The land of the Springwood estate was originally part of a land grant (the "Great Nine Partners Patent") which covered the area between the Hudson River in the west and the border of Connecticut in the East. While the early history of the house on the Springwood estate remains unclear, it is believed that the central portion of the present day house is formed by a large farmhouse which was constructed around the year 1800 in the Federal style. In 1845, the estate was purchased by Josiah Wheeler, a merchant from New York City. Wheeler undertook a remodeling of the house, giving it a then fashionable Italianate style with a three-story tower at the south end as well as front and rear piazzas spanning the entire length of the house. After this remodeling, the house comprised a total of 15 rooms.

The estate was bought in this condition by Franklin D. Roosevelt's father, James Roosevelt, in 1866 for a price of US$ 40,000 (at a time when a textile worker's earnings were less than a dollar a day). James Roosevelt made many improvements during his lifetime. He enlarged the servants' wing of the building and added two rooms. He also had a spacious carriage house built in the vicinity.

In 1915, Franklin D. Roosevelt, together with his mother Sara, undertook a final major enlargement and remodeling of the home. This was done in order to accommodate his growing family, but also to create an environment for entertaining his political associates which fitted his ambitions. Roosevelt contributed many ideas for the new design, but since the building work was paid for by his mother Sara, she had to find compromises which also took the financial aspect into account. She commissioned the design work the firm of Hoppin and Koen from New York City. The size of the house was more than doubled by adding two large fieldstone wings (designed by Roosevelt), a tower, and a third story with a flat roof. The clapboard exterior of the house was replaced with stucco and most of the porch was replaced with a fieldstone terrace with a balustrade and a small columned portico around the entrance. These alterations gave the exterior of the house the look of a mansion in Colonial Revival Style. The interior retained much of the layout of the old family home and was designed primarily with housing Roosevelt's growing collections of books, paintings, stamps, and coins. The remodeling work was finished within one year in 1916. Roosevelt also changed the appearance of the surrounding land by extensive planting of trees.

In 1943, Roosevelt donated the estate to the American people under the condition that his family maintained a life-time right to usage of the property. On November 21, 1945, after the family had relinquished their rights, the estate was transferred to the U.S. Department of the Interior. Since then, the estate has been administered by the National Park Service as a National Historic Site and is open to the public.