From 1990 to 2008, Roy built and sold multiple high-rise condominiums across the Florida coast. During the Great Recession, again moving ahead of a soon-to-arrive trend, he searched for non-performing loans and distressed properties, and in early 2013, acquired a property on the Las Olas Isles, where he built the first of five waterfront boutique condominiums in the acclaimed Aqua-series of luxury, boutique condominiums. Geared toward wealthy baby boomers that were downsizing, most of the award-winning buildings were sold out before they were built.