Greenbrier Mall opened in 1981 with two anchor stores and has been shedding and replacing them ever since. Three department stores still anchor the building today.
The fourth anchor space - the original Sears corner - has been empty since 2018 and is now the subject of a Costco proposal that has yet to clear the city's planning process.
The mall spans two levels across nearly 900,000 square feet, built into a hillside with entries on both floors.
It serves Chesapeake, the broader Hampton Roads region, and parts of eastern North Carolina via Greenbrier Parkway, Crossways Boulevard, and Eden Way North. With occupancy above 82 percent, it sold at auction for $22.3 million in early 2025.
The Hillside Mall That Chesapeake Built Its Identity Around
Park on the wrong side, and you walk in on the second floor. Park on the other side and you're already at ground level. Greenbrier Mall at Greenbrier Parkway South was built into a hill.
That hill never let anyone forget it - the building has entries on both levels, which is one of those things you stop noticing after the first dozen visits, but that strikes every first-timer as slightly wrong.
The mall opened on October 7, 1981, with Miller & Rhoads and Sears as its two anchors. Homart Development put it together.
The Greenbrier area had been filling in as a commercial district since the mid-1970s, and the mall locked it into place as Chesapeake's main retail destination.
The Greenbrier district now covers a study area of roughly 12 square miles, holds about 5.7 million square feet of retail space, and employs somewhere around 50,000 people on a typical weekday.
The mall's own footprint is 898,400 square feet across two levels.
It draws from Chesapeake, from the wider Hampton Roads region, and historically from parts of eastern North Carolina. In 1981, none of that scale existed yet.
Miller & Rhoads sold clothing and housewares. Sears sold everything else.
When Every Few Years Brought a New Sign Over the Same Door
Six years after it opened, Greenbrier got Hess's as a third department-store anchor. On September 7, 1988, Leggett - a division of Belk - opened as a fourth.
The food court filled up. Cinema Cafe opened with a format that combined dinner service with a movie screen.
Smokey Bones, Olive Garden, and Red Robin moved into outparcel spots around the edges of the property.
Then the consolidation started. Miller & Rhoads was sold to Hecht's in 1990. Proffitt's bought the Hess's space in 1993. Dillard's took over from Proffitt's in 1996.
The Leggett store had briefly run under the Belk name before Dillard's absorbed that space too in 1998, folding it into a men's and children's auxiliary location.
At one point, Dillard's controlled two of the building's major anchor spots simultaneously. Hecht's was still in the former Miller & Rhoads corner.
Sears still had its original end. JCPenney hadn't arrived yet. Every one of these changes came out of mergers and portfolio deals made in corporate offices, nowhere near Chesapeake.
The walls stayed the same. The parking lot still filled up on Saturdays. The stores just had different names.
A Gut Renovation and a $102.5 Million Sale
The 2003 renovation was the most structurally important thing that happened to Greenbrier Mall by the early 2000s.
Dillard's pulled back from two locations to one, consolidating into the former Proffitt's space at the east end of the building - about 160,000 square feet of reconstruction.
That left the old Leggett/Belk/Dillard's auxiliary building empty, and it became a JCPenney. The mall also got a new color scheme and the "G" logo it still uses today.
In April 2004, CBL & Associates Properties bought the property for $102.5 million from Gregory Greenfield & Associates.
CBL owned regional malls across the country and added Greenbrier to a portfolio that already spanned multiple states.
In 2006, Hecht's became Macy's as part of a national conversion that swept through dozens of cities at once, and the anchor lineup settled into Sears, Dillard's, JCPenney, and Macy's - four department stores in a two-level building that had worked through ten brand names in twenty-five years.
The 2013 renovation was a smaller job - new carpet on the upper level, fresh paint, restroom work, better landscaping, a redesigned food court with new seating - all of it surface work that touched what shoppers actually saw without moving a single wall.
The Sears End Went Dark in 2018 and Stayed That Way
Sears opened with Greenbrier Mall and held its place there for thirty-seven years. In 2015, the chain shifted its real-estate holdings, including the Greenbrier site, into a new company called Seritage Growth Properties.
The move split the land and building from the retail operation.
The store kept its lights on for three more years. On June 28, 2018, Sears set the closing. By September, the space stood empty. A new use surfaced in 2020.
The plan put Rosie's Gaming Emporium into the former Sears footprint, with around 700 historical horse-racing stations, a brewery on the second floor, four freestanding restaurants, and a four-story hotel nearby.
Chesapeake moved the proposal into public review.
