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Dempsey Hill is a leafy enclave of repurposed colonial barracks in the Tanglin area, tucked between the Botanic Gardens and Bukit Timah. Its low-rise whitewashed buildings, shaded by century-old rain trees, now house a curated mix of art galleries, restaurants, and antiques dealers.
Built in the 1860s as the Tanglin Barracks for the British military, the area was named after General Sir Miles Dempsey, who commanded the 14th Army. Decommissioned in the 1970s, it was gradually transformed into a lifestyle cluster from the 2000s onward.