Chesapeake Square is a fully enclosed regional shopping center in the Western Branch area of Chesapeake, Virginia, part of the Hampton Roads metro area, made up of independent cities and nearby counties.
The mall is located at 4200 Portsmouth Boulevard, close to where Portsmouth Boulevard meets Taylor Road. This location places it at a key western point for retail traffic moving through the Chesapeake area.
It serves shoppers from Western Branch, the rest of Chesapeake, and the wider Hampton Roads region. The property combines shopping, dining, and entertainment, with Target and a 12-screen Cinemark XD theater as its main active anchor stores.
The mall opened on October 11, 1989, developed by the Edward J. DeBartolo Corporation on land that was previously forest and swamp. The site is now undergoing a $30 million redevelopment into a mixed-use property.
How a Swamp Became the Center of Western Branch
In the late 1980s, the stretch of land along Portsmouth Boulevard in Chesapeake's Western Branch was still forest and swamp.
That changed when crews cleared the site and built a large enclosed mall, covering nearly one million square feet. It opened on October 11, 1989.
Almost right away, it started attracting shoppers who had been going to older retail centers in Portsmouth and elsewhere in Hampton Roads.
The mall was developed by the Edward J. DeBartolo Corporation. Its original anchor stores - JCPenney, Sears, Hess's, and Leggett - gave it the draw of a full regional destination.
Back then, 4200 Portsmouth Boulevard at the corner of Taylor Road was not known as a retail area. The mall established it as one.
Other shopping centers followed, including The Crossroads at Chesapeake Square across the street, built after the mall and influenced by its customer traffic, along with Chesapeake Center next door.
Chesapeake Square quickly became a major draw. As more shoppers headed west, older shopping centers in Portsmouth began losing tenants to the newer development.
Chesapeake Square's Anchor Lineup Keeps Reshuffling
Montgomery Ward arrived in 1992 as a fifth anchor, filling a new space that expanded the mall's footprint.
When Ward went under in 2001, its building sat vacant until Target moved in, opening in that expanded space on March 10, 2002.
The Hess's space changed hands in stages: it became Proffitt's and then, later in 1997, Dillard's took over Proffitt's locations at Chesapeake Square and several other Hampton Roads malls through a regional acquisition deal.
Hecht's opened a brand-new anchor store in October 1999, the same year the mall completed what would turn out to be its last major renovation.
That Hecht's location converted to Macy's in 2006 when the parent company rebranded the entire Hecht's chain. By the mid-2000s, Chesapeake Square had six active anchor spaces and appeared stable.
Within a decade, three of those six spaces would lose their anchor tenants, though the spaces did not all remain empty.
The $13.7 Million Bet on Entertainment and Burlington
Dillard's operated two anchor buildings at Chesapeake Square.
When the company announced in July 2009 that it would close both locations - affecting 45 employees - it left two large boxes on the mall's floor plan without tenants.
Burlington Coat Factory took the 81,700-square-foot former Dillard's South store and opened on September 24, 2010, bringing 70 jobs with it.
The second backfill was more ambitious.
Simon Property Group and Cinemark jointly committed $13.7 million to convert the former Dillard's east-wing building into a 12-screen, all-digital theater with stadium seating, IMAX 3D capability, and Cinemark's then-new NextGen design format.
The theater opened on December 16, 2011, with a Cinemark XD auditorium included.
The move made Chesapeake Square unusual: a mid-sized enclosed mall that had replaced a traditional department store with a cinema at the height of the entertainment-anchor trend.
How Chesapeake Square Lost Two Anchors in Two Years
In October 2014, Sears announced that its Chesapeake Square store and Sears Auto Center would close in mid-January 2015, with liquidation starting October 31.
Fourteen months later, in January 2016, Macy's announced it would also close, with 69 employees at the Chesapeake Square location and final clearance sales beginning January 11.
