This plaza is located close to the Pine Tree Shopping center, but on the north side of I-95. It opened in 1963 with Bradlees and Martin's Food which later became a Shop'n save supermarket. The Bradlees at Westbrook Plaza was the last in Maine after store closings in Windham, Lewiston and Topsham in the mid-90’s.  The chain declared bankruptcy in December 2000 and the Westbrook store closed early in 2001. The 52,000 sq.ft store stayed vacant for a while and Hannaford was thinking of moving out of their 38,000 sq.ft. store.

Hannaford finally moved to a new location elsewhere in town. Shaw’s supermarket, which had a location across the interstate at the Pine Tree Shopping Center, decided to move to the Westbrook Plaza. It became part of a redevelopment project of the plaza which was renamed Westbrook Crossing. In October 2004, Kohl’s opened a 90,000 sq.ft store on site of the former Bradlees and part of the former Hannaford. Shaw’s opened their new 68,000 sq.ft supermarket. The revamped shopping center also included a block of small stores. Chipotle opened in one half of the former Blockbuster Video. In May 2017, Payless Shoesource announced the closing of 387 U.S. stores including the Westbrook location. Ruby Tuesday eventually closed like many other locations in northern New England. Shaw's has closed its Westbrook location in February 2022.