At 66 Darling Point Road today you meet Winslow Gardens — a 1961 apartment block in the Chicago-school manner that took the name of the mansion it replaced. The original Winslow was one of those late-Victorian Darling Point residences that made the ridge feel like a private estate road. Dictionary of Sydney notes that politician and judge Sir Joseph George Long Innes bought the existing house in the last decades of the nineteenth century; he did not build it from scratch.

Innes (1834–1896) was solicitor-general and attorney-general under Parkes, then a Supreme Court judge from 1881 – a Reibey grandson on his mother’s side, and the man who helped settle Chisholm House as the site for today’s GPO. After he died in England in October 1896, the house emptied into the sale rooms. The auction catalogue below — Walter Bradley & Co., March 1897 — lists pictures, works of art and “very costly & elaborate household appointments” for sale at Winslow. That is the mansion speaking in its own voice: not a street number yet, but a named house on Darling Point.

Next door at 68 stands The Swifts, the Tooth/Resch baronial pile — still there. Winslow is the neighbour that the strata age erased. When you walk past 66, read the apartment name as a memorial plaque: the gardens are new; the name is the old house’s last trick.

Winslow - 66 Darling Point Road - Darling Point

Transcription (Auction catalogue cover, Walter Bradley & Co., March 1897)

CATALOGUE
OF THE
Late SIR GEORGE INNES' [handwritten: (died Octr 1896)]
Pictures and Works of Art
AND
VERY COSTLY & ELABORATE
Household Appointments

FOR SALE AT
"Winslow," Darling Point
ON
WEDNESDAY & THURSDAY,
7th & 8th MARCH,
AT ELEVEN O'CLOCK EACH DAY. [handwritten: (1897)]
Under Instructions from the Executrix in the Estate.

ON VIEW
TUESDAY, 6th MARCH,
10 A.M. TO 5 P.M.

WALTER BRADLEY & CO.,
Licensed Auctioneers & Valuators,
324 GEORGE STREET.

THE WOODHILL PRINTING WORKS, 127 YORK STREET, SYDNEY.

Potts Point And Darling Point with The Orgiinal Crown Grants & Early Historic Mansions

To Illustrate A Paper Read Before The Australian Historical Society
By Mr Arthur Dowling on 25th September 1906

The Land Grants shown in this map date back to the earliest times of the settlement since they include that of the Commissary General John Palmer at Woolloomooloo received in 1793.

The Map was compiled by Mr Normal Selfe, the well known engineer ( see Also 78156). It Illustrates a paper read before the Australian Historical Society in 1906 By Mr James Arthur Dowling, Grandson of Sir James Dowling, Chief Justice, who received in 1831 the grant shown at the corner of William Street & Forbes Street

Mrs Dowlings Paper Can Be seen in the Australian historical Society Volume 2 With Supp inVolume 13

Darling’s Seventeen Villa Allotments on Woolloomooloo Hill

If you stand on the Darlinghurst ridge and squint, you can still feel Governor Ralph Darling’s idea. In the late 1820s he picked the height then called Woolloomooloo Hill (soon Darlinghurst, associated with Eliza Darling) for a belt of gentlemen’s villas looking down on the town. Between about 1828 and 1831 he issued roughly seventeen grants of eight to ten acres, mainly to senior officials and favoured free settlers. Conditions were strict: plans needed his approval; each allotment was limited to a single substantial residence (commonly to a stated minimum of £1,000); houses were to face the town where practicable and sit in landscaped grounds.

Among the houses raised on those grants were places still remembered in street and suburb names — Craigend (Sir Thomas Mitchell), Barham (Edward Deas Thomson), Springfield, Rosebank, Orwell, Tusculum, Rockwall, Grantham, Brougham, Kellett and others. Most came down from the 1890s onward for terraces and flats. Only a handful survive: Barham inside SCEGGS Darlinghurst, Tusculum and Rockwall on the Potts Point ridge. Elizabeth Bay House sits in the same villa landscape story, though on its own closely related estate narrative.