, our top-down, objective approach will help you on your real estate journey.

I can help you by:

Offering Strategic Real Estate Advice – I can help create a comprehensive plan to guide you through your property journey.
Connecting Your Home with the Perfect Buyers – Through stunning visuals, an effective communication strategy, and an in-depth knowledge of the market, we’ll ensure your home is presented in the best possible way to fulfill your goals.

You May Also Like …

All Buying Tips Opinion

The High Price of Picking the Wrong Property in Singapore in 2025

Jayson Ang – January 9, 2025 –

The Steep Price Of Making A Mistake When Buying Property In Singapore Are you yearning for a condo, but the...

Mandarin Top 5

Top 5 Places to Buy Local Art in Singapore

Jayson Ang – August 27, 2024 –

Singapore, a melting pot of cultures and traditions, is not only known for its breathtaking cityscape, delectable food, and shopping...

All Blog Posts Buying Tips Opinion Reports

What Difference in One Year After the ABSD Hike in April 2023?

Jayson Ang – December 7, 2024 –

TLDR The recent hike in ABSD rates, especially the increase from 30% to 60% for foreign buyers, has dramatically affected...

Mandarin Top 5

Top 5 Must-Do Experiences in Singapore for First Timers

Jayson Ang – January 18, 2025 –

Singapore, a vibrant city-state known for its diverse culture and rich history, offers an array of unique experiences for first-time...

All Opinion

Reasons Why En-Bloc Sales Are Expected to Remain Slow in 2025

Jayson Ang – February 6, 2025 –

TLDR From 2014 to 2024, the en-bloc market has faced challenges due to fluctuating cooling measures and a shift from...

Mandarin Top 5

Top 5 Tips : How to Choose the Best Property Agent in Singapore – Insider Tips and Strategies!

Jayson Ang – September 30, 2024 –

Choosing the right property agent in Singapore can be a daunting task, especially with the plethora of options available. A...

All Buying Tips Opinion

Beyond Tenure: Why These Buyers Chose Older Leasehold Condos in Singapore

Jayson Ang – February 14, 2026 –

TLDR Older leasehold condos in Singapore may face skepticism but offer key benefits such as affordability, location, and flexibility. Three...

All Buying Tips Opinion

5 Frequently Heard Sales Pitches from Agents Encouraging You to Choose a New Development Instead of a Resale Condo: How Accurate Are They?

Jayson Ang – November 21, 2025 –

TLDR While some agents may discourage resale condos due to personal incentives, the difference in profits between resale and new...

All Buying Tips Opinion

What’s A Fair Price For An HDB Flat in 2025? A Savvy Buyer’s Guide

Jayson Ang – November 5, 2025 –

TLDR There’s no single “fair” price for HDB resale flats—what’s fair depends on your needs, motivation, and timing. To navigate...

All

Four Things to Avoid When Renting Out an HDB Flat

Jayson Ang – February 23, 2024 –

TLDR Renting out an HDB flat in Singapore can be a lucrative source of secondary income. Key considerations include adhering...

All Blog Posts Buying Tips

Will Your HDB Flat Provide For Your Retirement?

Jayson Ang – July 11, 2023 –

TLDR Singapore's property market presents challenges with high prices, particularly in private housing, while public housing remains relatively more affordable....

Mandarin Top 5

Top 5 Key Factors that Affect Singapore’s Property Prices?

Jayson Ang – February 9, 2025 –

Singapore's property market has always been a topic of interest for both local and international investors. The city-state's real estate...

All Buying Tips Opinion

4 Key Factors to Consider When Purchasing a Private Property for the First Time

Jayson Ang – August 27, 2023 –

TLDR When considering buying or selling property in Singapore, it's crucial to understand factors like Additional Buyer’s Stamp Duty, Loan-To-Value...