In Singapore’s competitive property market, buyers often find themselves caught between their aspirations and crushing reality. Budget constraints often force…
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!
Terrace houses.The terrace houses face the semi-Ds when you first drive in.Looking out to the “main” road, terrace houses on the left, semi-Ds on the right.It’s a really short street, so pretty soon you come to the end, where you find another street to the left.
The houses on this side street are next to Montfort Centre so they’re relatively more open. (Behind Montfort Centre is Boys Town.)
Again you find both semi-Ds and terrace houses here.
Let’s head back out to the main Chestnut Gardens road.
This is the last house of the row. As you can see, the garden is huge.Still the same garden, with no other houses in sight.
Let’s head out now and explore more.
First, let’s take a left to see the next road, Chestnut Drive.
The houses here are bigger. One was a construction site which might potentially mean noise although I didn’t hear any when visiting.To the left are the Chestnut Garden houses, so you can see that the first few terrace houses on Chestnut Gardens are single-loading (I.e. have no other houses directly next to them, without being separated by a road. This means that the airflow and light is usually better.)The single-loading houses.
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.
Looking back into Chestnut Gardens – as you can see, street parking is allowed. It’s usually quite fully occupied but I typically can find a space to park. (However, during festive seasons, your visitors will probably have to park elsewhere.)Another nice thing about the estate is the covered walkway right at the entrance.As you can see, it extends to both sides of Chestnut Gardens.Following the walkway down.More semi-Ds we pass along the way. (It’s always good to be a terrace house in an enclave of semi-Ds as that usually means the area is more spacious.)Nice initiative.That’s Jalan Pakis to the left. As shown, the land slopes down, so Chestnut Gardens is actually on slightly elevated land. (Also, see what I mean about this being a nice spacious and green area?)To the right is a school (Little Shepherd’s Schoolhouse.) School was in session when I visited and I could DEFINITELY hear the kids from this road, but I didn’t hear them when I was at Chestnut Gardens.To the left is a playground, the closest playground to the estate. (Chestnut Drive Playground.)Nothing out of the ordinary here.Opposite the playground are more rows of terrace houses. I’ve visited them all and, personally, I find Chestnut Gardens the best. Firstly because of the construction of the houses (brighter and more spacious but this could be personal preference) and secondly because of the location. These houses are practically next to CHIJ Our Lady Queen of Peace and I don’t think it’s much fun being next to a school when it’s in session!
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!
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Timothy Tay ·
11 Mar 2026 ·
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Look down the first row of terrace houses.Look down the second row of terrace houses. One of the rows of houses here is single-loading so it does have an advantage but personally, I still prefer Chestnut Gardens.Little Shepherds’ Schoolhouse has nice grounds!That’s the CHIJ I was referring to.If you keep walking down, you’ll eventually reach Upper Bukit Timah Road.Looking to the right.Can you see the elevation I was referring to?Looking to the left.The road is fairly busy but there’s not much within walking distance here. Let’s turn around and head to the right.This way lies the Catholic Theological Institute of Singapore. Also the closest eatery to Chestnuts Gardens, Benedito. It’s well-rated but it’s not open every day. (I wanted to visit but it was closed.)As you may have observed, one of the downsides of the estates is the lack of amenities. It’s great if you love nature and have a car but don’t have much to offer in terms of shops and restaurants. You’d most likely need a car, although the bus stop does have many buses stopping there. Another potential issue is (if you’re superstitious) that there may be a (small) cemetery nearby. When I was walking back to Chestnut Gardens, behind Little Shepherds’ I passed this area where you can see a few graves.
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!
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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
2 Comments
CC C
What are more elderly friendly estates (that are not newly built and super expensive)
Weiyong
i just got a small inter at cashew crescent. would love for u to visit!
2 Comments
What are more elderly friendly estates (that are not newly built and super expensive)
i just got a small inter at cashew crescent. would love for u to visit!