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)
Within the retail area from Copeland Road to south of Chapman Avenue, the distribution of shops has been as follows:
In 1900, the layout of the shops comprised, along Wongala Crescent, a butcher halfway between the fire station and Hannah Street and then closer to that corner a grocer with an estate agent on the corner. In Hannah Street there was a haberdasher on the northern side along Wongala closer to Chapman Avenue there was a bakehouse and along Beecroft Road there was a shoe repair man near the corner with Chapman and closer to Hannah there was a chemist.
During this time the retail area grew to comprise two green grocers, two garages to service the growing number of cars in the vicinity and a dentist.
Despite initial resentment at a growing commercial presence in Beecroft by 1922 6 retail premises were under construction in Wongala Crescent and a further 4 shops and a motor garage on Beecroft road. 
The new shops that opened at this time were a grocer and butcher in what is now known as The Treasure House Building, a butcher and a barber in the Boronia Cottage/St George building; a grocer, milk bar and greengrocer adjacent to the real estate agent on the corner of Hannah Street. In Hannah Street opposite the post office opened a ladies hairdresser, grocer and newsagent. The shoe repairer moved closer to the northern corner on Wongala and Hannah Street.
The purchasing power of the district at this times seems to have been dominated by a small number of wealthy residential owners and a large proportion of small farmers.
 Cumberland Argus and Fruitgrowers Advocate 9 December 1922 p6
The number of weekly ticket sales from Beecroft Railway Station peaked between 1945 (13, 040) and 1950 (16, 421) and then did not have the same rate of growth until 1970 (36, 921). The indicates a significant number of people travelling to the station and presumably also using the retail area. Due to two world wars and the Great Depression retail growth was slow within this period.
In this period the Bank of NSW opened on Beecroft Road just north of the corner with Hannah Street. South of the Post Office on Beecroft Road a grocer and further south a delicatessen opened. The butcher closest to the fire station closed and an engineering shop opened in its place. Between the green grocer and the estate agent on the corner of Wongala and Hannah a shoe store opened. The butcher in Boronia cottage closed and a library opened there. There was one garage on Beecroft Road and another on Wongala between the grocer and the bakehouse in the block between Hannah and Chapman.
The purchasing power of the district in this period was dominated by a steady increase in the residential population but with a preponderance of older, rather than young family, households.
Despite the growth of larger shopping centres in Eastwood, Epping and Pennant Hills and the growth in the number of households owning a motor car, the continued delivery service of a number of retail outlets in Beecroft appears to have maintained profitability in this centre.
The main growth in shops was along the northern side of Hannah Street with the opening of a chemist, the Commonwealth Bank, a hairdresser, grocer and electrical shop.
Throughout this period the shops included :
Beecroft Road (east side) between the fire station and Hannah Street was vacant Crown land; Geoff Smith’s cycle shop, Powell’s grocer and the post office on the corner.
Beecroft Road (east side) between Hannah Street and residential housing was the Bank of NSW on the corner then Ramsey’s garage and a draper shop that had once been Retchford’s chemist.
Hannah Street (south side) from the post office on the corner was vacant land then Chadwick’s library, a butcher, Sydenham’s real estate agency and Retchford’s chemist on the corner with Wongala Crescent.
Hannah Street (north side) from the Bank of NSW on the corner with Beecroft Road was Stewart’s cake shop; Alexnder’s newsagency, house of Miss Alcock; house of Dr Terry; Sackett’s grocery; a shop; Peg O’Neal’s haberdashery; Perry’s barber shop; Dr Seale the dentist; the Commonwealth Bank and Griffith’s pharmacy on the corner with Wongala.
Wongala Crescent (then Railway Parade) (west side) from the fire station was vacant crown land; the Ross blacksmith; Mills grocery; Luckey butcher; house; house of the Wordsworth family; Dalgerns hardware; Sutton fruit shop; Sparks bootmaker; Retchford Chemist on the corner with Hannah Street.
Wongala Crescent (then Railway Parade) (west side) from Hannah Street there was Griffith’s chemist on the corner; a laneway; Ireland garage; House and bakery of John Plant.
Wongala Crescent (east side) near the entry to the railway station was the taxi rank of Eric Mealey.
 information supplied by J Felton
This era saw a considerable growth in the retail area. Along Beecroft Road a third garage for the district was opened (in 1964) when the Caltex Garage opened between the delicatessen and the Post Office. Significantly the Village Arcade was built (in 1961) in this period (with its own carpark) between the hairdresser and greengrocer along the northern side of Hannah Street.
