Cooper returned to England in 1831 and on his death the major part of his estate was left to his nephew also a Daniel Cooper of the successful mercantile house of D. Cooper & co.[1] Although advertising for leasing of subdivision allotments of the "Point Piper Estate" can be found from May 1853, the property probably formed part of the group that was offered in the Sydney Morning Herald on 5 November 1856:[1] "choice building sites with water frontages to Rose and Double Bays, frontages to the South Head Roads, and situations easy of access; having magnificent views, embracing the ocean, the Harbour and Botany, with the City and Blue Mountains as a background.

Roads are now being formed and bridges built over the whole of this delightful estate, and it is impossible to imagine more beautiful situation for villa residences than exist thereon, their distances from the city averaging from one to four miles.

By 8 August 1864 it would appear general construction of the residence and perhaps outbuildings were completed for tenders were called for "gate pillars at Glenyarrah, Double Bay", applications to Mr Munro 64 Pitt Street.

[1] We may suggest therefore that Gordon was primarily the driving force in commissioning a purpose designed and built dwelling for himself; financed in large part by the lessor, Sir Daniel Cooper.

Munro may have sought his design inspiration from pattern books of the day for a close model for "Gladswood" may be found in JC Loudon's An Encyclopaedia of Cottage, Farm and Villa Architecture and Furniture, both in the 1833 and 1850 editions.

The central axial entry has been relocated to the side and the servant wing detached as in the following Design XXI, however, the plan arrangement of the rooms is a feature found at "Gladswood".

[1] Design XXI "a villa in the style of pointed architecture" shares the asymmetrical facade treatment, the central emphasis of the entry, the side ornamental screen fence wall and the detached service wing.

However, that Munro was consistent in his "Gothic" detailing is evidenced in his later design for St. Andrews College at Sydney University where similar elements found at "Gladswood" re-occur.

[1] Gordon's occupation continued until his death in 1882 and is recorded in his monogram incorporated in the strained glass window on either side of the entry vestibule and panels that light the main stair.

She was known for her charitable works and was the first honorary treasurer of the New South Wales division of the Red Cross Society and a life-governor of the Royal Alexandra Hospital for Children, Camperdown.

Brunton died in 1937 and the property was sold to Rose Bay builder Frederick Louis Perini who modified the building to become a guest house.

This, coupled with a personal interest in his client through his daughter's later marriage to Brunton's son, may have made him more amicable to compromising his own strongly held beliefs for architecture.

Similar consistent detailing to Joseland's general work is witnessed in the external treatment of the southern wing and extension of the stairwell which are clad in timber shingle.

The extension on the south of the front facade dates from this period and much of the internal refurbishment and joinery fittings within the original fabric may be attributed to Joseland.

The extent of Brunton's changes to the building were considerable these included the construction of a southern wing providing a formal dining room and ballroom as well as refurbishment of most of the ground and first floor areas.

[1][4]: 3–14  The Woollahra History & Heritage Society attribute the extensions to architect G. Flen Gilling, noting they included a fireplace and oak panelling from 14th century England.

It appears that Maas had some difficulty getting subdivision plans approved by Council, numerous disputes arising, primarily with regard to the extent and costs of road works.

[1] Perini commissioned the architect JA Dobson to convert the residence and provide a substantial western addition for "multiple occupancy" use; Council approved plans for these works date from February 1938.

[6][1] Constructed of sandstone, it features two wings, a verandah with three bays, a slate roof, Tudor chimneys and a fireplace that is thought to go back to 14th century England.

[17] "Gladswood House" represents one of the examples of picturesque Gothic that was a favoured style of "romantic embellishment" to the Sydney foreshore dating back to the earliest colonial period.

Unlike Lindesay and Carthona, Gladswood has lost its close relationship of the original building to a harbour view, a fundamental feature in the prescriptive siting of Loudon.

The bottom sash of these windows also contain Gordon's monogram and motto "in deo fiducia est mia", (In God is my trust) surrounded my motifs depicting Australian flora and fauna.

It contains some of the principal features of the house, its plastered relief ceilings, oak dado wall panelling and large ornate carved timber fireplace, all date from the 1913 renovations.

The existing solid timber doors with their deeply moulded architraves also date from the Brunton renovations and are in contrast to the more simple Victorian trims on the First Floor some of which may be original.

The contention that the ornate fireplace found in the ground floor entrance hall was not part of the original fabric is verified by the reinforced concrete support base for the hearth.

[1] The dining room/ballroom forms the Ground Floor area of a wing that was added at the time of Brunton's renovation and all the finishes including the fireplace were designed by Howard Joseland.

Within the four window panels are stained glass emblems, two of which contain the arms of Victoria and NSW, no doubt indicative of the Brunton family business associations.

The continuation of the stair width to a secondary service space and the visual cutting of the stained glass window is uncharacteristic of the earlier period.

The placement of an electrical bell board at the top of the stairs support such a contention, as does the dormer window on the northern section of the roof which does not appear on the photograph of the property dating c. 1913.

[1] The internal appearance of the front drawing room is a product of the 1913 renovation, however, it has been subdivided into two spaces with the installation of a partition wall that stops short of the ceiling.