Chestnut Hill has high local significance as an example of a 1920s Californian Bungalow in a garden setting with some plantings which may date from the pre-First World War era. The historic house is architecturally significant for its intact interior which includes decorative timber work and panelling to the walls and ceilings. The property contains a cottage also built in the 1920s, Boroni Cottage (now Chestnut Cottage), constructed for Angelo Boroni, resident Italian gardener employed by Elizabeth Kennon (widow of Squire Kennon) for whom the present house was built c1923. The garden is said to be one of the finest in the Dandenongs. A number of significant trees are listed with the National Trust.

Chestnut Hill is a large property which includes two substantial houses, a small cottage and a Chapel. These buildings are well hidden from Main Road and the driveway is marked by stone gateposts and a low stone retaining wall. The approach to the house is along a curved driveway which is shaded by a variety of substantial, mature deciduous trees. An extensive and spectacular garden surrounds the various buildings which includes a number of significant trees some of which have been listed by the National Trust.

The historic house, dating from the 1920s is located to the north of the driveway and is elevated to accommodate the slope of the land. It is a rectangular plan, gable roofed, single storey building with two, irregularly spaced projecting bays to the south elevation and a single projecting bay to the north-west corner. A wide verandah encircles the house to the east and north. The corrugated iron roofs generally have a low pitch, and extend beyond the facade. The building is largely timber, with timber shingles to the gable ends and horizontal timber lining to the walls. The porch to the south west bay is constructed from brick, with brick verandah posts and floor lining. The windows include timber multi-pane windows to the north facade and double hung timber windows to the south.

The interior is largely intact and boasts a number of original features to the main rooms including polished timber coffered ceilings, arts and crafts inspired timber door and window surrounds and elaborate timber fireplace surrounds.

To the south of the driveway is a double storey modern building used as an entertainment and accommodation lodge. To the east is the modest c.1920s timber cottage and the Chapel.

Physical Conditions: Excellent

Integrity: Intact