Hi Sabinel,
I agree its nice to do the school run to get to know other parents.
However, most of the 6 & 9 year olds will be on the school bus. So it only really matters for the little one.
Just a few pointers on older condos nearby. Not sure what you are looking for but from experience, families wanting more space often overlook some older very good condos so I'll mention a few so that you can ask your agent to show you and so you have all cards in hand to compare.
Look up descriptions and budget on proertyguru, its usually the most updated website.
For condos walking distance:
Dover park view & Heritage view (older, slightly bigger). Interiors often quite dated.
The estate around dover court is run by the singapore land authority. You can bid for a house. A dear friend lives there and budget is under $12k for a 3 bed house, large garden. they ARE renovated (paint, bathrooms/kitchen/air con) and the DC walk to UWC. You'll know all your neighbours in no time.
here is the website
Pasir panjang/clementi:
varsity park is really nice (modern, great facilities and decent use of space)
Clementiwoods (new, behind varsity, smallish rooms comparatively)
Closer to the harbourfront end, you will find Pepys hill condo ( old but lots of space, a litle gem if you find a renovated unit with garden) and Mount Faber lodge (the biggest is a rare find in Sg: triplex living space over 3,500 soft at a decent price)
Holland road:
The closest area lies hidden on Mount Sinai.
Very short easy drive to Dover.
Very cose to Cold storage Jelita on Holland road.
Many options to choose from. Its a stone's throw from Buona vista mrt through a walkway/cycle path at the back.
The marbella is a popular choice among the newer built.
Glentrees (townhouses & flats) very good too. Ridgewood (also town houses) is older and delivers space + garden.
Lots of nice little house and great community feel with communal playground around grove drive/holland grove view.
Lots of play schools.
If you are considering a house, the sunset way area is good too (that's where playdays is) and still a short painless drive to school.
Am sure your agent will find more options but that should give them food for thought instead of just pushing you towards what's on their books.
Early december should be a good time for viewings but you will need to secure something quickly as there will be many families looking at that time ( near cut off for Australian new school year so many expat tenants have there contracts starting or being renewed at that time of year.)
good luck