JCPenney was the last original anchor standing. The losses at the tenant level matched deterioration at the ownership level.
Simon had spun off Washington Prime Group on May 28, 2014, separating its smaller and lower-performing enclosed malls into a new company.
Chesapeake Square was part of that portfolio. By 2015, the property had entered special servicing.
In April 2016, it was sold back to the lender through a foreclosure sale, with an outstanding loan balance of approximately $60.1 million.
The 2017 Sale Package Tells the Story in Numbers
The 2017 sale marketing package - produced for the sale of a distressed asset - captures exactly what Chesapeake Square had become.
The total mall measured 760,400 square feet, but only 613,800 square feet were included in the offering because Target and Cinemark both owned their spaces outright.
Of that offered space, only 58 percent was occupied. Macy's and Sears were already vacant. Burlington and JCPenney were included in the offering.
The mall still had roughly 100 stores, restaurants, and kiosks, plus a 10-unit food court.
The loan balance on the property was approximately $60 million.
The property was being offered as a repositioning opportunity, which in commercial real estate language means the seller does not expect a buyer to operate it as-is.
JLL had been managing the leasing and transition since 2016, after the special servicer takeover in 2015.
The gap between the $60 million loan balance and whatever the property would fetch at sale was the clearest single measure of how far it had fallen.
Kotarides Pays $12.9 Million for 68 Acres of Potential
Kotarides, a company based in Virginia Beach, completed its purchase of Chesapeake Square in February 2018 for $12.9 million.
At that point, the property was assessed at about $49 million, more than three times what was paid.
At the time of the sale, the mall's anchor tenants were JCPenney, Burlington, Target, and Cinemark. Target and Cinemark owned their own spaces. Inside the mall, roughly 100 stores and kiosks were still in operation.
In May 2018, Kotarides selected Cushman & Wakefield Thalhimer as the exclusive leasing representative for a redevelopment covering about 613,000 square feet across approximately 68 acres.
Early plans called for a phased approach that would keep Target, Cinemark, JCPenney, and Burlington while adding new uses such as restaurants, retail, office space, and other mixed-use development.
Later plans expanded the project into a larger mixed-use program under MX zoning. The proposal included residential units, office buildings, grocery-anchored retail, and entertainment spaces.
Burlington closed in 2023.
That left Target as the only traditional retail anchor still operating at the site. JCPenney had previously announced in October 2021 that it would leave.
Demolition Starts, and a $30 Million Redevelopment Takes Shape
In the week of April 7, 2025, RC Demolition crews from Norfolk started removing parts of Chesapeake Square.
The work centered on the west end, where the former Burlington location and the old Sears, Macy's, and JCPenney buildings were located.
The redevelopment plan, valued at $30 million, called for a grocery store and a sporting goods store to replace those structures, along with new outparcels.
Demolition was expected to finish by mid-May 2025. Site work would follow, with construction planned to begin in October.
Target and the 12-screen Cinemark XD continued operating during the process. At the time demolition began, about 30 tenants - including both national retailers and local restaurants - were still open at the property.
By January 2026, the project was still in progress. Completion was expected between summer and fall 2026.
The official mall directory from early 2026 still listed tenants such as AT&T, Bath & Body Works, Finish Line, Rack Room Shoes, SNIPES, Twisted Crab, and Nori Japan.
Why Chesapeake Square's Reported Size Keeps Changing
The size of Chesapeake Square changes depending on the source. In 1989, opening coverage listed it at 984,500 square feet.
A 2011 city report described an 804,000-square-foot mall on 82 acres. In 2017, sales materials gave a total of 760,400 square feet, with 613,800 square feet included in the offering.
By 2025, demolition coverage described the site as about 1 million square feet in total, with roughly 700,000 square feet counted as leasable.
These numbers are all valid within their context. They differ because of how the property is measured, the year of the measurement, and which parts of the site are included.
Target and Cinemark own their buildings, so some totals include those areas while others do not.
