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The estate was initiated by the Singapore Teachers’ Union (STU) in 1967, with the primary goal of building a clubhouse for its members. Due to financial constraints, the union decided to develop a housing estate around the clubhouse. The site, which was previously a gambier, pepper, and later a rubber plantation, was chosen for its affordability and proximity to other areas where teachers lived.
The estate consists of 256 double-storey terrace houses, with prices ranging from $24,500 to $30,000 when they were first sold. The STU sold these houses to fund the construction of the clubhouse, known as the Teachers’ Centre. The clubhouse included facilities such as a library, kindergarten, restaurant, swimming pool, tennis courts, and a multipurpose hall.
The estate quickly developed a strong sense of community among its residents, many of whom were teachers. The roads in the estate were named after poets and literary figures, such as Tagore Avenue, Tu Fu Avenue, and Munshi Abdullah Avenue. The residents organized various community activities, including outings, carpooling, and joint maintenance of their homes.
Over the years, some of the original houses have been replaced with three- and four-storey homes. Despite this, the estate retains its charm and community spirit. In 2004, the estate underwent an upgrade under the Estate Upgrading Programme, which included the creation of a new poetry gallery and refurbishment of parks. A new park is also planned for the area.
The properties in Teachers' Housing Estate have appreciated significantly over the years. For example, a corner terrace house that was originally purchased for $26,500 in 1969 had appreciated to about $1.4 million by 1995. Currently, houses in the estate can sell for millions, reflecting the area's popularity and the value of its freehold landed properties.