The land on which Southland was built was formerly a farm and English garden designed by artist Henrietta Maria Gulliver, and was a renowned show place in the area.

Architectural photographer Wolfgang Sievers took a series of striking images of the building soon after it opened and these are now held by the National Library of Australia.

[7] During Southland's history, many renovations and face-lifts have shaped the centre, such as the first expansion in 1987 and the development of a Village Cinemas complex and food court in 1990.

[8] Prior to the extension, the 70,000 m2 (750,000 sq ft) Southland shopping centre had very limited development options.

[9] In June 1991, Westfield developers began discussions with the City of Moorabbin about the rezoning of the 60,000 m2 (650,000 sq ft) Cheltenham market area in order for them to construct a multimillion-dollar extension of Southland as part of a major redevelopment.

The former cinemas and food court were demolished, and the wide, multi-level retail-pedestrian-vehicle bridge (largest of its kind in the Southern Hemisphere[11]) was added.

[9][13] Subsequently, another $13 million was used for additional work, which included construction of shaded car park areas, two new car park ramps as well as a large glass window attached to the second level of the retail bridge, which has views 16 kilometres in the distance of the Melbourne CBD.

[9][14] From 2002, the Victorian State Government has designated Southland as one of 26 Principal Activity Centres in the city, as described in the Melbourne 2030 Metropolitan Strategy.

[17] In 2015, the Victorian Government committed to building a railway station at Southland to serve the busy shopping centre.