Is trouble in store for proponents' linchpin downtown redevelopment project, known as Bedford Square, as the Planning and Zoning Commission prepares to scrutinize "retail" use of the upper levels of the Westport Weston Family Y and whether they apply to the proposed project?

The Y has sold the property to Bedford Square Associates and plans to leave the site next year for its new Mahackeno headquarters, and a critical element of the redevelopment plans is citation of earlier P&Z memos that had generally considered the second and third stories of the Y "retail" uses. That status would allow the developers' plans for upper-level retail space to be grandfathered into their Post Road East project.

Unless an applicant can prove a pre-existing retail use on levels above the ground level, however, local zoning regulations prohibit such enterprises townwide.

And blunt questions arose at June's P&Z meeting about whether retail use of the Y building's upper levels really meet the pre-existing standard.

The complicated issue for the P&Z in weighing the retail-use question dates to a 2008 decision by the commission, upheld in court after a lawsuit filed by opponents of the Y's Mahackeno project, stated the Y's facilities constitute non-commercial recreational use. That key decision enabled the "non-commercial" Y to move forward with its plan to construct its new home in a residential zone off Sunny Lane, despite opposition.

Earlier, however, the P&Z staff had maintained that recreational facilities on the second and third floors of the Y's downtown building did constitute retail space. Under that interpretation, the Bedford Square team would have the right to develop second- and third-story retail space because of pre-existing use for the same.

The question was broached by P&Z Commissioner Jack Whittle at last month's P&Z meeting, when the panel began its review of the Bedford Square proposal.

"The uses being conducted at the Y were not commercial," Whittle said. "The proposal includes second- and third-floor retail and a great deal of it," he said of the Bedford Square plans. "I'm thinking, `How is that possible?' "

"You do not really have a pre-existing retail use on the second and third floors that you get to continue," Whittle added. That's the nagging problem I've got in my mind."

Representatives of the Bedford Square partnership appeared to be caught off guard by Whittle's concerns at the June meeting, and voiced surprise that the matter was being brought up at what they considered a late date in the approval process. The P&Z is the last town board whose blessing the developers need for the plans to secure final approval.

"The question is, `Does this carry over to what goes on at Bedford Square or not?' " Laurence Bradley, director of planning and zoning, said of the upper-level retail proposal. "That's the question and it's not an easy question to answer."

"The Camp Mahackeno case has no legal bearing," Bedford Square Associates wrote in a June 28 memo to the P&Z discounting the non-commercial status of the Y cited in that ruling.

"The historic use of the Bedford building ... has been for uses that include retail services," the memo states. "This fact has been consistently acknowledged by everyone who has looked at the situation. One Superior Court case with a very different fact pattern does not alter this and therefore does not establish legal precedent relevant to BSA's pending application."

Bradley said that before he joined the Westport P&Z staff, it had staff determined the Y's upstairs facilities, for the most part, qualified as retail.

"If you went back and looked at the staff memos, in the past the staff has taken a position that this is retail use," he said. "In the purest sense, the activities themselves ... are retail in nature ... but you have to overlay that with what the Y does" as a nonprofit organization that offers recreation and education programs.

"It's a difficult call to make," Bradley said.

Representatives of Bedford Square declined to comment on the recent questions, but referred to the memo concerning retail that it had sent to the commission.

"The applicant can take a couple of positions," Bradley said. "They can say they relied upon the staff's interpretation ... or they may say that what happened at the YMCA Mahackeno decision really has no bearing here on the Post Road East decision."

"It will be part of our discussion at our next meeting," said P&Z Chairwoman Catherine Walsh, but added that neither she nor any other commissioners could make comments on a pending application prior to their vote.

The P&Z is expected to continue its hearing on the Bedford Square application when it meets July 17 and 18.

The questions about the Bedford Square request to develop upper-level retail space could even prompt the P&Z re-examine its townwide prohibition against such uses, Bradley said.

"There was a proposal ... last year by an architect who was proposing to change some of the requirements to allow some limited second-floor uses, and that request was denied by the Planning and Zoning Commission," Bradley said.

At the last P&Z meeting, one of the commission members --Ron Corwin -- said he now regrets voting against the change, and would not do so now.