Then traffic carried the fight. The question centered on what another major draw would do to Greenbrier Parkway, Crossways Boulevard, and Eden Way North.
The proposal stalled and did not advance. The Sears space stayed dark.
Greenbrier's loan had come due in December 2019 with about $61.6 million still on the balance. CBL defaulted. On March 10, 2022, the property entered receivership.
The Foreclosure, the Auction, and Michael Sifen's $22.3 Million
The mall ran in receivership for nearly three years before most of it went to auction in February 2025. The opening bid was $6 million.
It sold for $22.3 million to a buyer connected to Michael Sifen, a Virginia Beach general contractor and developer.
The deal covered about 55 acres, including the Macy's and JCPenney sections of the property. Dillard's, which owns its own parcel, was not part of it.
Occupancy at the time of the sale was above 82 percent.
H&M, Foot Locker, Victoria's Secret, Bath & Body Works, Kay Jewelers, Reeds Jewelers, Aéropostale - the tenant list ran to several dozen stores, plus food vendors, services, and two civic uses: Chesapeake Police Community Outreach and the American Red Cross.
Cinema Cafe was still running.
Next month, the city held a public meeting on the future of the Greenbrier area, with concepts for the mall site that included a grocery store, residential units, dining, and an event center.
On August 19, 2025, the Chesapeake City Council adopted the Greenbrier Area Plan as the governing framework for the district.
A Permit Application and a Warehouse Store That Could Change Everything
The former Sears site hadn't had a serious tenant proposal since the gaming emporium failed in 2020.
In early January 2026, a conditional-use permit application appeared in Chesapeake's planning files - a fueling station tied to a possible Costco Wholesale development at that same location.
No site plans had gone to the planning commission or city council for review, and the city had approved nothing yet.
At the end of 2022, Greenbrier's retail vacancy rate was 4.3 percent, and about 57 percent of that empty space was inside the mall itself.
Average asking rents in Greenbrier ran at $23 per square foot, against Chesapeake's average of $16.40 and Hampton Roads' average of $15.50.
From 2018 through 2022, the Greenbrier area added 187,000 square feet of new retail - 54 percent of all new retail built in Chesapeake during that time.
The district added more than half of the city's new retail construction while also holding most of its vacant space.
Projected demand through 2045 for the Greenbrier study area is 505,000 to 555,000 additional square feet.
A Costco at the former Sears site would absorb a large portion of that in one building.
Nine Jewelry Stores, a Piano Showroom, and a Police Outreach Office
Greenbrier Mall is open Monday through Thursday from 10:00 a.m. to 8:00 p.m., Friday and Saturday until 9:00 p.m., and Sunday from noon to 6:00 p.m.
The 2026 events calendar runs from Only for Her in May through Santa's Workshop in December, with Juneteenth in June, Boo Bash in October, and Shopping with Elves in November.
At least nine separate jewelry stores operate inside the building: Banter, Broadway Jewelers, Jewelry Palace, Kay Jewelers, New York Jewelers, Reeds Jewelers, Segal & Co. Fine Jewelry, SK Diamonds, and Zales.
Piano Showcase holds a permanent inline space. So does Family Pet Center and Collector's Heaven. The service section covers hair, nails, tailoring, watch repair, and phone repair.
Short-term leases - kiosks, carts, pop-up spaces - run anywhere from a few days to twelve months, which means the tenant mix on any given visit is never quite the same as the last.
A police community outreach office and an American Red Cross blood donation site share the building with stores selling candles and athletic shoes.
The former Sears end is still the open question, and the application filed in November 2025 is the most concrete answer anyone has offered for it.
Chesapeake's Plans for the District That Grew Up Around the Mall
Chesapeake adopted the Greenbrier Area Plan on August 19, 2025. Its borders ran to the Virginia Beach city line, Military Highway, Route 168, and Kempsville Road.
This planning area holds 73.4 percent of the city's office inventory and 70 percent of its hotel rooms, 3,079 rooms in total.
Demand projections through 2045 call for 2,100 to 2,400 new housing units, 725,000 to 775,000 additional square feet of office space, and 300 to 400 new hotel rooms.
The adopted plan includes a rendering of the mall site rebuilt as a mixed-use district.
Getting there requires the Costco proposal to clear, Sifen to produce a redevelopment plan, Dillard's to cooperate on its separate parcel, and a developer to commit to the grocery, housing, dining, and event-space concepts the city has put forward.
None of those conditions is settled. The site is 55 acres of active retail in the middle of Chesapeake's largest commercial district. As of May 2026, it was still mostly a mall.