In 1965 the arcade comprised the following shops (from Hannah Street) along the western side – delicatessen, drapery, ladies clothes, Health and bulk food, dentist, jeweller, milk bar, hardware, Worman’s supermarket, green grocer. Along the eastern side from Hannah Street were – dry cleaner, antiques, ladies hairdresser, pet shop, art supplies, orthodontist, chemist, men’s wear, butcher, cakes. The arcade led directly into the carpark with no “T” arcade.
The purchasing power of the district was starting to rapidly change with a number of new subdivisions being built and young families moving into the district. In 1969 Congalton ranked 368 Sydney suburbs and placed Beecroft at No. 54.  Equivalent suburbs were Strathfield, Hunters Hill and Chatswood. This is reflected in the range of shops available including the number of clothing stores, an antiques shop and arts and music stores.
During this time the use of delivery services ceased.
 A A Congalton, Status and Prestige in Australia (Cheshire, Melbourne) 1969
This period saw the second (and last) growth period in the shopping centre. During this period the complex set back from Wongala was built, the Module complex was constructed (in 1972, again with its own carpark) and the “T” section of the Village arcade was added. The Village arcade had no street egress as its car park was landlocked. Initially Hornsby Council leased land to permit egress onto Wongala Crescent but by 2000 the owner of the leased land wished to build what is now the podiatry centre over the drive. Special arrangements were necessarily found.
Memories of the shopping centre from the late 1950s to the mid 1960s can also be found at Shopping in 1950s-1970s
1] A Tink statement in the Legislative Assembly 8 June 2000 contained in https://www.parliament.nsw.gov.au/Hansard/Pages/HansardResult.aspz (accessed 12 March 2019).
This was a difficult time for retailers as a result of three separate changes. Firstly the impact of the motorway cutting off ready access of North Epping residents and others travelling along Sutherland Road to the Beecroft shops; a trend away from local retail shopping through access to large retail shopping areas at Carlingford, Castle Hill and Macquarie Centre; and finally the demolition of the Module and the building of Beecroft Place disrupted many using the local retail space which did not revive as anticipated upon completion of the development and the growth of unit dwellings (not only at Beecroft Place but also in Hannah Street and Chapman Avenue) in the suburb at the same time.
In 2018 the shops included:
Beecroft Road (east side) between the fire station and Hannah Street: a car park; Toys shop; Chinese restaurant; pizza takeaway; medical practice; Di Jones real estate agency.
Beecroft Road (east side) from Hannah street north: Stone Real Estate agency; allied health premises; vacant stores.Hannah Street (south side) from Beecoft Road east: Di Jones real estate; wholesale travel agent; hairdresser; dress shop; hairdresser; dress shop; optometrist; car park; real estate agency; shoe shop on the corner with Wongala.
Hannah Street (north side) from Beecroft Road east: Stone real estate; florist; Beecroft Place including a bottle shop and Woolworths; entry to Beecroft Place parking; real estate agency; upstairs an accountant and a lawyer; chicken shop; pizza restaurant; Servades restaurant; vacant shop; Salon de Ritz hairdresser; Beecroft arcade (including Beautiful Things, real estate agent, chemist, Merchant of Tennis, dentists, beauty salon, medical practice, children’s wear (The Bees Knees closed after 26 years in 2020), post office, travel agency, coffee shop, bootmaker, dress shop, Chinese restaurant, newsagency, coffee shop, bakery, Japanese restaurant, fish shop, Chinese traditional medicine, lawyer, Manchester, hairdresser, Carmichael’s jewellery; real estate agent, Café Longshot); taxi rank outside Café Longshot; Children’s Bookshop; Commonwealth Bank site (closed during the year); dress shop on the corner with Wongala.
Wongala Crescent (west side) starting at the fire station and heading north to Hannah: car park; complex of shops (including toy shop, café, hairdresser, household effects, Umun jeweller); hairdresser; Chicken and Fishhead children’s clothes and café; a complex of shops (including medical practice, beauty salon, vacant shop, Con’s delicatessen, household effects, baker, vacant shop), dress shop, Spark’s shoes, shoe store on the corner with Hannah.
Wongala Crescent (west side) starting at the Hannah Street corner a dress shop; dry cleaner /laundry; Chalio’s Thai restaurant; Russells music above; brothel operating some time (and always without Council permission) above; Porter’s liquor store; car park; podiatrist; medical practices.
Under the heading Changing Times / Commerce / Specific Stores there is additional detail on some of the Stores mentioned in the above article.