Should I upgrade to a bigger property or should I buy a second property ?

Should I upgrade to a bigger property or should I buy a second property ?

Table of Contents


To develop a meaningful discussion here, one with depth and free from generic information that skims the surface. 

We will need to assume that your current property is apt in serving your basic lifestyle needs. i.e There are enough rooms for each child and the location serves its purpose in catering to the family needs. 

The consideration revolving around whether to upgrade to a bigger property or to buy a second property is mainly driven by the motivation to reap greater investment returns. 

Quick intro – Decoupling Expertise

Quick introduction, before you decide to commit the next 5mins reading this article.

We are decoupling expertise, a team of specialist realtor that specialise in helping Singapore property owners derive the best strategy to purchase their second investment property without ABSD.

While decoupling property is often the go-to strategy that property owners adopt. We pride ourselves for helping our client explore and evaluate other alternatives that best suit individual circumstances and objectives. 

Drop us a text to explore the best strategy to minimise ABSD on your next property purchase.

So which is better from an investment perspective ? – To upgrade to a bigger property or buy a second property ?

So which option will add more to your financial situation and your lifestyle ? We address the question by sharing perspectives. 

Productive Investment Asset – Upgrading to a bigger property vs purchasing a 2nd property

Let’s review both options by evaluating its qualities as a productive investment asset.

A productive investment asset is an asset that is able to generate passive cash flow net of its liability.

It will appreciate in value and you are able to monetise this appreciation by selling off the asset at a time of your choice.

Your home stay property is not a productive investment asset 

The conventional societal understanding is that upgrading is always good, upgrading means that you are doing better in life and you are providing more for your family. 

Your property agent will say that because purchasing a bigger property equates to more commission. Your friends and relatives will say this because it justifies their own decision and action in buying a bigger property. 

But is that really true ? Are you really going to make more money and have a better life when you upgrade ? Let’s take a deeper look into this.

Upgrading to a bigger property equates to a bigger loan and bigger monthly mortgage

Buying a bigger 3 bedder or 4 bedder in a better location or a newer condo development naturally comes with a bigger price tag. 

A bigger price tag, entails a bigger loan with heftier monthly mortgage to be shouldered by both you and your spouse. 

Yes, it’s the same in the case of purchasing a second property, in fact the overall mortgage could be even greater if you were to purchase a second property. 

But in the dual property ownership setup, you will have the option to rent out the 2nd property, fully or partially offsetting the monthly mortgage. 

When will you ever reap the profit from a bigger homestay property ?

It is true that a bigger condo brings about a larger quantum profit, and also a greater ease of exit, as 3 and 4 bedder condos are more highly sought after than 1 and 2 bedder condos. 

But let’s think about when you will ever realistically reap this capital appreciation that you have made. i.e see the actual money in your bank account. 

When you have got one property and your family lives in it, the natural progression of things is that you will always keep redeploying your capital from one property into another bigger property or in a better location. 

The only time when you can see the capital gain in your bank account is when you decide it’s time to downgrade, downsizing to a smaller condo or moving back to a less central location. 

Imagine your wife and family, well adapted to the location and size of the larger condo and try convincing them to downsize so that you can reap the capital gain. Trust me it is not going to be an easy feat. 

Your second property as a productive investment asset 

On the flipside, let’s review the option of acquiring a second property. 

From a monthly mortgage standpoint, the additional monthly mortgage could be partially if not fully offset by your tenant’s rental payment. Depending on the rentability of your second property, you may even emerge with some positive cash flow monthly. 

You will have the flexibility to monetise the capital gain of your second property. Compared to owning one property, you do not have to uproot your family or convince them of downsizing in order to realise the capital gain in the property. 

A second property can operate independently from your homestay property, having its own sale and purchase cycle. Essentially you can keep buying, selling and buying based solely on financial gains and market opportunities, partitioning family needs and lifestyle considerations. 

Investment property selection – Upgrading to a bigger property vs purchasing a 2nd property 

Rehashing our focus on discussing the viability of upgrading to a bigger condo vs buying a 2nd property, from an investment perspective. 

A key component of what makes a real estate investment a success or failure hinges on your ability to be flexible in your property selection.

So if buyer demand favours property in a specific location or comparative pricing favours new launch over resale condos. You must be able to capture the opportunity.

Upgrading to a bigger condo provides access to bigger unit type 

Objectively, if you were to consolidate both you and your spouse’s financial resources, you will be able to purchase bigger unit types like 3 bedroom or 4 bedroom condos.

Historical performance has shown that bigger unit types geared towards family buying for their home stay tends to reap higher quantum profit.

In addition to that, it is much easier to resell a bigger unit as compared to a 1 or 2 bedroom condo, given the majority of buyers out the market are purchasing to address their family’s dwelling needs. 

And this is one of the benefits of upgrading instead of buying a second property.

Purchasing a second property provides access to new launch condo development

When you are purchasing a Single property for your homestay.  It is difficult to consider new launch developments as an option, due to the fact that you will need an immediate place to house you and your family. 

