During the early 1900s, Miami pioneer and railroad tycoon Henry Flagler used the property at US 1 and Southwest 102 Street as a staging area during the construction of the Overseas Railroad to the Florida Keys.

In the 1930s, the area’s growth continued and the community began to evolve around one of the first tourist attractions established in the Miami vicinity - Parrot Jungle and Gardens. The Parrot Jungle was founded in 1936 by Franz and Louise Scherr on twenty-acres of property located at Red Road and Southwest 111 Street and over the years became a world famous tourist attraction whose visitors included Sir Winston Churchill. Today it is the site of Pinecrest Gardens and the property was added to the National Register of Historic Places in 2011.

The Miami Serpentarium, another popular tourist attraction, was located on US 1, next to the current site of the Pinecrest Municipal Center, for many decades prior to closing in the mid-1980s.

During the 1950s and 1960s the area flourished with the development and construction of ranch-style homes on acre lots which laid the foundation for the community’s rural and lushly landscaped residential character.

Rapid growth and local issues during the 1990s inspired a movement led by residents Evelyn Langlieb Greer and Gary Matzner to incorporate the area. The Village of Pinecrest was officially incorporated on March 12, 1996. Greer was elected the first mayor and was succeeded by Matzner in 2004. The founding Village Council, including Greer, Cindie Blanck, Barry Blaxberg, Leslie Bowe, and Robert Hingston, are credited with establishing well-regarded municipal services including police, parks and recreation, building and planning services, and public works.

Today, the Village of Pinecrest is home to approximately 18,223 residents and is nationally recognized as a Tree City USA, a Playful City USA and a Community of Respect. In 2011, the South Florida Business Journal recognized Pinecrest as one of the ten best places in Florida for "quality of life."