Pine Tree Shopping center is one of the first shopping plazas in Maine. It opened in 1959 and was the first real suburban shopping center in the area. In the early days, it featured a Zayre department store, W.T. Grant, Woolworth's and Columbia Market food store. A 1962 newspaper article noted that the center was popular with families because stores were open at night and people could shop after work. Air conditioning was a big draw in the summer. That Zayre was one of the first 14 stores opened by the company. Child World and Rexall also had stores at the plaza. The original L-shaped layout of the plaza was a lot like the Broadway Plaza of Bangor and Marden's Plaza in Lewiston.

The center originally had 12 stores but grew in phases to 20 stores. In 2001-2002, the anchor stores were Ames, Shaw's, Marden's and A.J.Wright. A.J.Wright opened in the former Marden's Carpet in 2001 and also added space from the adjacent Little Caesar's. Applebees opened on a pad site the early 2000's. Ames went out of business in 2002 and the store closed in October. Not long after, Shaw’s decided to close their supermarket and to relocate to the redeveloped Westbrook Plaza across Interstate 95.

With the two main anchors gone, action was needed to revitalize the plaza. Packard Development came with a proposal to renovate the old shopping center. The building from Shaw's to Ames was demolished in 2003 and the space became home to a 168,400 sq.ft. Lowe's. A.J.Wright closed and was eventually replaced by Big Lots. The parking lot and storefronts of the plaza have been upgraded with a more modern style in 2007. Below is the original storefront of Jo-Ann Fabrics and adjacent stores before renovations.

With the opening of a new 119,000 sq.ft. Marden's store in Scarborough, the company closed the smaller Portland store during summer 2010. Dollar Tree then opened in part of the former Marden's. In 2012, Fashion Bug closed all of its stores including the Portland location. In August 2024, Big Lots announced the closing of hundreds os stores including the Portland location.