Winter may be closing in fast on Boston, but suddenly, things are heating up on Summer Street.

The thoroughfare, which cuts a swath through the heart of the city’s Downtown Crossing district, is undergoing a series of changes that will alter the landscape dramatically, some by addition and others by subtraction. A main catalyst in the activity, for example, occurred last week when Syms Clothing finally shuttered its five-level store at 55 Summer St. after two years of hemorrhaging red ink from that operation.

The Syms failure has apparently not tainted the building as a retail destination, however, with industry sources maintaining that CVS Pharmacy will lease nearly 15,000 square feet of retail and storage space in the basement and ground floor of the 65,000-square-foot building. The Rhode Island-based company, already a ubiquitous presence in Downtown Crossing, reportedly would then close its 5,000-square-foot store across the street at 52 Summer St.

At this point, no one involved in the deal appears ready to discuss the matter. Although sources said a final agreement could be completed as early as this week, landlord Rosalind Gorin of the H.N. Gorin Co. would not comment, saying only, “We don’t have any signed leases.” CVS spokesman Michael DeAngelis also refused to acknowledge the negotiations.

The building’s leasing broker, Mark Browne of Browne Realty Advisors, was equally mum. “We’ve had a strong interest level in the space,” was all Browne would offer. The demand, he said, includes the upper floors, which are being converted for office use. Sources said Gorin has already found takers for all but one of the upper floors, leaving just 12,000 square feet available. Rents are said to be in the high $40 per-square-foot range, with some deals supposedly exceeding $50 per square foot later in the lease cycle.

The motivation for CVS, according to some, would likely be the prospect of doubling the existing store. Feeding off thousands of workers from the surrounding office buildings, the Summer Street CVS is often jammed full during peak hours, a situation that became so unwieldy that the store this year added bank-style customer ropes to guide people to the cash registers.

Beyond maneuverability, one broker following the deals suggested that CVS may also be concerned about the planned opening of a Walgreen’s Pharmacy a few doors down at the former Herman’s Sporting Goods store. That deal, first reported by B&T in July, would mark the arrival of the first non-CVS drugstore in Downtown Crossing.

“That’s a good strategic move,” the broker said of the CVS migration. “There’s a lot of reasons why it makes sense.”

Although the store would certainly give a new look for 55 Summer St., some suggest that the departure from 52 Summer St. could ultimately benefit that property as well. Owned by the Druker Co., the building is leased entirely to CVS, said principal Ronald Druker, even though the store itself is located only on the ground floor. According to industry observers, a CVS move would present Druker with a chance to redevelop 52 Summer St. and convert it into office space.

While insisting that CVS has not
approached him about getting out of its lease, Druker agreed it would not be
the worst outcome for his company, a major landlord throughout Downtown Crossing.

“If CVS goes, we’ll have an opportunity to do something,” said Druker. “If they stay, we’ll be happy to have them stay.”

According to one of the sources, the switch is all but imminent, with CVS hoping to be in 55 Summer St. quickly enough to thwart off any Walgreen’s insurgence. Druker said his building is currently about 20,000 square feet. It is unclear whether any floors could be built on top of the existing structure, but the source maintained that there is potential to add space.

One benefit for CVS is that the Walgreen’s would only be about 5,000 square feet. Despite that smaller size, it would finally put the former Herman’s property back into circulation four years after that chain closed the store as part of a liquidation.

Syms Swan Song
Meanwhile, pharmacies are not the only businesses marching onto Summer Street. Along with the recent opening of a Wendy’s Restaurant, a new 7-11 convenience store is headed to 56 Summer St. Also, Sebastian’s Catering is leasing approximately 3,000 square feet of revamped space in the ground floor of 100 Summer St. A spokeswoman for the landlord, Equity Office Properties, acknowledged last week that the deal is completed. The catering concern, a subsidiary of Fidelity Investments, will run a retail food service from the location.

While declining to discuss 55 Summer St., Browne said he does believe the street itself is on the upswing, with several closed or underperforming stores now being revitalized. Among the supposed reasons are the prolonged economic boom and the arrival of several thousand workers to Lafayette Corporate Center after that former mall was renovated into an office/retail complex. Lafayette itself is finally securing commitments from retailers, having recently inked Eddie Bauer to a 9,000-square-foot deal and now supposedly about to get Staples Inc. to sign a 12,000-square-foot deal. Officials at Schaffer & Assoc., the retail broker leasing that space, declined to comment on the situation.

As for Syms, the removal of its final merchandise last week marked the end of a brief but disastrous foray into Boston that began exactly two years ago this month. Despite a national operation of clothing stores, including the simultaneous opening of shops in downtown Chicago and New York, Syms struggled from the outset in the Hub, losing an estimated $3 million annually before opting to pull the plug. Earlier this month, for example, Syms officials announced a $10.5 million writeoff to get out of the 15-year lease and prepare the building for its next life.

According to Browne, it is unclear just what caused the company’s problems. Among the potential reasons, he said, may have been a misreading of the local demographics, consumer changes from more formal to casual clothing, plus the cavernous five-story operation itself. After trying various strategies to improve the traffic flow, Browne said Syms “begrudgingly accepted their fate.”

Had the company so desired, Gorin could have refused to negotiate a termination agreement with Syms, but Browne said the surging office market and demand as a retail property made such a stance unnecessary.

“We’re very happy,” Browne said. “With the market the way it is right now, it has worked out well.”