John Oxley was the first person to occupy land in Bowral as a cattle run and Governor Macquarie promised him land in 1819. A grant of 2400 acres was issued to Oxley on the 30th June 1823 with the land being named "Weston". Governor Brisbane authorised Oxley to buy 5000 acres of land at a rate of 5/- per acre but no deed was issued before his death as he had only paid £125 of the purchase money. This land is now known as Bowral. In November 1828 Governor Darling recommended that the land be a gift to Oxley's sons, HM and JN Oxley, as an acknowledgment of their fathers service to the country. On the 23rd of June 1829 the Secretary of the State authorised the issue of a grant with the deposit of £125 being refunded in 1830. On the 15th of August 1855 the deeds were issued in accordance with a decision of the Court of Claims. The grant was made up of two portions with 4200 acres in the Parish of Mittagong and 800 acres in the Parish of Berrima.
The first reference of Bowral is recorded in one of the field books belonging to Major TL Mitchell.
E Riley, James Comer, William Walker, John Golledge, Rev JJ Therry, R Loseby and Dr Wm Sherwin held large portions of land to the east and south east of the Oxley grants with William Hutchinson having substantial holdings to the south.
Grazing was the main use for these lands with wheat growing also being carried out. Little traffic travelled through the Old Highway after the road through Berrima was opened and the district, which it ran through, became deserted. In 1849 Surveyor Mann was instructed to mark a road from Mittagong to Bong Bong following a track at the western end of Gibraltar Hill. The survey was carried out and in February 1852 the road was proclaimed but the people around Bong Bong protested and claimed that it would be impassable for a part of the year as the Wingecarribee flats would be flooded.
In 1863 Surveyor Campbell said a radius of twelve miles from Bong Bong was the most fertile and prosperous part of the Camden County. After the opening of the new road traffic through Bong Bong increased considerably especially since a tollgate had opened on the Southern Road.
Edward Riley's son George, a Sydney businessman, came to the district in 1831 and settled on a property called "Bloomfield", the north western boundary is the road over the Gib. Riley opened the first store in the Bowral - Bong Bong district in 1837 where he advertised that he had a large variety of stock. He also continued to carry out farming and grazing on his property and was interested in horse breeding and racing which he was quite successful at. He claimed to be the first man in New South Wales to export sheep and cattle to New Zealand. Riley lived on "Bloomfield" until it was subdivided in the 1880's. He went and lived with one of his sons in Bowral. Riley married Phyllis Hanks at Bong Bong and she bore him 12 children and died in 1866. In June 1888 at the age of 88 Riley died.
"Bloomfield" remained in tact until 1883 when Samuel Horden purchased 760 acres for £5000. Cattle, horses and dogs were imported in 1891 and placed on the land, which was named "Retford Park". The stud was established in 1891with a horse named Nordenfeldt being purchased and 12 mares from England. Sir Samuel Horden completed a year's experiment in soil regeneration in 1932 with the poorest paddock being selected and being broken up with a rotary hoe in December 1930 and shell lime was worked into the land then rolled. Special fertiliser was added to 17 acres with 12 acres being sown with a mixture of perennial rye grass, Wimmera rye grass, Italian rye grass, and cocksfoot and white and red subterranean clovers. "Retford Park" increased to 1620 acres and had a modern dairy, which supplied nearby towns with milk and cream. The homestead is one of the finest in the Southern Highlands and had 10 staff cottages.
HM Oxley conveyed his share of the 4200-acre grant to his brother JN Oxley for £7350 plus 10/- to Emma Oxley, John Oxley's widow to release her interest in February 1858. JN Oxley had 200 acres of the property subdivided, as the railway would be constructed through the district. The subdivision went from the corner of Bong Bong and Bowral Sts to the Imperial Hotel corner. The blocks sold privately for £10 each and were 66 feet by 330 feet.
The area was called the "Village of Wingecarribee" and then the "Village of Burradoo" but in 1867 in legal transactions it was called the "Village of Bowral".
