Everyone knows that one neighbour who has stayed in the same block forever, and the same goes for condos, where some choose to live in the same estate for decades. For them, it’s not about the lack of better options, but instead staying because their home ticked all the right boxes.
Over the years, living in the same condo teaches valuable lessons about long-term living you won’t get from moving between new developments. Here are 7 pros and cons of living in the same condo for decades, with the lessons learned along the way.
Pros of living in the same condo for decades
Older condos are 10% larger than newer condos
Image credit: PIU Interior Design
If it feels like newer developments are shrinking, you’re probably right. According to The Straits Times, the typical size of new condos has shrunk by 10.6% falling from 1,012sqft in 2010 to 904 sqft in 2024. Older condos tend to be more spacious and feature more interesting, like duplex units and larger balconies—unlike newer projects with more compact and shoebox-style units.
For instance, Windy Heights from the 1970s only has 4-room units starting from 2,400sqft, a floor plan size that’s rarely found today unless you’re ready to fork out a premium. As Redditor u/ghostofwinter88 points out, “Try finding a 3 bedder new condo that’s larger than 1100 sqft. Near impossible. Meanwhile, older condos can have units as big as 3000-6000 sqft. It is impossible to find this in newer units.
Enjoying such luxury of space, staying in the same condo for decades becomes a huge perk—especially if you’re holding onto a freehold unit or a unit with a great view. With home sizes shrinking and prices climbing, staying put just makes more sense.
Stability of living in the same neighbourhood
Image credit: Lentor Modern
Staying in the same neighbourhood for years builds a unique sense of belonging — not just with your home, but also with the people and places around you. Over time, you get to know the faces in your block and settle into daily routines. Each shortcut and transport route becomes ingrained in you, enabling you to navigate anywhere with ease.
As the years pass, the neighbourhood will grow with new faces moving in and new places opening up, and you get to witness the area’s evolution.
Long-term condo living becomes a family strategy
Image credit: SRX
Especially for freehold or centrally-located condos, staying for years is more than a lifestyle choice, but also a strategic financial asset for generational planning. As long as the property is well-maintained, it can form part of a family’s long-term financial plans—even serving as a retirement nest egg for older owners, such as retired parents.
Well-maintained condo facilities also play a key role in making long-term stays a viable option. Features such as playgrounds and pools for kids, fitness corners for adults, can keep multiple generations satisfied without leaving the comfort of your estate.
One long-term resident summed it up: “Well-managed, with timely upgrades to cater to the evolving needs of residents. Well-maintained facilities. No problematic neighbours. Luxury of space, amenities that aren’t overcrowded. Well-connected for family members who don’t drive.” When your home ticks all these boxes, there’s little reason to trade convenience and space for a smaller and pricier unit elsewhere.
Cons of living in the same condo for decades
Ageing pains
Image credit: eLitigation
Staying in the same place for 2 decades means that you’ll inevitably bear witness to your condo slowly showing its age, even if your condo is well-maintained. This is most commonly seen in the wear and tear of facilities, such as peeling paint, outdated lifts, and worn-out pool tiles.
As u/-avenged- on Reddit describes, older condos would have ageing facilities that have a less pleasant user experience, such as “funky smelling common rooms, old equipment (e.g. gym, pool room); ageing design (e.g. rubbish chute in unit); ageing facade (looks a bit dirtier, yellow and brown).”
With these age-related problems cropping up the longer you stay in the condo, more work is required to maintain these facilities. Overhauling and repair could last for weeks, causing inconvenience and disruptions to residents.
Monthly maintenance fees will only go up
Image credit: Pool Party
Older condos often face higher maintenance fees—usually from $300 to $700 a month, funding increased upkeep and major estate works. In particular, boutique developments with fewer residents may feel the pinch even more, with a smaller pool of households taking on a larger cost burden.
While some estates manage to keep their facilities well-maintained and looking fresh, others inevitably show their age. If the development’s sinking fund isn’t well-maintained, owners could be caught off guard by unexpected one-off payments to cover urgent repairs.
The en bloc question
Image credit: I Love Mandarin Gardens on Facebook
Once your condo crosses the 25-year mark, the big en bloc question often starts to loom. For some, it’s a payday opportunity, while for others planning to stay for the long term, it’s an unwanted disruption.
Speculation can also create tension within the estate. Some neighbours might vote against raising the sinking fund or funding necessary major repairs, thinking that there’s no point upgrading these facilities if the building is sold in the near future. With a lack of maintenance or upkeep, the condo’s facade and facilities could be left neglected.
If a collective sale attempt does happen, not everyone will agree to sell. Residents can split into pro-sale and anti-sale camps, possibly straining previously friendly relations. And if the deal falls through, it can get awkward between neighbours on opposing sides.
For homeowners, the possibility of en bloc can even influence personal decisions, such as deciding whether to invest in a major home renovation or start to look for a new home.
Keeping your living space feeling fresh
Living in the same condo for decades means that you’ll need the occasional revamp to keep your space feeling fresh. Renovations are an unavoidable part of the process to address older structural issues like plumbing and electrical work, or adapting parts of the home to suit evolving family needs, such as baby-proofing or elder-proofing the home.
One long-term resident shared how they tackled this over the years: “We renovated the kitchen and some of the bathrooms about 10 years ago, combining the kitchen and yard into a larger area with more countertop space. Most of our furniture are classic investment pieces that have stood the test of time. The only pieces of furniture that have been updated several times are the sofa and coffee table, but it does change the look of the house whenever we do that.”
Even small changes, such as seasonal decorations and furniture swaps, can make a big difference in keeping a home feeling fresh over the years.
Lessons learned from living in the same condo after 20 years
Staying in the same condo for 20 years isn’t just about convenience, it also brings stability and familiarity with the neighbourhood, letting you grow with a space through different stages of life.
Of course, there will be trade-offs: ageing facilities, rising maintenance needs, or even the possibility of an en bloc sale. Experiencing these pros and cons over the years shapes how you think about future homes and what truly matters in a home. And even if you eventually decide to move, you’ll be better equipped to spot the long-term qualities of a home to support your family and lifestyle for years to come.
For more articles on condo living:
- 2025 Singapore condo launch guide
- Is 2025 the right time to upgrade from HDB to a resale condo?
- A first-time buyer’s guide to choosing a condo in Singapore
Cover image adapted from: Gallant Investment Pte Ltd, eLitigation
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