Retail and commercial activity in Cheltenham has been minimal during its history. The Cheltenham Recreation Club has maintained a bar and, for some decades until the 1990s, poker machines. At various times it has hosted coffee shops and restaurants.
There was a motor garage and service station on the north western corner of Beecroft Road and Cheltenham Avenue until the 1990s.
Some of the lots that were originally subdivided by Mr Chorley do have a covenant on them that they can only be used for residential purposes.
A proposal to build a dairy in 1924 was defeated. 
A Kindergarten was opened in the The Promenade Cheltenham in the 1940s as a war memorial. The former Congregational Church on the southern corner of The Promenade and Beecroft Road is being converted for use as a child care centre. 
 Cumberland Argus and Fruitgrowers Advocate 12 April 1924 p8
 See elsewhere on this web site for Kindergartens and child care centres.
Outside of the existing retail area there were at various early times Higgins general store (by 1970s a liquor store) on the corner with Mary Street, two shops near the School of Arts and two further shops south along Beecroft Road.
 This introduction was initially based upon the essay of Andrew R Conrow “Changes in the composition of the Beecroft Shopping Centre during this century and the influences of these changes” (1972, a student work typescript)
Originally known as West Epping Shopping Centre these retail and commercial premises were initially built at a critical watershed in how we shopped.
Built upon land of the Wallumeda (Dharug speaking) people, it was then part of a grant in 1856 of 56 acres to John McRoberts. It remained within the broader Mc Roberts and related families until 1959 when just over 5 acres was purchased by Robert John Lees a neighbouring poultry farmer and the parcel of just over 4 acres comprising what is the majority of the commercial space was purchased by Contemporary Timber Homes Pty Ltd. Between 1961 and 1963 the land was subdivided into largely the current commercial configuration anchored by the petrol station on the corner of Pennant Parade and North Rocks Road.
The watershed that was happening at this time was the shift from stand alone department stores (like David Jones, Farmers, Anthony Horderns) and shopping strips with shops fronting a road or other public space and servicing a local community, and the development of a shopping mall which was inward facing and centred around a supermarket or department store. In 1959 the first Westfield shopping mall was constructed by John Saunders and Frank Lowry in Blacktown. In 1961 the Village Arcade was built in Beecroft – with a small supermarket located in the ‘centre’ of the arcade. In 1963 Anthony Horderns built its first department store in a Sydney suburban shopping centre at West Ryde. Then 2 years later Carlingford Village (now Carlingford Court) opened with Farmers department store as the anchor. In the early 1970s Westfield built its mall in North Rocks and in 1972, the Module was built in Beecroft.
Contrary to these developments these shops formed part of retail history built around a strip and which was designed to serve only the immediate neighbourhood.
The initial strip of shops was (from 1962) were built and owned by Edward Poulton and were then extended eastward by West Epping Shopping Centre Limited.
After pressure from the local community, the shopkeepers and the local State member, Andrew Tink, from 2005 vehicular access and parking was immeasurably improved to enhance the use of this shopping precinct. This contributed to the change in these shops as their reliance on the local neighbourhood started to diminish and instead customers had to be attracted from further afield. The shopping strip started instead to become a hub.