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If you are comfortable with your current location and the amenities it offers, you can choose to continue living in your 3-room HDB flat. Dawson is a well-connected area with good schools and amenities, which might be convenient for your family.
If you have an alternative place to stay, such as with relatives or if you are posted overseas, you can rent out the entire HDB flat. However, this option is only available to Singapore Citizens, and there are specific requirements and restrictions to adhere to, such as a minimum lease period of 6 months and compliance with ethnic quotas and tenant quotas.
You might consider upgrading to a larger HDB flat, such as a 4-room or 5-room flat, to accommodate your growing family. This could be either a new Build-To-Order (BTO) flat or a resale HDB flat. Keep in mind that you will need to sell your current HDB flat within 6 months of collecting the keys to the new flat, and you may need to pay a Resale Levy if you are purchasing a second subsidized HDB flat.
If your financial situation allows, you could upgrade to an Executive Condominium (EC) or a private property. ECs offer a more luxurious living environment compared to HDB flats but still come with some subsidies. Private properties, such as condominiums, provide even more amenities and potentially better living conditions, but they are generally more expensive.
Given that you have young children, it might be beneficial to look for housing options that are close to good schools, childcare facilities, and family-friendly amenities. Areas like Queenstown, Bukit Timah, and the East Coast are known for their good schools and family-friendly environments.
Before making any decision, it is crucial to assess your financial situation. Consider factors such as the sale proceeds of your current flat, any outstanding mortgage, and the costs associated with purchasing a new property, including additional fees like agent fees and stamp duties.