Cockade House was originally built in the 1700's as a sugar plantation and is set within 2.5 acres. The original house was a part of Bennetts Plantation. Between 1960 and 1972 the home changed hands a couple of times when it was purchased by Derek Grewcock (who was involved in the Alaska Pipeline) for his friend Polly Haywood who commissioned the renowned English theatre designer, Oliver Messel, to redesign the house. Oliver Messel reconfigured the interior of the house, raised the height of the ceilings, added the verandahs, redid façade and incorporated a pool. He also designed the ruin/folly at the north end of the pool.
In the mid 1980's Barbadian architect, Michael Gomes built a cottage to the south west of the property to a design left by Oliver Messel. This is known as Oliver's Cottage. Nick Parravicino was instrumental in purchasing additional land from Bennetts plantation and the property now sits on 5.524 acres.
Cockade's present owner also enlisted Michael Gomes to modernise the existing bathrooms and kitchen and build two additional cottages. Oliver's cottage can be refurbished to have a further bedroom and bathroom suite, in total Cockade now consist of 7 en-suite bedrooms. The Owner has leased part of the land to the Cricket Academy for the use of young Barbadians, with the remainder of the property well landscaped with mahogany trees lining the long driveway and beautiful gardens.