Hi Stacked, I have been following your articles and would appreciate it if you can help analyse our present home situation. My husband and I own a unit in Windermere and a 5-room flat at Yew Tee, which are both fully paid. We are in our late 50s: one is retired and the other is semi-retired. 

Our flat is currently rented and the two of us stay in Windermere. Due to the ageing of Windermere, we wonder if we should (1) sell it and shift back to our 5-room flat, (2) carry on with our present living arrangement, or (3) sell both (since both units are old) and shift to a smaller HDB flat, which could be a resale or BTO flat. Hope to hear from you soon. Thank you in advance! 

Good day and thanks for reaching out to us! Based on your current stage in life, the key concern should not be which property performs best in an investment sense, instead we should examine which option best supports you over the next 20 to 30 years of your lives together. The arrangement should be comfortable for your post-retirement income, lifestyle, and peace of mind. 

We'll begin by examining both of the properties you own 

This is the 10-year performance of Windermere, a 395-unit leasehold condo in District 23. From records, we can see that the development was built in 1999. 

(Source: Stacked)

Over the past decade, Windermere's annualised price growth of 3.91 per cent has trailed the wider 99-year private residential leasehold market, as well as the leasehold residential properties in District 23. However, this is not particularly unusual for an older leasehold condo.

What's important is that Windermere still hits new price highs. So, while its growth has become more modest, the momentum of its resale volume means that it hasn't lost out in the resale market. That means it still has relevance to buyers for now and is an "exitable" asset.

As the majority of units in Windermere are three-bedroom layouts, we presume this is also the unit type you own. Based on transactions lodged in 2025, the average transacted price for a three-bedder in this condo is around $1,413,500.

Now let's look at the 5-room flats in Yew Tee that have sold over the past 10 years:

(Source: Stacked)

Average resale prices of five-room flats in Yew Tee have broadly moved in line with the price trend of the HDB resale market. They trail slightly, by less than a percentage point, which we think isn’t too significant in the context of this analysis. 

Based on transactions lodged in 2025, the average transacted price of a 5-room flat in Yew Tee is around $650,335.

We'll use $1,413,500 (Windermere) and $650,335 (the 5-room flat) as the price benchmarks for our projects going forward.

This gives you an estimated total asset value of ($1,413,500 + $650,335) = $2,063,835

Now let’s look at your considerations for each property, and the relevant approaches:

Windermere

As with most condos, Windermere offers more privacy compared to HDB developments. Condo facilities also make it easier to accommodate family activities. 

Some retirees, for instance, find that family BBQs, or the grandchildren coming over to use the pool for swimming lessons, play a role in family bonding and inter-generational ties.

That said, as the development continues to age, maintenance-related issues tend to become more frequent and MCST fees may rise over time. Facilities that once felt like a major draw may also see reduced usage, especially as you grow older. Everyone ages differently, but it's generally true that older residents make less use of some facilities like tennis courts and diving pools.

In terms of lifestyle fit, Windermere works well if privacy and a gated community environment are important to your lifestyle. However, as mobility becomes an important consideration in the years to come, factors such as proximity to daily amenities, transport nodes, and healthcare services may end up being more important factors.

A few years ago, we reviewed what it felt like to live at Windermere. 

5-room flat in Yew Tee

The 5-room flat presents a different set of trade-offs. From a liveability perspective, HDB flats are often — though not always — more practical as residents age. Town councils are usually more conscious of issues like lift access, barrier-free features, and stronger integration with neighbourhood amenities.

Everyday needs such as food options, clinics, and public transport are easier to access, as HDB estates are built with these in mind. That said, a 5-room layout may feel larger than necessary for a two-person household in the long term.

Financially, the flat plays a clear role as a stable income-generating asset. Running costs for HDB flats are relatively low, which helps preserve net rental income. Conservancy charges are lower than the maintenance fees of even the smallest condo units.

However, tenant management, occasional vacancies, and the administrative aspects of being a landlord can be burdensome in your later years. You may want to consider asking for help from a trustworthy, younger family member who can assist and keep track of these things for you.

From a lifestyle standpoint, the flat offers a more community-oriented living environment, which some retirees appreciate. At the same time, this comes with living in a higher density environment and less privacy compared to a condominium, which may not align with how you want to live in the coming years.

Now let's examine the options you’re considering. 

The figures used here are not meant to be exact projections, but rather broad guides to frame the potential costs, trade-offs, and outcomes. Actual results will vary depending on factors such as timing, market conditions, unit attributes, and personal preferences — all of which can be addressed by your realtor. 

Option 1: Sell Windermere, then move back to the HDB flat

Selling Windermere would potentially unlock around $1,413,500 in gross sale proceeds, based on the average transacted price of three-bedroom units at the condo in 2025. 

As we don’t know how much CPF was used for the purchase of Windermere, we can’t tell the exact cash amount you would receive after refunding your CPF; you can check the exact amount on the CPF website with your Singpass.

