Akaroa has a special character because of its attractive environs and many historic buildings. It is the cottages, many with attractive small-scale gardens, which make a major contribution to this character. The example at 162 Rue Jolie is typical.

Six acres of land bounded by Beach Road, Bruce Terrace and Rue Jolie was granted to C. B. Robinson, magistrate, in 1853. In 1862 the block was sold to Edward Latter, who sold it to Henry Wagstaff in 1873. Wagstaff built a hotel on part of the block, then sold sections along Rue Jolie in 1875.

The property that became 162 Rue Jolie was purchased for £60 by gardener James Harris in December 1875. In 1878 Harris took out a mortgage for £200, which suggests the building of a house at this time. Harris sold the property to James Garwood in March 1881 for £270. Garwood owned a good deal of Akaroa property, and probably leased this house to the MacGregor family, who then purchased it in May 1893. Alexander Innes MacGregor was the Member of Parliament for Akaroa for a period. An enthusiastic botanist, he was responsible for much of the planting in the 'Gardens' of Tane', a reserve across the road from the house. It is planted with a range of exotic trees and is accessed by a network of paths, providing a special amenity for the community.

When MacGregor died in 1901, the property was transferred to his daughter Annie. Annie married builder Thomas Penlington, who extended the house at the rear - adding a large kitchen, a pantry and a bathroom. Annie Penlington died in 1946, leaving the house to daughters Joan Penlington and Kath Chapman. The Penlington/MacGregor connection ceased in 1981, when the house was sold to the present owners who use it as a holiday residence.