The Cleveland House is a heritage-listed former residence, hospital, convent and aged care facility and now vacant building located at 146–164 Chalmers Street, Surry Hills, Sydney, Australia.

The house was built on about five hectares (twelve acres) of land which was originally granted to Charles Smith by Governor Macquarie in 1809.

Upon his purchase of the land Cooper spent A£4,000 on construction of the house, believed to be the work of architect Francis Greenway.

This caused Surry Hills to be built out and changed its character from a picturesque "village" to a high density suburb.

The section containing the house and the outbuildings, lots 7, 8 and 12, were sold as a single property to Isaac Levey and inherited by his son, Montague, in 1860.

Uses included a school, laundry, boarding house, gentlemen's apartment and a government labour bureau.

[1][2]: 8 The property was sold in 1988 to Denerin Pty Ltd and all the buildings with the exception of Cleveland House were demolished and further subdivisions have occurred.

It is today owned by LGS Enterprise, which runs a medical education business InViVo Communications from the building.

[3][1] Cleveland House is a two-storey stucco building, built in brick on stone foundations, in the Colonial Georgian style.

Its lack of setting and state of disrepair do not do justice to its history as a prominent house on a large city estate.

[1] As at 6 July 2007, Cleveland House is of State significance as a rare surviving gentlemen's residence of the 1820s, built for a prominent convict emancipist merchant Daniel Cooper.

Changes in its usage and modifications, such as subdivision as well as erection of new and extension of existing buildings, reflect the history of this inner city of Sydney suburb.

[1] Cleveland House was listed on the New South Wales State Heritage Register on 2 April 1999 having satisfied the following criteria.

The House is of State significance for its direct connection to Francis Greenway, a pioneering architect and emancipist.

[1] The place is important in demonstrating aesthetic characteristics and/or a high degree of creative or technical achievement in New South Wales.

The house is simple and symmetrical in design and sought to incorporate elements of English architecture with practical consideration of the Australian climate.

[1] The place possesses uncommon, rare or endangered aspects of the cultural or natural history of New South Wales.

[1] This Wikipedia article was originally based on Cleveland House, entry number 65 in the New South Wales State Heritage Register published by the State of New South Wales (Department of Planning and Environment) 2018 under CC-BY 4.0 licence, accessed on 13 October 2018.