Greenwood House was built in 1888 in Clear Water Harbor, the same year the Orange Belt Railway arrived, when fewer than 20 families lived along the shoreline. One of the earliest structures on the bluffs above the water, this wood-frame home originally had only 3 rooms with a shared fireplace between the 2 front rooms and was more sophisticated than the simpler log cabins and cottages built before the railway came. By 1910, as waterfront property values increased, developers removed structures that stood in the way of plans for prime real estate, and this modest home was moved about a mile from the waterfront to the edge of town, where it became part of a growing blue-collar working-class neighborhood. Over the years, the Crawford, Waldrop, and Fullop families lived here. David Crawford worked in nearby citrus groves, and he and his wife Emma were active in the local Methodist Church. Railway superintendent Leland Waldrop and his wife Nannie owned the home for about 15 years but were only occasional residents as he traveled around the South with the railroad. Tradesman Louis Fullop and his wife Bernice bought the house in 1943, raised chickens and small livestock on the property, and heated water on the kitchen stove for winter baths. In the 1940s, their son Bob helped raise chickens bought each year from a feed store on Park Street in Clearwater by feeding and watering them and collecting the eggs, and his mother made him shirts from chicken feed sacks.