Situated near the coastline on the Gulf Coast, it serves over 9 million customers every year, and is home to five anchor stores, a 12-screen CMX Cinemas, numerous restaurants, and an ice skating rink.

Sears shrunk for Nordstrom Rack and Whole Foods Market and closed in 2018, Maas Brothers is now a Macy's (formerly Burdines), and J. W. Robinson's is now a Dillard's (formerly Maison Blanche).

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.

In 2012, Westfield Countryside also added Bar Louie, BJ's Brewhouse & Restaurant, Grimaldi's Coal Fired Pizzeria, and Red Robin Gourmet Burgers.

[5] In late 2015, Nordstrom Rack opened their first and only Pinellas County location at Westfield Countryside in the former Sears Auto Center.