Fraud Blocker
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 Comments

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:

  1. Offering Strategic Real Estate Advice – I can help create a comprehensive plan to guide you through your property journey.
  2. 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 …


Why Buying an Older EC Can Beat a Million‑Dollar HDB Today
All Buying Tips Opinion

Why Buying an Older EC Can Beat a Million‑Dollar HDB Today

TLDR With resale HDB flats crossing the million‑dollar mark, older Executive Condominiums (ECs) have become a compelling alternative. At similar...
Read More
5 Essential Tips for Renting Property in Singapore as a Foreigner: A Guide for Newcomers
Buying Tips Mandarin Top 5

5 Essential Tips for Renting Property in Singapore as a Foreigner: A Guide for Newcomers

TLDR Renting property in Singapore as a foreigner can be challenging due to the high cost of living. To navigate...
Read More
Understanding Government Land Sales (GLS) and Their Influence on Singapore’s Property Market
All Buying Tips Opinion Selling Tips

Understanding Government Land Sales (GLS) and Their Influence on Singapore’s Property Market

TLDR Singapore’s Government Land Sales (GLS) Programme is a key tool used by the government to manage land supply and...
Read More
Top 5 Places to Watch Fireworks in Singapore
Mandarin Top 5

Top 5 Places to Watch Fireworks in Singapore

Singapore is known for its stunning skyline and vibrant celebrations, especially during events like National Day and New Year's Eve....
Read More
5 Critical Mistakes to Avoid When Investing in Singapore Property: Insights and Advice from Experts
Mandarin Top 5

5 Critical Mistakes to Avoid When Investing in Singapore Property: Insights and Advice from Experts

Investing in Singapore property can be a lucrative venture for investors, but it's important to avoid common mistakes that can...
Read More
4 Key Factors to Consider When Purchasing a Private Property for the First Time
All Buying Tips Opinion

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

TLDR When considering buying or selling property in Singapore, it's crucial to understand factors like Additional Buyer’s Stamp Duty, Loan-To-Value...
Read More
Top 5 Factors : Investing In Luxury Singapore Properties: Is It Worth It?
Mandarin Top 5

Top 5 Factors : Investing In Luxury Singapore Properties: Is It Worth It?

Investing in luxury properties has always been an attractive option for high-net-worth individuals seeking to diversify their investment portfolios. Singapore,...
Read More
Top 5 : Greatest Challenges That Investors Face In Singapore’s Real Estate Market
Mandarin Top 5

Top 5 : Greatest Challenges That Investors Face In Singapore’s Real Estate Market

Singapore's real estate market is a dynamic and attractive investment landscape for both local and international investors. Known for its...
Read More
Top 5 : Potential Risks Should Be Considered When Investing Property Within Singapore’s Competitive Real Estate Markets
Mandarin Top 5

Top 5 : Potential Risks Should Be Considered When Investing Property Within Singapore’s Competitive Real Estate Markets

Singapore, a bustling financial hub in Southeast Asia, has seen its real estate market flourish over the years. The city-state's...
Read More
7 Essential Considerations to Keep in Mind When Assessing a Floor Plan for a New Condominium Development
All Buying Tips Opinion

7 Essential Considerations to Keep in Mind When Assessing a Floor Plan for a New Condominium Development

TLDR When selecting a property unit, carefully examine the floor plan beyond aesthetics. Consider non-living spaces like ledges and void...
Read More
5 Things to Know About the Singapore Property Tax System
Mandarin Top 5

5 Things to Know About the Singapore Property Tax System

5 Things to Know About the Singapore Property Tax System Here are 5 things you need to know about the...
Read More
The Top 5 Tax Considerations When Investing In Singapore Property
Mandarin Top 5

The Top 5 Tax Considerations When Investing In Singapore Property

When investing in Singapore property, it is essential to be aware of the various tax implications and considerations. Here are...
Read More
Beware of These 7 Deceptive Tricks In Showflat Condo Sales
All Blog Posts Buying Tips

Beware of These 7 Deceptive Tricks In Showflat Condo Sales

TLDR When navigating the complexities of the real estate market, it's crucial to be wary of hidden marketing tricks when...
Read More
4 Simple Strategies to Help Future Homeowners Save Money
All Blog Posts Buying Tips

4 Simple Strategies to Help Future Homeowners Save Money

TLDR When it comes to being a new homeowner, it's essential to prioritize regular maintenance to avoid costly repairs down...
Read More
Discover Singapore: 5 Must-See Attractions for a Culture Lovers’ Paradise
Mandarin Top 5

Discover Singapore: 5 Must-See Attractions for a Culture Lovers’ Paradise

TLDR Singapore stands out as a top destination for culture lovers, offering a rich blend of heritage and modernity through...
Read More
Why Seletar Could Be Singapore’s Next Up-And-Coming Property Hotspot
All Buying Tips

Why Seletar Could Be Singapore’s Next Up-And-Coming Property Hotspot

TLDR Seletar, once seen as a remote enclave defined by its Aerospace Park and colonial bungalows, is on track to...
Read More
5 Risks Upgraders Should Be Aware of To Avoid Financial Troubles When Progressing Their Property
All Blog Posts Buying Tips

5 Risks Upgraders Should Be Aware of To Avoid Financial Troubles When Progressing Their Property

TLDR The article delves into the intricacies of property asset progression in Singapore's real estate market. It highlights the risks...
Read More
Top 5 Places to Watch the Sunset in Singapore
Mandarin Top 5

Top 5 Places to Watch the Sunset in Singapore

Singapore, a bustling city-state known for its modern architecture and vibrant culture, is also home to some of the most...
Read More
When Should You Consider Investing in Singapore Property, and When Should You Avoid It?
All Buying Tips Selling Tips

When Should You Consider Investing in Singapore Property, and When Should You Avoid It?

TLDR Investing in real estate is a complex decision influenced by personal goals, investment horizon, rental plans, and financial liquidity....
Read More
Making Sense of 99-Year Landed Home Investments in Singapore
All Buying Tips Opinion

Making Sense of 99-Year Landed Home Investments in Singapore

TLDR Investing in a 99-year leasehold landed property in Singapore can be a lucrative venture due to the country's land...
Read More

Compare Listings