The treatment of CPF refunds will also depend on the year in which you turned 55, as the Full Retirement Sum (FRS) varies across cohorts:

(Source: ) 

If you have met the FRS, you will be able to withdraw the excess funds, which could help with the purchase and renovation of your replacement home.

The monthly cost of moving back to an HDB flat is also very low, compared to a condo:

As everything is already paid for, and the monthly expenses are low, this pathway will allow you to unlock a significant amount of funds. This could be handy for aspirational goals, legacy planning, and an all-around more comfortable retirement lifestyle. 

Option 2: Keep your current arrangement

Under this option, you would continue living in Windermere while renting out the five-room HDB flat at Yew Tee.

Based on rental transactions in Q4 2025, the average rent for a 5-room flat in Yew Tee is approximately $3,181 per month. For the purpose of this projection, we will assume this is about the monthly rental rate for your flat.

Next, let's project the recurring costs you face for both units:

5-room flat

Windermere

Now let’s look at the net income after these costs:

Monthly income from HDB

As we noted earlier, resale prices at both Windermere and the Yew Tee flat have broadly moved in line with their overall resale markets, respectively. This suggests there is no immediate urgency to sell, assuming you won’t need a large amount of capital for any upcoming milestones.

That said, this pathway does not unlock any additional funds. Instead, it prioritises income continuity over unlocking more capital. Whether a monthly surplus of around $1,978 is sufficient depends on your lifestyle expectations and expenses. 

However, do keep in mind that certain expenses, such as healthcare costs, tend to rise significantly with age. So what is sufficient for now may not be in the future. 

Another consideration, which numbers cannot quantify, is the complexity of tenant management, vacancy risk, having to vet new tenants, etc. Some landlords find this too demanding in their later years. So as we mentioned, consider if someone trustworthy is available to help you later on.

Option 3: Sell both properties and right-size to a smaller HDB flat

Selling both Windermere and the 5-room flat would potentially unlock approximately $2,063,835 in gross proceeds.

This represents a significant pool of capital and it could likely be a game-changer in terms of retirement planning. It could be a buffer for future healthcare needs, a huge boost in legacy planning, or a big lifestyle upgrade in your twilight years.

In addition, a smaller home is generally easier to maintain over time.

That said, this is a highly personal decision. Some households continue to value a more spacious living environment even in retirement, and some find peace of mind in retaining an investment property; they may feel they have something to sell and fall back on.

This option also involves giving up both a familiar living environment and a recurring rental income stream. As an aside, it's worth bearing in mind that the Additional Buyer's Stamp Duty (ABSD) for Singapore Citizens currently stands at 20 per cent for a second residential property. 

For some households, this effectively means that once a rental asset is surrendered later in life it may be difficult, or impractical, to ever buy a second property again. 

Another consideration are the logistics of getting a smaller replacement flat

Another important consideration to remember is that after selling a private property, former private homeowners are generally required to observe a 30-month wait-out period before applying for a BTO flat, unless they are eligible seniors right-sizing to a short-lease 2-room Flexi flat or a Community Care Apartment, which are exempt from this requirement.

That said, here are the other considerations:

The combination of uncertainty and an extended waiting period for a BTO flat can take a mental toll, so you might want to consider resale instead. As you age past 55 years, there is no wait-out period for you to rightsize to a 4-room or smaller resale flat, and the only thing you need to wait for is renovations to be done.

That said, rightsizing is a personal judgement and what feels right will vary from one individual to another.

Based on transactions recorded in 2025, the table below shows the average prices of 3- and 4-room flats across various towns. You can use this as a broad reference for what right-sizing might result for you financially.

(Source: Stacked)

As you are familiar with the Yew Tee area, we'll assume as an example that you right-size to a 4-room flat in Choa Chu Kang, purchased at the average transacted price of approximately $559,030.

After completing the purchase, this would leave around ($2,063,835 – $573,400) = $1,490,435 in remaining funds.

Again, the monthly cost on the HDB flat is just around $164 (referring to the table we used in 'Option 1' section of this article), so this move unlocks a significant amount of capital for other needs. 

What should you do?

There is no clear right or wrong decision here. The best option is ultimately the one that aligns most closely with your retirement goals, risk comfort, and desired lifestyle.

What we can say for sure is that both properties are still moving broadly in line with the resale market, so there is no immediate pressure to sell, especially if the rental income from your HDB flat could help to support your retirement needs. 

Under this scenario, you can continue enjoying the privacy and facilities of condo living, while benefiting from a steady passive income stream.

On the other hand, if greater liquidity and simplicity are priorities, selling one or both properties would unlock a substantial amount of capital. 

Whether you choose to sell Windermere and move back into your HDB flat, or sell both properties and right-size to a smaller resale flat, you are likely to end up capitalising on the value of your properties while keeping monthly housing cost relatively low. Depending on the eventual purchase price of the smaller flat, the latter option may leave you with slightly more cash on hand.

Ultimately, the right path forward depends on what gives you greater peace of mind: maintaining your current lifestyle with ongoing rental income, or simplifying your property holdings while boosting your available savings in retirement.