14 West 68th Street is the oldest private house on the West Side. It was originally a magnificent five story country house. The front wing was built around 1875; a back wing was added in 1895. The occupants, Mary Harney and her son John, owned the entire block, as well as the next block to the north, from Central Park West to Broadway. The house originally commanded a view across a large front garden into Central Park. In 1899, the front lots were sold to the Christian Science Church, which built the present church. In the 'teens, townhouses were built on the other side down 68th street towards Columbus Avenue.

In 1914, the the house was divided up into 12 apartments. An elevator replaced an original bank of fireplaces. The servants' entrance became the main entrance, and the balcony entrance became a "greenhouse" for Apartment 4. In 1922, a second building, 12 West 68th Street, was built on the back of the lot. It originally contained 18 studio apartments; combinations over the years have reduced the number to 10 apartments.

In 1965, Dr. Thomas Haines and his late wife, artist Adrian Rappin, bought the two buildings. The property had by then become a rent-controlled slum, but the construction of Lincoln Center nearby promised to turn the neighborhood around. Initially, they used a top floor apartment for her painting studio. In 1970, they moved into Apartment 4, a large apartment on the second floor of 14 West. In 1986, following his wife's tragic death in 1985, Thomas Haines married Polly Cleveland. Together they designed and supervised a major renovation of the buildings. In 1988, they began offering short-term furnished rentals.