Pleasantville Lodge, upon the petition of 32 Master Masons, was instituted in July 1910 and received its Charter in May 1911, with a membership of 51 and Wilson R. Yard as the first Master. Its original designation was Pleasantville #886. The lodge first met in the Mount Pleasant Bank (later Pleasantville Village Hall).

In 1922, the lodge was established in the Pleasantville Masonic Lodge Community House in Depot Square, thanks to the generous contributions of brother James Sutherland. The Community House was located adjacent to the  Pleasantville train station. 

Pleasantville #886 moved to a new home at 283 Manville Road in 1940. The laying of the cornerstone was widely attended by area residents.

In 1991, Pleasantville #886 merged with Hiawatha #434 (Chartered in 1857 and originally based in Mt. Vernon) and became officially known as Pleasantville Hiawatha #434.