Chesapeake Square Mall
A regional shopping mall in Chesapeake, Virginia, undergoing redevelopment after the departure of most of its former department-store anchors.
Last updated August 25, 2026
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Overview
Chesapeake Square Mall is a regional shopping center in the Western Branch area of Chesapeake, Virginia, part of the Hampton Roads metropolitan region. The property opened in October 1989 on land that had previously been forest and swamp. It was developed by the Edward J. DeBartolo Corporation and was designed to serve the retail needs of western Chesapeake and nearby communities. At opening, its major department-store anchors included JCPenney, Sears, Hess's, and Leggett. The mall expanded its anchor mix during the 1990s and 2000s. Montgomery Ward opened in 1992, and after that retailer closed in 2001, its building was enlarged and converted for Target. Hecht's joined the center in 1999 and became Macy's in 2006 as part of the nationwide conversion of Hecht's stores. The former Leggett and Hess's spaces later passed through other department-store operators, including Belk and Proffitt's, before being occupied by Dillard's. Dillard's announced in 2009 that it would close both of its Chesapeake Square locations, leaving two large vacant anchor buildings. Burlington Coat Factory subsequently replaced the former Dillard's men's location. Entertainment became an important part of the property's repositioning. Cinemark moved into the former Dillard's women's and Hess's anchor space in 2010, and its twelve-screen theater, including an XD auditorium and stadium seating, opened in December 2011. The earlier Cinemark building was demolished in December 2017. The mall's tenant mix also included a food court and restaurants such as Big Woody's and Twisted Crab, while Target and Cinemark became particularly visible remaining destinations. Ownership and anchor departures have shaped the mall's more recent history. The property was previously associated with Simon Property Group and was transferred to Washington Prime Group in Simon's 2014 portfolio spin-off. Jones Lang LaSalle owned and managed the property before Virginia Beach-based Kotarides acquired it in February 2018. Macy's announced its closure in 2015, Sears announced the closure of its store in late 2014, and JCPenney announced that it would leave by 2022. JCPenney's departure removed the last of the mall's original opening anchors. Burlington closed in 2023, leaving Target as the only remaining retail store identified as an anchor in the available reference material. The property is now being reshaped through a large-scale redevelopment program rather than operating as the fully anchored department-store mall that existed in earlier decades. In December 2022, Kotarides Development president Pete Kotarides said that the former Macy's, JCPenney, and Sears buildings could be demolished and replaced by new retailers. Demolition work began in April 2025 on former department-store space, including areas associated with the former Burlington, JCPenney, and Macy's buildings. Plans described in a Cushman & Wakefield | Thalhimer flyer call for new retail development anchored by a grocery store and a sporting-goods store, with completion expected in fall 2026. The project indicates a transition from a traditional enclosed department-store mall toward a more mixed and redevelopment-oriented retail destination. The center's reported size is approximately 717,282 square feet, or about 66,638 square meters, and its historical tenant base has included roughly 70 stores.
History
Chesapeake Square was developed by the Edward J. DeBartolo Corporation and opened in October 1989 in Chesapeake's Western Branch section. The center was built on former forest and swamp land and became a regional shopping destination in the Hampton Roads area. Its initial anchor lineup consisted of JCPenney, Sears, Hess's, and Leggett, reflecting the department-store-centered format common to large enclosed malls of the period. The property added Montgomery Ward in 1992. After Montgomery Ward closed in 2001, its building was expanded and converted for Target. The mall's anchor roster continued to change as retail chains consolidated or rebranded. A Hecht's location opened in 1999 and was converted to Macy's in 2006. The former Hess's and Leggett spaces also changed operators, becoming associated with Proffitt's, Belk, and later Dillard's. Dillard's operated separate men's and women's locations, but announced in July 2009 that both Chesapeake Square stores would close. The men's building closed in September of that year, followed shortly by the women's building. Burlington Coat Factory replaced the former Dillard's men's location in September 2010. The former Dillard's women's and Hess's space was subsequently used for a Cinemark theater. Cinemark's twelve-screen venue opened in December 2011 and included stadium seating and an XD auditorium. The mall's older Cinemark building was demolished in December 2017, illustrating the continuing adaptation of the site as its retail and entertainment uses changed. The ownership structure also evolved. Chesapeake Square had previously been owned by Simon Property Group. In 2014, numerous properties were spun off from Simon to Washington Prime Group. Jones Lang LaSalle was associated with ownership and management before Kotarides acquired the property in February 2018. The acquisition placed the center under the control of a Virginia Beach-area developer as the traditional department-store model was weakening. Anchor closures accelerated during the 2010s and early 2020s. Sears announced the closure of its Chesapeake Square store in late 2014. Macy's was announced for closure in September 2015, with the store expected to leave by early 2016. In October 2021, JCPenney was reported to be leaving by 2022, ending the presence of the last original opening anchor. Burlington later closed in 2023. The available reference material identifies Target as the remaining retail anchor or major retail occupant after these departures, while Cinemark remained an important entertainment use during the mall's later history. The owner began planning a substantial redevelopment of the former anchor areas. In December 2022, Pete Kotarides, president of Kotarides Development, said that the former Macy's, JCPenney, and Sears buildings could be demolished and replaced by unnamed retailers. Demolition work began on April 7, 2025, when RC Demolition started removing former department-store space at the approximately 717,282-square-foot property. A flyer from Cushman & Wakefield | Thalhimer described plans for new retail development anchored by a grocery store and a sporting-goods store. The projected completion date was fall 2026. These plans represent a shift from a conventional enclosed mall dependent on multiple department stores toward a redevelopment model based on fewer, larger contemporary retail uses.
