This new house construction in an Anglo-Caribbean style was initially a 1950s-era single-story house, accompanied by a pool and a detached garage situated in the absolute center of a very deep lot. The clients wanted us to take full advantage of the depth’s opportunities, including generous space for indoor and outdoor entertaining. We designed several interconnected spaces throughout to tie together the common areas. A covered breezeway leads from the entry hall, between a courtyard and a garden, and into a stand-alone guest cottage. A pergola on the primary axis of the residence connects the main house with the pool yard and the master suite with the north courtyard.