You will not be able to wait out for 3 years for the new launch condo to be constructed. On the contrary if you were to own two properties, then you will have the option to purchase a new launch condo as a second property.

The advantages of getting a new launch condo includes 

  • Reduced interest outlay due to the progressive payment scheme
  • The option to own a brand new property that is attractive to buyer upon its completion in construction
  • Longer remaining lease life compared to a resale condo

As a side note, refer to our writeup on new launch vs resale property, with article link inline.

Purchasing a second property does not impose any constraints in location

The option of upgrading to a bigger condo places restrictions on locale selection. You would be restricted to consider a location that is proximate to your child’s school or place of work.

Where else, have your homestay property remain status quo and purchasing a second property allows you the freedom to select any location that is most advantageous from an investment perspective. 

You will have the flexibility to tap on any location with the following attribute

  • Location with new transport infrastructure development
  • Location with new district development or transformation
  • Location that is proximate to any highly sought after primary school 

As a side note, check out our separate write up on the best condo around some of the much sought after primary schools in Singapore. 

Risk – Upgrading to a bigger property vs purchasing a 2nd property 

In every investment decision to be made, the upside and advantage that is brought forth by a particular option, comes along with its own set of risks. 

Let’s expose the different risk that comes with the option of purchasing a 2nd property vs upgrading to a bigger condo. 

Much higher risk if you were to upgrade your current property and purchase another property at the same time.

The risk you shoulder when you upgrade both your current property and purchase a second property at the same time, will definitely outweigh the risk of simply upgrading to a bigger property. 

This happens as you and your spouse both take on a greater mortgage for both the home stay and investment property.

What about staying status quo for your homestay property and purchasing another investment property ?

Still in line with the idea of purchasing a second property, the risk can be considerably lower. if you are comfortable with maintaining the status quo for your current homestay property.

Reduce its outstanding loan to a manageable amount and focus your financial resources on the second property. 

The ideal outcome of heading down this path is that you might eventually fully pay down your homestay property, and only bear the mortgage risk for your second property. 

Greater risk if you were to take up a higher quantum mortgage on one property 

Consider the case, whereby you and your spouse take up a bigger loan simply to purchase a bigger property for homestay. This is a property that you will try not to liquidate in times of financial hardship.

Imagine, the situation whereby one of you starts disliking your job and would like to explore a career switch. You will always be restrained by the need to fulfil the monthly mortgage obligation for your property that you are living in. 

As compared to having a second property, you have the option to exit the investment by selling it off and call it quits and move on to explore other options in life. 

Two options that leads to different financial pathway in life – Your choice 

To summarise, there is no definite right or wrong answer in evaluating the decision. 

Each of these options leads to a different financial pathway and lifestyle. 

Purchasing second property while keeping the current property status quo

Gives you the option of potentially becoming debt free by paying down the homestay property.

And addressing the mortgage of the second investment property, you have the option to manage it with a combination of subsidising it with tenant’s rental and paying down its loan progressive to achieve a positive cash flow scenario.

Think about it this way, by buying a second property you are essentially creating a second source of income. 

When done right, you will be able to flip the 2nd property for a $200k to $300k profit every 3 to 4 years, similar to creating an additional stream of annual bonus. 

In some ways, psychologically it takes some stress away from your main job as you are no longer reliant on a single source of income for financial upside. 

Upgrading to a bigger property and keeping to one property only

On the flip side, things can be much simpler, if you simply upgrade to one bigger property. You won’t have to worry over the selection of the 2nd property, the managing of tenants etc.

You can simply focus on getting a bigger and better place for your family to live in. For those that are uninterested in real estate investing this option is much simpler and straightforward in terms of management and execution. 

How to own 2 properties in Singapore ? – Next Steps

Having committed the last 10 mins to reading, let’s take the research to the next steps. 

Drop us a text to share what’s on your mind and gather some 2nd opinions and ideals on whether your plan is the best way to purchase the 2nd property without ABSD.

Methods to purchase second property without ABSD

Then the following methods to acquire a second property without ABSD could be relevant to your cause. 

Consideration to purchasing second property 

Financial Consideration to purchasing second property 

Second property Selection


  • Jue Wen

    Jue Wen is the content marketing lead. This means he spend his waking hours researching and writing all things real estate. He believes life is a hustle and there is no joy in grinding away daily in our little rat races. He believes making wise moves in real estate investment can be a game changer. Aside from writing all things real estate, you can find him in your nearest bouldering gym.

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Jue Wen


Jue Wen is the property analyst and content marketing lead at decoupling expertise.
He specialises in helping clients overcome the complexities involved in owning their second private property in Singapore.
He had over 10 years of experience in real estate investing and have written over 40 detail guides on decoupling and minimising ABSD. He is a licensed real estate consultant and holds a Bachelor degree in Business Management from the Nanyang Technological University.



Kenji is the Group Division Director of ERA Realty Network.
He have got over 20 years of experience in real estate and have successfully helped over 50 couples purchased their second property. He specialises in helping client achieve the best approach towards acquiring their ideal investment properties while minimising ABSD.