The commission held an application for 5 Orange Street after the Historic Structures Advisory Group and commissioners voiced opposition to proposed skylights, a second-floor balcony and modern French doors on a rear conservatory.

The applicant's agent, Luke, described a plan that would demolish a later rear porch and replace it with a fully glazed conservatory with 12-foot doors, a second-floor deck and five skylights on a shallow-pitch roof. He said the owners plan to plant Leland cypress along Orange Street for screening.

Mickey Roland, representing the Historic Structures Advisory Group, told the commission the original arched, character-defining windows were more appropriate and that the proposed balcony and skylights were "definitely not appropriate." "Leland cypress do not belong downtown," Mickey said, adding that the back area should remain largely as-is.

Commissioners echoed the advisory group's concerns. Commissioner Angus said the five skylights did not meet local customary criteria ("one skylight per roof plane up toward the ridge") and called the balcony and French doors "very contemporary" and out of keeping with the structure. Several commissioners asked that original fenestration details be reinstated and that skylight count be reduced to traditional local practice.

The commission's motion directed the applicant to return with revisions that restore character-defining details (arched fenestration or compatible alternatives), eliminate or minimize skylights consistent with local guidelines, and rework the proposed deck to reduce visibility from public ways. The motion to hold for revisions carried unanimously.