Once a part of the historic Wooldon Manor estate, a former playhouse was renovated and expanded for a renowned American women’s footwear designer and shoe industry executive. Taking cues from the original large center room with the three-story ceiling, the house was doubled in size with an addition of the upper floor, a new kitchen and breakfast room, media room, paneled library, and staff quarters. Originally built in the 1920s in a classic English Tudor style, the expanded house looks like it’s always been there. Inside this Southhampton Estate English Tudor, its fine details like vaulted ceilings, limestone floors, Delft tile, and custom bronze doors are complemented by British Raj-style furniture that is beach-appropriate and lends the traditional house a slightly modern feel.