Touring Chestnut Gardens: A Small Enclave Of 999-Year Landed Homes That Are Elderly-Friendly In D23


TJ's interest in property was sparked after returning from the UK- where balconies are not counted in one's square footage!- and finding that the Singapore property had totally changed in the 7 years she was away. When not reading and watching articles & videos about property, she is busy cooking and baking for friends, family & her blog Greedygirlgourmet
Chestnut Gardens, a charming collection of terrace houses and semi-detached homes, recently captured my attention. These residences, constructed in the 80s or 90s, intriguingly don’t feature elevators – a common trait for buildings of that era. However, what’s particularly notable is that, according to a homeowner I conversed with, these houses were designed with stairwells spacious enough to accommodate a lift installation. This foresight makes them remarkably senior-friendly. Another aspect that appeals to me is the design of the stairs themselves: they are tiered or winding, rather than being a single, steep incline, which is a common feature in newer properties. As we know, the risk of falls increases with age, making such a design more practical and safer for families with elderly members.
However please note, that it’s essential to validate this information with a professional contractor. While homeowners’ insights are valuable, they might be biased, especially when making a sale. Regrettably, I don’t have any interior photos of the property to offer as an illustration. The specific house I visited has already been sold, but I can provide a video for a better visual understanding of the area and its unique features:
In addition, I liked how the living room was double volume, helping to make the space feel light and bright despite it being a terrace house. There’s also an option of building a walkway across the living room to connect with the porch roof to create a balcony (see the photo above.) Or, for those who really need a lot of space, you could potentially just extend the floor and do away with the double volume ceiling.
Some history: according to the owner I spoke to, the houses were constructed by a family for themselves, with only a few units sold to outsiders.
I also liked how spacious the area was – not many high-rise buildings in sight. But let me first show you the properties then take you around the estate so you can judge for yourself!






The houses on this side street are next to Montfort Centre so they’re relatively more open. (Behind Montfort Centre is Boys Town.)


Let’s head back out to the main Chestnut Gardens road.




Let’s head out now and explore more.
First, let’s take a left to see the next road, Chestnut Drive.



OK now that we’ve seen this, let’s head back to Chestnut Gardens and continue walking down the road to the right, which will take you to Upper Bukit Timah Road.
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Or during the pick-up and drop-off hours! Luckily there are several ways to enter this estate. However, I’d strongly suggest visiting during school pick-up and drop-off hours before committing to anything!














Now that you’ve seen the estate and maybe the video of the house, how did you find it? Let me know in the comments whether you think the double-volume ceiling is a plus or a space waster!
TJ
TJ's interest in property was sparked after returning from the UK- where balconies are not counted in one's square footage!- and finding that the Singapore property had totally changed in the 7 years she was away. When not reading and watching articles & videos about property, she is busy cooking and baking for friends, family & her blog GreedygirlgourmetRead next from Editor's Pick

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What are more elderly friendly estates (that are not newly built and super expensive)