In the late nineteenth century, a school building was constructed in the current neighborhood of New Brighton. The school, Public School 17, underwent many renovations and additions while it stood. Almost one century after the 
school was initially built, a schoolyard and tot lot were constructed next to the building, above Arnold Street and to the east of Clyde Place. Not long after the construction of the schoolyard and tot lot, a fire destroyed the school building and it was replaced by Public School 31, which was constructed further northeast in the neighborhood. Although the school was no longer in use, maintenance of the tot lot was taken up by the current Cottages Hill Tenant Association, a community group.
The New York City Department of Parks and Recreation sought to develop the school property and tot lot as parkland in the late 1980s. By 1993, they finally acquired the land from the New York City Board of Education. Once the park was opened in 1994, it became known as Cottages Hill-Brighton Park. When it first opened, Cottages Hill-Brighton Park included tennis courts and a picnic area, along with benches scattered among the
 plant life within the park.
In 1996, New York City Department of Parks and Recreation Commissioner Henry J. Stern went around appropriately renaming parks in the city. At that time, Cottages Hill-Brighton Park was renamed as Skyline Park. This is because the park is 206 feet above sea level-much higher than most other parks in New York City. From this park, visitors are able to see the Manhattan skyline. Today, Skyline Playground has more than just tennis courts. It has bocce courts, playgrounds, and spray showers. Additionally, the Cottages Hill Tenant Association holds community events at Skyline Park each year.
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