The mall opened on September 8, 1975. Opening anchors included Maas Brothers and Sears, with JCPenney and J. W. Robinson's opening a year later. Out of the four original anchors, only JCPenney currently remains. Sears shrunk for Nordstrom Rack and Whole Foods Market and closed in 2018, Maas Brothers is now a Macy's, and J. W. Robinson's is now a Dillard's. A six screen movie theater was built next to the mall across from JCPenney. However, declining attendance led it to close in 2000; it has since become an LA Fitness center. In 2002, as part of their expansion into the United States, Westfield Group acquired Countryside Mall in a $4.8 billion deal that involved 13 other shopping centers. The mall was renamed "Westfield Countryside" by the new owners, dropping the "Shoppingtown" name in June 2005. In April 2009, work for a $12 million renovation project began. The mall's interior look was completely updated with new relocated escalators, new flooring and ceilings, additional skylights, an expanded children's play area, and a completely redesigned food court. Dozens of planters and fake columns were removed, and an entourage of new stores were brought to the mall. The renovations were completed in November 2009. In December 2011, Countryside Cobb-12 Cinema was added to the 2nd level of the mall. In 2012, Westfield Countryside also added Bar Louie, BJ's Brewhouse & Restaurant, Grimaldi's Coal Fired Pizzeria, and Red Robin Gourmet Burgers. In 2013, PF Chang's China Bistro was added to finish out "Restaurant Row". Pinellas County's first and only Whole Foods Market opened in September 2014 on the first floor's western portion of the Sears space. In 2015, Sears Holdingsspun off 235 of its properties, including the Sears at Westfield Countryside, into Seritage Growth Properties. In late 2015, Nordstrom Rack opened their first and only Pinellas County location at Westfield Countryside in the former Sears Auto Center. On April 23, 2018, Sears announced that its store would be closing as part of a plan to close 42 stores nationwide. The store closed on July 15, 2018.
Anchors
Current anchors
Dillard's, opened 1976 as J.W. Robinsons, sold to Maison Blanche in 1987, and to Dillard's in 1991
JCPenney, opened 1976
Macy's, opened 1975 as Maas Brothers, then Burdines in 1991, and Macy's in 2005
Nordstrom Rack, opened 2015 in former Sears Auto Center
Whole Foods Market, opened 2014 in part of Sears space
Former anchors
Burdines
Maas Brothers
Maison Blanche
J.W. Robinson's
Sears, opened 1975, formerly 223,184 sq ft., and shrunk in 2013 to make way for Whole Foods Market in 2014 - closed July 15, 2018