Chimney Company in Medford, NY

The Long Island Rail Road established the Medford station in 1843 in a flat wilderness in the Long Island Central Pine Barrens. The station connected to the Patchogue Stage Road between Patchogue and Port Jefferson, and a post office was established.

In 1907 the LIRR established the Medford Prosperity Farm (officially called Experimental Station #2) on 80 acres (320,000 m²) to show that crops could be raised in the Pine Barrens. Theodore Roosevelt visited the station in August 1910. As the car drove across a trail between Medford and Wading River, it got stuck in the mud and Roosevelt was said to take a “flying leap” to get out.

By the mid-to-late-20th century, developers were building new neighborhoods within Medford. Eagle Estates was built along Horse Block Road east of NY 112 in 1963, although it was planned as far back as the 1930s. The development included a Blue Jay Market shopping center on Horseblock Road west of Eagle Avenue, and a youth baseball and athletic field east of Sipp Avenue between Wave and Race avenues. The Long Island Expressway was built through Medford in 1970, with interchanges at New York State Route 112 and Horseblock Road, the latter of which is close to an older interchange with Horseblock Road and Long Island Avenue, and was not completed until 1999. The Pines was established in the 1970s east of Buffalo Avenue, south of Jamaica Avenue, north of Woodside Avenue and far west of Patchogue-Yaphank Road.