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

Posted by Jayson Ang on May 24, 2026

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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.

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