- 2025
Redevelopment demolition begins
[1]RC Demolition begins removing former department-store space for a redevelopment expected to include grocery and sporting-goods anchors.
- 2023
Burlington closes
[1]Burlington Coat Factory leaves the mall.
- 2018
Kotarides acquires the property
[1]Kotarides acquires Chesapeake Square for a reported $12.9 million.
- 2014
Property portfolio shifts to Washington Prime Group
[1]The mall is among properties spun off from Simon Property Group to Washington Prime Group.
- 2011
New Cinemark theater opens
[1]Cinemark opens a twelve-screen theater with stadium seating and an XD auditorium in a former department-store space.
- 2010
Burlington replaces former Dillard's men's space
[1]Burlington Coat Factory opens in the former Dillard's men's building.
- 2009
Dillard's exits
[1]Dillard's closes both its men's and women's locations at the mall.
- 2006
Hecht's converts to Macy's
[1]The Hecht's store is converted to Macy's as part of a broader chainwide rebranding.
- 2001
Montgomery Ward closes
[1]After Montgomery Ward closes, its building is expanded and adapted for Target.
- 1999
Hecht's becomes an anchor
[1]Hecht's opens at Chesapeake Square and later becomes Macy's in 2006.
Products and positioning
A regional retail and entertainment center serving Chesapeake and the wider Hampton Roads area, historically organized around department-store anchors and now repositioning through redevelopment, grocery, sporting-goods, and other replacement retail uses.
General merchandise retail · 2001
Target
Target occupies the former Montgomery Ward building, which was expanded after Montgomery Ward closed in 2001. It became the principal remaining retail anchor identified in the available history after the departures of Sears, Macy's, JCPenney, and Burlington.
Cinema and entertainment · 2011
Cinemark Theatres
Cinemark moved into a former Dillard's women's and Hess's anchor space. The twelve-screen theater opened in December 2011 and featured stadium seating and an Extreme Digital auditorium, providing an entertainment use within the mall's changing tenant mix.
Dining
Food court and restaurants
The mall has historically offered food-court dining and standalone restaurants. Reference material identifies Big Woody's and Twisted Crab among the restaurants located at or near the mall's main entry.
Brand decisions
2022
Redevelopment of former department-store areasStrategyBackground
The mall had lost Sears, Macy's, JCPenney, and later Burlington, leaving substantial former anchor space available for reuse.
Action taken
Kotarides Development outlined potential demolition of former Macy's, JCPenney, and Sears buildings and replacement with new retail uses.
Aftermath
Demolition began in April 2025, with plans calling for grocery and sporting-goods anchors and an expected fall 2026 completion.
2018
Kotarides purchases Chesapeake SquareM&ABackground
The transaction followed earlier ownership and portfolio changes involving Simon Property Group, Washington Prime Group, and Jones Lang LaSalle, during a period of anchor-store contraction.
Action taken
Kotarides acquired the mall in February 2018.
Aftermath
The property subsequently moved toward redevelopment after further anchor departures.
Acquisition price. $12.9 million (February 2018)
Sources1 sources
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