Assuming price is the same and both are a 10 minute walk from the nearest MRT, which would you pick- a smaller condo at CBD fringe (550 sq ft) or a larger one in a location like Clementi (958 sq ft)?

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This seems like a simple more space vs less space scenario, in which case, go for the bigger condo in Clementi. If you have a family, there are more schools nearby in this area too. Unless you're a single professional and would rather live closer to your workplace in the CBD. Factors that may affect your lifestyle is also important to consider before buying a property.