The 12th of August 1863 saw the first land conveyance after the original subdivision from JN Oxley to a widow Emma Foulkes at a price of £20. The land was in section 3 on the corner of Bong Bong and Boolwey Sts and consisted of two blocks number 6 and 7 in the township of Bowral. Emma Foulkes husband built a hotel on the land. J Robinson had the Wingecarribee Inn and in the Sydney Morning Herald on the 18th August 1866 Robinson's Hotel and store situated in section 3 on the corner of Bong Bong and Boolwey Sts and consisted of two blocks number 6 and 7 in the township of Bowral were offered for sale which were the lots sold to Mrs Foulkes. In 1937 HM Oxley stated in a letter that there were two business places in town kept by Robinson and they were known as "Upper and Lower Robinsons". Upper Robinson was at the corner of Bong Bong and Boolwey Sts and had a hotel and store. Whilst out shooting Robinson accidentally killed himself.
Navvies employed to construct the railway line to the south had camps at Mittagong and Bowral. A number of hotels got licenses to cater for the increased population. In 1865 William Chalker held a license for the Prince of Wales, George Larkin for the Gibraltar Inn and J Robinson for the Wingecarribee Inn. The first brick building in Bowral was Chalkers Hotel and it adjoined a butchery that he carried on before he built the inn.
JJ Campbell in Bong Bong Street built Bowral's second house. In 1869 Bowral had two hotels, Wm Gleeson had the Prince Alfred Inn, which was originally the Wingecarribee Inn and William Chalkers Prince of Wales Inn. David Harrison was also an early settler and opened a shop in 1863 and also had a blacksmith shop and shoeing forge
A deputation presented a petition to the Minister for Works in June 1865 which was signed by over 300 persons requesting the opening of a station at "Bowrel" that was referred to as a small village about 4 miles past the Fitzroy Miles". The petitioners also pointed out that it necessary to have a new road formed from Kangaloon to Bowral to afford an outlet for the free selectors. When the Mittagong to Moss Vale line opened in December 1867 a station was built in Bowral.
Slowly the village developed and in 1871 it had a population of 133 with it increasing ten years later to 363.
After the opening of the railway line people from Sydney began to spend their holidays in the Berrima district. Bowral was reported as growing rapidly in January 1875 and Randolph Nott from Sydney built some nice houses on Wards Hill. By November 1881 houses being built were being occupied straight away. In 1883 it was necessary for publicans to increase the size of their premises. In 1884 many small residences were being built with S Horden, BM Osbourne, W Angus, A Lamb, JL Campbell and other well-known men erecting large country residences. New shops were being built in 1884 with the village growing in 1885. A large store went up in the main street and boarding houses were increasing their accommodation.
In 1886 there was a huge demand for land but the price was to high with a number of auctions failing to reach the reserve. In the same year a local syndicate bought Jamieson Hill Estate for £8000 or £9000 in order to subdivide it.
In September 1889 many houses were being constructed and there were many visitors to the town. Many businesses had commenced like an architect, a jeweller, a bookmaker, a hairdresser and a Chinese goods store. In 1890 the building trade was still going strong and land in Bong Bong Street was selling for £30 per foot with it keeping up in price in early 1891. Vendors chartered two trains to transport buyers from Sydney with a lot of business being done.
Twelve blocks were sold at the Amos Estate in April 1917 for £40 - £120 each. GE Marshall bought a block bounded by Merrigang, Holly, Shepherd and Una Sts for £2260 in April 1918 with some of these blocks being purchased later in the year for 25/- to 30/- per foot. Early 1919 saw some portions of the Woodbine property, bounded by Bendooley, Merrigang and Burradoo (now Bundaroo) Sts, sold at prices ranging from £2/1/- to £5/2/6 per foot. In 1920 lots in Bendooley and Bowral Sts were sold for £2/15/- to £3/15/- per foot. Eight blocks in the Glebe subdivision sold for £2/15/- to £3/10/- a foot in 1921. In January 1922 fifteen blocks on the Gib were sold for £35 to £65 per lot. Shops in Bong Bong St were selling for £111 per foot including the building. January 1923 saw two lots in the Golf Links subdivision sell for £1000, two in St Jude St for £840 and two in Bowral St for £630. The price of land in Bong Bong St in 1927 was said to be excessive at £50 per foot.
After World War 1 a building boom developed with brick makers in the area finding it hard to keep up with demand in 1923. In 1927 steady progress was being made and remodelling of businesses was being carried out. Between the years 1926 to 1928, over 200 new homes were built.