A native of Manhattan, Theodore Roosevelt first came to Oyster Bay, Long Island on summer vacations with his family in the 1870s. The teenage boy grew to love the area's natural beauty and enjoyed the opportunities it afforded for such pastimes as hiking, rowing, swimming and riding.

In his early 20s when Roosevelt had finished college and was beginning to start a family, he thought that the best possible place to settle with his wife and to raise children would be Oyster Bay. He purchased farmland in Cove Neck, a peninsula just east of Oyster Bay village and envisioned building a large, sturdy, modern home. He hired New York City architects Lamb and Rich to design such a house, and construction based on their Queen Anne-style sketches began in 1884.