Maymont's original 100 acres are intact and retain the architectural and landscape features in place at the time of Mrs. Dooley's death. More than 25 original buildings and garden structures are preserved.
The Normandy-style Carriage House (built of James River granite), the three-storied Stone Barn and the Water Tower were designed by Noland and Baskervill and constructed in the early 20th century. These principal buildings (in addition to the three-storied Garage, a granite compost house, chicken coop and gatehouse) all were connected by the old service road that begins at Maymont's Hampton Street entrance. Arrayed along a high ridge, this village-like assemblage of picturesque outbuildings would have been visible to guests entering along the magnolia-lined drive. These buildings have been adaptively renovated as public spaces and for institutional use.
Other original structures can be found throughout the estate. They include the Dooleys' Doric temple-style mausoleum, gates, bridges and gazebos of differing styles including Italian Neoclassical, Victorian and rustic or Adirondack.